Butoconazole

HCID 47472CAS 64872-76-0
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기본 정보

표준 SMILES
Clc1ccc(CCC(Cn2ccnc2)Sc2c(Cl)cccc2Cl)cc1
InChIKey
SWLMUYACZKCSHZ-UHFFFAOYSA-N
분자식
C19H17Cl3N2S
평균 분자량
411.8 g/mol
단동위원소 질량
410.01780258

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
영어명
Butoconazole
분자식
C19H17Cl3N2S
분자량
411.78

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
BUTONAZOLEButooonazoleButoconazole USP/EP/BP1-[4-(4-Chlorophenyl)-2-(2,6-dichlorophenyl)sulfanyl-butyl]imidazole1-(4-(4-Chlorophenyl)-2-((2,6-dichlorophenyl)thio)butyl)-1H-imidazole1-[2-[(2,6-Dichlorophenyl)thio]-4-(4-chlorophenyl)butyl]-1H-imidazole1-[(2S)-4-(4-chlorophenyl)-2-[(2,6-dichlorophenyl)thio]butyl]imidazole(±)-1-[4-(4-Chlorophenyl)-2-[(2，6-dichlorophenyl)thio]butyl]-1H-imidazole1-[4-(4-Chlorophenyl)-2-[(2,6-dichlorophenyl)thio]butyl]-1H-imidazole (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

데이터베이스 식별자

CAS
64872-76-0、64872-77-1
PubChem CID
47472
DTXSID
DTXSID2048537
ChEMBL
CHEMBL1295
ChEBI
CHEBI:3240
UNII
0Q771797PH
Nikkaji
J418.220K

물성

구조 계산 물성

XLogP
6.4
극성 표면적
43.1 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
2
회전 가능 결합 수
7
무거운 원자 수
25

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

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

물리화학적 성질

녹는점
68 · 68-70.5°
끓는 점
566.9 · 566.9±50.0 °C(Predicted)
밀도
1.32 · 1.32±0.1 g/cm3(Predicted)
저장 조건
-20 °C · Store at -20°C
용해도
82 mg/mL · DMSO: 82 mg/mL (199.14 mM);;
산도 계수 (pKa)
6.74 · 6.74±0.12(Predicted)

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 <i>in vitro</i> against <i>Candida</i> spp. and has been demonstrated to be clinically effective against vaginal infections due to <i>Candida albicans</i>. <i>Candida albicans</i> 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 14&alpha;-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.
응용 분야 · 2건

개요Butoconazole is an imidazole that is pharmacologically quite comparable to clotrimazole. It is a vaginal antifungal agent that increases cell membrane permeability in susceptible fungi. It is indicated for local treatment of vulvovaginal candidiasis (moniliasis).

용도Butoconazole is a fungostatic drug, and it is formally classified as an imidazole, but only because of the presence of an imidazole ring in the structure. It is believed that butoconazole, like miconazole, econazole, and other “pure” representatives of the imidazole class, also inhibits the biosynthesis of estrosterin in the cytoplasmatic membrane of fungi; however, it is very possible that this is not the only mechanism of its action. It is effective for vaginal infections caused by various types of candida. It is also used only externally and vaginally. Synonyms of this drug are femstat, listomin, and others.

상·하류 제품 정보

공급사50 곳

成都超九八生物科技有限公司13348960310 13348960310 · [email protected]
山东海舟生物工程有限公司130-0567-0367 13006570367 · [email protected]
上海毕得医药科技股份有限公司400-1647117 13681763483 · [email protected]
陕西缔都化学有限公司029-029-81123119 17391733320 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
추가 설명 · 1건

정의ChEBI: 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 sa t in gynaecology for treatment of vulvovaginal infections caused by Candida species, particularly Candida albicans.

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