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Details

Stereochemistry ACHIRAL
Molecular Formula C6H8N2O2S
Molecular Weight 172.2062
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SULFANILAMIDE

SMILES

c1cc(ccc1N)S(=O)(=O)N

InChI

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

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

-1.44374399E11
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
Use of antibiotics to treat bacteriuria of pregnancy in the Nordic countries. Which antibiotics are appropriate to treat bacteriuria of pregnancy?
2001 Apr
Persistence of sulphonamide resistance in Escherichia coli in the UK despite national prescribing restriction.
2001 Apr 28
Carbonic anhydrase inhibitors: metal complexes of a sulfanilamide derived Schiff base and their interaction with isozymes I, II and IV.
2001 Dec
5-HT(6) receptor antagonists: lead optimisation and biological evaluation of N-aryl and N-heteroaryl 4-amino-benzene sulfonamides.
2001 Feb
Primary prevention with cotrimoxazole for HIV-1-infected adults: results of the pilot study in Dakar, Senegal.
2001 Feb 1
Salt effects in capillary zone electrophoresis. V. Adsorption and retention of electrically neutral analytes.
2001 Sep 21
Molecular epidemiology of cystic fibrosis-linked Burkholderia cepacia complex isolates from three national referral centres in Ireland.
2002
Pneumocystis pneumonia.
2002 Dec
Test strip for determination of nitrite in water.
2002 Jul
Spectrophotometric determination of serum nitrite and nitrate by copper-cadmium alloy.
2002 Jul 1
Improving broad specificity hapten recognition with protein engineering.
2002 Jul 17
Release characteristics of pectin microspheres prepared by an emulsification technique.
2002 Jul-Aug
Liquid chromatographic-tandem mass spectrometric determination of selected sulphonamides in milk.
2002 Jun 25
The sorption and transport of a sulphonamide antibiotic in soil systems.
2002 May 10
'In vitro' study of chemotherapeutic activity of sulphimidazole on some sensitive and metronidazole-resistant Trichomonas vaginalis strains.
2002 Nov
Idiosyncratic NSAID drug induced oxidative stress.
2002 Nov 10
Iron (III) aquacomplexes as effective photocatalysts for the degradation of pesticides in homogeneous aqueous solutions.
2002 Oct 21
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
Diagnostic, prognostic and therapeutic implications of carbonic anhydrases in cancer.
2003 Jul 7
Preserving the chromatographic integrity of high-speed supercritical fluid chromatography separations using time-of-flight mass spectrometry.
2003 Jul-Aug
Drug-induced bilateral transient myopia with the sulphonamide sulphasalazine.
2003 Nov
Facilitation of addition-elimination reactions in pyrimidines and purines using trifluoroacetic acid in trifluoroethanol.
2003 Nov 21
Validated HPLC method for the determination of ranitidine in plasma.
2003 Oct
Carbonic anhydrase inhibitors: inhibition of human and murine mitochondrial isozymes V with anions.
2003 Sep 1
High-performance liquid chromatography/inductively coupled plasma mass spectrometry and tandem mass spectrometry for the detection of carbon-containing compounds.
2004
Quantitative analysis of twelve sulfonamides in honey after acidic hydrolysis by high-performance liquid chromatography with post-column derivatization and fluorescence detection.
2004 Aug 20
A new method for purification of carbonic anhydrase isozymes by affinity chromatography.
2004 Feb
Carbonic anhydrase inhibitors: the first selective, membrane-impermeant inhibitors targeting the tumor-associated isozyme IX.
2004 Feb 23
Carbonic anhydrase inhibitors. Inhibition of mitochondrial isozyme V with aromatic and heterocyclic sulfonamides.
2004 Feb 26
Effects of pig slurry on the sorption of sulfonamide antibiotics in soil.
2004 Jul
Carbonic anhydrase inhibitors. Inhibition of cytosolic isozyme XIII with aromatic and heterocyclic sulfonamides: a novel target for the drug design.
2004 Jul 16
Plasmodium falciparum carbonic anhydrase is a possible target for malaria chemotherapy.
2004 Jun
Emerging issues in infective endocarditis.
2004 Jun
Contamination of honey by the herbicide asulam and its antibacterial active metabolite sulfanilamide.
2004 Jun
Drug interaction with T-cell receptors: T-cell receptor density determines degree of cross-reactivity.
2004 Mar
Synthesis and cytotoxic activity of lipophilic sulphonamide derivatives of the benzo[b]thiophene 1,1-dioxide.
2004 Mar 1
Lessons unlearned.
2004 May-Jun
Carbonic anhydrase inhibitors: synthesis and inhibition of cytosolic/tumor-associated carbonic anhydrase isozymes I, II, and IX with sulfonamides incorporating 1,2,4-triazine moieties.
2004 Nov 1
Drinking-water nitrate, methemoglobinemia, and global burden of disease: a discussion.
2004 Oct
Theoretical study of gas-phase acidity, pKa, lipophilicity, and solubility of some biologically active sulfonamides.
2004 Oct 15
Pharmacokinetics of the nonsteroidal steroid sulphatase inhibitor 667 COUMATE and its sequestration into red blood cells in rats.
2004 Oct 4
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
EP   HSDB   INN   MART.   MI   ORANGE BOOK   VANDF   WHO-DD  
INN  
Official Name English
SULFADIMETHOXINE IMPURITY E [EP]
Common Name English
BENZENESULFONAMIDE, 4-AMINO-
Systematic Name English
NSC-7618
Code English
SULFANILAMIDE [WHO-DD]
Common Name English
SULPHANILAMIDUM
HPUS  
Common Name English
SULFANILAMIDE MELTING POINT STANDARD
USP-RS  
Common Name English
AVC
Brand Name English
SULFANILAMIDE [USP-RS]
Common Name English
(4-(AMINOSULFONYL)PHENYL)AMINE
Systematic Name English
P-AMINOBENZENESULFAMIDE
Common Name English
4-SULFAMOYLANILINE
Systematic Name English
SULFANILAMIDE [MI]
Common Name English
P-AMINOBENZENESULFONAMIDE
Common Name English
SULFACETAMIDE SODIUM IMPURITY A [EP]
Common Name English
SULFANILAMIDE [ORANGE BOOK]
Common Name English
PRONTOSIL I
Common Name English
4-AMINOPHENYLSULFONAMIDE
Systematic Name English
SULFADIMIDINE IMPURITY D [EP]
Common Name English
PRONTYLIN
Common Name English
SULFANILAMIDE [VANDF]
Common Name English
SULFANILAMIDE [EP MONOGRAPH]
Common Name English
SULFANILAMIDE [MART.]
Common Name English
ANILINE-P-SULFONIC AMIDE
Common Name English
SULFANILAMIDE [INN]
Common Name English
4-(AMINOSULFONYL)ANILINE
Systematic Name English
SULFANILAMIDE [HSDB]
Common Name English
SULPHANILAMIDUM [HPUS]
Common Name English
4-AMINOBENZENE-1-SULFONAMIDE
Systematic Name English
SULFADIMETHOXINE SODIUM FOR VETERINARY USE IMPURITY E [EP]
Common Name English
SULFAMINE
Common Name English
STREPTOCID
Brand Name English
SULFAMETHOXAZOLE IMPURITY E [EP]
Common Name English
SULFONAMIDE
Common Name English
4-AMINOBENZENESULFONAMIDE
Systematic Name English
Classification Tree Code System Code
CFR 21 CFR 310.527
Created by admin on Fri Jun 25 21:19:10 UTC 2021 , Edited by admin on Fri Jun 25 21:19:10 UTC 2021
WHO-ATC J01EB06
Created by admin on Fri Jun 25 21:19:10 UTC 2021 , Edited by admin on Fri Jun 25 21:19:10 UTC 2021
WHO-VATC QJ01EQ06
Created by admin on Fri Jun 25 21:19:10 UTC 2021 , Edited by admin on Fri Jun 25 21:19:10 UTC 2021
WHO-VATC QD06BA05
Created by admin on Fri Jun 25 21:19:10 UTC 2021 , Edited by admin on Fri Jun 25 21:19:10 UTC 2021
CFR 21 CFR 862.3850
Created by admin on Fri Jun 25 21:19:10 UTC 2021 , Edited by admin on Fri Jun 25 21:19:10 UTC 2021
EPA PESTICIDE CODE 77902
Created by admin on Fri Jun 25 21:19:10 UTC 2021 , Edited by admin on Fri Jun 25 21:19:10 UTC 2021
WHO-ATC D06BA05
Created by admin on Fri Jun 25 21:19:10 UTC 2021 , Edited by admin on Fri Jun 25 21:19:10 UTC 2021
NCI_THESAURUS C29739
Created by admin on Fri Jun 25 21:19:10 UTC 2021 , Edited by admin on Fri Jun 25 21:19:10 UTC 2021
Code System Code Type Description
INN
426
Created by admin on Fri Jun 25 21:19:10 UTC 2021 , Edited by admin on Fri Jun 25 21:19:10 UTC 2021
PRIMARY
USP_CATALOG
1633007
Created by admin on Fri Jun 25 21:19:10 UTC 2021 , Edited by admin on Fri Jun 25 21:19:10 UTC 2021
PRIMARY USP-RS
DRUG BANK
DB00259
Created by admin on Fri Jun 25 21:19:10 UTC 2021 , Edited by admin on Fri Jun 25 21:19:10 UTC 2021
PRIMARY
EPA CompTox
63-74-1
Created by admin on Fri Jun 25 21:19:10 UTC 2021 , Edited by admin on Fri Jun 25 21:19:10 UTC 2021
PRIMARY
FDA UNII
21240MF57M
Created by admin on Fri Jun 25 21:19:10 UTC 2021 , Edited by admin on Fri Jun 25 21:19:10 UTC 2021
PRIMARY
CAS
63-74-1
Created by admin on Fri Jun 25 21:19:10 UTC 2021 , Edited by admin on Fri Jun 25 21:19:10 UTC 2021
PRIMARY
EVMPD
SUB10718MIG
Created by admin on Fri Jun 25 21:19:10 UTC 2021 , Edited by admin on Fri Jun 25 21:19:10 UTC 2021
PRIMARY
MERCK INDEX
M10327
Created by admin on Fri Jun 25 21:19:10 UTC 2021 , Edited by admin on Fri Jun 25 21:19:10 UTC 2021
PRIMARY Merck Index
DRUG CENTRAL
2521
Created by admin on Fri Jun 25 21:19:10 UTC 2021 , Edited by admin on Fri Jun 25 21:19:10 UTC 2021
PRIMARY
NCI_THESAURUS
C47738
Created by admin on Fri Jun 25 21:19:10 UTC 2021 , Edited by admin on Fri Jun 25 21:19:10 UTC 2021
PRIMARY
WIKIPEDIA
SULFANILAMIDE
Created by admin on Fri Jun 25 21:19:10 UTC 2021 , Edited by admin on Fri Jun 25 21:19:10 UTC 2021
PRIMARY
USP_CATALOG
1632004
Created by admin on Fri Jun 25 21:19:10 UTC 2021 , Edited by admin on Fri Jun 25 21:19:10 UTC 2021
PRIMARY USP-RS
HSDB
223
Created by admin on Fri Jun 25 21:19:10 UTC 2021 , Edited by admin on Fri Jun 25 21:19:10 UTC 2021
PRIMARY
MESH
C036944
Created by admin on Fri Jun 25 21:19:10 UTC 2021 , Edited by admin on Fri Jun 25 21:19:10 UTC 2021
PRIMARY
PUBCHEM
5333
Created by admin on Fri Jun 25 21:19:10 UTC 2021 , Edited by admin on Fri Jun 25 21:19:10 UTC 2021
PRIMARY
RXCUI
10184
Created by admin on Fri Jun 25 21:19:10 UTC 2021 , Edited by admin on Fri Jun 25 21:19:10 UTC 2021
PRIMARY RxNorm
ECHA (EC/EINECS)
200-563-4
Created by admin on Fri Jun 25 21:19:10 UTC 2021 , Edited by admin on Fri Jun 25 21:19:10 UTC 2021
PRIMARY
ChEMBL
CHEMBL21
Created by admin on Fri Jun 25 21:19:10 UTC 2021 , Edited by admin on Fri Jun 25 21:19:10 UTC 2021
PRIMARY