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

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

Description

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.

Originator

Approval Year

1936
7
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 43.7 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8429
AVC

Approved Use

For the treatment of vulvovaginitis caused by Candida albicans.

Launch Date

1965
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2.08 μg/mL
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/27010464
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
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/27010464
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
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/27010464
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/006530s019lbl.pdf
unhealthy, adult
Health Status: unhealthy
Condition: bacterial infection (Candida albicans)
Age Group: adult
Sex: F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/006530s019lbl.pdf
Other AEs: Local reaction...
Other AEs:
Local reaction (0.2%)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/006530s019lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/006530s019lbl.pdf
unhealthy, adult
Health Status: unhealthy
Condition: bacterial infection (Candida albicans)
Age Group: adult
Sex: F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/006530s019lbl.pdf
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:45373
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:45373
ChemicalBook
CB6212562
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB6212562
MolPort
MolPort-000-871-476
https://www.molport.com/shop/molecule-link/MolPort-000-871-476
Selleck Chemicals
Sulfanilamide
http://www.selleckchem.com/products/Sulfanilamide.html
ZINC
ZINC000000002101
http://zinc15.docking.org/substances/ZINC000000002101
eMolecules
474316
https://www.emolecules.com/cgi-bin/more?vid=474316
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
Molecular and crystal structures of N-arylglycopyranosylamines formed by reaction between sulfanilamide and D-ribose, D-arabinose and D-mannose.
2001 Apr 12
Persistence of sulphonamide resistance in Escherichia coli in the UK despite national prescribing restriction.
2001 Apr 28
Molecular epidemiology of cystic fibrosis-linked Burkholderia cepacia complex isolates from three national referral centres in Ireland.
2002
Drug release properties of pectinate microspheres prepared by emulsification method.
2002 Aug 21
Release characteristics of pectin microspheres prepared by an emulsification technique.
2002 Jul-Aug
Role of carbon dioxide and ion transport in the formation of sub-embryonic fluid by the blastoderm of the Japanese quail.
2002 Mar
The sorption and transport of a sulphonamide antibiotic in soil systems.
2002 May 10
Chronic gastric ulcer healing in rats subjected to selective and non-selective cyclooxygenase-2 inhibitors.
2002 May 3
Sulphonamide resistant commensal Neisseria with alterations in the dihydropteroate synthase can be isolated from carriers not exposed to sulphonamides.
2002 Nov 18
Preserving the chromatographic integrity of high-speed supercritical fluid chromatography separations using time-of-flight mass spectrometry.
2003 Jul-Aug
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
Generation of group-specific antibodies against sulfonamides.
2003 Sep 24
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
Cyclooxygenase-2 selective inhibition with NS-398 suppresses proliferation and invasiveness and delays liver metastasis in colorectal cancer.
2004 Feb 9
Effects of pig slurry on the sorption of sulfonamide antibiotics in soil.
2004 Jul
Sorption of sulfonamide pharmaceutical antibiotics on whole soils and particle-size fractions.
2004 Jul-Aug
Plasmodium falciparum carbonic anhydrase is a possible target for malaria chemotherapy.
2004 Jun
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

Patents

03963706
5
04895842
4
JP2002327050A
4
JP2007530485A
10
JP2008543916A
10
JP2009241188A
4
JP2011524365A
34
JPH01248059A
4
JPH05156013A
4
JPH08198840A
4
JPS6130768A
4
JPS62221431A
4

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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 Sat Dec 16 15:51:25 GMT 2023
Edited
by admin
on Sat Dec 16 15:51:25 GMT 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 Sat Dec 16 15:51:27 GMT 2023 , Edited by admin on Sat Dec 16 15:51:27 GMT 2023
WHO-ATC J01EB06
Created by admin on Sat Dec 16 15:51:27 GMT 2023 , Edited by admin on Sat Dec 16 15:51:27 GMT 2023
WHO-VATC QJ01EQ06
Created by admin on Sat Dec 16 15:51:27 GMT 2023 , Edited by admin on Sat Dec 16 15:51:27 GMT 2023
WHO-VATC QD06BA05
Created by admin on Sat Dec 16 15:51:27 GMT 2023 , Edited by admin on Sat Dec 16 15:51:27 GMT 2023
CFR 21 CFR 862.3850
Created by admin on Sat Dec 16 15:51:27 GMT 2023 , Edited by admin on Sat Dec 16 15:51:27 GMT 2023
EPA PESTICIDE CODE 77902
Created by admin on Sat Dec 16 15:51:27 GMT 2023 , Edited by admin on Sat Dec 16 15:51:27 GMT 2023
WHO-ATC D06BA05
Created by admin on Sat Dec 16 15:51:27 GMT 2023 , Edited by admin on Sat Dec 16 15:51:27 GMT 2023
NCI_THESAURUS C29739
Created by admin on Sat Dec 16 15:51:27 GMT 2023 , Edited by admin on Sat Dec 16 15:51:27 GMT 2023
Code System Code Type Description
INN
426
Created by admin on Sat Dec 16 15:51:27 GMT 2023 , Edited by admin on Sat Dec 16 15:51:27 GMT 2023
PRIMARY
DRUG BANK
DB00259
Created by admin on Sat Dec 16 15:51:27 GMT 2023 , Edited by admin on Sat Dec 16 15:51:27 GMT 2023
PRIMARY
EPA CompTox
DTXSID4023622
Created by admin on Sat Dec 16 15:51:27 GMT 2023 , Edited by admin on Sat Dec 16 15:51:27 GMT 2023
PRIMARY
FDA UNII
21240MF57M
Created by admin on Sat Dec 16 15:51:27 GMT 2023 , Edited by admin on Sat Dec 16 15:51:27 GMT 2023
PRIMARY
CAS
63-74-1
Created by admin on Sat Dec 16 15:51:27 GMT 2023 , Edited by admin on Sat Dec 16 15:51:27 GMT 2023
PRIMARY
NSC
7618
Created by admin on Sat Dec 16 15:51:27 GMT 2023 , Edited by admin on Sat Dec 16 15:51:27 GMT 2023
PRIMARY
EVMPD
SUB10718MIG
Created by admin on Sat Dec 16 15:51:27 GMT 2023 , Edited by admin on Sat Dec 16 15:51:27 GMT 2023
PRIMARY
RS_ITEM_NUM
1632004
Created by admin on Sat Dec 16 15:51:27 GMT 2023 , Edited by admin on Sat Dec 16 15:51:27 GMT 2023
PRIMARY
RS_ITEM_NUM
1633007
Created by admin on Sat Dec 16 15:51:27 GMT 2023 , Edited by admin on Sat Dec 16 15:51:27 GMT 2023
ALTERNATIVE
MERCK INDEX
m10327
Created by admin on Sat Dec 16 15:51:27 GMT 2023 , Edited by admin on Sat Dec 16 15:51:27 GMT 2023
PRIMARY Merck Index
DRUG CENTRAL
2521
Created by admin on Sat Dec 16 15:51:27 GMT 2023 , Edited by admin on Sat Dec 16 15:51:27 GMT 2023
PRIMARY
NCI_THESAURUS
C47738
Created by admin on Sat Dec 16 15:51:27 GMT 2023 , Edited by admin on Sat Dec 16 15:51:27 GMT 2023
PRIMARY
WIKIPEDIA
SULFANILAMIDE
Created by admin on Sat Dec 16 15:51:27 GMT 2023 , Edited by admin on Sat Dec 16 15:51:27 GMT 2023
PRIMARY
HSDB
223
Created by admin on Sat Dec 16 15:51:27 GMT 2023 , Edited by admin on Sat Dec 16 15:51:27 GMT 2023
PRIMARY
MESH
C036944
Created by admin on Sat Dec 16 15:51:27 GMT 2023 , Edited by admin on Sat Dec 16 15:51:27 GMT 2023
PRIMARY
SMS_ID
100000083274
Created by admin on Sat Dec 16 15:51:27 GMT 2023 , Edited by admin on Sat Dec 16 15:51:27 GMT 2023
PRIMARY
PUBCHEM
5333
Created by admin on Sat Dec 16 15:51:27 GMT 2023 , Edited by admin on Sat Dec 16 15:51:27 GMT 2023
PRIMARY
RXCUI
10184
Created by admin on Sat Dec 16 15:51:27 GMT 2023 , Edited by admin on Sat Dec 16 15:51:27 GMT 2023
PRIMARY RxNorm
ECHA (EC/EINECS)
200-563-4
Created by admin on Sat Dec 16 15:51:27 GMT 2023 , Edited by admin on Sat Dec 16 15:51:27 GMT 2023
PRIMARY
ChEMBL
CHEMBL21
Created by admin on Sat Dec 16 15:51:27 GMT 2023 , Edited by admin on Sat Dec 16 15:51:27 GMT 2023
PRIMARY
CHEBI
45373
Created by admin on Sat Dec 16 15:51:27 GMT 2023 , Edited by admin on Sat Dec 16 15:51:27 GMT 2023
PRIMARY
Related Record Type Details
Structure of SULFANILAMIDE SODIUM
SALT/SOLVATE -> PARENT
Structure of SULFANILAMIDE HYDROCHLORIDE
SALT/SOLVATE -> PARENT
Structure of Sulfanilamide sodium mesylate
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of SULFAMIDOCHRYSOIDINE HYDROCHLORIDE
PARENT -> METABOLITE
Related Record Type Details
Structure of SULFADIMETHOXINE SODIUM
PARENT -> IMPURITY
FOR VETERINARY USE
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of SULFADIAZINE
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of SULFAMETHAZINE
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of SULFADIMETHOXINE
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of SILVER SULFADIAZINE
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of SULFACETAMIDE SODIUM
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
Structure of SULFAMETHOXAZOLE
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
Structure of SULFANILAMIDE
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