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

Details

Stereochemistry ACHIRAL
Molecular Formula C6H7N2O2S.Na
Molecular Weight 194.187
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SULFANILAMIDE SODIUM

SMILES

[Na+].NC1=CC=C(C=C1)S([NH-])(=O)=O

InChI

InChIKey=CGRKCGWEOIQFRD-UHFFFAOYSA-N
InChI=1S/C6H7N2O2S.Na/c7-5-1-3-6(4-2-5)11(8,9)10;/h1-4H,7H2,(H-,8,9,10);/q-1;+1

HIDE SMILES / InChI

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

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
Should celecoxib be contraindicated in patients who are allergic to sulfonamides? Revisiting the meaning of 'sulfa' allergy.
2001
Use of antibiotics to treat bacteriuria of pregnancy in the Nordic countries. Which antibiotics are appropriate to treat bacteriuria of pregnancy?
2001 Apr
Neurology was there in the 1930s.
2001 Jun
Characterisation of carbonic anhydrase in Plasmodium falciparum.
2001 May 15
E7070, a novel sulphonamide agent with potent antitumour activity in vitro and in vivo.
2001 Nov
Antibiotic resistance in bacteria from magpies (Pica pica) and rabbits (Oryctolagus cuniculus) from west Wales.
2001 Oct
Trichinella britovi in domestic pig--a case report.
2002
Molecular epidemiology of cystic fibrosis-linked Burkholderia cepacia complex isolates from three national referral centres in Ireland.
2002
Antimicrobial resistance and plasmid profiles of Campylobacter jejuni and Campylobacter coli from human and animal sources.
2002
Effects of anion and cation inhibitors and carbonic anhydrase inhibitors upon the activity of the gypsy moth (Lepidoptera: Lymantriidae) nucleo-polyhedrovirus.
2002 Apr
Sulphonamide residues in eggs following drug administration via the drinking water.
2002 Apr
Drug release properties of pectinate microspheres prepared by emulsification method.
2002 Aug 21
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
Liquid chromatographic-tandem mass spectrometric determination of selected sulphonamides in milk.
2002 Jun 25
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
Evidence for a membrane site of action for 14,15-EET on expression of aromatase in vascular smooth muscle.
2002 Nov
The enhancement of the hyperglycemic effect of S-nitrosoglutathione and S-nitroso-N-acetylpenicillamine by vitamin C in an animal model.
2002 Sep 13
Exposure to receptor-activator of NFkappaB ligand renders pre-osteoclasts resistant to IFN-gamma by inducing terminal differentiation.
2003
Measurement of physiological S-nitrosothiols: a problem child and a challenge.
2003 Aug
Risk factors for antibiotic resistance in Campylobacter spp. isolated from raw poultry meat in Switzerland.
2003 Dec 9
Polyelectrolyte Complexes: Interactions between Lignosulfonate and Chitosan.
2003 Mar-Apr
Early manifestation of nephropathy in rats with arterial calcinosis.
2003 May
Facilitation of addition-elimination reactions in pyrimidines and purines using trifluoroacetic acid in trifluoroethanol.
2003 Nov 21
Investigation of structural and dynamic features of the radicals produced in gamma irradiated sulfanilamide: an ESR study.
2003 Nov 28
Validated HPLC method for the determination of ranitidine in plasma.
2003 Oct
High-performance liquid chromatography/inductively coupled plasma mass spectrometry and tandem mass spectrometry for the detection of carbon-containing compounds.
2004
Integron analysis and genetic mapping of antimicrobial resistance genes in Salmonella enterica serotype Typhimurium.
2004
Simultaneous determination of cefatrizine and clavulanic acid in dog plasma by HPLC.
2004 Apr 1
4-sulphamoylphenyl semicarbazones with anticonvulsant activity.
2004 Aug
A new method for purification of carbonic anhydrase isozymes by affinity chromatography.
2004 Feb
Carbonic anhydrase inhibitors. Inhibition of mitochondrial isozyme V with aromatic and heterocyclic sulfonamides.
2004 Feb 26
Carbonic anhydrase inhibitors: N-(p-sulfamoylphenyl)-alpha-D-glycopyranosylamines as topically acting antiglaucoma agents in hypertensive rabbits.
2004 Jan 5
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
Effects of polymorphic differences for sulfanilamide, as seen through 13C and 15N solid-state NMR, together with shielding calculations.
2004 Mar
An experimental animal model of aseptic loosening of hip prostheses in sheep to study early biochemical changes at the interface membrane.
2004 Mar 3
Defective DNA repair as a potential mechanism for the rapid development of drug resistance in Plasmodium falciparum.
2004 May 4
Lessons unlearned.
2004 May-Jun
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
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 Fri Dec 15 15:05:45 GMT 2023
Edited
by admin
on Fri Dec 15 15:05:45 GMT 2023
Record UNII
4ZB6W6B524
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SULFANILAMIDE SODIUM
Systematic Name English
SODIUM SULFANILAMIDE
Systematic Name English
SULFANILAMIDE, MONOSODIUM SALT
Common Name English
SULFANILAMIDE MONOSODIUM
Systematic Name English
Code System Code Type Description
FDA UNII
4ZB6W6B524
Created by admin on Fri Dec 15 15:05:45 GMT 2023 , Edited by admin on Fri Dec 15 15:05:45 GMT 2023
PRIMARY
EPA CompTox
DTXSID00143688
Created by admin on Fri Dec 15 15:05:45 GMT 2023 , Edited by admin on Fri Dec 15 15:05:45 GMT 2023
PRIMARY
PUBCHEM
12226950
Created by admin on Fri Dec 15 15:05:45 GMT 2023 , Edited by admin on Fri Dec 15 15:05:45 GMT 2023
PRIMARY
CAS
10103-15-8
Created by admin on Fri Dec 15 15:05:45 GMT 2023 , Edited by admin on Fri Dec 15 15:05:45 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY