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HCID 2812생성일: 2026년 10월 27일

클로트라이마졸

클로트라이마졸 · CLOTRIMAZOL · clotrimazole powder · (2-Chlorophenyl)diphenyl-1-imidazolylmethane · CLT · myclo · hemagglutinin · mycelex-g

https://huagongshe.com/ko/chemical/2812

클로트라이마졸 분자 구조식

식별자 및 물리적 특성

CAS No.23593-75-1
분자식C22H17ClN2
평균 분자량344.8 g/mol
단동위원소 질량344.10802622 g/mol
SMILESClc1ccccc1C(c1ccccc1)(c1ccccc1)n1ccnc1
InChIKeyVNFPBHJOKIVQEB-UHFFFAOYSA-N
PubChem CID2812
ChEMBLCHEMBL104
ChEBICHEBI:3764
EC No.245-764-8
DTXSIDDTXSID7029871
현지명클로트라이마졸

화학 및 물리적 성질

XLogP5
극성 표면적17.8
수소 결합 공여자 수0
수소 결합 수용자 수1
회전 가능 결합 수4
무거운 원자 수25
형식 전하0
복잡도396
의약품PharmaceuticalsPharmaceuticals -> AntibioticsPharmaceuticals -> Listed in ZINC15
화장품AntimicrobialAntidandruff
pHWEAK BASE
LogP(분배 계수)4.75
냄새Odorless
Color/FormCrystalsWhite to pale yellow crystalline powder
용해도SOL IN ACETONE, CHLOROFORM, ETHYL ACETATESLIGHTLY SOL IN WATER, BENZENE, TOLUENEFreely soluble in alcoholsoluble in polyethylene glycol 400Slightly soluble in ether3.7 [ug/mL] (The mean of the results at pH 7.4)클로로포름, DMSO, DMF 및 알코올에 용해됨
Human DrugsBreast FeedingLactationMilk, HumanAntifungal AgentsDermatologic AgentsFDA approved drugs -> Active ingredientAntifungal medicines
Animal DrugsActive Ingredients (Clotrimazole) -> FDA GreenbookPharmaceuticals -> UK Veterinary Medicines Directorate List
녹는점147-149 °C148 °C147-149°C
Physical DescriptionSolid
Dissociation Constants4.1
끓는 점501.14°C (rough estimate)
밀도1.1095 (rough estimate)
굴절률1.5940 (estimate)
저장 조건2-8°C
pKa(산도 계수)pKa 4.7(EtOH 50%aq ) (Uncertain)
물리적 상태Solid
색상흰색에서 거의 흰색
용해도<10mg/L(25℃)
Merck14,2417
주요 응용제약소분자 약용
화장품 원료 기능항균항지루성
InChIInChI=1S/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
InChIKeyVNFPBHJOKIVQEB-UHFFFAOYSA-N
SMILESC1N(C(C2=CC=CC=C2Cl)(C2=CC=CC=C2)C2=CC=CC=C2)C=CN=1
NISTClotrimazole(23593-75-1)

화학적 성질

White or pale yellow, crystalline powder.

안전 및 규제

GHS 분류This chemical does not meet GHS hazard criteria for 1.5% (3 of 196) of reports.DangerH302 (96.9%): Harmful if swallowed [Warning Acute toxicity, oral]P203, P260, P262, P264, P264+P265, P270, P273, P280, P301+P317, P302+P352, P305+P351+P338, P316, P318, P319, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P391, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 196 reports by companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
규제 정보Hazard Traits - BioaccumulationEnvironmental PersistenceClotrimazole: Does not have an individual approval but may be used under an appropriate group standard
기타 안전 정보IMAP assessments - 1H-Imidazole, 1-[(2-chlorophenyl)diphenylmethyl]-: Environment tier I assessment
FDA 요건Clotrimazole 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.
Hazard Classes and CategoriesAcute Tox. 4 (96.9%)
Skin, Eye, and Respiratory IrritationsAdverse effects after topical use of clotrimazole include stinging.
상호 작용A synergistic effect of clotrimazole and certain anionic surfactants against a strain of Candida albicans was confirmed. Measurement of apparent partition coefficients indicated that lipophilic ion pairs between clotrimazole and anionic surfactants were formed. It is suggested that the synergistic effect of the drugs may be due to ion pair formation.
HepatotoxicityTransient elevations in serum aminotransferase levels occur in up to 15% of patients treated with clotrimazole orally. The elevations are generally mild-to-moderate in degree and resolve spontaneously with or without discontinuation. Despite decades of widespread use, clotrimazole has not been linked to instances of clinically apparent hepatotoxicity.

용도

개요

Clotrimazole is an imidazole antifungal that is active against a wide variety of fungal forms and is effective in many types of fungal infections. It tightly binds sterol 14-α demethylase isoform B from A. fumigatus (KD = 103 nM) and, like other imidazoles, disturbs the fungal cell membrane. In mammalian cells, clotrimazole potently inhibits the calcium-dependent potassium channels Kv1.3 and IK-1 (IC50 = 6.0 and 0.07 μM, respectively).

용도

Clotrimazole is an antifungal agent.

일반 설명

Chemical structure: imidazole

유해 작용The adverse effects of the oral formulation include itching, nausea, and vomiting. More than 10% of patients receiving oral clotrimazole (troche) may have abnormal liver function tests. For this reason, patients receiving oral clotrimazole (troche) should have their liver function tests periodically monitored.
노출 경로Poorly and erratically absorbed orally, minimal vaginal or topical absorption.
독성 요약When clotrimazole is applied locally and topically, toxic effects such as pelvic cramps, hives, skin rash, occasional headache, itching, and irritation of the vulva and vagina may be observed. Therapy should be halted if there are any adverse effects.Clotrimazole interacts with yeast 14-&alphademethylase, a cytochrome P-450 enzyme that converts lanosterol to ergosterol, an essential component of the membrane. In this way, clotrimazole inhibits ergosterol synthesis, resulting in increased cellular permeability. Clotrimazole may also inhibit endogenous respiration, interact with membrane phospholipids, inhibit the transformation of yeasts to mycelial forms and the uptake of purine, impair triglyceride and/or phospholipid biosynthesis, and inhibit the movement of calcium and potassium ions across the cell membrane by blocking the ion transport pathway known as the Gardos channel.
Signs and SymptomsSymptoms of overdose include erythema, stinging, blistering, peeling, edema, pruritus, urticaria, burning, and general irritation of the skin, and cramps.
Human Toxicity ExcerptsIn a small fraction of recipients, clotrimazole on the skin may cause stinging, erythema, edema, vesication, desquamation, pruritus, and urticaria. Applied to the vagina, about 1.6% of recipients complain of a mild burning sensation and, rarely, of lower abdominal cramps, slight increase in urinary frequency, or skin rash. Occasionally, the sexual partner may experience penile or urethral irritation. By the oral route, clotrimazole can cause mild gastrointestinal irritation. In patients using troches, the incidence is about 5%.No adverse effects have been reported to date in humans when clotrimazole was administered intravaginally in the second or third trimesters of pregnancyhowever, intravaginal use of the drug during the first trimester of pregnancy has not been studied. Since clotrimazole is absorbed in small amounts from the vagina, the drug should not be used intravaginally in the first trimester of pregnancy unless the drug is considered essential to the welfare of the patient.Adverse effects after topical use of clotrimazole include erythemastinging, blistering, and peeling of the skinand urticaria. Adverse reactions after use of the troche form include nausea and vomiting (incidence, about 5%). Reversible elevation of SGOT to abnormal levels has occurred in 15% of patients receiving troches. The manufacturer recommends periodic assessment of hepatic function, particularly in patients with pre-existing hepatic impairment. The safety and effectiveness of clotrimazole troches in children less than 3 years has not been establishedtherefore, use of this dosage form in these patients is not recommended.Seventy three patients with rheumatoid arthritis were randomized in a double blind study to receive either clotrimazole (20 mg/kg/day) 2 days/wk for 12 wk or matching placebo. Patients receiving clotrimazole had significant improvements (p< 0.05) from baseline in measurements of grip strength, joint count, and patient assessment of pain, but did not show significant improvement over patients treated with placebo. More adverse experiences, predominantly gastrointestinal complaints, occurred in patients taking clotrimazole resulting in 9 patients discontinuing therapy.For more Human Toxicity Excerpts (Complete) data for CLOTRIMAZOLE (6 total), please visit the HSDB record page.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver InjuryDrug Induced Liver Injury Rank (DILIrank 2.0)ClotrimazolevLess-DILI-concern3Warnings & precautionsDOI:10.1016/j.drudis.2016.02.015
Non-Human Toxicity ExcerptsSHOWED MODERATE TOXICITY AFTER ORAL ADMIN. SOLN OR CREAM WERE WELL TOLERATED BY SKIN OF RABBIT & CONJUNCTIVA.Clotrimazole inhibits or kills many fungi, including yeast and dermatophytes. The drug is also active against some gram positive bacteria. In vitro, clotrimazole concentrations of 1 ug/ml or less inhibit most strains of Trichlophyton rubrum, T. mentagrophytes, Epidermophyton floccosum, and Microsporum canis. At a concentration of 3 ug/ml or less, clotrimazole inhibits most other susceptible organisms including Malassezia furfur (Pityrosporum orbiculare), Aspergillus fumigatus, Candida albicans, some strains of Staphylococcus aureaus and Streptococcus pyogenes, and a few strains of Proteus vulgaris and Salmonella in vitro. Clotrimazole is also active in vitro against Sporothrix, Cryptococcus, Cephalosporium, and Fusarium. Clotrimazole concentrations of 100 ug/ml are required to inhibit Trichomonas vaginalis.Clotrimazole has been shown to be embryotoxic in rats and mice when given in oral doses 100 times the usual human dosethis effect may be secondary to maternal toxicity. Clotrimazole has not been teratogenic in mice, rabbits, or rats when given in oral doses up to 200, 180, or 100 times the human dose, respectively. In addition, reproduction studies in mice using oral clotrimazole, at a dosage 120 times the usual human dose and administered from 9 weeks prior to mating through weaning, resulted in impairment of mating, decreased number of viable young, and decreased survival to weaningno effects were observed when doses 60 times the usual human dose were used. In similar studies in rats using oral doses 50 times the usual human dose, there was a slight decrease in the number of pups per litter and decreased pup viability.Clotrimazole is embryotoxic in rats and mice when given in doses 100 times the adult human dose (in mg/kg), possibly secondary to maternal toxicity. The drug was not teratogenic in mice, rabbits, and rats when given in doses up to 200 times the human dose.
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation◈ What is clotrimazole?
Non-Human Toxicity ValuesLD50 Rat, male oral 708 mg/kgLD50 Mouse, male oral 923 mg/kg
수질 위해 등급(WGK)3
RTECS 번호NI4377000
독성LD50 in male mice, rats (mg/kg): 923, 708 orally (Tettenborn)
관세 코드29332900
위험 문구(R)22-36/38
위험 표시Xn
안전 문구(S)26-36
위험 등급Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Eye Irrit. 2Skin Irrit. 2
저장 분류11 - Combustible Solids
유해 물질 데이터23593-75-1(Hazardous Substances Data)