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Details

Stereochemistry RACEMIC
Molecular Formula C19H17Cl3N2S
Molecular Weight 411.7773
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BUTOCONAZOLE

SMILES

c1cc(c(c(c1)Cl)SC(CCc2ccc(cc2)Cl)Cn3ccnc3)Cl

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
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

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
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

1.33729917E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
4471.25 pg/mL
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
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
113290.135 pg × h/mL
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
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
17.834 h
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

Doses

DosePopulationAdverse 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:
unknown, adult
n = 314
Health Status: unknown
Age Group: adult
Sex: M+F
Population Size: 314
Sources:
Disc. AE: Vaginal pain or burning, Abdominal pain...
AEs leading to
discontinuation/dose reduction:
Vaginal pain or burning
Abdominal pain
Cramp
Sources:
AEs

AEs

AESignificanceDosePopulation
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:
unknown, adult
n = 314
Health Status: unknown
Age Group: adult
Sex: M+F
Population Size: 314
Sources:
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:
unknown, adult
n = 314
Health Status: unknown
Age Group: adult
Sex: M+F
Population Size: 314
Sources:
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:
unknown, adult
n = 314
Health Status: unknown
Age Group: adult
Sex: M+F
Population Size: 314
Sources:
PubMed

PubMed

TitleDatePubMed
1-[4-(4-Chlorophenyl)-2-(2,6-dichlorophenylthio)-n-butyl]-1H-imidazole nitrate, a new potent antifungal agent.
1978 Aug
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
An evaluation of butoconazole nitrate 2% site release vaginal cream (Gynazole-1) compared to fluconazole 150 mg tablets (Diflucan) in the time to relief of symptoms in patients with vulvovaginal candidiasis.
2005 Dec
[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
Screening of a chemical library reveals novel PXR-activating pharmacologic compounds.
2015 Jan 5
Patents

Sample Use Guides

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
INN   MI   VANDF   WHO-DD  
INN  
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
BUTOCONAZOLE [WHO-DD]
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
NSC-758658
Code English
Classification Tree Code System Code
WHO-VATC QG01AF15
Created by admin on Fri Jun 25 22:12:27 UTC 2021 , Edited by admin on Fri Jun 25 22:12:27 UTC 2021
NDF-RT N0000175487
Created by admin on Fri Jun 25 22:12:27 UTC 2021 , Edited by admin on Fri Jun 25 22:12:27 UTC 2021
WHO-ATC G01AF15
Created by admin on Fri Jun 25 22:12:27 UTC 2021 , Edited by admin on Fri Jun 25 22:12:27 UTC 2021
NDF-RT N0000008217
Created by admin on Fri Jun 25 22:12:27 UTC 2021 , Edited by admin on Fri Jun 25 22:12:27 UTC 2021
NCI_THESAURUS C514
Created by admin on Fri Jun 25 22:12:27 UTC 2021 , Edited by admin on Fri Jun 25 22:12:27 UTC 2021
Code System Code Type Description
EPA CompTox
64872-76-0
Created by admin on Fri Jun 25 22:12:27 UTC 2021 , Edited by admin on Fri Jun 25 22:12:27 UTC 2021
PRIMARY
DRUG BANK
DB00639
Created by admin on Fri Jun 25 22:12:27 UTC 2021 , Edited by admin on Fri Jun 25 22:12:27 UTC 2021
PRIMARY
CAS
64872-76-0
Created by admin on Fri Jun 25 22:12:27 UTC 2021 , Edited by admin on Fri Jun 25 22:12:27 UTC 2021
PRIMARY
ChEMBL
CHEMBL1295
Created by admin on Fri Jun 25 22:12:27 UTC 2021 , Edited by admin on Fri Jun 25 22:12:27 UTC 2021
PRIMARY
WIKIPEDIA
Butoconazole
Created by admin on Fri Jun 25 22:12:27 UTC 2021 , Edited by admin on Fri Jun 25 22:12:27 UTC 2021
PRIMARY
NCI_THESAURUS
C79927
Created by admin on Fri Jun 25 22:12:27 UTC 2021 , Edited by admin on Fri Jun 25 22:12:27 UTC 2021
PRIMARY
INN
4496
Created by admin on Fri Jun 25 22:12:27 UTC 2021 , Edited by admin on Fri Jun 25 22:12:27 UTC 2021
PRIMARY
DRUG CENTRAL
450
Created by admin on Fri Jun 25 22:12:27 UTC 2021 , Edited by admin on Fri Jun 25 22:12:27 UTC 2021
PRIMARY
EVMPD
SUB06026MIG
Created by admin on Fri Jun 25 22:12:27 UTC 2021 , Edited by admin on Fri Jun 25 22:12:27 UTC 2021
PRIMARY
PUBCHEM
47472
Created by admin on Fri Jun 25 22:12:27 UTC 2021 , Edited by admin on Fri Jun 25 22:12:27 UTC 2021
PRIMARY
FDA UNII
0Q771797PH
Created by admin on Fri Jun 25 22:12:27 UTC 2021 , Edited by admin on Fri Jun 25 22:12:27 UTC 2021
PRIMARY
RXCUI
19884
Created by admin on Fri Jun 25 22:12:27 UTC 2021 , Edited by admin on Fri Jun 25 22:12:27 UTC 2021
PRIMARY RxNorm
MESH
C017125
Created by admin on Fri Jun 25 22:12:27 UTC 2021 , Edited by admin on Fri Jun 25 22:12:27 UTC 2021
PRIMARY
LACTMED
Butoconazole
Created by admin on Fri Jun 25 22:12:27 UTC 2021 , Edited by admin on Fri Jun 25 22:12:27 UTC 2021
PRIMARY
MERCK INDEX
M2801
Created by admin on Fri Jun 25 22:12:27 UTC 2021 , Edited by admin on Fri Jun 25 22:12:27 UTC 2021
PRIMARY Merck Index