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Your Location：Home>Product Center >> Pharmaceutical API >> Clotrimazole
  • Clotrimazole
Name:Clotrimazole
CAS No:23593-75-1

PRODUCT DESCRIPTION

【Name】
Clotrimazole
【CAS Registry number】
23593-75-1
【Synonyms】
Diphenyl(2-chlorophenyl)(1-imidazolyl)methane
Bay-B 5097
BAYb 5097
Mycelex (TN)
(2-Chlorophenyl)diphenyl-1-imidazolylmethane
Lotrimin (TN)
Clotrimazol [INN-Spanish]
Gyne-Lotrimin
1-[(2-chlorophenyl)(diphenyl)methyl]-1H-imidazole
Mycelex Troches
1H-Imidazole, 1-[ (2-chlorophenyl)diphenylmethyl]-
Imidazole, 1- (o-chloro-.alpha.,.alpha.-diphenylbenzyl)-
Bis-fenil-(2-clorofenil)-1-imidazolil-metano [Italian]
Lotrimin AF Cream
1-(alpha-(2-Chlorophenyl)benzhydryl)imidazole
Lotrimax
Prestwick_120
FB 5097
Monobaycuten
1-(o-Chloro-.alpha., .alpha.-diphenylbenzyl)imidazole
Trimysten
Bis-phenyl-(2-chlorophenyl)-1-imidazoyl)methane
BAY b5097
Mykosporin
Mycelex G
【EINECS(EC#)】
245-764-8
【Molecular Formula】
C22H17ClN2 (Products with the same molecular formula)
【Molecular Weight】
344.84
【Inchi】
InChI=1/C22H17ClN2/c23-21-14-8-7-13-20(21)22(25-16-15-24-17-25,18-9-3-1-4-10-18)19-11-5-2-6-12-19/h1-17H
【InChIKey】
VNFPBHJOKIVQEB-UHFFFAOYSA-N
【Canonical SMILES】
C1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=CC=C3Cl)N4C=CN=C4
【MOL File】
23593-75-1.mol

Chemical and Physical Properties

【Appearance】
Crystals. Odorless.
【Density】
1.13g/cm3
【Melting Point】
147-149℃
【Boiling Point】
482.3°Cat760mmHg
【Vapour】
5.42E-09mmHg at 25°C
【Refractive Index】
1.616
【Flash Point】
245.5°C
【Solubilities】
Slightly soluble
【Color/Form】
Crystals
White to pale yellow crystalline powder
【Stability】
No data.
【Storage temp】
Store at RT.
【Computed Properties】
Molecular Weight:344.83678 [g/mol]
Molecular Formula:C22H17ClN2
XLogP3:5
H-Bond Donor:0
H-Bond Acceptor:0
Rotatable Bond Count:4
Exact Mass:344.108026
MonoIsotopic Mass:344.108026
Topological Polar Surface Area:17.8
Heavy Atom Count:25
Formal Charge:0
Complexity:396
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Cation Count:1
Feature 3D Ring Count:4
Effective Rotor Count:4
Conformer Sampling RMSD:0.8
CID Conformer Count:3

Safety and Handling

【Hazard Codes】
Xn: Harmful;
【Risk Statements】
R22
【Safety Statements 】
26-36
【Safety】

Safety Information of?Mycosporin (CAS NO.23593-75-1):
Hazard Codes:Xn? 
Risk Statements:22-36/38
22:Harmful if swallowed
36/38:Irritating to eyes and skin?? 
Safety Statements:26-36
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice? 
36:Wear suitable protective clothing? 
WGK Germany:3
RTECS:NI4377000
Hazardous Substances Data:23593-75-1(Hazardous Substances Data) 
Poison by intraperitoneal route. Moderately toxic by ingestion. An experimental teratogen. Human systemic effects by intrvaginal route: primary skin irritations. Experimental reproductive effects. A fungicide. When heated to decomposition it emits very toxic fumes of Cl? and NOx.

【Skin, Eye, and Respiratory Irritations】
Adverse effects after topical use of clotrimazole include stinging.
【Formulations/Preparations】
Topical: Lotrimin (Schering), Mycelex (Miles). Cream 1% in 15, 30, 45 (Lotrimin only), and 90 g containers; solution 1% in 10 and 30 ml containers; and lotion 1% (Lotrimin only) in 30 ml containers; intravaginal: Gyne-Lotrimin (Schering) Cream (vaginal) 1% in 45 g containers; tablets (vaginal) 100 and 500 mg; Mycelex-G (Miles) cream (vaginal) 1% in 45 and 90 g containers; tablets 100 and 500 mg; and 500 mg with cream 1% in 7 g containers. Oral: troche 10 mg.
Mycelex 1% cream
【Exposure Standards and Regulations】
Clotrimazole cream. (a) Specifications: Each g of cream contains 10 mg of clotrimazole ... (c) Conditions of use: Apply 1/4 in ribbon of cream per sq in of lesion for 2 to 4 wk ... For the treatment of fungal infections of dogs and cats caused by Microsporum canis and Trichophyton mentagrophytes ... Wash hands thoroughly after use to avoid spread of infection. Federal law restricts this drug to use by or on the order of a licensed veterinarian.
【Protective Equipment and Clothing】
Adverse effects after topical use of clotrimazole include stinging.

Use and Manufacturing

【Usage】

Medication, fungicide.

Biomedical Effects and Toxicity

【Pharmacological Action】
- Compounds that specifically inhibit STEROL 14-DEMETHYLASE. A variety of azole-derived ANTIFUNGAL AGENTS act through this mechanism.
- Substances used on humans and other animals that destroy harmful microorganisms or inhibit their activity. They are distinguished from DISINFECTANTS, which are used on inanimate objects.
- 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.
【Therapeutic Uses】
Anti-Infective Agents, Local; Antifungal Agents; Growth Inhibitors
CLOTRIMAZOLE IS A CHLORINATED IMIDAZOLE DERIVATIVE THAT IS USED TO TREAT TOPICAL FUNGAL, DERMATOPHYTE, & YEAST INFECTIONS. WHILE CLOTRIMAZOLE HAS MARKED IN VITRO ACTIVITY AGAINST MANY FUNGI, IT IS OF LITTLE VALUE IN TREATMENT OF SYSTEMIC MYCOSES.
VAGINAL: 1 TABLET (100 MG) IS INSERTED DAILY FOR 1 WK FOR CANDIDAL VAGINITIS. TOPICAL: SUFFICIENT CREAM OR SOLN IS APPLIED TWICE DAILY TO SKIN INFECTED WITH CANDIDA ALBICANS, TRICOPHYTON, OR MICROSPORUM SPECIES. 2 WK OF THERAPY IS USUALLY SUFFICIENT.
CLOTRIMAZOLE HAS BEEN USED INVESTIGATIONALLY FOR ORAL TREATMENT OF MUCOCUTANEOUS CANDIDIASIS.
MEDICATION (VET): ANTIFUNGAL
Medication: Clotrimazole is a broad spectrum antifungal agent ... /for/ topical treatment of tinea pedis, tinea curis, tinea corporis ... candidiaisis due to Candida albicans, and tinea versicolor due to Pityrosporon obiculare; also for local treatment of vulvovaginal candidiasis
Based on the available data, the most appropriate treatment for acute, uncomplicated vulvovaginal candidiasis appears to be single day therapy with 500 mg clotrimazole (Gyne-Lotrimin; Mycelex) vaginal tablets.
An open study designed to compare the effectiveness and safety of clotrimazole troches with nystatin oral suspension in the prevention of oropharyngeal candidiasis was conducted. This study was performed as the troche form of clotrimazole was easier to administer and less costly than nystatin oral suspension. Sixty assessable patients were randomized to receive either clotrimazole troches (n= 32) or nystatin oral suspension (n= 28) for a 60 day period after receiving a renal allograft. The two groups were comparable in age, sex, type of transplant, and amount of immunosuppression. Both regimens were 100% effective in preventing the development of thrush in the patients studied. Adverse effects were infrequently seen in either group (one case of mild nausea in the clotrimazole group and three cases in the nystatin group). One patient chose to withdraw from the clotrimazole group, and eight patients withdrew from the nystatin group before completing 60 days of therapy (p= .002). Reasons given for withdrawal were the unpleasant taste of the drugs, or an inability to comply with the protocol. The cost of clotrimazole troches in the prophylactic doses given in this study was approximately one tenth that of nystatin oral suspension. Clotrimazole troches are effective, less expensive, and easier to self administer than nystatin oral suspension. [Gombert ME et al; JAMA 258 (18): 2553-5 (1987)]
【Biomedical Effects and Toxicity】
GIVEN ORALLY OR IV WAS ABSORBED, DISTRIBUTED, ELIMINATED READILY. EXCRETED AS INACTIVE METABOLITE IN BILE, LITTLE IN URINE.
Absorption of clotrimazol is less than 0.5% after application to the intact skin: from the vagina, it is 3 to 10%. Fungicidal concentrations remain in the vagina for as long as 3 days after application of the drug. The small amount absorbed is metabolized in the liver and excreted in bile. In adults, an oral dose of 200 mg per day will give rise to plasma concentrations of 0.2 to 0.35 ug/ml.
Only very small amounts of clotrimazole appear to be absorbed systemically following topical application to the skin. Following application to the skin, highest concentrations of clotrimazole are present in the stratum corneum; lower drug concentrations occur in the stratum spinosum and the papillary and reticular dermis. Small amounts of clotrimazole are absorbed systemically when the drug is administered intravaginally. Following intravaginal administration of radiolabeled clotrimazole in patients with normal or inflamed vaginal mucosa, peak serum concentrations of clotrimazole 24 hours after insertion of a single 100 mg tablet of the drug are 0.03 ug/ml and peak serum concentrations 24 hours after administration of a cream containing 50 mg of the drug are 0.01 ug/ml. About 3-10% of an intravaginal dose of the drug reaches systemic circulation, principally as metabolites.
Clotrimazole is absorbed from the gastrointestinal tract ... and excreted in the feces and urine. When applied topically clotrimazole penetrates the epidermis but there is little if any systemic absorption. Slight absorption has been reported following the administration of vaginal tablets.

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