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

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

Molecular Formula	C19H17Cl3N2S
Molecular Weight	411.776
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description

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	Inhibitor 8,504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Vulvovaginal candidiasis 13	Curative		Approved 8,583	GYNAZOLE-1

C_max

Value	Dose	Analyte	Population
4471.25 pg/mL	100 mg single, vaginal	BUTOCONAZOLE plasma	Homo sapiens
0.895 ng/mL	0.05 g single, vaginal	BUTOCONAZOLE plasma	Homo sapiens
1.74 ng/mL	0.1 g single, vaginal	BUTOCONAZOLE plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
113290.135 pg × h/mL	100 mg single, vaginal	BUTOCONAZOLE plasma	Homo sapiens
36.38 ng × h/mL	0.05 g single, vaginal	BUTOCONAZOLE plasma	Homo sapiens
73.48 ng × h/mL	0.1 g single, vaginal	BUTOCONAZOLE plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
17.834 h	100 mg single, vaginal		BUTOCONAZOLE plasma	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
5 g 1 times / day single, vaginal Recommended	unknown, adult	Disc. AE: Vaginal pain or burning, Abdominal pain...

Showing 1 to 1 of 1 entries

Previous1Next

AEs

Show entries

AE	Significance	Dose	Population
Abdominal pain	Disc. AE	5 g 1 times / day single, vaginal Recommended	unknown, adult
Cramp	Disc. AE	5 g 1 times / day single, vaginal Recommended	unknown, adult
Vaginal pain or burning	Disc. AE	5 g 1 times / day single, vaginal Recommended	unknown, adult

Showing 1 to 3 of 3 entries

Previous1Next

Sourcing

Sourcing

Show entries

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
eMolecules	901494	https://www.emolecules.com/cgi-bin/more?vid=901494
MolPort	MolPort-003-666-530	https://www.molport.com/shop/molecule-link/MolPort-003-666-530

Showing 1 to 4 of 4 entries

Previous1Next

PubMed

Show entries

Title	Date	PubMed
1-[4-(4-Chlorophenyl)-2-(2,6-dichlorophenylthio)-n-butyl]-1H-imidazole nitrate, a new potent antifungal agent.	1978 Aug	357722
[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

Showing 1 to 3 of 3 entries

Previous1Next

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.