SULFANILAMIDE

US Previously Marketed

First marketed in 1936

Details

Stereochemistry	ACHIRAL
Molecular Formula	C6H8N2O2S
Molecular Weight	172.2062
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

c1cc(ccc1N)S(=O)(=O)N

InChI

InChIKey=FDDDEECHVMSUSB-UHFFFAOYSA-N

InChI=1S/C6H8N2O2S/c7-5-1-3-6(4-2-5)11(8,9)10/h1-4H,7H2,(H2,8,9,10)

HIDE SMILES / InChI

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/006530s019lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/15279950

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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial dihydropteroate synthase 42 Target ID: CHEMBL2364668 Sources: http://www.cyto.purdue.edu/cdroms/cyto2/17/chmrx/sulfashd.htm	Inhibitor 7728		43.7 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Vulvovaginal candidiasis 7 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/006530s019lbl.pdf	Curative		Approved 8043	AVC Approved Use For the treatment of vulvovaginitis caused by Candida albicans. Launch Date -1.44374399E11

C_max

Value	Dose	Co-administered	Analyte	Population
2.08 μg/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/27010464	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

Value	Dose	Co-administered	Analyte	Population
81.3 μg × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/27010464	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
3.71 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/27010464	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

Dose	Population	Adverse events
15 % 1 times / day steady, topical Recommended Dose: 15 %, 1 times / day Route: topical Route: steady Dose: 15 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/006530s019lbl.pdf	unhealthy, adult Health Status: unhealthy Condition: bacterial infection (Candida albicans) Age Group: adult Sex: F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/006530s019lbl.pdf	Other AEs: Local reaction... Other AEs: Local reaction (0.2%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/006530s019lbl.pdf

AEs

AE	Significance	Dose	Population
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/006530s019lbl.pdf	unhealthy, adult Health Status: unhealthy Condition: bacterial infection (Candida albicans) Age Group: adult Sex: F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/006530s019lbl.pdf

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:45373	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:45373
ChemicalBook	CB6212562	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB6212562
MolPort	MolPort-000-871-476	https://www.molport.com/shop/molecule-link/MolPort-000-871-476
Selleck Chemicals	Sulfanilamide	http://www.selleckchem.com/products/Sulfanilamide.html
ZINC	ZINC000000002101	http://zinc15.docking.org/substances/ZINC000000002101
eMolecules	474316	https://www.emolecules.com/cgi-bin/more?vid=474316

PubMed

Title	Date	PubMed
Use of antibiotics to treat bacteriuria of pregnancy in the Nordic countries. Which antibiotics are appropriate to treat bacteriuria of pregnancy?	2001 Apr	11295409
Persistence of sulphonamide resistance in Escherichia coli in the UK despite national prescribing restriction.	2001 Apr 28	11343738
Carbonic anhydrase inhibitors: metal complexes of a sulfanilamide derived Schiff base and their interaction with isozymes I, II and IV.	2001 Dec	12164389
5-HT(6) receptor antagonists: lead optimisation and biological evaluation of N-aryl and N-heteroaryl 4-amino-benzene sulfonamides.	2001 Feb	11311747
Primary prevention with cotrimoxazole for HIV-1-infected adults: results of the pilot study in Dakar, Senegal.	2001 Feb 1	11242179
Salt effects in capillary zone electrophoresis. V. Adsorption and retention of electrically neutral analytes.	2001 Sep 21	11594392
Molecular epidemiology of cystic fibrosis-linked Burkholderia cepacia complex isolates from three national referral centres in Ireland.	2002	11972706
Pneumocystis pneumonia.	2002 Dec	12674864
Test strip for determination of nitrite in water.	2002 Jul	12110981
Spectrophotometric determination of serum nitrite and nitrate by copper-cadmium alloy.	2002 Jul 1	12069417
Improving broad specificity hapten recognition with protein engineering.	2002 Jul 17	12105945
Release characteristics of pectin microspheres prepared by an emulsification technique.	2002 Jul-Aug	12396387
Liquid chromatographic-tandem mass spectrometric determination of selected sulphonamides in milk.	2002 Jun 25	12150549
The sorption and transport of a sulphonamide antibiotic in soil systems.	2002 May 10	11988355
'In vitro' study of chemotherapeutic activity of sulphimidazole on some sensitive and metronidazole-resistant Trichomonas vaginalis strains.	2002 Nov	12419652
Idiosyncratic NSAID drug induced oxidative stress.	2002 Nov 10	12399153
Iron (III) aquacomplexes as effective photocatalysts for the degradation of pesticides in homogeneous aqueous solutions.	2002 Oct 21	12449339
Design and synthesis of fluorescent beta-cyclodextrins for the enantioselective sensing of alpha-amino acids.	2003	12884372
Sulphonamide resistance gene sul3 found in Escherichia coli isolates from human sources.	2003 Dec	14585855
Diagnostic, prognostic and therapeutic implications of carbonic anhydrases in cancer.	2003 Jul 7	12838292
Preserving the chromatographic integrity of high-speed supercritical fluid chromatography separations using time-of-flight mass spectrometry.	2003 Jul-Aug	12857113
Drug-induced bilateral transient myopia with the sulphonamide sulphasalazine.	2003 Nov	14622362
Facilitation of addition-elimination reactions in pyrimidines and purines using trifluoroacetic acid in trifluoroethanol.	2003 Nov 21	14651112
Validated HPLC method for the determination of ranitidine in plasma.	2003 Oct	14609279
Carbonic anhydrase inhibitors: inhibition of human and murine mitochondrial isozymes V with anions.	2003 Sep 1	14611844
High-performance liquid chromatography/inductively coupled plasma mass spectrometry and tandem mass spectrometry for the detection of carbon-containing compounds.	2004	15216511
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	15481463
A new method for purification of carbonic anhydrase isozymes by affinity chromatography.	2004 Feb	15000690
Carbonic anhydrase inhibitors: the first selective, membrane-impermeant inhibitors targeting the tumor-associated isozyme IX.	2004 Feb 23	15012984
Carbonic anhydrase inhibitors. Inhibition of mitochondrial isozyme V with aromatic and heterocyclic sulfonamides.	2004 Feb 26	14971907
Effects of pig slurry on the sorption of sulfonamide antibiotics in soil.	2004 Jul	15346776
Carbonic anhydrase inhibitors. Inhibition of cytosolic isozyme XIII with aromatic and heterocyclic sulfonamides: a novel target for the drug design.	2004 Jul 16	15203157
Plasmodium falciparum carbonic anhydrase is a possible target for malaria chemotherapy.	2004 Jun	15499996
Emerging issues in infective endocarditis.	2004 Jun	15207065
Contamination of honey by the herbicide asulam and its antibacterial active metabolite sulfanilamide.	2004 Jun	15204534
Drug interaction with T-cell receptors: T-cell receptor density determines degree of cross-reactivity.	2004 Mar	15007356
Synthesis and cytotoxic activity of lipophilic sulphonamide derivatives of the benzo[b]thiophene 1,1-dioxide.	2004 Mar 1	14980609
Lessons unlearned.	2004 May-Jun	15233251
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	15454239
Drinking-water nitrate, methemoglobinemia, and global burden of disease: a discussion.	2004 Oct	15471727
Theoretical study of gas-phase acidity, pKa, lipophilicity, and solubility of some biologically active sulfonamides.	2004 Oct 15	15388166
Pharmacokinetics of the nonsteroidal steroid sulphatase inhibitor 667 COUMATE and its sequestration into red blood cells in rats.	2004 Oct 4	15328524

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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.

Name

Type

Language

SULFANILAMIDE

Official Name

English

SULFADIMETHOXINE IMPURITY E [EP]

Common Name

English

BENZENESULFONAMIDE, 4-AMINO-

Systematic Name

English

NSC-7618

Code

English

SULFANILAMIDE [WHO-DD]

Common Name

English

SULPHANILAMIDUM

Common Name

English

SULFANILAMIDE MELTING POINT STANDARD

Common Name

English

AVC

Brand Name

English

SULFANILAMIDE [USP-RS]

Common Name

English

(4-(AMINOSULFONYL)PHENYL)AMINE

Systematic Name

English

P-AMINOBENZENESULFAMIDE

Common Name

English

4-SULFAMOYLANILINE

Systematic Name

English

SULFANILAMIDE [MI]

Common Name

English

P-AMINOBENZENESULFONAMIDE

Common Name

English

SULFACETAMIDE SODIUM IMPURITY A [EP]

Common Name

English

SULFANILAMIDE [ORANGE BOOK]

Common Name

English

PRONTOSIL I

Common Name

English

4-AMINOPHENYLSULFONAMIDE

Systematic Name

English

SULFADIMIDINE IMPURITY D [EP]

Common Name

English

PRONTYLIN

Common Name

English

SULFANILAMIDE [VANDF]

Common Name

English

SULFANILAMIDE [EP MONOGRAPH]

Common Name

English

SULFANILAMIDE [MART.]

Common Name

English

ANILINE-P-SULFONIC AMIDE

Common Name

English

SULFANILAMIDE [INN]

Common Name

English

4-(AMINOSULFONYL)ANILINE

Systematic Name

English

SULFANILAMIDE [HSDB]

Common Name

English

SULPHANILAMIDUM [HPUS]

Common Name

English

4-AMINOBENZENE-1-SULFONAMIDE

Systematic Name

English

SULFADIMETHOXINE SODIUM FOR VETERINARY USE IMPURITY E [EP]

Common Name

English

SULFAMINE

Common Name

English

STREPTOCID

Brand Name

English

SULFAMETHOXAZOLE IMPURITY E [EP]

Common Name

English

SULFONAMIDE

Common Name

English

4-AMINOBENZENESULFONAMIDE

Systematic Name

English

Classification Tree Code System Code

CFR

21 CFR 310.527