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Nystatin(CAS No. 1400-61-9)

Nystatin C47H75NO17 (cas 1400-61-9) Molecular Structure

1400-61-9 Structure

Identification and Related Records

【Name】
Nystatin
【Iupac name】
(4E,6E,8E,10E,14E,16E,18S,19R,20R,21S,35S)-3-[(2S,3S,4S,5S,
6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-19,25,27,29,32,33,35,
37-octahydroxy-18,20,21-trimethyl-23-oxo-22,
39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10,14,
16-hexaene-38-carboxylic acid
【CAS Registry number】
1400-61-9
【Synonyms】
Biofanal
Candio-Hermal
Diastatin
Flagystatin
Fungicidin
L-Nystatin
Moronal (antibiotic)
Myconystatin
Mycostatin
MycostatinPastilles
Mykostatyna
Nistatin
Nyotran
Nysfungin
Nystacid
Nystan
Nystavescent
Nystex
Nystop
O-V Statin
Stamycin
【EINECS(EC#)】
215-749-0
【Molecular Formula】
C47H75NO17 (Products with the same molecular formula)
【Molecular Weight】
926.1
【Inchi】
InChI=1/C47H75NO17/c1-27-17-15-13-11-9-7-5-6-8-10-12-14-16-18-34(64-46-44(58)41(48)43(57)30(4)63-46)24-38-40(45(59)60)37(54)26-47(61,65-38)25-36(53)35(52)20-19-31(49)21-32(50)22-33(51)23-39(55)62-29(3)28(2)42(27)56/h5-6,8,10-18,27-38,40-44,46,49-54,56-58,61H,7,9,19-26,48H2,1-4H3,(H,59,60)/b6-5+,10-8+,13-11+,14-12+,17-15+,18-16+/t27-,28-,29-,30+,31?,32?,33?,34?,35?,36?,37?,38?,40?,41-,42+,43+,44-,46+,47+/m0/s1
【Canonical SMILES】
CC1C=CC=CCCC=CC=CC=CC=CC(CC2C(C(CC(O2)(CC(C(CCC(CC(CC(CC(=O)OC(C(C1O)C)C)O)O)O)O)O)O)O)C(=O)O)OC3C(C(C(C(O3)C)O)N)O
【Isomers smiles】
C[C@H]1/C=C/C=C/CC/C=C/C=C/C=C/C=C/C(CC2C(C(C[C@](O2)(CC(C(CCC(CC(CC(CC
(=O)O[C@H]([C@@H]([C@@H]1O)C)C)O)O)O)O)O)O)O)C(=O)O)O[C@@H]3[C@H]([C@H](
[C@@H]([C@H](O3)C)O)N)O
【MOL File】
1400-61-9.mol

Chemical and Physical Properties

【Appearance】
yellow suspension
【Density】
g/cm3
【Melting Point】
Gradually decomp above 160 deg C without melting by 250 deg C
【Boiling Point】
476°Cat760mmHg
【Vapour】
1.6E-07mmHg at 25°C
【Refractive Index】
1.503
【Flash Point】
127.3°C
【Solubilities】
insoluble in water
【Color/Form】
yellow
【Storage temp】
?20°C
【Spectral properties】
Optical rotation at 25 deg C/D: -10 deg (glacial acetic acid); +21 deg (pyridine); +12 deg (dimethylformamide); max absorption (ethanol): 290, 307 and 322 nm; optical rotation at 25 deg C/D: -7 deg (0.1 N HCl in methanol)
【Computed Properties】
Molecular Weight:926.0949 [g/mol]
Molecular Formula:C47H75NO17
XLogP3-AA:-0.2
H-Bond Donor:12
H-Bond Acceptor:18
Rotatable Bond Count:3
Tautomer Count:2
Exact Mass:925.5035
MonoIsotopic Mass:925.5035
Topological Polar Surface Area:320
Heavy Atom Count:65
Formal Charge:0
Complexity:1620
Isotope Atom Count:0
Defined Atom Stereocenter Count:10
Undefined Atom Stereocenter Count:9
Defined Bond Stereocenter Count:6
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1

Safety and Handling

【Hazard Codes】
F, C
【Risk Statements】
R11
【Safety Statements 】
S22;S24/25
【Safety】
Poison by intraperitoneal and intravenous routes. Moderately toxic by subcutaneous route. Mildly toxic by ingestion. An experimental teratogen. Mutation data reported. An antibiotic. When heated to decomposition it emits toxic fumes of NOx.
【Formulations/Preparations】
Tablets, dragees, lozenges, suspensions, drops, ointments, powders, gels, creams, ovulas, and vaginal tablets of different concentrations. There are also formulations available in combination with antibiotics and/or steroids such as tetracycline, neomycin, gramicidin, and cortisone. Dosages are often expressed in IE (100 000 IE = 22.73 mg nystatin A1).
Trade Names: Adiclair (Ardeypharm), Biofanal (Pfleger), Candex (Dome), Candio-Hermal (Hermal, Merck), Canstat (Lederle), Diastatin (Pfizer), Fungicidin (Spofa), Fungireduct (Azupharma), Herniocid (Mayrhofer), Korostatin (Holland-Rantos), Lederlind (Lederle), Lystin (Mekim), Mikostatin (Squibb), Moronal (Heyden, Squibb), Multilind (Bristol-Myers Squibb, Fair), Mycostatin (Bristol-Myers Squibb, Heyden, Sanofi Winthrop, Westwood-Squibb), Mykinac (NMC), MycoPosterine N (Kade), Mykundex (Jossa), Nadostine (Pan-Well), Nilstat (Lederle), Nyaderm (Taro), Nysert (Norwich Eaton), Nystacid (Farmos Group), Nystaderm (Dermapharm), Nysta-Dome (Dome), Nystan (Squibb), Nystat-Rx (Pharma-Tek), Nystavescent (Squibb), Nystex (Savage), Oranyst (Taro), O-V Statin (Squibb), Restatin (Remedica), Rivostatin (Rivopharm) Stereomycin (Medica).
Nystatin is commercially available as a cream, ointment, or powder for topical application to the skin; as a powder for oral suspension, oral suspension, or film-coated tablets for oral administration; as oral lozenges for oral topical administration; and as tablets for intravaginal administration.
Oral: For suspension 50 million units Nystatin Powder, Paddock Nystat-Rx, (Pharma-Tek); 150 million units Nystatin Powder, Paddock Nystat-Rx, (Pharma-Tek); 500 million units Nystatin Powder, Paddock Nystat-Rx, (Pharma-Tek); 1 billion units Nystat-Rx, (Pharma-Tek); 2 billion units Nystatin Powder, (Paddock); 5 billion units Nystatin Powder, (Paddock). Oral: Suspension: 100,000 units/mL Mycostatin ( with =1% alcohol parabens and sucrose 50%), (Bristol-Myers Squibb). Oral: Tablets, film-coated 500,000 units Mycostatin Filmlok ( with povidone), (Bristol-Myers Squibb)
【Exposure Standards and Regulations】
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl nystatin, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses, as described below. However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: nystatin is included in topical antifungal drug products.
A tolerance of zero is established for residues of nystatin in or on eggs and the uncooked edible tissues of swine and poultry.
New animal drugs for use in animal feeds. Requirement of a medicated feed mill license. Nystatin is included on this list.
New animal drugs for use in animal feeds. Nystatin. ... It is used in chickens and turkeys as follows: ... aid in control of crop mycosis and mycotic diarrhea (Candida albicans) ... treatment of crop mycosis and mycotic diarrhea (Candida albicans).
Ophthalmic and topical dosage form new animal drugs. Nystatin, neomycin, thiostrepton, and triamcinolone acetonide ointment. ... Indications for use. (i) Topically: Use either ointment in dogs and cats for anti-inflammatory, antipruritic, antifungal, and antibacterial treatment of superficial bacterial infections, and for dermatologic disorders characterized by inflammation and dry or exudative dermatitis, particularly associated with bacterial or candidal (Candida albicans) infections. (ii) Otitis, cysts, and anal gland infections: Use petrolatum base ointment in dogs and cats for the treatment of acute and chronic otitis and interdigital cysts, and in dogs for anal gland infections.
Ophthalmic and topical dosage form new animal drugs. Nystatin, neomycin, thiostrepton, and triamcinolone acetonide ophthalmic ointment. ... The drug is recommended for ophthalmic use as an anti-inflammatory, antipruritic, antifungal (Candida albicans), and antibacterial ointment for local therapy in keratitis and conjunctivitis in cats and dogs and for infectious kerato-conjunctivitis (pink eye) in cattle.
【Specification】

The IUPAC name of?Nystatin is?(4E,6E,8E,10E,14E,16E,18S,19R,20R,21S,35S)-3-[(2S,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-19,25,27,29,32,33,35,37-octahydroxy-18,20,21-trimethyl-23-oxo-22,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10,14,16-hexaene-38-carboxylic acid. With the?CAS registry number 1400-61-9, it?is also named as?Biofanal.?It is?yellow suspension which is insoluble in water. Additionally,?this chemical should?be sealed in the container and stored at the temperature of -20 °C.

The other characteristics of this product can be summarized as:?(1)ACD/LogP: 0.62; (2)# of Rule of 5 Violations: 3; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 1; (5)ACD/KOC (pH 5.5): 1; (6)ACD/KOC (pH 7.4): 1; (7)#H bond acceptors: 18; (8)#H bond donors: 13; (9)#Freely Rotating Bonds: 14 ; (10)Index of Refraction: 1.598; (11)Molar Refractivity: 240.74 cm3; (12)Molar Volume: 705.3 cm3; (13)Polarizability: 95.43×10-24 cm3; (14)Surface Tension: 69.5 dyne/cm; (15)Enthalpy of Vaporization: 188.49 kJ/mol; (16)Vapour Pressure: 0 mmHg at 25°C; (17)Rotatable Bond Count: 3; (18)Tautomer Count: 2; (19)Exact Mass: 925.5035; (20)MonoIsotopic Mass: 925.5035; (21)Topological Polar Surface Area: 320; (22)Heavy Atom Count: 65; (23)Complexity: 1620.

Uses of Nystatin:?It is often used as prophylaxis in patients who are at risk for fungal infections, such as AIDS patients with a low CD4+ count and patients receiving chemotherapy.?It is also used in cellular biology as an inhibitor of the lipid raft-caveolae endocytosis pathway on mammalian cells, at concentrations around 3 μg/mL.?In addition, it is?used as a tool by scientists performing "perforated" patch-clamp electrophysiologic recordings of cells.

When you are using this chemical, please be cautious about it as the following:
It is highly flammable and can cause burns,?so people should keep it away from sources of ignition. When use it, people?do not breathe dust and avoid contact with skin and eyes.?In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection.?In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

People can use the following data to convert to the molecule structure.?
1. SMILES:O=C2OC(C)C(C)C(O)C(C=CC=CCCC=CC=CC=CC=CC(OC1O[C@@H]([C@@H](O)[C@H](N)[C@@H]1O)C)CC(O)C(C(=O)O)C(O)CC(=O)CC(O)C(O)CCC(O)CC(O)CC(O)C2)C
2. InChI:InChI=1/C47H75NO17/c1-27-17-15-13-11-9-7-5-6-8-10-12-14-16-18-35(65-47-45(60)42(48)44(59)30(4)64-47)26-39(56)41(46(61)62)38(55)24-34(52)23-37(54)36(53)20-19-31(49)21-32(50)22-33(51)25-40(57)63-29(3)28(2)43(27)58/h5-6,8,10-18,27-33,35-39,41-45,47,49-51,53-56,58-60H,7,9,19-26,48H2,1-4H3,(H,61,62)/t27,28,29,30-,31,32,33,35,36?,37,38,39,41,42+,43,44-,45+,47/m1/s1
?

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 4400ug/kg (4.4mg/kg) ? Journal of Pharmaceutical Sciences. Vol. 65, Pg. 905, 1976.
mouse LD50 intravenous 3mg/kg (3mg/kg) ? Journal of Antibiotics. Vol. 32, Pg. 1230, 1979.
mouse LD50 oral 8gm/kg (8000mg/kg) ? Progress in Medical Chemistry. Vol. 14, Pg. 105, 1977.
mouse LD50 subcutaneous 120mg/kg (120mg/kg) ? Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 53, Pg. 228S, 1957.
rat LD50 intraperitoneal 24305ug/kg (24.305mg/kg) ? Antibiotics Annual. Vol. 3, Pg. 697, 1955/1956.
rat LD50 oral 10gm/kg (10000mg/kg) ? Acta Poloniae Pharmaceutica. For English translation, see APPFAR. Vol. 30, Pg. 81, 1973.

【Octanol/Water Partition Coefficient】
log Kow = 7.08 (est)
【Report】

The IUPAC name of?Nystatin is?(4E,6E,8E,10E,14E,16E,18S,19R,20R,21S,35S)-3-[(2S,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-19,25,27,29,32,33,35,37-octahydroxy-18,20,21-trimethyl-23-oxo-22,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10,14,16-hexaene-38-carboxylic acid. With the?CAS registry number 1400-61-9, it?is also named as?Biofanal.?It is?yellow suspension which is insoluble in water. Additionally,?this chemical should?be sealed in the container and stored at the temperature of -20 °C.

The other characteristics of this product can be summarized as:?(1)ACD/LogP: 0.62; (2)# of Rule of 5 Violations: 3; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 1; (5)ACD/KOC (pH 5.5): 1; (6)ACD/KOC (pH 7.4): 1; (7)#H bond acceptors: 18; (8)#H bond donors: 13; (9)#Freely Rotating Bonds: 14 ; (10)Index of Refraction: 1.598; (11)Molar Refractivity: 240.74 cm3; (12)Molar Volume: 705.3 cm3; (13)Polarizability: 95.43×10-24 cm3; (14)Surface Tension: 69.5 dyne/cm; (15)Enthalpy of Vaporization: 188.49 kJ/mol; (16)Vapour Pressure: 0 mmHg at 25°C; (17)Rotatable Bond Count: 3; (18)Tautomer Count: 2; (19)Exact Mass: 925.5035; (20)MonoIsotopic Mass: 925.5035; (21)Topological Polar Surface Area: 320; (22)Heavy Atom Count: 65; (23)Complexity: 1620.

Uses of Nystatin:?It is often used as prophylaxis in patients who are at risk for fungal infections, such as AIDS patients with a low CD4+ count and patients receiving chemotherapy.?It is also used in cellular biology as an inhibitor of the lipid raft-caveolae endocytosis pathway on mammalian cells, at concentrations around 3 μg/mL.?In addition, it is?used as a tool by scientists performing "perforated" patch-clamp electrophysiologic recordings of cells.

When you are using this chemical, please be cautious about it as the following:
It is highly flammable and can cause burns,?so people should keep it away from sources of ignition. When use it, people?do not breathe dust and avoid contact with skin and eyes.?In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection.?In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

People can use the following data to convert to the molecule structure.?
1. SMILES:O=C2OC(C)C(C)C(O)C(C=CC=CCCC=CC=CC=CC=CC(OC1O[C@@H]([C@@H](O)[C@H](N)[C@@H]1O)C)CC(O)C(C(=O)O)C(O)CC(=O)CC(O)C(O)CCC(O)CC(O)CC(O)C2)C
2. InChI:InChI=1/C47H75NO17/c1-27-17-15-13-11-9-7-5-6-8-10-12-14-16-18-35(65-47-45(60)42(48)44(59)30(4)64-47)26-39(56)41(46(61)62)38(55)24-34(52)23-37(54)36(53)20-19-31(49)21-32(50)22-33(51)25-40(57)63-29(3)28(2)43(27)58/h5-6,8,10-18,27-33,35-39,41-45,47,49-51,53-56,58-60H,7,9,19-26,48H2,1-4H3,(H,61,62)/t27,28,29,30-,31,32,33,35,36?,37,38,39,41,42+,43,44-,45+,47/m1/s1
?

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 4400ug/kg (4.4mg/kg) ? Journal of Pharmaceutical Sciences. Vol. 65, Pg. 905, 1976.
mouse LD50 intravenous 3mg/kg (3mg/kg) ? Journal of Antibiotics. Vol. 32, Pg. 1230, 1979.
mouse LD50 oral 8gm/kg (8000mg/kg) ? Progress in Medical Chemistry. Vol. 14, Pg. 105, 1977.
mouse LD50 subcutaneous 120mg/kg (120mg/kg) ? Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 53, Pg. 228S, 1957.
rat LD50 intraperitoneal 24305ug/kg (24.305mg/kg) ? Antibiotics Annual. Vol. 3, Pg. 697, 1955/1956.
rat LD50 oral 10gm/kg (10000mg/kg) ? Acta Poloniae Pharmaceutica. For English translation, see APPFAR. Vol. 30, Pg. 81, 1973.

【Disposal Methods】
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.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Vandeputte, US patent 2,832,719 (1958 to Olin Mathieson); Renella, US patent 3,517,100 (1970 to American Cyanamid)
Polyene antifungal antibiotic complex containing 3 biologically active compounds, A1,A2,A3. Produced by Streptomyces noursei, S. aureus and other Streptomyces spp.

Biomedical Effects and Toxicity

【Pharmacological Action】
- Substances that reduce the growth or reproduction of BACTERIA.
- 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.
- Chemical agents that increase the permeability of biological or artificial lipid membranes to specific ions. Most ionophores are relatively small organic molecules that act as mobile carriers within membranes or coalesce to form ion permeable channels across membranes. Many are antibiotics, and many act as uncoupling agents by short-circuiting the proton gradient across mitochondrial membranes.
【Therapeutic Uses】
Antibiotics, Antifungal; Antibiotics, Macrolide; Ionophores
MEDICATION (VET):Antifungal; growth promotant
MEDICATION (VET): /Used in treatment of/ intestinal mycosis due to Candida albicans in poultry; occasionally orally in cats and dogs in suspected Candida intestinal overgrowth following antibiotic therapy, and also topically ... as cream or ointment on skin lesions ...
Nystatin vaginal tablets are used as lozenges to treat oropharyngeal candidiasis since their slow dissolution rate provides prolonged oral contact. /NOT included in US product labeling/
Vaginal nystatin is indicated in the local treatment of vulvovaginal candidiasis caused by Candida albicans and other Candida species. /Included in US product labeling/
Topical nystatin is used in the treatment of tinea barbae and tinea capitis. /NOT included in US product labeling/
Topical nystatin is indicated in the treatment of cutaneous and mucocutaneous mycotic infections caused by Candida (Monilia) albicans and other Candida species. /Included in US product labeling/
Nystatin oral suspension, lozenges (pastilles), and nystatin for oral suspension are used in the prophylaxis of oropharyngeal candidiasis. /NOT included in US product labeling/
Nystatin lozenges (pastilles), nystatin oral suspension, and nystatin for oral suspension are indicated in the local treatment of fungal infections of the oral cavity caused by Candida albicans and other Candida species. /Included in US product labeling/
【Biomedical Effects and Toxicity】
Nystatin penetrates eye poorly.
Nystatin is poorly absorbed from the GI tract, and detectable blood concentrations are not obtained after usual doses. Following oral administration, nystatin is excreted almost entirely in feces as unchanged drug.
In healthy individuals, mean salivary nystatin concentrations in excess of those required in vitro for growth inhibition of clinically important Candida persist for approximately 2 hours after the beginning of oral dissolution of two nystatin lozenges (400,000 units) administered simultaneously.
Not absorbed following topical application to intact skin or mucous membranes.
Excreted in feces as unchanged drug.
Persons with renal insufficiency may occasionally develop significant plasma concn of nystatin while taking conventional doses by mouth.

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 170(SRC), determined from a water solubility of 3.60X10+2 mg/L(2) and a regression-derived equation(3), indicates that nystatin is expected to have moderate mobility in soil(SRC). Volatilization of nystatin from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.0X10-7 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Nystatin is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 8.68X10-7 mm Hg(SRC), determined from a fragment constant method(5). A 4% degradation in 28 days using the Closed Bottle test(6) indicates that biodegradation is not an important environmental fate process in soil.
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 170(SRC), determined from a water solubility of 3.60X10+2 mg/L(2) and a regression-derived equation(3), indicates that nystatin is expected to adsorb slightly to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.0X10-7 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 22(SRC), from its water solubility and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). A 4% degradation in 28 days using the Closed Bottle test(7) indicates that biodegradation is not an important environmental fate process in water.
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), nystatin, which has an estimated vapor pressure of 8.7X10-7 mm Hg at 25 deg C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere.Vapor-phase nystatin is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 1.5 hours(SRC), calculated from its rate constant of 2.5X10-10 cu cm/molec-sec at 25 deg C(SRC), that was derived using a structure estimation method(3). Vapor-phase nystatin is degraded in the atmosphere by reaction with ozone(SRC); the half-life for this reaction in air is estimated to be 2.6 hours(SRC), calculated from its rate constant of 1.1X10-16 cu cm/molec-sec at 25 deg C(SRC), that was derived using a structure estimation method(4). Particulate-phase nystatin may be removed from the air by wet or dry deposition(SRC). The rate of nystatin decomposition is affected by light(5) and therefore the compound may be susceptible to direct photolysis by sunlight.

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