1-[4-(4-chlorophenyl)-2-[(2,6-dichlorophenyl)sulfanyl]butyl]-1H-imidazole

• ChemBase ID: 521
• Molecular Formular: C19H17Cl3N2S
• Molecular Mass: 411.77568
• Monoisotopic Mass: 410.01780259
• SMILES: Clc1c(SC(CCc2ccc(Cl)cc2)Cn2ccnc2)c(Cl)ccc1
• Canonical SMILES: Clc1ccc(cc1)CCC(Sc1c(Cl)cccc1Cl)Cn1cncc1
• InChI: InChI=1S/C19H17Cl3N2S/c20-15-7-4-14(5-8-15)6-9-16(12-24-11-10-23-13-24)25-19-17(21)2-1-3-18(19)22/h1-5,7-8,10-11,13,16H,6,9,12H2
• InChIKey: SWLMUYACZKCSHZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[4-(4-chlorophenyl)-2-[(2,6-dichlorophenyl)sulfanyl]butyl]-1H-imidazole
• IUPAC Traditional name: butoconazole
• Brand Name: Femstat; Femstat 3; Gynazole-1
• Synonyms: Butoconazol [INN-Spanish]; Butoconazole nitrate; Butoconazolum [INN-Latin]; Butoconazole; 1-(4-(4-chlorophenyl)-2-(2,6-dichlorophenyl)sulfanyl-butyl)imidazole; Butoconazole nitrate

Database IDs

• CAS Number: 64872-76-0; 64872-77-1
• PubChem SID: 160963984; 46508016
• PubChem CID: 47472

CALCULATED PROPERTIES

JChem

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 6.0206056
• LogD (pH = 7.4): 6.4849215
• Log P: 6.5524845
• Molar Refractivity: 108.986 cm^3
• Polarizability: 42.21479 Å^3
• Polar Surface Area: 17.82 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 6.7
• LOG S: -5.7
• Solubility (Water): 8.18e-04 g/l

PROPERTIES

Physical Property

• Solubility: Nitrate salt: 0.26 mg/ml (practically insoluble)
• Hydrophobicity(logP): 6.7

Product Information

• Purity: 98%

DETAILS

DrugBank - DB00639

• Drug Groups: approved
• Description: Butoconazole is an imidazole antifungal used in gynecology.
• Indication: For the local treatment of vulvovaginal candidiasis (infections caused by Candida)
• Pharmacology: 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.
• Toxicity: Oral, rat: LD₅₀ = >1720 mg/kg.
• Affected Organisms: Fungi, yeast and protozoans
• Absorption: Following 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.
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com