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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

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
63.35 h
1000 mg single, oral
dose: 1000 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
SULFANILAMIDE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
27.37%
1000 mg single, oral
dose: 1000 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
SULFANILAMIDE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
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
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
Age Group: adult
Sex: F
Sources:
PubMed

PubMed

TitleDatePubMed
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.
2004-11-01
Theoretical study of gas-phase acidity, pKa, lipophilicity, and solubility of some biologically active sulfonamides.
2004-10-15
Pharmacokinetics of the nonsteroidal steroid sulphatase inhibitor 667 COUMATE and its sequestration into red blood cells in rats.
2004-10-04
Drinking-water nitrate, methemoglobinemia, and global burden of disease: a discussion.
2004-10
Molecular characterization of bifunctional hydroxymethyldihydropterin pyrophosphokinase-dihydropteroate synthase from Plasmodium falciparum.
2004-09
Quantitative analysis of twelve sulfonamides in honey after acidic hydrolysis by high-performance liquid chromatography with post-column derivatization and fluorescence detection.
2004-08-20
4-sulphamoylphenyl semicarbazones with anticonvulsant activity.
2004-08
Sorption of sulfonamide pharmaceutical antibiotics on whole soils and particle-size fractions.
2004-07-16
Carbonic anhydrase inhibitors. Inhibition of cytosolic isozyme XIII with aromatic and heterocyclic sulfonamides: a novel target for the drug design.
2004-07-16
Lessons unlearned.
2004-07-06
Effects of pig slurry on the sorption of sulfonamide antibiotics in soil.
2004-07
Glucose 6 phosphate dehydrogenase deficiency in adults.
2004-07
Plasmodium falciparum carbonic anhydrase is a possible target for malaria chemotherapy.
2004-06
Emerging issues in infective endocarditis.
2004-06
Contamination of honey by the herbicide asulam and its antibacterial active metabolite sulfanilamide.
2004-06
Enhancement of host fitness by the sul2-coding plasmid p9123 in the absence of selective pressure.
2004-06
Defective DNA repair as a potential mechanism for the rapid development of drug resistance in Plasmodium falciparum.
2004-05-04
Simultaneous determination of cefatrizine and clavulanic acid in dog plasma by HPLC.
2004-04-01
An experimental animal model of aseptic loosening of hip prostheses in sheep to study early biochemical changes at the interface membrane.
2004-03-03
Synthesis and cytotoxic activity of lipophilic sulphonamide derivatives of the benzo[b]thiophene 1,1-dioxide.
2004-03-01
[Preparation of monoclonal antibody against sulfadiazine and development of an ELISA kit].
2004-03
Drug interaction with T-cell receptors: T-cell receptor density determines degree of cross-reactivity.
2004-03
Effects of polymorphic differences for sulfanilamide, as seen through 13C and 15N solid-state NMR, together with shielding calculations.
2004-03
Carbonic anhydrase inhibitors. Inhibition of mitochondrial isozyme V with aromatic and heterocyclic sulfonamides.
2004-02-26
Carbonic anhydrase inhibitors: the first selective, membrane-impermeant inhibitors targeting the tumor-associated isozyme IX.
2004-02-23
Cyclooxygenase-2 selective inhibition with NS-398 suppresses proliferation and invasiveness and delays liver metastasis in colorectal cancer.
2004-02-09
A new method for purification of carbonic anhydrase isozymes by affinity chromatography.
2004-02
Engineering of a broad specificity antibody for simultaneous detection of 13 sulfonamides at the maximum residue level.
2004-01-14
Carbonic anhydrase inhibitors: N-(p-sulfamoylphenyl)-alpha-D-glycopyranosylamines as topically acting antiglaucoma agents in hypertensive rabbits.
2004-01-05
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
Risk factors for antibiotic resistance in Campylobacter spp. isolated from raw poultry meat in Switzerland.
2003-12-09
Sulphonamide resistance gene sul3 found in Escherichia coli isolates from human sources.
2003-12
Investigation of structural and dynamic features of the radicals produced in gamma irradiated sulfanilamide: an ESR study.
2003-11-28
Facilitation of addition-elimination reactions in pyrimidines and purines using trifluoroacetic acid in trifluoroethanol.
2003-11-21
[Treatment of sulfanilamide production wastewater by resin adsorption technique].
2003-11
Drug-induced bilateral transient myopia with the sulphonamide sulphasalazine.
2003-11
Validated HPLC method for the determination of ranitidine in plasma.
2003-10
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.
2003-10
Generation of group-specific antibodies against sulfonamides.
2003-09-24
Carbonic anhydrase inhibitors: inhibition of human and murine mitochondrial isozymes V with anions.
2003-09-01
[Treatment of patients with acute pneumonia].
2003-08-02
Measurement of physiological S-nitrosothiols: a problem child and a challenge.
2003-08
Preserving the chromatographic integrity of high-speed supercritical fluid chromatography separations using time-of-flight mass spectrometry.
2003-07-15
Diagnostic, prognostic and therapeutic implications of carbonic anhydrases in cancer.
2003-07-07
[Integrons and antimicrobial resistance gene cassettes in Shigella flexneri strains ].
2003-07
[Adverse cutaneous reaction to celecoxib: 6 cases].
2003-05
Early manifestation of nephropathy in rats with arterial calcinosis.
2003-05
Design and synthesis of fluorescent beta-cyclodextrins for the enantioselective sensing of alpha-amino acids.
2003
Exposure to receptor-activator of NFkappaB ligand renders pre-osteoclasts resistant to IFN-gamma by inducing terminal differentiation.
2003
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 Mon Mar 31 17:57:43 GMT 2025
Edited
by admin
on Mon Mar 31 17:57:43 GMT 2025
Record UNII
R2MR7LN8WP
Record Status Validated (UNII)
Record Version
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Name Type Language
SULFANILAMIDE HYDROCHLORIDE
Systematic Name English
BENZENESULFONAMIDE, 4-AMINO-, MONOHYDROCHLORIDE
Preferred Name English
PABIAMID
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 Mon Mar 31 17:57:43 GMT 2025 , Edited by admin on Mon Mar 31 17:57:43 GMT 2025
PRIMARY
FDA UNII
R2MR7LN8WP
Created by admin on Mon Mar 31 17:57:43 GMT 2025 , Edited by admin on Mon Mar 31 17:57:43 GMT 2025
PRIMARY
PUBCHEM
80197
Created by admin on Mon Mar 31 17:57:43 GMT 2025 , Edited by admin on Mon Mar 31 17:57:43 GMT 2025
PRIMARY
CAS
6101-31-1
Created by admin on Mon Mar 31 17:57:43 GMT 2025 , Edited by admin on Mon Mar 31 17:57:43 GMT 2025
PRIMARY
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