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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 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 ClH
Molecular Weight 36.461
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
[Clinico-immunologic effect of immunomodulin and bactim in duodenal ulcer under environmental pollution conditions].
2002
[Structure and function of integrons].
2002 Aug-Sep
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
Release characteristics of pectin microspheres prepared by an emulsification technique.
2002 Jul-Aug
Development and validation of limited sampling strategies for prediction of the systemic exposure to the novel anticancer agent E7070 (N-(3-chloro-7-indolyl)-1,4-benzenedisulphonamide).
2002 Nov
'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
Idiosyncratic NSAID drug induced oxidative stress.
2002 Nov 10
Sulphonamide resistant commensal Neisseria with alterations in the dihydropteroate synthase can be isolated from carriers not exposed to sulphonamides.
2002 Nov 18
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
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
Risk factors for antibiotic resistance in Campylobacter spp. isolated from raw poultry meat in Switzerland.
2003 Dec 9
[Integrons and antimicrobial resistance gene cassettes in Shigella flexneri strains ].
2003 Jul
Diagnostic, prognostic and therapeutic implications of carbonic anhydrases in cancer.
2003 Jul 7
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
Early manifestation of nephropathy in rats with arterial calcinosis.
2003 May
[Treatment of sulfanilamide production wastewater by resin adsorption technique].
2003 Nov
Drug-induced bilateral transient myopia with the sulphonamide sulphasalazine.
2003 Nov
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
Generation of group-specific antibodies against sulfonamides.
2003 Sep 24
Simultaneous determination of cefatrizine and clavulanic acid in dog plasma by HPLC.
2004 Apr 1
4-sulphamoylphenyl semicarbazones with anticonvulsant activity.
2004 Aug
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
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
Carbonic anhydrase inhibitors: N-(p-sulfamoylphenyl)-alpha-D-glycopyranosylamines as topically acting antiglaucoma agents in hypertensive rabbits.
2004 Jan 5
Carbonic anhydrase inhibitors. Inhibition of cytosolic isozyme XIII with aromatic and heterocyclic sulfonamides: a novel target for the drug design.
2004 Jul 16
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
Emerging issues in infective endocarditis.
2004 Jun
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
Lessons unlearned.
2004 May-Jun
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

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 15:26:16 UTC 2023
Edited
by admin
on Fri Dec 15 15:26:16 UTC 2023
Record UNII
R2MR7LN8WP
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SULFANILAMIDE HYDROCHLORIDE
Systematic Name English
PABIAMID
Common Name English
BENZENESULFONAMIDE, 4-AMINO-, MONOHYDROCHLORIDE
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 Fri Dec 15 15:26:16 UTC 2023 , Edited by admin on Fri Dec 15 15:26:16 UTC 2023
PRIMARY
FDA UNII
R2MR7LN8WP
Created by admin on Fri Dec 15 15:26:16 UTC 2023 , Edited by admin on Fri Dec 15 15:26:16 UTC 2023
PRIMARY
PUBCHEM
80197
Created by admin on Fri Dec 15 15:26:16 UTC 2023 , Edited by admin on Fri Dec 15 15:26:16 UTC 2023
PRIMARY
CAS
6101-31-1
Created by admin on Fri Dec 15 15:26:16 UTC 2023 , Edited by admin on Fri Dec 15 15:26:16 UTC 2023
PRIMARY
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