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Details

Stereochemistry ACHIRAL
Molecular Formula C6H8N2O2S
Molecular Weight 172.205
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SULFANILAMIDE

SMILES

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

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

Molecular Formula C6H8N2O2S
Molecular Weight 172.205
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Primary prevention with cotrimoxazole for HIV-1-infected adults: results of the pilot study in Dakar, Senegal.
2001 Feb 1
E7070, a novel sulphonamide agent with potent antitumour activity in vitro and in vivo.
2001 Nov
Epidemiological analysis of Salmonella enteritidis isolates in Singapore.
2001 Oct
Effects of anion and cation inhibitors and carbonic anhydrase inhibitors upon the activity of the gypsy moth (Lepidoptera: Lymantriidae) nucleo-polyhedrovirus.
2002 Apr
Pneumocystis pneumonia.
2002 Dec
An outbreak of multidrug-resistant Salmonella enterica subsp. enterica serotype Typhimurium, DT104L linked to dried anchovy in Singapore.
2002 Feb
Spectrophotometric determination of serum nitrite and nitrate by copper-cadmium alloy.
2002 Jul 1
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
Evidence for a membrane site of action for 14,15-EET on expression of aromatase in vascular smooth muscle.
2002 Nov
Sulphonamide resistant commensal Neisseria with alterations in the dihydropteroate synthase can be isolated from carriers not exposed to sulphonamides.
2002 Nov 18
[Treatment of patients with acute pneumonia].
2003 Apr-Jun
[Adverse cutaneous reaction to celecoxib: 6 cases].
2003 May
Investigation of structural and dynamic features of the radicals produced in gamma irradiated sulfanilamide: an ESR study.
2003 Nov 28
Synthesis and applications of poly(acryl p-aminobenzenesulfonamideamidine- p-aminobenzenesulfonylamide) chelating fiber for pre-concentrating and separating trace Bi(III), Hg(III), Au(III) and Pd(IV) from solution samples.
2003 Oct
Simultaneous determination of cefatrizine and clavulanic acid in dog plasma by HPLC.
2004 Apr 1
4-sulphamoylphenyl semicarbazones with anticonvulsant activity.
2004 Aug
Carbonic anhydrase inhibitors. Inhibition of mitochondrial isozyme V with aromatic and heterocyclic sulfonamides.
2004 Feb 26
Engineering of a broad specificity antibody for simultaneous detection of 13 sulfonamides at the maximum residue level.
2004 Jan 14
[Preparation of monoclonal antibody against sulfadiazine and development of an ELISA kit].
2004 Mar
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
Molecular characterization of bifunctional hydroxymethyldihydropterin pyrophosphokinase-dihydropteroate synthase from Plasmodium falciparum.
2004 Sep
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.
Substance Class Chemical
Created
by admin
on Thu Jul 06 21:23:47 UTC 2023
Edited
by admin
on Thu Jul 06 21:23:47 UTC 2023
Record UNII
21240MF57M
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SULFANILAMIDE
EP   HSDB   INN   MART.   MI   ORANGE BOOK   VANDF   WHO-DD  
INN  
Official Name English
BENZENESULFONAMIDE, 4-AMINO-
Systematic Name English
NSC-7618
Code English
SULPHANILAMIDUM
HPUS  
Common Name English
SULFANILAMIDE MELTING POINT STANDARD
USP-RS  
Common Name English
SULFADIMIDINE IMPURITY D [EP IMPURITY]
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
SULFANILAMIDE [ORANGE BOOK]
Common Name English
PRONTOSIL I
Common Name English
SULFADIMETHOXINE IMPURITY E [EP IMPURITY]
Common Name English
4-AMINOPHENYLSULFONAMIDE
Systematic Name English
PRONTYLIN
Common Name English
SULFANILAMIDE [VANDF]
Common Name English
SULFANILAMIDE [EP MONOGRAPH]
Common Name English
SULFAMETHOXAZOLE IMPURITY E [EP IMPURITY]
Common Name English
SULFANILAMIDE [MART.]
Common Name English
SULFADIAZINE IMPURITY D [EP IMPURITY]
Common Name English
ANILINE-P-SULFONIC AMIDE
Common Name English
sulfanilamide [INN]
Common Name English
4-(AMINOSULFONYL)ANILINE
Systematic Name English
Sulfanilamide [WHO-DD]
Common Name English
SULFANILAMIDE [HSDB]
Common Name English
SULPHANILAMIDUM [HPUS]
Common Name English
SULFADIMETHOXINE SODIUM FOR VETERINARY USE IMPURITY E [EP IMPURITY]
Common Name English
4-AMINOBENZENE-1-SULFONAMIDE
Systematic Name English
SULFAMINE
Common Name English
STREPTOCID
Brand Name English
SULFACETAMIDE SODIUM IMPURITY A [EP IMPURITY]
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 Thu Jul 06 21:23:48 UTC 2023 , Edited by admin on Thu Jul 06 21:23:48 UTC 2023
WHO-ATC J01EB06
Created by admin on Thu Jul 06 21:23:48 UTC 2023 , Edited by admin on Thu Jul 06 21:23:48 UTC 2023
WHO-VATC QJ01EQ06
Created by admin on Thu Jul 06 21:23:48 UTC 2023 , Edited by admin on Thu Jul 06 21:23:48 UTC 2023
WHO-VATC QD06BA05
Created by admin on Thu Jul 06 21:23:48 UTC 2023 , Edited by admin on Thu Jul 06 21:23:48 UTC 2023
CFR 21 CFR 862.3850
Created by admin on Thu Jul 06 21:23:48 UTC 2023 , Edited by admin on Thu Jul 06 21:23:48 UTC 2023
EPA PESTICIDE CODE 77902
Created by admin on Thu Jul 06 21:23:48 UTC 2023 , Edited by admin on Thu Jul 06 21:23:48 UTC 2023
WHO-ATC D06BA05
Created by admin on Thu Jul 06 21:23:48 UTC 2023 , Edited by admin on Thu Jul 06 21:23:48 UTC 2023
NCI_THESAURUS C29739
Created by admin on Thu Jul 06 21:23:48 UTC 2023 , Edited by admin on Thu Jul 06 21:23:48 UTC 2023
Code System Code Type Description
INN
426
Created by admin on Thu Jul 06 21:23:48 UTC 2023 , Edited by admin on Thu Jul 06 21:23:48 UTC 2023
PRIMARY
DRUG BANK
DB00259
Created by admin on Thu Jul 06 21:23:48 UTC 2023 , Edited by admin on Thu Jul 06 21:23:48 UTC 2023
PRIMARY
EPA CompTox
DTXSID4023622
Created by admin on Thu Jul 06 21:23:48 UTC 2023 , Edited by admin on Thu Jul 06 21:23:48 UTC 2023
PRIMARY
FDA UNII
21240MF57M
Created by admin on Thu Jul 06 21:23:48 UTC 2023 , Edited by admin on Thu Jul 06 21:23:48 UTC 2023
PRIMARY
CAS
63-74-1
Created by admin on Thu Jul 06 21:23:48 UTC 2023 , Edited by admin on Thu Jul 06 21:23:48 UTC 2023
PRIMARY
NSC
7618
Created by admin on Thu Jul 06 21:23:48 UTC 2023 , Edited by admin on Thu Jul 06 21:23:48 UTC 2023
PRIMARY
EVMPD
SUB10718MIG
Created by admin on Thu Jul 06 21:23:48 UTC 2023 , Edited by admin on Thu Jul 06 21:23:48 UTC 2023
PRIMARY
RS_ITEM_NUM
1632004
Created by admin on Thu Jul 06 21:23:48 UTC 2023 , Edited by admin on Thu Jul 06 21:23:48 UTC 2023
PRIMARY
RS_ITEM_NUM
1633007
Created by admin on Thu Jul 06 21:23:48 UTC 2023 , Edited by admin on Thu Jul 06 21:23:48 UTC 2023
ALTERNATIVE
MERCK INDEX
M10327
Created by admin on Thu Jul 06 21:23:48 UTC 2023 , Edited by admin on Thu Jul 06 21:23:48 UTC 2023
PRIMARY Merck Index
DRUG CENTRAL
2521
Created by admin on Thu Jul 06 21:23:48 UTC 2023 , Edited by admin on Thu Jul 06 21:23:48 UTC 2023
PRIMARY
NCI_THESAURUS
C47738
Created by admin on Thu Jul 06 21:23:48 UTC 2023 , Edited by admin on Thu Jul 06 21:23:48 UTC 2023
PRIMARY
WIKIPEDIA
SULFANILAMIDE
Created by admin on Thu Jul 06 21:23:48 UTC 2023 , Edited by admin on Thu Jul 06 21:23:48 UTC 2023
PRIMARY
HSDB
223
Created by admin on Thu Jul 06 21:23:48 UTC 2023 , Edited by admin on Thu Jul 06 21:23:48 UTC 2023
PRIMARY
MESH
C036944
Created by admin on Thu Jul 06 21:23:48 UTC 2023 , Edited by admin on Thu Jul 06 21:23:48 UTC 2023
PRIMARY
SMS_ID
100000083274
Created by admin on Thu Jul 06 21:23:48 UTC 2023 , Edited by admin on Thu Jul 06 21:23:48 UTC 2023
PRIMARY
PUBCHEM
5333
Created by admin on Thu Jul 06 21:23:48 UTC 2023 , Edited by admin on Thu Jul 06 21:23:48 UTC 2023
PRIMARY
RXCUI
10184
Created by admin on Thu Jul 06 21:23:48 UTC 2023 , Edited by admin on Thu Jul 06 21:23:48 UTC 2023
PRIMARY RxNorm
ECHA (EC/EINECS)
200-563-4
Created by admin on Thu Jul 06 21:23:48 UTC 2023 , Edited by admin on Thu Jul 06 21:23:48 UTC 2023
PRIMARY
ChEMBL
CHEMBL21
Created by admin on Thu Jul 06 21:23:48 UTC 2023 , Edited by admin on Thu Jul 06 21:23:48 UTC 2023
PRIMARY
CHEBI
45373
Created by admin on Thu Jul 06 21:23:48 UTC 2023 , Edited by admin on Thu Jul 06 21:23:48 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
PARENT -> METABOLITE
Related Record Type Details
PARENT -> IMPURITY
FOR VETERINARY USE
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
PARENT -> IMPURITY
correction factor: for the calculation of the content, multiply the peak area of impurity A by 0.5
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY