CAS 67085-13-6 Butoconazole (HCID 178765343)

기본 정보

CAS: 67085-13-6
표준 SMILES: Clc1ccc(CCC(Cn2ccnc2)Sc2c(Cl)cccc2Cl)cc1
InChIKey: SWLMUYACZKCSHZ-UHFFFAOYSA-N
분자식: C19H17Cl3N2S
평균 분자량: 411.8 g/mol

개요

Butoconazole is a member of the class of imidazoles that is 1H-imidazole in which the hydrogen attached to the nitrogen is substituted by a 4-(4-chlorophenyl)-2-[(2,6-dichlorophenyl)sulfanyl]butyl group. An antifungal agent, it is used as its nitrate salt in gynaecology for treatment of vulvovaginal infections caused by Candida species, particularly Candida albicans. It is a dichlorobenzene, a member of imidazoles, an aryl sulfide, a member of monochlorobenzenes, an imidazole antifungal drug and a conazole antifungal drug. It is a conjugate base of a butoconazole(1+).

이름 및 식별자

우선 이름: Butoconazole
IUPAC: 1-[4-(4-chlorophenyl)-2-(2,6-dichlorophenyl)sulfanylbutyl]imidazole
현지명: 부토코나졸
영어명: Butoconazole
분자식: C19H17Cl3N2S
분자량: 411.77568

이름 및 동의어

Butoconazole64872-76-0ButoconazolButoconazolumGynofortRS 35887-10-3NSC-7586580Q771797PH1-[4-(4-chlorophenyl)-2-[(2,6-dichlorophenyl)sulfanyl]butyl]-1H-imidazoleCHEBI:32401-{4-(4-chlorophenyl)-2-[(2,6-dichlorophenyl)sulfanyl]butyl}-1H-imidazole1H-Imidazole, 1-(4-(4-chlorophenyl)-2-((2,6-dichlorophenyl)thio)butyl)-, (+-)-

이름 더 보기

부토코나졸1H-Imidazole, 1-(4-(4-chlorophenyl)-2-((2,6-dichlorophenyl)thio)butyl)-, nitrateButoconazoleQ: What is Butoconazole Q: What is the CAS Number of Butoconazole Q: What is the storage condition of Butoconazole Q: What are the applications of Butoconazole

1-[4-(4-Chloro-phenyl)-2-(2,6-dichloro-phenylsulfanyl)-butyl]-1H-imidazole(+-)-1-[4-(4-Chlorophenyl)-2-[(2,6-dichlorophenyl)thio]butyl]-1H-imidazole1-(4-(4-chlorophenyl)-2-((2,6-dichlorophenyl)sulfanyl)butyl)-1H-imidazole(+-)-1-(4-(4-Chlorophenyl)-2-((2,6-dichlorophenyl)thio)butyl)-1H-imidazole1-(4-(4-Chloro-phenyl)-2-(2,6-dichloro-phenylsulfanyl)-butyl)-1H-imidazole1-(4-(4-Chlorophenyl)-2-(2,6-dichlorophenylthio)-n-butyl)-1H-imidazoleRefChem:56483G01AF15

물성

구조 계산 물성

XLogP: 6.4
극성 표면적: 43.1 Å²
수소 결합 공여자 수: 0
수소 결합 수용자 수: 2
회전 가능 결합 수: 7
무거운 원자 수: 25
형식 전하: 0
복잡도: 383

실험 및 물리화학적 성질

LogP6.7

Solubility · 2건

Nitrate salt: 0.26 mg/ml (practically insoluble)

8.18e-04 g/L

Human DrugsBreast Feeding; Lactation; Anti-Infective Agents; Antifungal Agents; Dermatologic Agents;

Melting Point · 2건

~159°C with decomposition (nitrate salt)

159 °C (decomposition)

Physical DescriptionSolid

Collision Cross Section · 2건

185.55 Å² [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

186.5 Å² [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

안전 및 규제

독성 정보

Drug Induced Liver Injury · 5건

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

butoconazole

DILI Negative

Vaginal

DOI:10.1016/j.drudis.2019.09.022

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

화학 및 산업

약리 정보

ATC Code · 3건

G01AF15

G - Genito urinary system and sex hormones

QG - Genito urinary system and sex hormones

Pharmacodynamics · 1건

Butoconazole is an imidazole derivative that has fungicidal activity in vitro against Candida spp. and has been demonstrated to be clinically effective against vaginal infections due to Candida albicans. Candida albicans has been identified as the predominant species responsible for vulvovaginal candidasis.

Mechanism of Action · 1건

The exact mechanism of the antifungal action of butoconazole is unknown, however, it is presumed to function as other imidazole derivatives via inhibition of steroid synthesis. Imidazoles generally inhibit the conversion of lanosterol to ergosterol via the inhibition of the enzyme cytochrome P450 14α-demethylase, resulting in a change in fungal cell membrane lipid composition. This structural change alters cell permeability and, ultimately, results in the osmotic disruption or growth inhibition of the fungal cell.

FDA Pharmacological Classification · 5건

0Q771797PH

BUTOCONAZOLE

Established Pharmacologic Class [EPC] - Azole Antifungal

Chemical Structure [CS] - Azoles

Butoconazole is an Azole Antifungal.

MeSH Pharmacological ClassificationSubstances 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.

Absorption, Distribution and ExcretionFollowing vaginal administration of butoconazole nitrate vaginal cream, 2% to 3 women, 1.7% (range 1.3-2.2%) of the dose was absorbed on average.

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