Synonym: Pyrazinamide, Pyrazinoic acid amide
|Related Categories||Antibacterial, Antibiotics, Antibiotics A to Z, Antibiotics N-S, Antimycobacterial,|
10, 25, 100 g in poly bottle
Pyrazinamide is used therapeutically as an antitubercular agent. Pyrazinamide is used to form polymeric copper complexes, create pyrazine carboxamide scaffolds useful as FXs inhibitors, and as a component of mycobacteria identification kits. It is used to study liver toxicity prevention 1 and mechanisms of resistance 2.
Pyrazinamide is used to form polymeric copper complexes, create pyrazine carboxamide scaffolds useful as FXs inhibitors, and as a component of mycobacteria identification kits.
The active moiety of pyrazinamide is pyrazinoic acid (POA). POA is thought to disrupt membrane energetics and inhibit membrane transport function at acid pH in Mycobacterium tuberculosis. Iron enhances the antituberculous activity of pyrazinamide 3. Pyrazinamide and its analogs have been shown to inhibit the activity of purified FAS I.
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1. Human and Experimental Toxicology. Terminalia chebula (fruit) prevents liver toxicity caused by sub-chronic administration of rifampicin, isoniazid and pyrazinamide in combination S A Tasduq, K Singh, N K Satti, et al. Hum. Exp. Toxicol. 25, 111-118, (2006)
2. Mechanisms of pyrazinamide resistance in mycobacteria: importance of lack of uptake in addition to lack of pyrazinamidase activity Catherine Raynaud, Marie-Antoinette Lanéelle, et a Microbiology 145, 1359-1367, (1999)
Factors associated with the rapid implementation process of the fixed-dose combination RHZE tuberculosis regimen in Brazil: an ecological study. Braga JU, da Conceição DA, and Trajman A BMC Public Health 13, 321, (2013)
Oral bioavailability of rifampicin, isoniazid, ethambutol, and pyrazinamide in a 4-drug fixed-dose combination compared with the separate formulations in healthy Chinese male volunteers. Xu J, Jin H, Zhu H, et al. Clin. Ther. 35(2), 161-8, (2013)
Tuberculous lymphadenopathy: a multicentre operational study of 6-month thrice weekly directly observed treatment. Jindal SK, Aggarwal AN, Gupta D, et al. Int. J. Tuberc. Lung Dis. 17(2), 234-9, (2013)
Efficacy of the 6-month thrice-weekly regimen in the treatment of new sputum smear-positive pulmonary tuberculosis under clinical trial conditions. Banu Rekha VV, Rajaram K, Kripasankar AS, et al. Natl. Med. J. India 25(4), 196-200, (2012)
Tuberculosis treatment survival of HIV positive TB patients on directly observed treatment short-course in Southern Ethiopia: a retrospective cohort study. Shaweno D and Worku A BMC Res. Notes 5, 682, (2012)
Leprosy and tuberculosis co-infection: clinical and immunological report of two cases and review of the literature. Trindade MÂ, Miyamoto D, Benard G, et al. Am. J. Trop. Med. Hyg. 88(2), 236-40, (2013)
A time-to-event pharmacodynamic model describing treatment response in patients with pulmonary tuberculosis using days to positivity in automated liquid mycobacterial culture. Chigutsa E, Patel K, Denti P, et al. Antimicrob. Agents Chemother. 57(2), 789-95, (2013)
Analogs of the antituberculous agent pyrazinamide are competitive inhibitors of NADPH binding to M. tuberculosis fatty acid synthase I. Sayahi H, Pugliese KM, Zimhony O, et al. Chem. Biodivers. 9(11), 2582-96, (2012)
Prevention of false resistance results obtained in testing the susceptibility of Mycobacterium tuberculosis to pyrazinamide with the Bactec MGIT 960 system using a reduced inoculum. Piersimoni C, Mustazzolu A, Giannoni F, et al. J. Clin. Microbiol. 51(1), 291-4, (2013)
Isoniazid- and streptomycin-resistant miliary tuberculosis complicated by intracranial tuberculoma in a Japanese infant. Ishiwada N, Tokunaga O, Nagasawa K, et al. Tohoku J. Exp. Med. 229(3), 221-5, (2013)
Inadequate therapeutic response to a recommended antituberculosis fixed-dose combination regimen in an overweight patient with Mycobacterium bovis infection. Lloret-Linares C, Mouly S, Hoang-Nguyen DT, et al. Ann. Pharmacother. 47(1), e4, (2013)
Impact of pharmacogenetic markers of CYP2B6, clinical factors, and drug-drug interaction on efavirenz concentrations in HIV/tuberculosis-coinfected patients. Manosuthi W, Sukasem C, Lueangniyomkul A, et al. Antimicrob. Agents Chemother. 57(2), 1019-24, (2013)
Microwave prompted multigram synthesis, structural determination, and photo-antiproliferative activity of fluorinated 4-hydroxyquinolinones. Kapil Arya et al Bioorg. Med. Chem. Lett. 17, 86-93, (2007)
Pyrrolidine dithiocarbamate and diethyldithiocarbamate are active against growing and nongrowing persister Mycobacterium tuberculosis. Sean T Byrne et al Antimicrob. Agents Chemother. 51, 4495-7, (2007)
A microwave-assisted facile regioselective Fischer indole synthesis and antitubercular evaluation of novel 2-aryl-3,4-dihydro-2H-thieno[3,2-b]indoles. Subramanian Vedhanarayanan Karthikeyan et al Bioorg. Med. Chem. Lett. 19, 3006-9, (2009)
Prediction of volume of distribution values in human using immobilized artificial membrane partitioning coefficients, the fraction of compound ionized and plasma protein binding data. Xiaofan Sui et al Eur. J. Med. Chem. 44, 4455-60, (2009)
Pharmacokinetics-pharmacodynamics of pyrazinamide in a novel in vitro model of tuberculosis for sterilizing effect: a paradigm for faster assessment of new antituberculosis drugs. Tawanda Gumbo et al Antimicrob. Agents Chemother. 53, 3197-204, (2009)
Role of porins in the susceptibility of Mycobacterium smegmatis and Mycobacterium chelonae to aldehyde-based disinfectants and drugs. Zuzana Svetlíková et al Antimicrob. Agents Chemother. 53, 4015-8, (2009)
Selective one-pot multicomponent synthesis and anti-tubercular evaluation of 5-(aryl/cyclohexylsulfanyl)-2-alkoxy-4,6-diarylnicotinonitriles. Ramaiyan Manikannan et al Bioorg. Med. Chem. Lett. 20, 3352-5, (2010)
A highly atom economic, chemo-, regio- and stereoselective synthesis and evaluation of spiro-pyrrolothiazoles as antitubercular agents. Subramanian Vedhanarayanan Karthikeyan et al Bioorg. Med. Chem. Lett. 20, 350-3, (2010)
Novel three-component domino reactions of ketones, isatin and amino acids: synthesis and discovery of antimycobacterial activity of highly functionalised novel dispiropyrrolidines. Raju Suresh Kumar et al Eur. J. Med. Chem. 45, 411-22, (2010)
Emergence and molecular characterization of extensively drug-resistant Mycobacterium tuberculosis clinical isolates from the Delhi Region in India. Alka Khanna et al Antimicrob. Agents Chemother. 54, 4789-93, (2010)
Mutually exclusive genotypes for pyrazinamide and 5-chloropyrazinamide resistance reveal a potential resistance-proofing strategy. Anthony D Baughn et al Antimicrob. Agents Chemother. 54, 5323-8, (2010)
Pyrazinamide, but not pyrazinoic acid, is a competitive inhibitor of NADPH binding to Mycobacterium tuberculosis fatty acid synthase I. Halimah Sayahi et al Bioorg. Med. Chem. Lett. 21, 4804-7, (2011)
Synthesis, antibacterial and antimycobacterial activities of some new 4-aryl/heteroaryl-2,6-dimethyl-3,5-bis-N-(aryl)-carbamoyl-1,4-dihydropyridines. Kalam Sirisha et al Eur. J. Med. Chem. 46, 1564-71, (2011)
Camphorsulfonic acid catalysed facile tandem double Friedlander annulation protocol for the synthesis of phenoxy linked bisquinoline derivatives and discovery of antitubercular agents. Nidhin Paul et al Bioorg. Med. Chem. Lett. 22, 1643-8, (2012)
Aldrich MSDS 1, 1556:C / Corp MSDS 1 (2), 2986:A / FT-IR 2 (3), 3887:B / FT-IR 1 (2), 844:D / FT-NMR 1 (3), 410:A / IR-Spectra (3), 1378:A / IR-Spectra (2), 1200:G / NMR-Reference 2 (2), 723:D / RegBook 1 (2), 2595:F / Sax 6, 2323 / Sigma FT-IR 1 (2), 865:C / Structure Index 1, 410:C:6
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