(+)-Griseofulvin

Iupac Name：(2S,5'R)-7-chloro-3',4,6-trimethoxy-5'-methylspiro[1-benzofuran-2,4'-cyclohex-2-ene]-1',3-dione

Molecular Weight：352.77

Modify Date.: 2023-02-14 09:18

Introduction: Griseofulvin is a non-polyene class antifungal antibiotics; it can strongly inhibit the mitosis of fungal cell and interfere with the fungal DNA synthesis; it can also bind to tubulin to prevent fungal cell division. It has been applied to clinical medicine since 1958 and has currently been widely used for treating the fungal infections of the skin and the stratum corneum with strong inhibitory effects on Trichophyton rubrum and Trichophyton tonsorans, etc. Griseofulvin is not only a widely used antibiotic for clinical treatment of fungal infections of the skin and cuticle, but also applied in agriculture for prevention and treatment of fungal diseases; for example, it has a special efficacy on treating a kind of candidiasis in apple which can cause infection during pollination. View more+

Request For Quotation

1. Names and Identifiers

1.1 Name: (+)-Griseofulvin
1.2 Synonyms: (1&rsquoS,6&rsquoR)-7-chloro-2&rsquo,4,6-trimethoxy-6&rsquo-methylspiro[benzofuran-2(3H),1&rsquo-[2]cyclohexene]-3,4&rsquo-dione (1&rsquoS-trans)- 7-chloro-2&rsquo,4,6-trimethoxy-6&rsquo-methylspiro[benzofuran-2(3H),1&rsquo-cyclohex-2&rsquo-ene]-3,4&rsquo-dione (1'S-trans)-7-Chloro-2',4,6-trimethoxy-6'-methylspiro[benzofuran-2(3H),1'-[2]cyclohexene]-3,4'-dione (2S,5'R)-7-chloro-3',4,6-trimethoxy-5'-methylspiro[1-benzofuran-2,4'-cyclohex-2-ene]-1',3-dione (2S,6'R)-7-Chloro-2',4,6-trimethoxy-6'-methyl-3H,4'H-spiro[1-benzofuran-2,1'-cyclohex[2]ene]-3,4'-dione 7-chloranyl-3',4,6-trimethoxy-5'-methyl-spiro[1-benzofuran-2,4'-cyclohexane]-1',3-dione 7-Chloro-2',4,6-trimethoxy-6'b-methylspiro[benzofuran-2(3H),1'-[2]cyclohexene]-3,4'-dione 7-Chloro-2,4,6-trimethoxy-6-methyl-, (1S-trans)-Spiro(benzofuran-2(3H),1-(2)cyclohexene)-3,4-dione 7-Chloro-2',4,6-trimethoxy-6'-methyl-3H,4'H-spiro[1-benzofuran-2,1'-cyclohexane]-3,4'-dione 7-chloro-3',4,6-trimethoxy-5'-methylspiro[benzofuran-2,4'-cyclohexane]-1',3-dione 7-chloro-4,6-dimethoxycoumaran-3-one-2-spiro-1&rsquo-(2&rsquo-methoxy-6&rsquo-methylcyclohex-2&rsquo-en-4&rsquo-one) amudane Curling factor EINECS 204-767-4 Fulcin Fulvicin Grifulvin Grisact Grisactin Griseofulvin Griseofulvin (200 mg) Griseofulvin Permeability Diameter GRISEOFULVIN(RG) Griseofulvin, (2S)-trans-7-Chloro-2μ,4,6-trimethoxy-6μ-methylspiro(benzofuran-2[3H],1μ-[2]cyclohexene)-3,4μ-dione Grisovi Grisovin Grizeofulvin Lamoryl Likuden Likunden MFCD00082343 Polygris Poncyl Spiro[benzofuran-2(3H),1'-cyclohex[2]ene]-3,4'-dione, 7-chloro-2',4,6-trimethoxy-6'-methyl-, (2S,6'R)- Spiro[benzofuran-2(3H),1'-cyclohexane]-3,4'-dione, 7-chloro-2',4,6-trimethoxy-6'-methyl- Spirofulvin Sporostatin UNII-32HRV3E3D5

1.3 CAS No.: 126-07-8

1.4 CID: 441140

1.5 EINECS(EC#): 204-767-4

1.6 Molecular Formula: C17H17ClO6 (isomer)

1.7 Inchi: InChI=1S/C17H17ClO6/c1-8-5-9(19)6-12(23-4)17(8)16(20)13-10(21-2)7-11(22-3)14(18)15(13)24-17/h6-8H,5H2,1-4H3/t8-,17+/m1/s1

1.8 InChkey: DDUHZTYCFQRHIY-RBHXEPJQSA-N

1.9 Canonical Smiles: CC1CC(=O)C=C(C12C(=O)C3=C(O2)C(=C(C=C3OC)OC)Cl)OC

1.10 Isomers Smiles: C[C@@H]1CC(=O)C=C([C@]12C(=O)C3=C(O2)C(=C(C=C3OC)OC)Cl)OC

2. Properties

2.1 Density: 1.2579 (rough estimate)

2.1 Melting point: 218-220 °C(lit.)

2.1 Boiling point: 469.04°C (rough estimate)

2.1 Refractive index: 1.4429 (estimate)

2.1 Flash Point: 228°C

2.1 Precise Quality: 352.07100

2.1 PSA: 71.06000

2.1 logP: 2.81030

2.1 Λmax: 321nm(CHCl3)(lit.)

2.2 AnalyticLaboratory Methods: AOAC METHOD NO. 968.49. DETERMINATION IN FEEDS, APPLICABLE TO CONCN GREATER THAN OR EQUAL TO 10 MG/OZ; CHROMATOGRAPHY; SPECTROPHOTOMERY, READING AT 290 & 320 NM.

2.3 Appearance: White to pale cream-colored crystalline powder. Odorless or almost odorless. Tasteless.

2.4 Storage: Keep Cold.

2.5 Chemical Properties: Griseofulvin pure product is colorless crystal, being neutral, and insoluble in water with a strong systemic property. It is stable both in vitro and in vivo of plants and is also stable to the various environment factors between pH3.0~8.8. It can be used for prevention and treatment of a variety of fungal plant diseases. The main species china applied for production of griseofulvin is Penicillium nigricans and Penicillium urticae. When grown at the medium, Penicillium nigricans is fuzzy with fresh culture being pure gray and aging culture being dark gray with its back being deep orange-red to the back orange brown. The fungi lawn of Penicillium urticae is yellowish green to pure light gray, thick and dense with the back being pale yellow to brownish; their aerial hyphae has a broom-like shape.

2.6 Color/Form: Powder

2.7 Odor: ODORLESS

2.8 Physical: PHYSICAL DESCRIPTION: White to pale cream-colored crystalline powder. Odorless or almost odorless. Tasteless. Sublimes without decomposition at 410°F. (NTP, 1992)

2.9 Water Solubility: practically insoluble

2.10 Spectral Properties: MAX ABSORPTION: 286 NM, 325 NM
SPECIFIC OPTICAL ROTATION: +370 DEG @ 17 DEG C/D (SATURATED CHLOROFORM SOLN)
INDEX OF REFRACTION: 1.5403 @ 25 DEG C/D
MAX ABSORPTION (ALCOHOL): 291 NM (LOG E= 4.37); 325 NM (LOG E= 3.77); SPECIFIC OPTICAL ROTATION: +337 DEG @ 21 DEG C/D (ACETONE)
IR: 5182 (Coblentz Society Spectral Collection)
UV: 6-726 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York)
MASS: 2748 (National Bureau of Standards EPA-NIH Mass Spectra Data Base, NSRDS-NBS-63)

2.11 Stability: Stable under normal temperatures and pressures.

2.12 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 Definition: ChEBI: An oxaspiro compound produced by Penicillium griseofulvum. It is used by mouth as an antifungal drug for infections involving the scalp, hair, nails and skin that do not respond to topical treatment.

3.2 General Description: Griseofulvin is a non-polyene class antifungal antibiotics; it can strongly inhibit the mitosis of fungal cell and interfere with the fungal DNA synthesis; it can also bind to tubulin to prevent fungal cell division. It has been applied to clinical medicine since 1958 and has currently been widely used for treating the fungal infections of the skin and the stratum corneum with strong inhibitory effects on Trichophyton rubrum and Trichophyton tonsorans, etc. Griseofulvin is not only a widely used antibiotic for clinical treatment of fungal infections of the skin and cuticle, but also applied in agriculture for prevention and treatment of fungal diseases; for example, it has a special efficacy on treating a kind of candidiasis in apple which can cause infection during pollination.

3.3 GHS Classification: Signal: Danger
GHS Hazard Statements
Aggregated GHS information provided by 81 companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria by 1 of 81 companies. For more detailed information, please visit ECHA C&L website

Of the 12 notification(s) provided by 80 of 81 companies with hazard statement code(s):

H317 (86.25%): May cause an allergic skin reaction [Warning Sensitization, Skin]
H351 (97.5%): Suspected of causing cancer [Warning Carcinogenicity]
H360 (98.75%): May damage fertility or the unborn child [Danger Reproductive toxicity]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P201, P202, P261, P272, P280, P281, P302+P352, P308+P313, P321, P333+P313, P363, P405, and P501

3.4 Methods of Manufacturing: ANTIBIOTIC SUBSTANCE PRODUCED BY PENICULLIUM GRISEOFULVUM DIERCKX AND BY P. JANCZEWSKII ZAL. (= P. NIGRCANS (BANIER) THOM.). ISOLATION: OXFORD ET AL, BIOCHEM J 33, 240 (1939); BRIAN ET AL, TRANS BRIT MYCOL SOC 29, 173 (1946); HOCKENHULL, DOREY ET AL, US PATENT 3,069,328-9 (1962 TO GLAXO).

3.5 Produe Method: Griseofulvin is a antibiotic produced from the culture fermentation broth of Penicillium griseofulvum.

3.6 Purification Methods: Crystallise it from *benzene or EtOH. Purify 2g of griseofulvin by chromatography on Alumina (40 x 1.5cm) and elute with *C6H6/MeOH (199:1) and follow the UV blue fluorescent band. [MacMillan J Chem Soc 1823 1959, Beilstein 18 III/IV 3160, 18/5 V 150.]

3.7 Usage: adrenegic blocker, Ca channel blocker, coronary vasodilator, antiarrhythmic

4. Safety and Handling

4.1 Symbol: GHS07;GHS08;

4.1 Hazard Codes: T,Xn

4.1 Signal Word: DANGER

4.1 Risk Statements: 60-61-40-43-45

4.1 Safety Statements: 53-22-36/37/39-45

4.1 Exposure Standards and Regulations: Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

4.2 Octanol/Water Partition Coefficient: LogP = 2.18

4.3 Fire Hazard: Flash point data for (+)-Griseofulvin are not available. (+)-Griseofulvin is probably combustible.

4.4 Other Preventative Measures: PRECAUTIONS FOR "CARCINOGENS": Smoking, drinking, eating, storage of food or of food & beverage containers or utensils, & the application of cosmetics should be prohibited in any laboratory. All personnel should remove gloves, if worn, after completion of procedures in which carcinogens have been used. They should ... wash ... hands, preferably using dispensers of liq detergent, & rinse ... thoroughly. Consideration should be given to appropriate methods for cleaning the skin, depending on nature of the contaminant. No standard procedure can be recommended, but the use of organic solvents should be avoided. Safety pipettes should be used for all pipetting. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": In animal laboratory, personnel should remove their outdoor clothes & wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... Clothing should be changed daily but ... discarded immediately if obvious contamination occurs ... /also,/ workers should shower immediately. In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. If gowns are of distinctive color, this is a reminder that they should not be worn outside of lab. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": ... Operations connected with synth & purification ... should be carried out under well-ventilated hood. Analytical procedures ... should be carried out with care & vapors evolved during ... procedures should be removed. ... Expert advice should be obtained before existing fume cupboards are used ... & when new fume cupboards are installed. It is desirable that there be means for decreasing the rate of air extraction, so that carcinogenic powders can be handled without ... powder being blown around the hood. Glove boxes should be kept under negative air pressure. Air changes should be adequate, so that concn of vapors of volatile carcinogens will not occur. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": Vertical laminar-flow biological safety cabinets may be used for containment of in vitro procedures ... provided that the exhaust air flow is sufficient to provide an inward air flow at the face opening of the cabinet, & contaminated air plenums that are under positive pressure are leak-tight. Horizontal laminar-flow hoods or safety cabinets, where filtered air is blown across the working area towards the operator, should never be used ... Each cabinet or fume cupboard to be used ... should be tested before work is begun (eg, with fume bomb) & label fixed to it, giving date of test & avg air-flow measured. This test should be repeated periodically & after any structural changes. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": Principles that apply to chem or biochem lab also apply to microbiological & cell-culture labs ... Special consideration should be given to route of admin. ... Safest method of administering volatile carcinogen is by injection of a soln. Admin by topical application, gavage, or intratracheal instillation should be performed under hood. If chem will be exhaled, animals should be kept under hood during this period. Inhalation exposure requires special equipment. ... Unless specifically required, routes of admin other than in the diet should be used. Mixing of carcinogen in diet should be carried out in sealed mixers under fume hood, from which the exhaust is fitted with an efficient particulate filter. Techniques for cleaning mixer & hood should be devised before expt begun. When mixing diets, special protective clothing &, possibly, respirators may be required. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": When ... admin in diet or applied to skin, animals should be kept in cages with solid bottoms & sides & fitted with a filter top. When volatile carcinogens are given, filter tops should not be used. Cages which have been used to house animals that received carcinogens should be decontaminated. Cage-cleaning facilities should be installed in area in which carcinogens are being used, to avoid moving of ... contaminated /cages/. It is difficult to ensure that cages are decontaminated, & monitoring methods are necessary. Situations may exist in which the use of disposable cages should be recommended, depending on type & amt of carcinogen & efficiency with which it can be removed. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": To eliminate risk that ... contamination in lab could build up during conduct of expt, periodic checks should be carried out on lab atmospheres, surfaces, such as walls, floors & benches, & ... interior of fume hoods & airducts. As well as regular monitoring, check must be carried out after cleaning-up of spillage. Sensitive methods are required when testing lab atmospheres. ... Methods ... should ... where possible, be simple & sensitive. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": Rooms in which obvious contamination has occurred, such as spillage, should be decontaminated by lab personnel engaged in expt. Design of expt should ... avoid contamination of permanent equipment. ... Procedures should ensure that maintenance workers are not exposed to carcinogens. ... Particular care should be taken to avoid contamination of drains or ventilation ducts. In cleaning labs, procedures should be used which do not produce aerosols or dispersal of dust, ie, wet mop or vacuum cleaner equipped with high-efficiency particulate filter on exhaust, which are avail commercially, should be used. Sweeping, brushing & use of dry dusters or mops should be prohibited. Grossly contaminated cleaning materials should not be re-used ... If gowns or towels are contaminated, they should not be sent to laundry, but ... decontaminated or burnt, to avoid any hazard to laundry personnel. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": Doors leading into areas where carcinogens are used ... should be marked distinctively with appropriate labels. Access ... limited to persons involved in expt. ... A prominently displayed notice should give the name of the Scientific Investigator or other person who can advise in an emergency & who can inform others (such as firemen) on the handling of carcinogenic substances. /Chemical Carcinogens/

4.5 Hazard Declaration: H317; H351; H360

4.5 Cleanup Methods: PRECAUTIONS FOR "CARCINOGENS": A high-efficiency particulate arrestor (HEPA) or charcoal filters can be used to minimize amt of carcinogen in exhausted air ventilated safety cabinets, lab hoods, glove boxes or animal rooms ... Filter housing that is designed so that used filters can be transferred into plastic bag without contaminating maintenance staff is avail commercially. Filters should be placed in plastic bags immediately after removal ... The plastic bag should be sealed immediately ... The sealed bag should be labelled properly ... Waste liquids ... should be placed or collected in proper containers for disposal. The lid should be secured & the bottles properly labelled. Once filled, bottles should be placed in plastic bag, so that outer surface ... is not contaminated ... The plastic bag should also be sealed & labelled. ... Broken glassware ... should be decontaminated by solvent extraction, by chemical destruction, or in specially designed incinerators. /Chemical Carcinogens/

4.6 DisposalMethods: SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
PRECAUTIONS FOR "CARCINOGENS": There is no universal method of disposal that has been proved satisfactory for all carcinogenic compounds & specific methods of chem destruction ... published have not been tested on all kinds of carcinogen-containing waste. ... summary of avail methods & recommendations ... /given/ must be treated as guide only. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": ... Incineration may be only feasible method for disposal of contaminated laboratory waste from biological expt. However, not all incinerators are suitable for this purpose. The most efficient type ... is probably the gas-fired type, in which a first-stage combustion with a less than stoichiometric air:fuel ratio is followed by a second stage with excess air. Some ... are designed to accept ... aqueous & organic-solvent solutions, otherwise it is necessary ... to absorb soln onto suitable combustible material, such as sawdust. Alternatively, chem destruction may be used, esp when small quantities ... are to be destroyed in laboratory. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": HEPA (high-efficiency particulate arrestor) filters ... can be disposed of by incineration. For spent charcoal filters, the adsorbed material can be stripped off at high temp & carcinogenic wastes generated by this treatment conducted to & burned in an incinerator. ... LIQUID WASTE: ... Disposal should be carried out by incineration at temp that ... ensure complete combustion. SOLID WASTE: Carcasses of lab animals, cage litter & misc solid wastes ... should be disposed of by incineration at temp high enough to ensure destruction of chem carcinogens or their metabolites. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": ... Small quantities of ... some carcinogens can be destroyed using chem reactions ... but no general rules can be given. ... As a general technique ... treatment with sodium dichromate in strong sulfuric acid can be used. The time necessary for destruction ... is seldom known ... but 1-2 days is generally considered sufficient when freshly prepd reagent is used. ... Carcinogens that are easily oxidizable can be destroyed with milder oxidative agents, such as saturated soln of potassium permanganate in acetone, which appears to be a suitable agent for destruction of hydrazines or of compounds containing isolated carbon-carbon double bonds. Concn or 50% aqueous sodium hypochlorite can also be used as an oxidizing agent. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": Carcinogens that are alkylating, arylating or acylating agents per se can be destroyed by reaction with appropriate nucleophiles, such as water, hydroxyl ions, ammonia, thiols & thiosulfate. The reactivity of various alkylating agents varies greatly ... & is also influenced by sol of agent in the reaction medium. To facilitate the complete reaction, it is suggested that the agents be dissolved in ethanol or similar solvents. ... No method should be applied ... until it has been thoroughly tested for its effectiveness & safety on material to be inactivated. For example, in case of destruction of alkylating agents, it is possible to detect residual compounds by reaction with 4(4-nitrobenzyl)-pyridine. /Chemical Carcinogens/

4.7 RIDADR: UN 1648 3 / PGII

4.7 Caution Statement: P201-P280-P308 + P313

4.7 Formulations/Preparations: DUSTS 1.5-3.5% WT/WT FOR USE AT 75 LB/ACRE. WETTABLE POWDERS, DISPERSIBLE CONCENTRATES (SOLN IN DIMETHYL FORMAMIDE WITH DISPERSING AGENT). /SRP: NOT APPROVED FOR USE ON CROPS IN US./
GRISEOFULVIN, USP (FULVICIN U/F, GRIFULVIN V, GRISACTIN), IS MARKETED IN CAPSULES CONTAINING 125 OR 250 MG & IN TABLETS CONTAINING 125, 250, OR 500 MG; IT IS ALSO AVAIL AS ORAL SUSPENSION (125 MG/5 ML). ... TABLETS INCORPORATING ULTRAMICROSIZED PREPN (FULVICIN P/G, GRIS-PEG) CONTAIN 125 OR 250 MG OF GRISEOFULVIN (EQUIVALENT TO 250 OR 500 MG OF PREPN...ABOVE).
BIOAVAILABILITY OF A 500 MG MICROSIZE FORMULATION WAS COMPARED TO 2 NEW ULTRAMICROSIZE FORMULATIONS. ONE 330 MG ULTRAMICROSIZE TABLET IS BIOEQUIVALENT TO 2 165 MG ULTRAMICROSIZE TABLETS & EITHER ULTRAMICROSIZE DOSAGE REGIMEN IS BIOEQUIVALENT TO 500 MG OF THE MICROSIZE FORMULATION. [LIN C ET AL; J INT MED RES 10 (4): 274 (1982)] PubMed Abstract
THE BIOAVAILABILITY OF GRISEOFULVIN TABLETS SPRAY DRIED WITH 20% METHYLCELLULOSE WAS DETERMINED IN 10 RABBITS. COMPARED TO REGULAR TABLETS, DRUG ABSORPTION WAS GREATER IN THE SPRAY DRIED PREPN.
Tablet, 250 mg, 500 mg; suspension, 250 mg/ml /Grifulvin V/

4.8 WGK Germany: 3

4.8 RTECS: WG9800000

4.8 Toxicity

CHEMICAL IDENTIFICATION

RTECS NUMBER :: WG9800000

CHEMICAL NAME :: Spiro(benzofuran-2(3H),1'-(2)cyclohexene)-3,4'-dione, 7-chloro-2'4,6-trimethoxy-6'-beta- methyl-

CAS REGISTRY NUMBER :: 126-07-8

BEILSTEIN REFERENCE NO. :: 0095226

LAST UPDATED :: 199801

DATA ITEMS CITED :: 53

MOLECULAR FORMULA :: C17-H17-Cl-O6

MOLECULAR WEIGHT :: 352.79

WISWESSER LINE NOTATION :: T56 BOXVJ FO1 HO1 IG C-& DL6V DX BUTJ CO1 E1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >10 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 400 mg/kg

TOXIC EFFECTS :: Blood - changes in cell count (unspecified) Blood - changes in bone marrow (not otherwise specified)

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >50 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 200 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >12 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 280 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 109 gm/kg/52W-C

TOXIC EFFECTS :: Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 462 gm/kg/2Y-I

TOXIC EFFECTS :: Tumorigenic - neoplastic by RTECS criteria Blood - lymphoma, including Hodgkin's disease

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 440 gm/kg/52W-C

TOXIC EFFECTS :: Tumorigenic - neoplastic by RTECS criteria Liver - tumors

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 120 mg/kg/49W-I

TOXIC EFFECTS :: Tumorigenic - neoplastic by RTECS criteria Liver - tumors

TYPE OF TEST :: TD - Toxic dose (other than lowest)

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 730 gm/kg/52W-C

TOXIC EFFECTS :: Tumorigenic - neoplastic by RTECS criteria Liver - tumors

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1250 mg/kg

SEX/DURATION :: female 6-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Newborn - viability index (e.g., # alive at day 4 per # born alive)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 2 gm/kg

SEX/DURATION :: female 11-14 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - urogenital system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 12500 mg/kg

SEX/DURATION :: female 6-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Specific Developmental Abnormalities - musculoskeletal system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 500 mg/kg

SEX/DURATION :: female 9 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - eye/ear

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 10 gm/kg

SEX/DURATION :: female 8-9 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1 gm/kg

SEX/DURATION :: female 48-52 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system

TYPE OF TEST :: Specific locus test

TYPE OF TEST :: DNA repair

TYPE OF TEST :: Cytogenetic analysis

TYPE OF TEST :: Cytogenetic analysis

TYPE OF TEST :: Sister chromatid exchange

TYPE OF TEST :: Sex chromosome loss and nondisjunction

TYPE OF TEST :: Sperm Morphology

MUTATION DATA

TYPE OF TEST :: Cytogenetic analysis

TEST SYSTEM :: Bird - chicken Fibroblast

DOSE/DURATION :: 50 mg/L

REFERENCE :: NATUAS Nature. (Nature Subscription Dept., POB 1018, Manasguan, NJ 08736) V.1- 1869- Volume(issue)/page/year: 253,361,1975 *** REVIEWS *** IARC Cancer Review:Animal Sufficient Evidence IMSUDL IARC Monographs, Supplement. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) No.1- 1979- Volume(issue)/page/year: 7,391,1987 IARC Cancer Review:Human No Adequate Data IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 7,391,1987 IARC Cancer Review:Group 2B IMSUDL IARC Monographs, Supplement. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) No.1- 1979- Volume(issue)/page/year: 7,56,1987 TOXICOLOGY REVIEW LLOYA2 Lloydia. (Cincinnati, OH) V.1-41, 1938-78. For publisher information, see JNPRDF. Volume(issue)/page/year: 38,21,1975 TOXICOLOGY REVIEW 32XPAD "Teratology," Berry, C.L., and D.E. Poswillo, eds., New York, Springer, 1975 Volume(issue)/page/year: -,49,1975 TOXICOLOGY REVIEW ARMIAZ Annual Review of Microbiology. (Annual Reviews, Inc., POB 10139, Palo Alto, CA 94303) V.1- 1947- Volume(issue)/page/year: 26,279,1972 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X3685 No. of Facilities: 58 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 1656 (estimated) No. of Female Employees: 774 (estimated)

View all

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin sensitization, Category 1

Carcinogenicity, Category 2

Reproductive toxicity, Category 1B

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H317 May cause an allergic skin reaction H351 Suspected of causing cancer H360 May damage fertility or the unborn child
Precautionary statement(s)
Prevention	P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P272 Contaminated work clothing should not be allowed out of the workplace. P280 Wear protective gloves/protective clothing/eye protection/face protection. P201 Obtain special instructions before use. P202 Do not handle until all safety precautions have been read and understood.
Response	P302+P352 IF ON SKIN: Wash with plenty of water/... P333+P313 If skin irritation or rash occurs: Get medical advice/attention. P321 Specific treatment (see ... on this label). P362+P364 Take off contaminated clothing and wash it before reuse. P308+P313 IF exposed or concerned: Get medical advice/ attention.
Storage	P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

View all

6. NMR Spectrum

13C NMR : in CDCl3

13C NMR : Predict

1H NMR : 400 MHz in CDCl3

1H NMR : Predict

Predict 1H proton NMR

IR : KBr disc

IR : nujol mull

Mass

Mass spectrum (electron ionization)

7. Synthesis Route

126-07-8Total: 1 Synthesis Route

7776-77-4

2151-17-9

17793-63-4

126-07-8 264 Suppliers

Literatures:
Sato; Oda; Saito Chemical and Pharmaceutical Bulletin, 1981 , vol. 29, # 8 p. 2313 - 2321
Yield: null

8. Other Information

8.0 Merck: 14,4549

8.1 BRN: 95226

8.2 General description: Griseofulvin is a non-polyene class antifungal antibiotics; it can strongly inhibit the mitosis of fungal cell and interfere with the fungal DNA synthesis; it can also bind to tubulin to prevent fungal cell division. It has been applied to clinical medicine since 1958 and has currently been widely used for treating the fungal infections of the skin and the stratum corneum with strong inhibitory effects on Trichophyton rubrum and Trichophyton tonsorans, etc. Griseofulvin is not only a widely used antibiotic for clinical treatment of fungal infections of the skin and cuticle, but also applied in agriculture for prevention and treatment of fungal diseases; for example, it has a special efficacy on treating a kind of candidiasis in apple which can cause infection during pollination.

8.3 Physical and Chemical Properties: Griseofulvin pure product is colorless crystal, being neutral, and insoluble in water with a strong systemic property. It is stable both in vitro and in vivo of plants and is also stable to the various environment factors between pH3.0~8.8. It can be used for prevention and treatment of a variety of fungal plant diseases. The main species china applied for production of griseofulvin is Penicillium nigricans and Penicillium urticae. When grown at the medium, Penicillium nigricans is fuzzy with fresh culture being pure gray and aging culture being dark gray with its back being deep orange-red to the back orange brown. The fungi lawn of Penicillium urticae is yellowish green to pure light gray, thick and dense with the back being pale yellow to brownish; their aerial hyphae has a broom-like shape.

8.4 Pharmacological effects: In medicine, this product mainly has good antibacterial effect against Trichophyton, Microspores, and Epidermophyton fungi. However, it has no anti-bacterial effect on Candida, Cryptococcus, Histoplasma, Sporothrix, Blastomyces, and Coccidioides and so on. Mechanism of action of is drug is through interfering with the biosynthesis of nucleic acids of fungal and further inhibiting of its growth.
In agriculture, this product has good inhibitory effect on the Ascomycetes, Basidiomycetes, Deuteromycetes and some kinds of algae. However, it is not effective in treating oomycetes whose cell wall containing no chitin content. After spraying melons and other crops, it can be transferred into the branch, leaves and fruits through inner absorption, the absorption of water via rrot, as well as transpiration effect, and further preventing the fungal diseases; according to the study of Brandeis et al. (1946), at a concentration as low as even 10 mg/L or 1 mg/L, griseofulvin can already can make the mycelium of Bctrytis allill be stout, deformed and exhibit spiral bending, also cause: large number of abnormal branching; the development retardation of germinated spores, and loss of apical dominance; thus it has uptake therapeutic effects on a variety of plant diseases, especially powdery mildew, gray mold diseases; Griseofulvin has a more prominent antibacterial activity than the bactericidal activity.

8.5 Pharmacokinetics: The absorption of orally administration of this drug varies according to the difference in preparation, the micro-particle of this drug can be absorbed by 25% to 70%; its ultrafine particles can almost all absorbed after oral administration. Eating fat can significantly increase the extent of absorption. The product has a serum protein binding rate of being 80%. After its absorption, this product can be deposited in the skin, hair, nail cuticle and combine with keratin to prevent the further invasion of sensitive dermatophytes; at the same time, the pathogenic fungi locate in superficial stratum corneum will leave the body together with the fall-off of the skin or hair with only a very small amount being distribution in other body fluids and tissues. This product can also enter into the fetal circulation and be secreted from the milk. This product is inactivated through metabolism in the liver with the main metabolite being 6-methyl griseofulvin and glucuronic acylate; the blood elimination half-life is 14 to 24 hours. The percentage of product secreted from the urine in its prototype is less than 1% with about 16% to 36% of the prototype being discharged from the feces.

8.6 Indications: In medicine, this product is suitable for the treatment of a variety of ringworm, including tinea capitis, tinea barbae, body tinea, jock itch, foot tinea and onychomycosis. The various kinds of tinea mentioned are caused by various fungi including Trichophyton rubrum, Trichophyton tonsorans, Trichophyton mentagrophytes, Fingers Trichophyton, etc., and Microsporon audouini, Microsporon canis, Microsporon gypseum and Epidermophyton floccosum, etc. due. This product is not suitable for treatment in mild cases, localized infection cases and cases which can be treated with topical antifungal agents. Griseofulvin is not effective in treating the infections of a various kinds of fungi such as Candida, Histoplasma, Actinomyces, Sporothrix species, Blastomyces, Coccidioides, Nocardio and Cryptococcus species as well as treating tinea versicolor.
In agriculture, this product is first introduced by Brian et al (1951) for control of plant diseases. According to previous studies, it can be used for prevention of melon (melon) vine blight, crack spread disease, watermelon blight, anthracnose, apple blossom rot, apple cold rot, apple rot, cucumber downy mildew , strawberry gray mold, gourds hanging blight, powdery mildew of roses, chrysanthemums powdery mildew, rot flower lettuce, early tomato blight, tulip fire blight and other fungal diseases.

8.7 Side effects: 1. Nervous system headache is relatively common with about 10% of patients experiencing headaches; it is a bit severe at initial stage, but will be alleviated with the continuing administration of drug; other reactions also include lethargy and fatigue. Occasional dizziness, ataxia, and peripheral neuritis may also occur.
2. For Digestive system; a small number of patients may undergo abdominal discomfort, nausea or diarrhea, usually mild which can be tolerated by the patient.
3. Allergies can occur in about 3% of patients which suffers rash; occasionally angioneurotic edema, persistent urticaria, and exfoliative dermatitis can also occur; in very rare cases, photosensitive dermatitis can occur at a small number of patients.
4. This product can sometimes cause reduction of the number of peripheral blood leukocyte; sometime can even cause liver toxicity and proteinuria.

8.8 Precautions: 1. Cross allergy; because griseofulvin is obtained from Penicillium, which indicated that the drug may have cross-allergy with penicillin or penicillamine, however, this kinds of hypothesis hasn’t been confirmed by clinical cases; but patients allergic to penicillin should still apply with caution and subject to careful observation.
2. Griseofulvin can cause tumor in animal experiments.
3. This product can occasionally cause liver toxicity; patients with original liver disease or liver damage should decide whether to choose to apply this drug after thinking twice.
4. It can induce porphyria and lupus; lupus patients who have index should have trade-off decision before applying this drug.
5. During the treatment, regular testing of peripheral blood, liver function, blood nitrogen content in urea, creatinine and urine routine are demanded.
6. It can be administrated either simultaneously with meal or after the meal with high-fat meal being the best, because they can reduce the gastrointestinal side effects and increase drug absorption.
7. In order to prevent relapse, treatment should be continued until clinical symptoms and laboratory tests confirmed that the pathogen has been completely eradicated. Usually treatment course is: tinea capitis: 8 to 10 weeks; tinea: 2 to 4 weeks; tinea pedis: 4-8 weeks; finger nail tinea: at least four months; nail psoriasis: at least six months, although still with a high recurrence rate.
8. A suitable topical administration is usually necessary at the same time; this is particularly important for athlete's foot.
9. During the treatment or at least 6 months of post-treatment, male patients should take contraceptive measures for prevention of pregnancy.

8.9 Drug Interactions: 1. Combination of this product together with ethanol can cause tachycardia, sweating, flushing of the skin, etc., so avoid taking them at the same time.
2. Combination with anticoagulant drugs such as warfarin, and coumarin can enhance the hepatic metabolism and leaving the efficacy of anticoagulation being weakened; so it is necessary to adjust the dose by monitoring the prothrombin time at the same time.
3. Combination with primidone, and phenobarbital can decrease the antifungal effect of this product which may be due to that absorption of barbiturates may reduce the absorption of this drug as well as the increased rate of its inactivation due to the induction of hepatic enzyme which causes the decreased blood concentration; thus should avoid this kind of combination of drugs.
4. Combination of estrogen-class contraceptive with the product can reduce the effect of orally administrated contraceptives which may be due to that the product may strengthen the metabolism of contraceptive drugs in the live, causing its decreased blood concentration; thus should avoid using them simultaneously.

8.10 Toxicity: Griseofulvin has a relatively low toxicity to warm-blooded animals; intraperitoneal injection of both sexes of Waster rats found that they could both withstand a dosage of per 100ml/kg (some damage effects on the seminal vesicles and the intestinal epithelium were observed). Although intravenous injection can cause the temporary inhibition of cells mitosis (especially bone marrow some cells), the rates were almost unaffected under normal conditions. Moreover, after 24 hours, the rats began to rapidly recover; its LD50 is 400ml/kg body weight. Furthermore, even a large dose of griseofulvin only has a very small toxicity to the plants. It will be slowly degraded in the body with a faster degradation rate in soil; so there are no issues about residue and environmental pollution problems. However, the property of its fast degradation also limits their application of antimicrobial activity in agriculture.

8.11 Pediatric medication: We are lack of information about the medication on children under 2 years.

8.12 Elderly medication: There are still no existing information about its application in Elderly people and the relation with their ages.

8.13 Chemical Properties: It is white or white-like powder. Melting point is 218-224 °C. It is highly soluble in tetrachloroethane, soluble in acetone or chloroform, slightly soluble in methanol or ethanol, and very slightly soluble in water. It is odorless or almost odorless with slightly bitter taste. It is stable to heat.

8.14 Production methods: Griseofulvin is a antibiotic produced from the culture fermentation broth of Penicillium griseofulvum.

8.15 Category: Pesticide

8.16 Toxicity grading: Low toxicity

8.17 Acute toxicity: Oral-rat LD50: 10000 mg/kg; Oral-Mouse LD50: 50000 mg/kg

8.18 Flammability hazard characteristics: Combustion can produce toxic chloride gas

8.19 Storage Characteristics: Treasury: ventilation low-temperature an dry; it should be separately stored and transported from raw materials of food.

8.20 Extinguishing agent: Dry powder, foam, sand

8.21 Chemical Properties: Crystalline Solid

8.22 Originator: Grifulvin,McNeil,US,1959

8.23 Uses: adrenegic blocker, Ca channel blocker, coronary vasodilator, antiarrhythmic

8.24 Uses: antifungal, inhibits mitosis in metaphase

8.25 Uses: Griseofulvin is a spirobenzofuran produced by a number of Penicillium species, first isolated in the 1930s by Raistrick's group. Griseofulvin is a selective antifungal agent used to treat skin infections in animals and humans. Griseofulvin acts by binding to fungal tubulin and inhibiting the mitotic spindle. Griseofulvin's ability to bind to keratin is considered an important aspect of the metabolite's access to dermatophytic fungi. More recently, griseofulvin has become an important phenotypic marker in Penicillium taxonomy.

8.26 Uses: An antifungal and antiproliferative agent that affects microtubules.

8.27 Uses: It is an antifungal drug. It is used both in animal and in humans, to treat rigworm infections of the skin and nails. It is derived from the mold Penicillium griseofulvum.Environmental contaminants; Food contaminants.

8.28 Definition: ChEBI: An oxaspiro compound produced by Penicillium griseofulvum. It is used by mouth as an antifungal drug for infections involving the scalp, hair, nails and skin that do not respond to topical treatment.

8.29 Indications: Griseofulvin (Fulvicin, Grifulvin V) has been used safely and effectively for decades for dermatophyte infections of scalp and nails and for more widespread skin eruptions. However, infections in certain sites (e.g.. toenails) respond poorly. The drug is generally well tolerated, even in the long-term courses necessary for nail disease.

8.30 Indications: Griseofulvin (Gris-PEG, Grifulvin, Grisactin, Fulvicin) is an oral fungistatic agent used in the long-term treatment of dermatophyte infections caused by Epidermophyton, Microsporum, and Trichophyton spp. Produced by the mold Penicillium griseofulvin, this agent inhibits fungal growth by binding to the microtubules responsible for mitotic spindle formation, leading to defective cell wall development.
Ineffective topically, griseofulvin is administered orally but has poor gastrointestinal absorption; absorption can be improved by microcrystalline processing of the drug and by taking the drug with fatty meals. Peak serum levels occur 4 hours after dosing. Griseofulvin is metabolized in the liver and has a half-life of 24 to 36 hours. The drug binds to keratin precursor cells and newly synthesized keratin in the stratum corneum of the skin, hair, and nails, stopping the progression of dermatophyte infection.

8.31 Manufacturing Process: The experiment was carried out on the 1,000 gallon scale. Three impellers 1'8" diameter at 220 rpm were employed. The air rates were 0 to 5 hours, 40 cfm, 5 to 10 hours, 80 cfm and after 10 hours, 125 cfm. The inoculum rate was 10% v/v. It was prepared by the standard inoculum development technique on the following medium:
This was inoculated with a spore suspension of P. patulurn (1 liter containing 3-5 x 107 spores/ml) and grown at 25°C in 100 gallon tank. The inoculum is transferred at 40 hours or when the mycelial volume (after spinning 10 minutes at 3,000 rpm) exceeds 25%. The fermentation is conducted as near to the ideal pH curve as possible by addition of crude glucose, according to US Patent 3,069,328.

8.32 Brand name: Fulvicin Bolus [Veterinary] (Schering-Plough Animal Health); Fulvicin-P/G (Schering); Fulvicin-U/F (Schering); Fulvicin-U/F Powder and Tablets [Veterinary] (Schering-Plough Animal Health); Grifulvin V (Ortho Pharmaceutical); Grisactin (Wyeth- Ayerst); Gris-PEG (Allergan Herbert);B-gf;Delmofluvina;Flugolin;Fulcine-125;Fulcine-s;Fulvicin p/g;Fulvicin u/f;Fulvicina;Gefulvine;Grfulvin v;Grisaltin;Grisefalin;Grisefulvin;Griseomed;Griseostatin;Grisovina fp;Grisovine;Grisovin-fp;Grisowen;Lamoryl-novum;Lamoyl;Likuden m;Microcidal;Neo fulcin;Neo-filcin;Norofluvin;Ocufen;Sulvina.

8.33 Usage: Griseofulvin is an antifungal drug. It is used both in animal and in humans, to treat ringworm infections of the skin and nails.

8.34 Therapeutic Function: Antifungal

8.35 World Health Organization (WHO): Griseofulvin, isolated from a penicillin producing mould, has been widely used as a systemically administered antifungal agent in man for over 20 years. It is effective in dermatophyte infections (including tinea barbae and tinea capitis) but it is inactive against yeasts and bacteria. Evidence that very high doses of griseofulvin are carcinogenic, teratogenic and fetotoxic in laboratory animals has led to an acceptance that it should not be used to treat trivial infections that respond to topical therapy. Oral formulations of griseofulvin are included in the WHO Model List of Essential Drugs. (Reference: (WHTAC1) The Use of Essential Drugs, 2nd Report of the WHO Expert Committee, 722, , 1985)

8.36 Antimicrobial activity: The spectrum of useful activity is restricted to dermatophytes causing skin, nail and hair infections (Epidermophyton, Microsporum and Trichophyton spp.). Resistance has seldom been reported.

8.37 General Description: White to pale cream-colored crystalline powder. Odorless or almost odorless. Tasteless. Sublimes without decomposition at 410°F.

8.38 Air & Water Reactions: Insoluble in water.

8.39 Reactivity Profile: (+)-Griseofulvin is incompatible with strong oxidizing agents. .

8.40 Hazard: Possible carcinogen.

8.41 Fire Hazard: Flash point data for (+)-Griseofulvin are not available. (+)-Griseofulvin is probably combustible.

8.42 Pharmaceutical Applications: A fermentation product of various species of Penicillium, including Pen. griseofulvum. Available as fine-particle or ultrafine- particle formulations for oral use.

8.43 Mechanism of action: The mechanism of action of griseofulvin is through binding to the protein tubulin, which interferes with the function of the mitotic spindle and, thereby, inhibits cell division. Griseofulvin also may interfere directly with DNA replication. Griseofulvin is gradually being replaced by newer agents .

8.44 Pharmacokinetics: Absorption from the gastrointestinal tract is dependent on drug formulation. Administration with a high-fat meal will increase the rate and extent of absorption, but individuals tend to achieve consistently high or low blood concentrations. It appears in the stratum corneum within 4–8 h as a result of secretion in perspiration. However, levels begin to fall soon after the drug is discontinued, and within 48–72 h it can no longer be detected. It is metabolized in the liver, the metabolites being excreted in the urine. The elimination half-life is 9–21 h.

8.45 Clinical Use: In the treatment of ringworm of the beard, scalp, and other skin surfaces, 4 to 6 weeks of therapy is often required. Therapy failure may be to the result of an incorrect diagnosis; superficial candidiasis, which may resemble a dermatophyte infection, does not respond to griseofulvin treatment. Onychomycosis responds very slowly to griseofulvin (1 year or more of treatment is commonly required) and cure rates are poor; itraconazole and terbinafine hydrochloride are more effective than griseofulvin for onychomycosis.

8.46 Clinical Use: Dermatophyte infections of hair, skin and nail

8.47 Side effects: Adverse reactions occur in about 15% of patients and include headache, nausea, vomiting, rashes and photosensitivity.

8.48 Side effects: Griseofulvin is usually well tolerated. Headache is common with initiation of therapy. Hepatotoxicity (especially in patients with acute intermittent porphyria), dermatitis, and gastrointestinal distress also occur. Griseofulvin increases warfarin metabolism, and griseofulvin metabolism is increased by phenobarbital.

8.49 Chemical Synthesis: Griseofulvin, 7-chloro-2,4,6-trimethoxy-6-methylspiro[benzofuran- 2(3H),1-[2]-cyclohexen]-3,4-dione (35.4.1), is an antibiotic produced by the mycelial fungus Penicillium patulum.

8.50 Veterinary Drugs and Treatments: In veterinary species, griseofulvin is approved for use in dogs and cats to treat dermatophytic fungal (see below) infections of the skin, hair and claws, and to treat ringworm (caused by T. equinum and M. gypseum) in horses. It has also been used in laboratory animals and ruminants for the same indications. The oral tablets approved for dogs and cats are no longer marketed in the USA, but human dosage forms are available.

8.51 Metabolism: Griseofulvin is metabolized by the liver, and its metabolites are excreted in the urine. It is highly protein bound and, therefore, may have high tissue levels. However, tissue levels decrease and fall as soon as griseofulvin is discontinued such that its presence is no longer detectable 2 to 3 days after cessation of therapy.

8.52 Purification Methods: Crystallise it from *benzene or EtOH. Purify 2g of griseofulvin by chromatography on Alumina (40 x 1.5cm) and elute with *C6H6/MeOH (199:1) and follow the UV blue fluorescent band. [MacMillan J Chem Soc 1823 1959, Beilstein 18 III/IV 3160, 18/5 V 150.]

8.53 Dosage forms: The average treatment time for tinea capitis is 4 to 6 weeks; for tinea corporis, 2 to 4 weeks; and for tinea pedis, 4 to 8 weeks. Because of the low cure rate and length of therapy, griseofulvin is not commonly used for onychomycosis of the fingernails or toenails. Complete blood count (CBC) is monitored every 3 months during long-term therapy.

9. Computational chemical data

Molecular Weight: 352.77g/mol
Molecular Formula: C₁₇H₁₇ClO₆
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 352.0713660
Monoisotopic Mass: 352.0713660
Complexity: 575
Rotatable Bond Count: 3
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 6
Topological Polar Surface Area: 71.1
Heavy Atom Count: 24
Defined Atom Stereocenter Count: 2
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADceB4OAAEAAAAAAAAAAAAAAAAASAAAAAwQAAAAAAAAEgBAAAAGgIAAAAADUaAmCIyBoAABACIAqBSAAICCAAkJEAAiAFGC8gNJzeFNh6COWCl4BUKqQfK7vzuoCAAKAAICABAQABQABAQAAAAAAAAAA==

10. Recommended Suppliers

Global246SuppliersView all >>

Hanhong Medicine Technology (Hubei) Co., Ltd. Diamond member

2YRS

Products:5413-05-8 Ethyl 2-phenylacetoacetate; 20320-59-6/5449-12-7 BMK powder; 28578-16-7 Pmk glycidate; 79099-07-3 N-BOC-4-piperidone; 49851-31-2 2-bromo-1-phenylpentan-1-one; 288573-56-8
Tel:86-27-86832068
Email:cynthia@hanhong-api.com

Griseofulvin

Purity:99%Packing: 200kg/bag FOB
Price: USD/kilogram
Time: 2023/05/30

Inquire

Hebei Fanggan New Material Technology Co., LTD Diamond member

1YR

Products:chemicals
Tel:0311-18503114-031178503114
Email:mandy@rilonchem.com

Hot selling Griseofulvin（126-07-8）

Purity:99%Packing: 200kg/bag FOB
Price: 60 USD/kg
Time: 2023/05/30

Inquire

Hebei Crovell Biotech Co. Ltd Diamond member

3YRS

Products:Cosmetic Raw Materials,solvents,etc.
Tel:86-311-66562153
Email:breeduan@crovellbio.com

griseofulvin Cas 126-07-8 from China

Purity:99%Packing: 200kg/bag FOB
Price: 10 USD/kilogram
Time: 2023/05/30

Inquire

Wuhan Xiju Biotechnology Co., Ltd. Diamond member

2YRS

Products:My whatsapp:+86 13043111536 cas no.1451-82-7,79099-07-3,5449-12-7,5337-93-9,49851-31-2,288573-56-8
Tel:86-311-13164690256
Email:liya@wh-xiju.com

Good Quality Antifungal Drug Griseofulvin CAS 126-07-8

Purity:99%Packing: 200kg/bag FOB
Price: 880 USD/kg
Time: 2023/05/30

Inquire

Wuhan Fortuna Chemical Co., Ltd. Diamond member

10YRS

Products:API,fine chemical&its intermediates,biological chemistry
Tel:0086-27-59207850
Email:info@fortunachem.com

Griseofulvin CAS 126-07-8

Purity:99%Packing: 200kg/bag FOB
Price: 10 USD/kg
Time: 2023/05/29

Inquire

11. Realated Product Infomation

6915-11-3 griseofulvin

1279033-22-5 GRISEOFULVIN-D3

Recently Updated : 848065-41-8 158819-67-1 149506-01-4 1824562-11-9 149505-86-2 1824189-94-7 114554-08-4 79583-58-7 1368226-38-3 1314933-74-8