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Butoconazole

Butoconazole structure

CAS No:
64872-76-0
Formula:
C19H17Cl3N2S
Chemical Name:
Butoconazole
Synonyms:
1H-Imidazole,1-[4-(4-chlorophenyl)-2-[(2,6-dichlorophenyl)thio]butyl]-;1H-Imidazole,1-[4-(4-chlorophenyl)-2-[(2,6-dichlorophenyl)thio]butyl]-,(±)-;1-[4-(4-Chlorophenyl)-2-[(2,6-dichlorophenyl)thio]butyl]-1H-imidazole;Butoconazole;Butaconazole;1-[2-(2,6-Dichlorophenylthio)-4-(4-chlorophenyl)-n-butyl]imidazole;67085-13-6;85496-23-7
Categories:
Active Pharmaceutical Ingredients > Synthetic Anti-infective Drugs

Description

ChEBI: 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.

Solid

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 member of imidazoles, an aryl sulfide, a dichlorobenzene, a member of monochlorobenzenes, an imidazole antifungal drug and a conazole antifungal drug. It is a conjugate base of a butoconazole(1+).|Butoconazole is an imidazole antifungal used in gynecology.

Butoconazole Basic Attributes

Molecular Weight：

411.78

Exact Mass：

411.78

EC Number：

613-721-6

NSC Number：

758658

DSSTox ID：

DTXSID2048537

ATC Code：

G01AF15|G - Genito urinary system and sex hormones

HScode：

2933290090

Characteristics

PSA：

43.1

XLogP3：

6.7

Appearance：

Solid

Density：

1.3±0.1 g/cm3

Melting Point：

68-70.5 °C

Boiling Point：

566.9±50.0 °C at 760 mmHg

Flash Point：

296.7±30.1 °C

Refractive Index：

1.634

Water Solubility：

Nitrate salt: 0.26 mg/ml (practically insoluble )

Collision Cross Section：

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

Safety Information

Packing level：

Hazard category：

Transport codes：

UN 3260 8/PG 2

wgk germany：

hazard class code：

R14:Reacts violently with water. R34:Causes burns. R40:Limited evidence of a carcinogenic effect. R42/43:May cause sensitization by inhalation and skin contact .

safety instructions：

S22-S26-S36/37/39-S45

Marks：

Toxicity

Toxicity Summary：

Oral, rat: LD50 = >1720 mg/kg.

Drug Information

Drug Indication：

For the local treatment of vulvovaginal candidiasis (infections caused by Candida)|FDA Label

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.

MeSH：

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. (See all compounds classified as Antifungal Agents.)

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.

Mechanism of Action：

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.

MeSH Entry Terms：

1-(4-(4-chlorophenyl)-2-(2,6-dichlorophenylthio)-n-butyl)-1H-imidazole

Butoconazole Use and Manufacturing

Uses

antineoplastic, pyrimidine antimetabolite

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:411.8
XLogP3:6.4
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:7
Exact Mass:410.017803
Monoisotopic Mass:410.017803
Topological Polar Surface Area:43.1
Heavy Atom Count:25
Complexity:383
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

tert-Butanol