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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

-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
Carbonic anhydrase inhibitors: metal complexes of a sulfanilamide derived Schiff base and their interaction with isozymes I, II and IV.
2001 Dec
[Repeat antibiotic prescriptions following treatment with sulfonamide or pivmecillinam. A survey of prescriptions among women aged 15-50 years in the county of Nordjylland].
2001 Dec 31
Epidemiological analysis of Salmonella enteritidis isolates in Singapore.
2001 Oct
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
The spectrum of allergic (cross-)sensitivity in clinical patch testing with 'para amino' compounds.
2002 Apr
[Structure and function of integrons].
2002 Aug-Sep
Pneumocystis pneumonia.
2002 Dec
An outbreak of multidrug-resistant Salmonella enterica subsp. enterica serotype Typhimurium, DT104L linked to dried anchovy in Singapore.
2002 Feb
A small-molecule inhibitor of skeletal muscle myosin II.
2002 Jan
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
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
Idiosyncratic NSAID drug induced oxidative stress.
2002 Nov 10
Susceptibility of Danish Escherichia coli strains isolated from urinary tract infections and bacteraemia, and distribution of sul genes conferring sulphonamide resistance.
2002 Oct
Iron (III) aquacomplexes as effective photocatalysts for the degradation of pesticides in homogeneous aqueous solutions.
2002 Oct 21
The enhancement of the hyperglycemic effect of S-nitrosoglutathione and S-nitroso-N-acetylpenicillamine by vitamin C in an animal model.
2002 Sep 13
[Treatment of patients with acute pneumonia].
2003 Apr-Jun
Measurement of physiological S-nitrosothiols: a problem child and a challenge.
2003 Aug
Sulphonamide resistance gene sul3 found in Escherichia coli isolates from human sources.
2003 Dec
Preserving the chromatographic integrity of high-speed supercritical fluid chromatography separations using time-of-flight mass spectrometry.
2003 Jul-Aug
Polyelectrolyte Complexes: Interactions between Lignosulfonate and Chitosan.
2003 Mar-Apr
[Adverse cutaneous reaction to celecoxib: 6 cases].
2003 May
[Treatment of sulfanilamide production wastewater by resin adsorption technique].
2003 Nov
Generation of group-specific antibodies against sulfonamides.
2003 Sep 24
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
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
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
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
Enhancement of host fitness by the sul2-coding plasmid p9123 in the absence of selective pressure.
2004 Jun
[Preparation of monoclonal antibody against sulfadiazine and development of an ELISA kit].
2004 Mar
Drug interaction with T-cell receptors: T-cell receptor density determines degree of cross-reactivity.
2004 Mar
Effects of polymorphic differences for sulfanilamide, as seen through 13C and 15N solid-state NMR, together with shielding calculations.
2004 Mar
Synthesis and cytotoxic activity of lipophilic sulphonamide derivatives of the benzo[b]thiophene 1,1-dioxide.
2004 Mar 1
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
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
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 UTC 2023
Edited
by admin
on Fri Dec 15 15:05:45 UTC 2023
Record UNII
4ZB6W6B524
Record Status Validated (UNII)
Record Version
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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 UTC 2023 , Edited by admin on Fri Dec 15 15:05:45 UTC 2023
PRIMARY
EPA CompTox
DTXSID00143688
Created by admin on Fri Dec 15 15:05:45 UTC 2023 , Edited by admin on Fri Dec 15 15:05:45 UTC 2023
PRIMARY
PUBCHEM
12226950
Created by admin on Fri Dec 15 15:05:45 UTC 2023 , Edited by admin on Fri Dec 15 15:05:45 UTC 2023
PRIMARY
CAS
10103-15-8
Created by admin on Fri Dec 15 15:05:45 UTC 2023 , Edited by admin on Fri Dec 15 15:05:45 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
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ACTIVE MOIETY