3D Mol Similar

Vagistat

: Iupac Name：1-[2-[(2-chlorothiophen-3-yl)methoxy]-2-(2,
4-dichlorophenyl)ethyl]imidazole; CAS No.: 65899-73-2; Molecular Weight：387.71122; Modify Date.: 2022-11-22 17:01; Introduction: Tioconazole is an antifungal agent, closely related tomiconazole. Tioconazole is effective in the topicaltreatment of superficial fungal infections and appears to be more potent thanmiconazole against Candida and Trichophyton species. View more+

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1. Names and Identifiers

: 1.1 Name; Vagistat; 1.2 Synonyms; (±)-1-[2-[(2-Chloro-3-thienyl)methoxy]-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole (+-)-1-(2,4-dichloro-beta-((2-chloro-3-ethenyl)oxy)phenethyl)imidazole 1-(2-((2-chloro-3-thienyl)methoxy)-2-(2,4-dichlorophenyl)ethyl)-1h-imidazol 1-[2,4-Dichloro-b-[(2-chloro-3-thenyl)oxy]phenethyl]imidazole 1-[2-[(2-Chloro-3-thienyl)methoxy]-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole 1-[2-[(2-chlorothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)-ethyl]imidazole 1-{2-[(2-Chloro-3-thienyl)methoxy]-2-(2,4-dichlorophenyl)ethyl}-1H-imidazole 1-{2-[(2-chloro-3-thienyl)methoxy]-2-(2,4-dichlorophenyl)ethyl}imidazole 1-{2-[(2-chlorothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl}-1H-imidazole 1H-Imidazole, 1-[2-[(2-chloro-3-thienyl)methoxy]-2-(2,4-dichlorophenyl)ethyl]- 1H-Imidazole, 1-[2-[(2-chloro-3-thienyl)methoxy]-2-(2,4-dichlorophenyl)ethyl]- (9CI) EINECS 265-973-8 Fungibacid Gyno-Trosyd MFCD00057276 TIOCONAZOLE Trosyd Zoniden; View all

1.3 CAS No.: 65899-73-2

1.4 CID: 5482

1.5 EINECS(EC#): 265-973-8

1.6 Molecular Formula: C16H13Cl3N2OS (isomer)

1.7 Inchi: InChI=1S/C16H13Cl3N2OS/c17-12-1-2-13(14(18)7-12)15(8-21-5-4-20-10-21)22-9-11-3-6-23-16(11)19/h1-7,10,15H,8-9H2

1.8 InChIkey: QXHHHPZILQDDPS-UHFFFAOYSA-N

1.9 Canonical Smiles: C1=CC(=C(C=C1Cl)Cl)C(CN2C=CN=C2)OCC3=C(SC=C3)Cl

1.10 Isomers Smiles: C1=CC(=C(C=C1Cl)Cl)C(CN2C=CN=C2)OCC3=C(SC=C3)Cl

2. Properties

2.1 Density: 1.44

2.1 Melting point: 78-87°C

2.1 Boiling point: 534.5°C at 760 mmHg

2.1 Refractive index: 1.654

2.1 Flash Point: 277°C

2.1 Precise Quality: 385.98100

2.1 PSA: 55.29000

2.1 logP: 5.86290

2.1 Appearance: white to off-white

2.2 Storage: Ambient temperatures.

2.3 Chemical Properties: White powder EINECS: 265-973-8

2.4 Color/Form: white to off-white

2.5 pKa: 6.66±0.12(Predicted)

2.6 Water Solubility: 1.65e-02 g/L

2.7 StorageTemp: Keep in dark place,Inert atmosphere,Room temperature

3. Use and Manufacturing

3.1 Definition: ChEBI: A member of the class of imidazoles that comprises 2-(2,4-dichlorophenyl)ethylimidazole carrying an additional (2-chloro-3-thienyl)methoxy substituent at position 2.

3.2 Usage: antithrombotic

4. Safety and Handling

4.1 Symbol: GHS07;

4.1 Hazard Codes: Xn

4.1 Signal Word: Warning

4.1 Risk Statements: 22

4.1 Safety Statements: 22

4.1 Hazard Declaration: H302

4.1 RIDADR: NONH for all modes of transport

4.1 Caution Statement: P301 + P312 + P330

4.1 WGK Germany: 3

4.1 RTECS: NI4480000

4.1 Safety: Moderately toxic by ingestion and intraperitoneal routes. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of Cl−, SOx, and NOx.

4.2 Toxicity

CHEMICAL IDENTIFICATION

RTECS NUMBER :: NI4480000

CHEMICAL NAME :: 1H-Imidazole, 1-(2-((2-chloro-3-thienyl)methoxy)-2-(2,4-dichlorophe nyl)ethyl)-

CAS REGISTRY NUMBER :: 65899-73-2

BEILSTEIN REFERENCE NO. :: 0573867

LAST UPDATED :: 199612

DATA ITEMS CITED :: 12

MOLECULAR FORMULA :: C16-H13-Cl3-N2-O-S

MOLECULAR WEIGHT :: 387.72

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 :: 770 mg/kg

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

REFERENCE :: YKYUA6 Yakkyoku. Pharmacy. (Nanzando, 4-1-11, Yushima, Bunkyo-ku, Tokyo, Japan) V.1- 1950- Volume(issue)/page/year: 35,1623,1984

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 730 mg/kg

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

REFERENCE :: YKYUA6 Yakkyoku. Pharmacy. (Nanzando, 4-1-11, Yushima, Bunkyo-ku, Tokyo, Japan) V.1- 1950- Volume(issue)/page/year: 35,1623,1984

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >10 gm/kg

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

REFERENCE :: YKYUA6 Yakkyoku. Pharmacy. (Nanzando, 4-1-11, Yushima, Bunkyo-ku, Tokyo, Japan) V.1- 1950- Volume(issue)/page/year: 35,1623,1984

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1870 mg/kg

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

REFERENCE :: YKYUA6 Yakkyoku. Pharmacy. (Nanzando, 4-1-11, Yushima, Bunkyo-ku, Tokyo, Japan) V.1- 1950- Volume(issue)/page/year: 35,1623,1984

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 508 mg/kg

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

REFERENCE :: YKYUA6 Yakkyoku. Pharmacy. (Nanzando, 4-1-11, Yushima, Bunkyo-ku, Tokyo, Japan) V.1- 1950- Volume(issue)/page/year: 35,1623,1984

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >10 gm/kg

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

REFERENCE :: YKYUA6 Yakkyoku. Pharmacy. (Nanzando, 4-1-11, Yushima, Bunkyo-ku, Tokyo, Japan) V.1- 1950- Volume(issue)/page/year: 35,1623,1984 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 300 mg/kg/30D-I

TOXIC EFFECTS :: Endocrine - changes in thymus weight Skin and Appendages - dermatitis, other (after systemic exposure) Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - transaminases

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 10,3849,1982

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1820 mg/kg/26W-I

TOXIC EFFECTS :: Blood - changes in leukocyte (WBC) count Skin and Appendages - dermatitis, other (after systemic exposure) Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - phosphatases

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 10,3849,1982 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 800 mg/kg

SEX/DURATION :: female 15-22 day(s) after conception

TOXIC EFFECTS :: Reproductive - Maternal Effects - parturition

REFERENCE :: TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 32,30A,1985

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 2490 mg/kg

SEX/DURATION :: male 9 week(s) pre-mating female 2 week(s) pre-mating - 7 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea) Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth)

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 10,3849,1982

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 330 mg/kg

SEX/DURATION :: female 7-17 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - stillbirth

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 10,3849,1982

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 810 mg/kg

SEX/DURATION :: female 17-22 day(s) after conception lactating female 21 day(s) post-birth

TOXIC EFFECTS :: Reproductive - Effects on Newborn - weaning or lactation index (e.g., # alive at weaning per # alive at day 4)

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 10,3849,1982

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Skin sensitization, Category 1

Reproductive toxicity, Category 2

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 1

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H302 Harmful if swallowed H317 May cause an allergic skin reaction H361 Suspected of damaging fertility or the unborn child H410 Very toxic to aquatic life with long lasting effects
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. 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. P273 Avoid release to the environment.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. 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. P391 Collect spillage.
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 : Predict

1H NMR : Predict

Predict 1H proton NMR

7. Other Information

7.0 靶点: Antifungal.

7.1 Description: Tioconazole is an antifungal agent, closely related to miconazole. Tioconazole is effective in the topical treatment of superficial fungal infections and appears to be more potent than miconazole against Candida and Trichophyton species.

7.2 Chemical Properties: White powder EINECS: 265-973-8

7.3 Originator: Pfizer (United Kiugdom)

7.4 Uses: antithrombotic

7.5 Uses: Tioconazole is an antifungal that is more active than Fluconazole (F421000) or Voriconazole (V760000) against Candida glabrata mutant strains. Antifungal (topical).

7.6 Definition: ChEBI: A member of the class of imidazoles that comprises 2-(2,4-dichlorophenyl)ethylimidazole carrying an additional (2-chloro-3-thienyl)methoxy substituent at position 2.

7.7 Manufacturing Process: A solution of 1-(2,4-dichlorophenyl)-2-(1-imidazolyl)ethanol (1.5 g, 5.8 mmol) dissolved in dry tetrahydrofuran (10 ml) was added to a stirred suspension of sodium hydride (0.39 g, as 80% dispersion in oil, 16 mmol) in dry tetrahydrofuran (10 ml) and warmed to 70°C for 90 minutes. The mixture was cooled in ice and a solution of 2-chloro-3- chloromethylthiophene (8.8 mmol) in dry tetrahydrofuran was added. The mixture was heated at 70°C for 3 hours and allowed to stir at room temperature overnight. The solvent was removed under vacuum and the residue stirred with dry ether (200 ml). The ether solution was filtered through Celite and saturated with hydrogen chloride gas to precipitate an oil which was solidified by trituration with ether and ethyl acetate. The solid product was collected and recrystallized from a mixture of acetone and diisopropyl ether to give the product, melting point 168°C to 170°C.

7.8 Brand name: TROSYL

7.9 Clinical Use: 1-[2-[(2-chloro-3-thienyl)methoxy]2-(2,4-dichlorophenyl)-ethyl]-1H-imidazole (Vagistat) is used for the treatment ofvulvovaginal candidiasis. A vaginal ointment containing6.5% of the free base is available. Tioconazole is more effectiveagainst Torulopsis glabrata than are other azoles.

7.10 Usage: Potent inhibitor of cytochrome-P450

7.11 Collision Cross Section: 180.7 ?2 [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

7.12 Mesh: Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues. (See all compounds classified as Antifungal Agents.)|Compounds that specifically inhibit STEROL 14-DEMETHYLASE. A variety of azole-derived ANTIFUNGAL AGENTS act through this mechanism. (See all compounds classified as 14-alpha Demethylase Inhibitors.)

7.13 Absorption: Systemic absorption following a single intravaginal application of tioconazole in nonpregnant patients is negligible.

7.14 Metabolism: Orally administered tioconazole is extensively metabolized. The major metabolites are glucuronide conjugates.

7.15 Mesh Entry Terms: Gyno-Trosyd

7.16 Use Classification: Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

8. Computational chemical data

Molecular Weight: 387.71122g/mol
Molecular Formula: C₁₆H₁₃Cl₃N₂OS
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 385.981417
Monoisotopic Mass: 385.981417
Complexity: 379
Rotatable Bond Count: 6
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 3
Topological Polar Surface Area: 55.3
Heavy Atom Count: 23
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 1
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADccB7IABGAAAAAAAAAAAAAAAAAWJAAAAwAAAAAAAAAAAB8AAAHgYAAAAADBbl2ia9kZcMFAikAjBnZAADgK0xH7BJyBgYOoiKbiKhuxmXMAAswAO4qCeQwKAOBAAAAACBAAAIAAAAAQIAAAAAAAAAAA==

9. Question & Answer

What is the content of the Vagistat suppository instructions? Apr 25 2022
The Vagistat suppository is a commonly used medication for the treatment of gynecological inflammatory diseases in women. It is widely used in clinical practice. However, it is important to read the i..
What is Tioconazole and How Does it Work? Mar 30 2022
Tioconazole is a substituted imidazole derivative that shares structural similarities with econazole, clotrimazole, and miconazole. It has a chemical formula of C16H13Cl3N2OS and exhibits a broad spec..
What diseases can Vagistat treat and how effective is it? Nov 08 2021
Many people wonder what diseases can be treated with Vagistat. Understanding this is crucial to determine its medicinal value. The following aspects can answer your questions. Vagistat can be used to..

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