BUTOCONAZOLE

Details

Stereochemistry	RACEMIC
Molecular Formula	C19H17Cl3N2S
Molecular Weight	411.776
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

ClC1=CC=C(CCC(CN2C=CN=C2)SC3=C(Cl)C=CC=C3Cl)C=C1

InChI

InChIKey=SWLMUYACZKCSHZ-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/19881slr009_gynazole_lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/2184984

Butoconazole, trade names Gynazole-1, an imidazole antifungal used in gynecology for the local treatment of vulvovaginal candidiasis (infections caused by Candida). The exact mechanism of the antifungal action of butoconazole nitrate 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, 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.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cytochrome P450 51 28 Target ID: CHEMBL1780 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2184984	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Vulvovaginal candidiasis 9 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/19881slr009_gynazole_lbl.pdf	Curative		Approved 8429	GYNAZOLE-1 Approved Use Gynazole·1® (butoconazole nitrate) vaginal cream, 2% is indicated for the local treatment of vulvovaginal candidiasis (infections caused by Candida). The diagnosis should be confirmed by KOH smears and/or cultures. Launch Date 2012

C_max

Value	Dose	Analyte	Population
4471.25 pg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24939312	100 mg single, vaginal dose: 100 mg route of administration: Vaginal experiment type: SINGLE co-administered:	BUTOCONAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
0.895 ng/mL EXPERIMENT https://www.researchgate.net/publication/289924108_Pharmacokinetics_of_butoconazole_nitrate_suppositories_in_human	0.05 g single, vaginal dose: 0.05 g route of administration: Vaginal experiment type: SINGLE co-administered:	BUTOCONAZOLE unknown	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
1.74 ng/mL EXPERIMENT https://www.researchgate.net/publication/289924108_Pharmacokinetics_of_butoconazole_nitrate_suppositories_in_human	0.1 g single, vaginal dose: 0.1 g route of administration: Vaginal experiment type: SINGLE co-administered:	BUTOCONAZOLE unknown	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
113290.135 pg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24939312	100 mg single, vaginal dose: 100 mg route of administration: Vaginal experiment type: SINGLE co-administered:	BUTOCONAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
36.38 ng × h/mL EXPERIMENT https://www.researchgate.net/publication/289924108_Pharmacokinetics_of_butoconazole_nitrate_suppositories_in_human	0.05 g single, vaginal dose: 0.05 g route of administration: Vaginal experiment type: SINGLE co-administered:	BUTOCONAZOLE unknown	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
73.48 ng × h/mL EXPERIMENT https://www.researchgate.net/publication/289924108_Pharmacokinetics_of_butoconazole_nitrate_suppositories_in_human	0.1 g single, vaginal dose: 0.1 g route of administration: Vaginal experiment type: SINGLE co-administered:	BUTOCONAZOLE unknown	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
17.834 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24939312	100 mg single, vaginal dose: 100 mg route of administration: Vaginal experiment type: SINGLE co-administered:		BUTOCONAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
5 g 1 times / day single, vaginal Recommended Dose: 5 g, 1 times / day Route: vaginal Route: single Dose: 5 g, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/19881slr009_gynazole_lbl.pdf	unknown, adult n = 314 Health Status: unknown Age Group: adult Sex: M+F Population Size: 314 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/19881slr009_gynazole_lbl.pdf	Disc. AE: Vaginal pain or burning, Abdominal pain... AEs leading to discontinuation/dose reduction: Vaginal pain or burning Abdominal pain Cramp Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/19881slr009_gynazole_lbl.pdf

AEs

AE	Significance	Dose	Population
Abdominal pain	Disc. AE	5 g 1 times / day single, vaginal Recommended Dose: 5 g, 1 times / day Route: vaginal Route: single Dose: 5 g, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/19881slr009_gynazole_lbl.pdf	unknown, adult n = 314 Health Status: unknown Age Group: adult Sex: M+F Population Size: 314 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/19881slr009_gynazole_lbl.pdf
Cramp	Disc. AE	5 g 1 times / day single, vaginal Recommended Dose: 5 g, 1 times / day Route: vaginal Route: single Dose: 5 g, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/19881slr009_gynazole_lbl.pdf	unknown, adult n = 314 Health Status: unknown Age Group: adult Sex: M+F Population Size: 314 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/19881slr009_gynazole_lbl.pdf
Vaginal pain or burning	Disc. AE	5 g 1 times / day single, vaginal Recommended Dose: 5 g, 1 times / day Route: vaginal Route: single Dose: 5 g, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/19881slr009_gynazole_lbl.pdf	unknown, adult n = 314 Health Status: unknown Age Group: adult Sex: M+F Population Size: 314 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/19881slr009_gynazole_lbl.pdf

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:3240	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:3240
ChemicalBook	CB3352597	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB3352597
MolPort	MolPort-003-666-530	https://www.molport.com/shop/molecule-link/MolPort-003-666-530
eMolecules	901494	https://www.emolecules.com/cgi-bin/more?vid=901494

PubMed

Title	Date	PubMed
1-[4-(4-Chlorophenyl)-2-(2,6-dichlorophenylthio)-n-butyl]-1H-imidazole nitrate, a new potent antifungal agent.	1978 Aug	357722
In vitro activity of cloconazole, sulconazole, butoconazole, isoconazole, fenticonazole, and five other antifungal agents against clinical isolates of Candida albicans and Candida spp.	1992 Apr	1406898
[The statement of Polish Gynecological Society Experts on the treatment of acute vulvovaginal candidiasis with prolonged releasing 2% butoconazole nitrate vaginal cream--state of art in 2008].	2009 Apr	19507567
Screening of a chemical library reveals novel PXR-activating pharmacologic compounds.	2015 Jan 5	25455453

Patents

Sample Use Guides

In Vivo Use Guide

The recommended dose of Gynazole·1 (butoconazole nitrate) is one applicatorful of cream (approximately 5 grams of the cream) intravaginally. This amount of cream contains approximately 100 mg of butoconazole nitrate.

Route of Administration: Vaginal

In Vitro Use Guide

Increasing levels of butoconazole were added to 150 microliters of a dilution in Roiron medium adjusted to 50,000 Trichomonas/ml. Results were read after 1, 2, 6 and 24 hours aerobic incubation at 37 degrees C. Minimum lethal concentration was 93 micrograms/microliters after one hour, 23 micrograms/microliter after six hours and 12 micrograms/microliters after 24 hours. These findings warrant in vivo studies of butoconazole against Trichomonas. This drug may prove very useful since concomitant infection of the genital tract by Trichomonas and Candida is common.

Name

Type

Language

BUTOCONAZOLE

Official Name

English

GYNOFORT

Brand Name

English

(±)-1-(4-(P-CHLOROPHENYL)-2-((2,6-DICHLOROPHENYL)THIO)BUTYL)IMIDAZOLE

Common Name

English

butoconazole [INN]

Common Name

English

1H-IMIDAZOLE, 1-(4-(4-CHLOROPHENYL)-2-((2,6-DICHLOROPHENYL)THIO)BUTYL)-, (±)-

Systematic Name

English

BUTOCONAZOLE [VANDF]

Common Name

English

BUTOCONAZOLE [MI]

Common Name

English

Butoconazole [WHO-DD]

Common Name

English

NSC-758658

Code

English

Classification Tree Code System Code

WHO-VATC

QG01AF15