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Details

Stereochemistry ACHIRAL
Molecular Formula C6H8N2O2S.CH3O3S.Na
Molecular Weight 290.292
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Sulfanilamide sodium mesylate

SMILES

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

InChI

InChIKey=BSIXAEHVYKHWGJ-UHFFFAOYSA-M
InChI=1S/C6H8N2O2S.CH4O3S.Na/c7-5-1-3-6(4-2-5)11(8,9)10;1-5(2,3)4;/h1-4H,7H2,(H2,8,9,10);1H3,(H,2,3,4);/q;;+1/p-1

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

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 CH3O3S
Molecular Weight 95.098
Charge -1
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
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
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
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
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
Salt effects in capillary zone electrophoresis. V. Adsorption and retention of electrically neutral analytes.
2001 Sep 21
Effects of anion and cation inhibitors and carbonic anhydrase inhibitors upon the activity of the gypsy moth (Lepidoptera: Lymantriidae) nucleo-polyhedrovirus.
2002 Apr
Tandem vicarious nucleophilic substitution of hydrogen/intramolecular Diels-Alder reaction of 1,2,4-triazines into functionalized cycloalkenopyridines.
2002 Apr
Sulphonamide residues in eggs following drug administration via the drinking water.
2002 Apr
The spectrum of allergic (cross-)sensitivity in clinical patch testing with 'para amino' compounds.
2002 Apr
Drug release properties of pectinate microspheres prepared by emulsification method.
2002 Aug 21
[Structure and function of integrons].
2002 Aug-Sep
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
Spectrophotometric determination of serum nitrite and nitrate by copper-cadmium alloy.
2002 Jul 1
The sorption and transport of a sulphonamide antibiotic in soil systems.
2002 May 10
'In vitro' study of chemotherapeutic activity of sulphimidazole on some sensitive and metronidazole-resistant Trichomonas vaginalis strains.
2002 Nov
Evidence for a membrane site of action for 14,15-EET on expression of aromatase in vascular smooth muscle.
2002 Nov
Susceptibility of Danish Escherichia coli strains isolated from urinary tract infections and bacteraemia, and distribution of sul genes conferring sulphonamide resistance.
2002 Oct
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
[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
Diagnostic, prognostic and therapeutic implications of carbonic anhydrases in cancer.
2003 Jul 7
Polyelectrolyte Complexes: Interactions between Lignosulfonate and Chitosan.
2003 Mar-Apr
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
Carbonic anhydrase inhibitors: inhibition of human and murine mitochondrial isozymes V with anions.
2003 Sep 1
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
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
Engineering of a broad specificity antibody for simultaneous detection of 13 sulfonamides at the maximum residue level.
2004 Jan 14
Glucose 6 phosphate dehydrogenase deficiency in adults.
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
Contamination of honey by the herbicide asulam and its antibacterial active metabolite sulfanilamide.
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
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
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 Sat Dec 16 19:18:24 UTC 2023
Edited
by admin
on Sat Dec 16 19:18:24 UTC 2023
Record UNII
5P7TK324BY
Record Status Validated (UNII)
Record Version
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Name Type Language
Sulfanilamide sodium mesylate
Common Name English
Benzenesulfonamide, 4-amino-, methanesulfonate, sodium salt (1:1:1)
Systematic Name English
Sodium sulfanilamide methanesulfonate
Common Name English
Sulfanilamide sodium mesilate
Common Name English
Benzenesulfonamide, 4-amino-, monomethanesulfonate, monosodium salt
Systematic Name English
Sulfanilamide sodium mesilate [WHO-DD]
Common Name English
Code System Code Type Description
PUBCHEM
164512883
Created by admin on Sat Dec 16 19:18:25 UTC 2023 , Edited by admin on Sat Dec 16 19:18:25 UTC 2023
PRIMARY
CAS
35915-69-6
Created by admin on Sat Dec 16 19:18:25 UTC 2023 , Edited by admin on Sat Dec 16 19:18:25 UTC 2023
PRIMARY
FDA UNII
5P7TK324BY
Created by admin on Sat Dec 16 19:18:25 UTC 2023 , Edited by admin on Sat Dec 16 19:18:25 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE