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

Details

Stereochemistry ACHIRAL
Molecular Formula C6H8N2O2S.ClH
Molecular Weight 208.666
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SULFANILAMIDE HYDROCHLORIDE

SMILES

Cl.NC1=CC=C(C=C1)S(N)(=O)=O

InChI

InChIKey=XZMIAZCXISFPEJ-UHFFFAOYSA-N
InChI=1S/C6H8N2O2S.ClH/c7-5-1-3-6(4-2-5)11(8,9)10;/h1-4H,7H2,(H2,8,9,10);1H

HIDE SMILES / InChI
Sulfanilamide is an anibiotic drug, which has been used for decades for the treatment of vulvovaginal candidiasis. The drug blocks folic acid synthesis in bacterias by inhibitin the enzyme dihydropteroate synthase.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
43.7 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
AVC

Approved Use

For the treatment of vulvovaginitis caused by Candida albicans.

Launch Date

1965
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2.08 μg/mL
10 mg/kg bw single, oral
dose: 10 mg/kg bw
route of administration: Oral
experiment type: SINGLE
co-administered:
SULFANILAMIDE plasma
Capra hircus
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
81.3 μg × h/mL
10 mg/kg bw single, oral
dose: 10 mg/kg bw
route of administration: Oral
experiment type: SINGLE
co-administered:
SULFANILAMIDE plasma
Capra hircus
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
3.71 h
10 mg/kg bw single, oral
dose: 10 mg/kg bw
route of administration: Oral
experiment type: SINGLE
co-administered:
SULFANILAMIDE plasma
Capra hircus
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
15 % 1 times / day steady, topical
Recommended
Dose: 15 %, 1 times / day
Route: topical
Route: steady
Dose: 15 %, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Condition: bacterial infection (Candida albicans)
Age Group: adult
Sex: F
Sources:
Other AEs: Local reaction...
AEs

AEs

AESignificanceDosePopulation
Local reaction 0.2%
15 % 1 times / day steady, topical
Recommended
Dose: 15 %, 1 times / day
Route: topical
Route: steady
Dose: 15 %, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Condition: bacterial infection (Candida albicans)
Age Group: adult
Sex: F
Sources:
PubMed

PubMed

TitleDatePubMed
[Repeat antibiotic prescriptions following treatment with sulfonamide or pivmecillinam. A survey of prescriptions among women aged 15-50 years in the county of Nordjylland].
2001 Dec 31
Primary prevention with cotrimoxazole for HIV-1-infected adults: results of the pilot study in Dakar, Senegal.
2001 Feb 1
Development of an ELISA for sulfachlorpyridazine and investigation of matrix effects from different sample extraction procedures.
2001 Jan
[Current approaches to treatment of secondary sulfonylamide drug resistance in Type II diabetes mellitus].
2001 Mar-Apr
Molecular epidemiology of cystic fibrosis-linked Burkholderia cepacia complex isolates from three national referral centres in Ireland.
2002
Antimicrobial use and antimicrobial resistance: a population perspective.
2002 Apr
Sulphonamide residues in eggs following drug administration via the drinking water.
2002 Apr
Pharmacokinetics of organic anions in rats with arterial calcinosis.
2002 Jan-Feb
Release characteristics of pectin microspheres prepared by an emulsification technique.
2002 Jul-Aug
The sorption and transport of a sulphonamide antibiotic in soil systems.
2002 May 10
Idiosyncratic NSAID drug induced oxidative stress.
2002 Nov 10
Sulphonamide resistant commensal Neisseria with alterations in the dihydropteroate synthase can be isolated from carriers not exposed to sulphonamides.
2002 Nov 18
The enhancement of the hyperglycemic effect of S-nitrosoglutathione and S-nitroso-N-acetylpenicillamine by vitamin C in an animal model.
2002 Sep 13
Design and synthesis of fluorescent beta-cyclodextrins for the enantioselective sensing of alpha-amino acids.
2003
Sulphonamide resistance gene sul3 found in Escherichia coli isolates from human sources.
2003 Dec
[Adverse cutaneous reaction to celecoxib: 6 cases].
2003 May
Generation of group-specific antibodies against sulfonamides.
2003 Sep 24
4-sulphamoylphenyl semicarbazones with anticonvulsant activity.
2004 Aug
A new method for purification of carbonic anhydrase isozymes by affinity chromatography.
2004 Feb
Glucose 6 phosphate dehydrogenase deficiency in adults.
2004 Jul
Emerging issues in infective endocarditis.
2004 Jun
Theoretical study of gas-phase acidity, pKa, lipophilicity, and solubility of some biologically active sulfonamides.
2004 Oct 15
Patents

Sample Use Guides

One applicatorful (about 6g) intravaginally once or twice daily. Improvements in symptoms should occur within a few days, but treatment should be continued for a period of 30 days.
Route of Administration: Vaginal
Antimicrobial activity of sulfanilamide was tested with different bacterial and yeast strains. MIC values were 8 ug/ml for Listeria innocua, Escherishia coli and Pseudomonas aeruginosa; 16 ug/ml for Staphylococcus aureu and Candida albicans; 100 ug/ml for Botrytis cinerea and Fusarium oxysporum culmorum.
Name Type Language
SULFANILAMIDE HYDROCHLORIDE
Systematic Name English
PABIAMID
Common Name English
BENZENESULFONAMIDE, 4-AMINO-, MONOHYDROCHLORIDE
Common Name English
BENZENESULFONAMIDE, 4-AMINO-, HYDROCHLORIDE (1:1)
Systematic Name English
SULFANILAMIDE, MONOHYDROCHLORIDE
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID50209889
Created by admin on Fri Dec 15 15:26:16 GMT 2023 , Edited by admin on Fri Dec 15 15:26:16 GMT 2023
PRIMARY
FDA UNII
R2MR7LN8WP
Created by admin on Fri Dec 15 15:26:16 GMT 2023 , Edited by admin on Fri Dec 15 15:26:16 GMT 2023
PRIMARY
PUBCHEM
80197
Created by admin on Fri Dec 15 15:26:16 GMT 2023 , Edited by admin on Fri Dec 15 15:26:16 GMT 2023
PRIMARY
CAS
6101-31-1
Created by admin on Fri Dec 15 15:26:16 GMT 2023 , Edited by admin on Fri Dec 15 15:26:16 GMT 2023
PRIMARY