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S9251 Sigma-Aldrich

Sulfanilamide

≥99%

Synonym: p-Aminobenzenesulfonamide

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Properties

Related Categories Antibacterial, Antibiotics, Antibiotics A to Z, Antibiotics N-S, Biochemicals and Reagents,
assay   ≥99%
mp   164-166 °C(lit.)
antibiotic activity spectrum   Gram-negative bacteria
  Gram-positive bacteria
Gene Information   human ... CA1(759), CA2(760), CA5A(763), CA5B(11238), CA9(768)
mouse ... Car13(71934), Car5a(12352)

Description

Biochem/physiol Actions

Sulfonamide antibiotic that blocks the synthesis of dihydrofolic acid by inhibiting the enzyme dihydropteroate synthase.
Mode of Action: A competitive inhibitor of dihydropteroate synthestase to block the synthesis of folic acid.
Anti-microbial Spectrum: Gram positive, Gram negative, Chlamydia
Mode of Resistance: Alteration of dihydropteroate synthase or alternative pathway for folic acid synthesis.

Packaging

100, 500 g in poly bottle

Price and Availability

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Safety & Documentation

Safety Information

WGK Germany 
3
RTECS 
WO8400000

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

Peer-Reviewed Papers

References

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Pneumocystis jiroveci dihydropteroate synthase polymorphisms confer resistance to sulfadoxine and sulfanilamide in Saccharomyces cerevisiae. Meneau, I. et al. Antimicrob. Agents Chemother. 48, 2610-6, (2004)

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Carbon-sensitized and nitrogen-doped TiO2 for photocatalytic degradation of sulfanilamide under visible-light irradiation. Wang P, Zhou T, Wang R, et al. Water Res. 45(16), 5015-26, (2011)

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Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species. Denis Fourches et al Chem. Res. Toxicol. 23, 171-83, (2010)

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Carbonic anhydrase inhibitors. Inhibition of the human cytosolic isozyme VII with aromatic and heterocyclic sulfonamides. Daniela Vullo et al Bioorg. Med. Chem. Lett. 15, 971-6, (2005)

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Carbonic anhydrase inhibitors. Characterization and inhibition studies of the most active beta-carbonic anhydrase from Mycobacterium tuberculosis, Rv3588c. Fabrizio Carta et al Bioorg. Med. Chem. Lett. 19, 6649-54, (2009)

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A predictive ligand-based Bayesian model for human drug-induced liver injury. Sean Ekins et al Drug Metab. Dispos. 38, 2302-8, (2010)

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Cloning, characterization, and inhibition studies of a beta-carbonic anhydrase from Brucella suis. Pascale Joseph et al J. Med. Chem. 53, 2277-85, (2010)

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Use of simple docking methods to screen a virtual library for heteroactivators of cytochrome P450 2C9. Charles W Locuson et al J. Med. Chem. 50, 1158-65, (2007)

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Carbonic anhydrase inhibitors. The mitochondrial isozyme VB as a new target for sulfonamide and sulfamate inhibitors. Isao Nishimori et al J. Med. Chem. 48, 7860-6, (2005)

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Cloning, characterization and sulfonamide inhibition studies of an ?-carbonic anhydrase from the living fossil sponge Astrosclera willeyana. Anna Ohradanova et al Bioorg. Med. Chem. 20, 1403-10, (2012)

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Carbonic anhydrase inhibitors: DNA cloning and inhibition studies of the alpha-carbonic anhydrase from Helicobacter pylori, a new target for developing sulfonamide and sulfamate gastric drugs. Isao Nishimori et al J. Med. Chem. 49, 2117-26, (2006)

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Carbonic anhydrase inhibitors. Synthesis and inhibition of cytosolic/tumor-associated carbonic anhydrase isozymes I, II, and IX with boron-containing sulfonamides, sulfamides, and sulfamates: toward agents for boron neutron capture therapy of hypoxic tumors. Jean-Yves Winum et al Bioorg. Med. Chem. Lett. 15, 3302-6, (2005)

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The coumarin-binding site in carbonic anhydrase accommodates structurally diverse inhibitors: the antiepileptic lacosamide as an example and lead molecule for novel classes of carbonic anhydrase inhibitors. Claudia Temperini et al J. Med. Chem. 53, 850-4, (2010)

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A sensitive emulsification liquid phase microextraction coupled with on-line phase separation followed by HPLC for trace determination of sulfonamides in water samples. Ebrahimpour B, Yamini Y, and Rezazadeh M Environ. Monit. Assess. 187(1), 4162, (2015)

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Purification and characterization of carbonic anhydrase from sheep kidney and effects of sulfonamides on enzyme activity. Demirdağ R, Çomaklı V, Şentürk M, et al. Bioorg. Med. Chem. 21(6), 1522-5, (2013)

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Two centuries of assessing drug risks. Avorn J N. Engl. J. Med. 367(3), 193-7, (2012)

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Trypanosoma congolense Infections: Induced Nitric Oxide Inhibits Parasite Growth In Vivo. Lu W J. Parasitol. Res. 2011, 316067, (2011)

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Stress degradation study on sulfadimethoxine and development of a validated stability-indicating HPLC assay. Louati K, Mistiri F, Kallel M, et al. Ann. Pharm. Fr. 69(2), 91-9, (2011)

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[Synthesis and investigation on antidiabetic activity of 4-(1-aryl-3-oxo-5-phenylpentylamino) benzenesulfonamide]. Yang DC, Yan JF, Xu J, et al. Yao Xue Xue Bao 45(1), 66-71, (2010)

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Natural product-based phenols as novel probes for mycobacterial and fungal carbonic anhydrases. Rohan A Davis et al J. Med. Chem. 54, 1682-92, (2011)

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Carbonic anhydrase inhibitors. Cloning, characterization, and inhibition studies of a new beta-carbonic anhydrase from Mycobacterium tuberculosis. Isao Nishimori et al J. Med. Chem. 52, 3116-20, (2009)

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Molecular cloning, characterization, and inhibition studies of the Rv1284 beta-carbonic anhydrase from Mycobacterium tuberculosis with sulfonamides and a sulfamate. Tomoko Minakuchi et al J. Med. Chem. 52, 2226-32, (2009)

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Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors. Lourdes Santana et al J. Med. Chem. 51, 6740-51, (2008)

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A new ?-carbonic anhydrase from Brucella suis, its cloning, characterization, and inhibition with sulfonamides and sulfamates, leading to impaired pathogen growth. Pascale Joseph et al Bioorg. Med. Chem. 19, 1172-8, (2011)

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Carbonic anhydrase inhibitors: inhibition of the transmembrane isozyme XIV with sulfonamides. Isao Nishimori et al Bioorg. Med. Chem. Lett. 15, 3828-33, (2005)

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Rapid and sensitive determination of sulfonamide residues in milk and chicken muscle by microfluidic chip electrophoresis. Wang L, Wu J, Wang Q, et al. J. Agric. Food Chem. 60(7), 1613-8, (2012)

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Fred Loe, MD, and the history of trachoma. Feibel RM Arch. Ophthal. 129(4), 503-8, (2011)

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Electrophilic trifluoromethanesulfanylation of organometallic species with trifluoromethanesulfanamides. Baert F, Colomb J, and Billard T Angew. Chem. Int. Ed. Engl. 51(41), 10382-5, (2012)

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Inhibition studies of a beta-carbonic anhydrase from Brucella suis with a series of water soluble glycosyl sulfanilamides. Daniela Vullo et al Bioorg. Med. Chem. Lett. 20, 2178-82, (2010)

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Synthesis of novel sulfanilamide-derived 1,2,3-triazoles and their evaluation for antibacterial and antifungal activities. Wang XL, Wan K, and Zhou CH Eur. J. Med. Chem. 45(10), 4631-9, (2010)

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In silico and in vitro filters for the fast estimation of skin permeation and distribution of new chemical entities. Giorgio Ottaviani et al J. Med. Chem. 50, 742-8, (2007)

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Phenylethynylbenzenesulfonamide regioisomers strongly and selectively inhibit the transmembrane, tumor-associated carbonic anhydrase isoforms IX and XII over the cytosolic isoforms I and II. Edward E Knaus et al Bioorg. Med. Chem. Lett. 21, 5892-6, (2011)

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Superelectrophilic activation in superacid HF/SbF(5) and synthesis of benzofused sultams. Liu F, Martin-Mingot A, Jouannetaud MP, et al. Org. Lett. 12(4), 868-71, (2010)

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Carbonic anhydrase inhibitors. DNA cloning, characterization, and inhibition studies of the human secretory isoform VI, a new target for sulfonamide and sulfamate inhibitors. Isao Nishimori et al J. Med. Chem. 50, 381-8, (2007)

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Control of the coordination status of the open metal sites in metal-organic frameworks for high performance separation of polar compounds. Fu YY, Yang CX, and Yan XP Langmuir 28(17), 6794-802, (2012)

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Carbonic anhydrase inhibitors. Identification of selective inhibitors of the human mitochondrial isozymes VA and VB over the cytosolic isozymes I and II from a natural product-based phenolic library. Rohan A Davis et al Bioorg. Med. Chem. 18, 14-8, (2010)

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Developing structure-activity relationships for the prediction of hepatotoxicity. Nigel Greene et al Chem. Res. Toxicol. 23, 1215-22, (2010)

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Carbonic anhydrase inhibitors: the beta-carbonic anhydrase from Helicobacter pylori is a new target for sulfonamide and sulfamate inhibitors. Isao Nishimori et al Bioorg. Med. Chem. Lett. 17, 3585-94, (2007)

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Carbonic anhydrase inhibitors. Inhibition of the membrane-bound human and bovine isozymes IV with sulfonamides. Alessio Innocenti et al Bioorg. Med. Chem. Lett. 15, 1149-54, (2005)

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Philornis sp. bot fly larvae in free living scarlet macaw nestlings and a new technique for their extraction. Olah G, Vigo G, Ortiz L, et al. Vet. Parasitol. 196(1-2), 245-9, (2013)

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Carbonic anhydrase inhibitors: cloning, characterization, and inhibition studies of the cytosolic isozyme III with sulfonamides. Isao Nishimori et al Bioorg. Med. Chem. 15, 7229-36, (2007)

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Carbonic anhydrase inhibitors: inhibition of the beta-class enzyme from the yeast Saccharomyces cerevisiae with sulfonamides and sulfamates. Semra Isik et al Bioorg. Med. Chem. 17, 1158-63, (2009)

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Carbonic anhydrase inhibitors. Novel sulfanilamide/acetazolamide derivatives obtained by the tail approach and their interaction with the cytosolic isozymes I and II, and the tumor-associated isozyme IX. Hasan Turkmen et al Bioorg. Med. Chem. Lett. 15, 367-72, (2005)

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Carbonic anhydrase inhibitors: synthesis and inhibition of cytosolic/tumor-associated carbonic anhydrase isozymes I, II, and IX with sulfonamides incorporating thioureido-sulfanilyl scaffolds. Luca Puccetti et al Bioorg. Med. Chem. Lett. 15, 2359-64, (2005)

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An evaluation of the chick cardiomyocyte micromass system for identification of teratogens in a blind trial. Hurst H, Clothier RH, and Pratten M Reprod. Toxicol. 28(4), 503-10, (2009)

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Carbonic anhydrase inhibitors. Inhibition and homology modeling studies of the fungal beta-carbonic anhydrase from Candida albicans with sulfonamides. Alessio Innocenti et al Bioorg. Med. Chem. 17, 4503-9, (2009)

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QSAR study on topically acting sulfonamides incorporating GABA moieties: a molecular connectivity approach. Vijay K Agrawal et al Bioorg. Med. Chem. Lett. 16, 2044-51, (2006)

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QSAR study on the antibacterial activity of some sulfa drugs: building blockers of Mannich bases. Dheeraj Mandloi et al Bioorg. Med. Chem. Lett. 15, 405-11, (2005)

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Carbonic anhydrase inhibitors: inhibition of the tumor-associated isozymes IX and XII with a library of aromatic and heteroaromatic sulfonamides. Ozen Ozensoy et al Bioorg. Med. Chem. Lett. 15, 4862-6, (2005)

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Cloning, expression, post-translational modifications and inhibition studies on the latest mammalian carbonic anhydrase isoform, CA XV. Mika Hilvo et al J. Med. Chem. 52, 646-54, (2009)

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Design and synthesis of thiourea compounds that inhibit transmembrane anchored carbonic anhydrases. Janina Moeker et al Bioorg. Med. Chem. 20, 2392-404, (2012)

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Characterization and inhibition studies of an α-carbonic anhydrase from the endangered sturgeon species Acipenser gueldenstaedti. Kolayli S, Karahalil F, Sahin H, et al. J. Enzyme Inhib. Med. Chem. 26(6), 895-900, (2011)

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Inhibition of β-carbonic anhydrases with ureido-substituted benzenesulfonamides. Pacchiano, F., et al. Bioorg. Med. Chem. Lett. 21, 102-105, (2011)

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Synthesis of a new class of 2-anilino substituted nicotinyl arylsulfonylhydrazides as potential anticancer and antibacterial agents. Ahmed Kamal et al Bioorg. Med. Chem. 15, 1004-13, (2007)

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Novel use of chemical shift in NMR as molecular descriptor: a first report on modeling carbonic anhydrase inhibitory activity and related parameters. Padmakar V Khadikar et al Bioorg. Med. Chem. Lett. 15, 931-6, (2005)

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Carbonic anhydrase inhibitors: cloning and sulfonamide inhibition studies of a carboxyterminal truncated alpha-carbonic anhydrase from Helicobacter pylori. Isao Nishimori et al Bioorg. Med. Chem. Lett. 16, 2182-8, (2006)

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Sulfonamides incorporating boroxazolidone moieties are potent inhibitors of the transmembrane, tumor-associated carbonic anhydrase isoforms IX and XII. Marouan Rami et al Bioorg. Med. Chem. Lett. 21, 2975-9, (2011)

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Carbonic anhydrase inhibitors. Inhibition studies with anions and sulfonamides of a new cytosolic enzyme from the scleractinian coral Stylophora pistillata. Anthony Bertucci et al Bioorg. Med. Chem. Lett. 21, 710-4, (2011)

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Identification and characterization of novel tissue-nonspecific alkaline phosphatase inhibitors with diverse modes of action. Sergienko E, Su Y, Chan X, et al. J. Biomol. Screen. 14(7), 824-37, (2009)

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Synthesis and biological study of medicinally important Mannich bases derived from 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a pentahydroxy naphthacene carboxamide. Sheela Joshi et al Bioorg. Med. Chem. Lett. 17, 645-8, (2007)

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Correlation analyses on binding affinity of substituted benzenesulfonamides with carbonic anhydrase using ab initio MO calculations on their complex structures (II). Yohei Munei et al Bioorg. Med. Chem. Lett. 21, 141-4, (2011)

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Kinetic modelling and residue depletion of drugs in eggs. Hekman P and Schefferlie GJ Br. Poult. Sci. 52(3), 376-80, (2011)

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Carbonic anhydrase inhibitors: design of thioureido sulfonamides with potent isozyme II and XII inhibitory properties and intraocular pressure lowering activity in a rabbit model of glaucoma. Francesco Mincione et al Bioorg. Med. Chem. Lett. 15, 3821-7, (2005)

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Convenient QSAR model for predicting the complexation of structurally diverse compounds with beta-cyclodextrins. Alfonso Pérez-Garrido et al Bioorg. Med. Chem. 17, 896-904, (2009)

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Synthesis and antidiabetic performance of β-amino ketone containing nabumetone moiety. Wang H, Yan JF, Song XL, et al. Bioorg. Med. Chem. 20(6), 2119-30, (2012)

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Carbonic anhydrase inhibitors. Inhibition studies of a coral secretory isoform by sulfonamides. Anthony Bertucci et al Bioorg. Med. Chem. 17, 5054-8, (2009)

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Inhibition studies of the ?-carbonic anhydrases from the bacterial pathogen Salmonella enterica serovar Typhimurium with sulfonamides and sulfamates. Isao Nishimori et al Bioorg. Med. Chem. 19, 5023-30, (2011)

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Conformational landscape, photochemistry, and infrared spectra of sulfanilamide. Borba A, Gómez-Zavaglia A, and Fausto R J. Phys. Chem. A 117(4), 704-17, (2013)

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Synthesis and in vitro study of novel Mannich bases as antibacterial agents. Sheela Joshi et al Bioorg. Med. Chem. Lett. 15, 221-6, (2005)

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Covalent binding of nitroso-sulfonamides to glutathione S-transferase in guinea pigs with delayed type hypersensitivity. Eyanagi R, Toda A, Imoto M, et al. Int. Immunopharmacol. 12(4), 694-700, (2012)

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Mutation of Phe91 to Asn in human carbonic anhydrase I unexpectedly enhanced both catalytic activity and affinity for sulfonamide inhibitors. Feray Kockar et al Bioorg. Med. Chem. 18, 5498-503, (2010)

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Synthesis, structure analysis, and antibacterial activity of some novel 10-substituted 2-(4-piperidyl/phenyl)-5,5-dioxo[1,2,4]triazolo[1,5-b][1,2,4]benzothiadiazine derivatives. Ahmed Kamal et al Bioorg. Med. Chem. Lett. 17, 5400-5, (2007)

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Aminobenzenesulfonamide functionalized SBA-15 nanoporous molecular sieve: a new and promising adsorbent for preconcentration of lead and copper ions. Hajiaghababaei L, Ghasemi B, Badiei A, et al. J. Environ. Sci. (China) 24(7), 1347-54, (2012)

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Carbonic anhydrase inhibitors: copper(II) complexes of polyamino-polycarboxylamido aromatic/heterocyclic sulfonamides are very potent inhibitors of the tumor-associated isoforms IX and XII. Marouan Rami et al Bioorg. Med. Chem. Lett. 18, 836-41, (2008)

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3D-QSAR study of benzene sulfonamide analogs as carbonic anhydrase II inhibitors. Kalyan K Sethi et al Bioorg. Med. Chem. Lett. 20, 3089-93, (2010)

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Application of sulphanilamides disazo dyes with Tropaeolin O for simple, rapid and sensitive spectrophotometric assay of medicines. Boiko M, Vrublevska T, Korkuna O, et al. Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 79(2), 325-31, (2011)

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Anti-mycobacterial activity of a bis-sulfonamide. Brendan L Wilkinson et al Bioorg. Med. Chem. Lett. 17, 1355-7, (2007)

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Computational approach for fast screening of small molecular candidates to inhibit crystallization in amorphous drugs. Pajula K, Lehto VP, Ketolainen J, et al. Mol. Pharm. 9(10), 2844-55, (2012)

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Mutation of active site residues Asn67 to Ile, Gln92 to Val and Leu204 to Ser in human carbonic anhydrase II: Influences on the catalytic activity and affinity for inhibitors. Sumeyye Turkoglu et al Bioorg. Med. Chem. 20, 2208-13, (2012)

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Spectrophotometric determination of drugs with iodine. Karuna T, et al. J. Sci. Ind. Res. 65(10), 808, (2006)

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Increasing throughput of surface plasmon resonance-based biosensors by multiple analyte injections. Mehand MS, De Crescenzo G, and Srinivasan B J. Mol. Recognit. 25(4), 208-15, (2012)

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Electric field-controlled benzoic acid and sulphanilamide delivery from poly(vinyl alcohol) hydrogel. Sittiwong J, Niamlang S, Paradee N, et al. AAPS PharmSciTech 13(4), 1407-15, (2012)

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Evaluation of phytochemical composition and antioxidant capacity of a decoction containing Adenanthera pavonina L. and Thespesia populnea L. Silva IK and Soysa P Pharmacogn. Mag. 7(27), 193-9, (2011)

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The last year before the dawn of antibiotics. Ellis H Br. J. Hosp. Med. (Lond.) 70(8), 475, (2009)

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Carbonic anhydrase inhibitors: inhibition of cytosolic carbonic anhydrase isozymes II and VII with simple aromatic sulfonamides and some azo dyes. Carta F, Pothen B, Maresca A, et al. Chem. Biol. Drug Des. 74(2), 196-202, (2009)

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Merck 14,8925

Beil. 14,IV,2658

FT-IR 1 (2), 532:B / FT-IR 2 (2), 3294:B / FT-NMR 1 (2), 1636:B / IR-Spectra (2), 1024:H / IR-Spectra (3), 1176:D / NMR-Reference 2 (2), 851:D / RegBook 1 (2), 2243:A / Sax 6, 2480 / Sigma FT-IR 1 (1), 716:C / Structure Index 1, 352:D:2

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