U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C19H17Cl3N2S.HNO3
Molecular Weight 474.789
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BUTOCONAZOLE NITRATE

SMILES

O[N+]([O-])=O.ClC1=CC=C(CCC(CN2C=CN=C2)SC3=C(Cl)C=CC=C3Cl)C=C1

InChI

InChIKey=ZHPWRQIPPNZNML-UHFFFAOYSA-N
InChI=1S/C19H17Cl3N2S.HNO3/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;2-1(3)4/h1-5,7-8,10-11,13,16H,6,9,12H2;(H,2,3,4)

HIDE SMILES / InChI
Molecular Formula HNO3
Molecular Weight 63.0128
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C19H17Cl3N2S
Molecular Weight 411.776
Charge 0
Count
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

1985
117
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
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

1.33729917E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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

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:
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

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:
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

Sourcing

Vendor/AggregatorIDURL
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

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

Patents

CN104744371A
2
EP0065385
2
WO2005070897A1
2

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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:59:53 UTC 2023
Edited
by admin
on Fri Dec 15 18:59:53 UTC 2023
Record UNII
4805237NP5
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BUTOCONAZOLE NITRATE
MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN  
Official Name English
BUTOCONAZOLE NITRATE [MI]
Common Name English
BUTOCONAZOLE NITRATE [USP-RS]
Common Name English
RS-35887
Code English
BUTOCONAZOLE NITRATE [ORANGE BOOK]
Common Name English
BUTOCONAZOLE NITRATE [VANDF]
Common Name English
BUTOCONAZOLE NITRATE [USAN]
Common Name English
Butoconazole nitrate [WHO-DD]
Common Name English
1H-IMIDAZOLE, 1-(4-(4-CHLOROPHENYL)-2-((2,6-DICHLOROPHENYL)THIO)BUTYL)-, MONONITRATE, (±)-
Systematic Name English
BUTOCONAZOLE NITRATE [USP MONOGRAPH]
Common Name English
BUTOCONAZOLE NITRATE [MART.]
Common Name English
(±)-1-(4-(P-CHLOROPHENYL)-2-((2,6-DICHLOROPHENYL)THIO)BUTYL)IMIDAZOLE MONONITRATE
Common Name English
GYNAZOLE
Brand Name English
FEMSTAT
Brand Name English
RS-35887-00-10-3
Code English
Classification Tree Code System Code
NCI_THESAURUS C514
Created by admin on Fri Dec 15 18:59:54 UTC 2023 , Edited by admin on Fri Dec 15 18:59:54 UTC 2023
Code System Code Type Description
CAS
64872-77-1
Created by admin on Fri Dec 15 18:59:53 UTC 2023 , Edited by admin on Fri Dec 15 18:59:53 UTC 2023
PRIMARY
ChEMBL
CHEMBL1295
Created by admin on Fri Dec 15 18:59:53 UTC 2023 , Edited by admin on Fri Dec 15 18:59:53 UTC 2023
PRIMARY
PUBCHEM
47471
Created by admin on Fri Dec 15 18:59:54 UTC 2023 , Edited by admin on Fri Dec 15 18:59:54 UTC 2023
PRIMARY
NCI_THESAURUS
C47427
Created by admin on Fri Dec 15 18:59:54 UTC 2023 , Edited by admin on Fri Dec 15 18:59:54 UTC 2023
PRIMARY
RXCUI
47464
Created by admin on Fri Dec 15 18:59:54 UTC 2023 , Edited by admin on Fri Dec 15 18:59:54 UTC 2023
PRIMARY RxNorm
DRUG BANK
DB00639
Created by admin on Fri Dec 15 18:59:53 UTC 2023 , Edited by admin on Fri Dec 15 18:59:53 UTC 2023
PRIMARY
EPA CompTox
DTXSID6045452
Created by admin on Fri Dec 15 18:59:53 UTC 2023 , Edited by admin on Fri Dec 15 18:59:53 UTC 2023
PRIMARY
SMS_ID
100000084860
Created by admin on Fri Dec 15 18:59:54 UTC 2023 , Edited by admin on Fri Dec 15 18:59:54 UTC 2023
PRIMARY
FDA UNII
4805237NP5
Created by admin on Fri Dec 15 18:59:53 UTC 2023 , Edited by admin on Fri Dec 15 18:59:53 UTC 2023
PRIMARY
DAILYMED
4805237NP5
Created by admin on Fri Dec 15 18:59:53 UTC 2023 , Edited by admin on Fri Dec 15 18:59:53 UTC 2023
PRIMARY
RS_ITEM_NUM
1082300
Created by admin on Fri Dec 15 18:59:54 UTC 2023 , Edited by admin on Fri Dec 15 18:59:54 UTC 2023
PRIMARY
MERCK INDEX
m2801
Created by admin on Fri Dec 15 18:59:53 UTC 2023 , Edited by admin on Fri Dec 15 18:59:53 UTC 2023
PRIMARY Merck Index
CHEBI
3241
Created by admin on Fri Dec 15 18:59:53 UTC 2023 , Edited by admin on Fri Dec 15 18:59:53 UTC 2023
PRIMARY
EVMPD
SUB00918MIG
Created by admin on Fri Dec 15 18:59:53 UTC 2023 , Edited by admin on Fri Dec 15 18:59:53 UTC 2023
PRIMARY
Related Record Type Details
Structure of BUTOCONAZOLE NITRATE, (S)-
ENANTIOMER -> RACEMATE
Structure of BUTOCONAZOLE
PARENT -> SALT/SOLVATE
Structure of BUTOCONAZOLE NITRATE, (R)-
ENANTIOMER -> RACEMATE
Related Record Type Details
Structure of BUTOCONAZOLE
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966