| Attributes | Values |
|---|
| rdf:type
| |
| http://linked.open...gbank/description
| - A pyrazine that is used therapeutically as an antitubercular agent. (en)
|
| http://linked.open...y/drugbank/dosage
| |
| http://linked.open...generalReferences
| - # Controlled trial of four thrice-weekly regimens and a daily regimen all given for 6 months for pulmonary tuberculosis. Lancet. 1981 Jan 24;1(8213):171-4. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/6109855 # Controlled clinical trial of 4 short-couse regimens of chemotherapy (three 6-month and one 8-month) for pulmonary tuberculosis. Tubercle. 1983 Sep;64(3):153-66. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/6356538 # A controlled trial of 6 months' chemotherapy in pulmonary tuberculosis. Final report: results during the 36 months after the end of chemotherapy and beyond. British Thoracic Society. Br J Dis Chest. 1984 Oct;78(4):330-6. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/6386028 # Yee D, Valiquette C, Pelletier M, Parisien I, Rocher I, Menzies D: Incidence of serious side effects from first-line antituberculosis drugs among patients treated for active tuberculosis. Am J Respir Crit Care Med. 2003 Jun 1;167(11):1472-7. Epub 2003 Jan 31. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/12569078 # Boshoff HI, Mizrahi V, Barry CE 3rd: Effects of pyrazinamide on fatty acid synthesis by whole mycobacterial cells and purified fatty acid synthase I. J Bacteriol. 2002 Apr;184(8):2167-72. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/11914348 # Zimhony O, Vilcheze C, Arai M, Welch JT, Jacobs WR Jr: Pyrazinoic acid and its n-propyl ester inhibit fatty acid synthase type I in replicating tubercle bacilli. Antimicrob Agents Chemother. 2007 Feb;51(2):752-4. Epub 2006 Nov 13. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/17101678 # Ngo SC, Zimhony O, Chung WJ, Sayahi H, Jacobs WR Jr, Welch JT: Inhibition of isolated Mycobacterium tuberculosis fatty acid synthase I by pyrazinamide analogs. Antimicrob Agents Chemother. 2007 Jul;51(7):2430-5. Epub 2007 May 7. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/17485499 # Shi W, Zhang X, Jiang X, Yuan H, Lee JS, Barry CE 3rd, Wang H, Zhang W, Zhang Y: Pyrazinamide inhibits trans-translation in Mycobacterium tuberculosis. Science. 2011 Sep 16;333(6049):1630-2. doi: 10.1126/science.1208813. Epub 2011 Aug 11. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/21835980 (en)
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| http://linked.open...gy/drugbank/group
| |
| http://linked.open...drugbank/halfLife
| - 9-10 hours (normal conditions) (en)
|
| http://linked.open...ugbank/indication
| - For the initial treatment of active tuberculosis in adults and children when combined with other antituberculous agents. (en)
|
| http://linked.open...bank/manufacturer
| |
| sameAs
| |
| Title
| |
| adms:identifier
| |
| http://linked.open...mechanismOfAction
| - Pyrazinamide diffuses into M. tuberculosis, where the enzyme pyrazinamidase converts pyrazinamide to the active form pyrazinoic acid. Under acidic conditions, the pyrazinoic acid that slowly leaks out converts to the protonated conjugate acid, which is thought to diffuse easily back into the bacilli and accumulate. The net effect is that more pyrazinoic acid accumulates inside the bacillus at acid pH than at neutral pH. Pyrazinoic acid was thought to inhibit the enzyme fatty acid synthase (FAS) I, which is required by the bacterium to synthesise fatty acids. However, this theory was thought to have been discounted (PMID: 11914348). However, further studies reproduced the results of FAS I inhibition as the putative mechanism first in whole cell assay of replicating M. tuberculosis bacilli which have shown that pyrazinoic acid and its ester inhibit the synthesis of fatty acids (PMID: 17101678). This study was followed by in vitro assay of tuberculous FAS I enzyme that tested the activity with pyrazinamide, pyrazinoic acid and several classes of pyrazinamide analogs. Pyrazinamide and its analogs inhibited the activity of purified FAS I (PMID: 17485499). It has also been suggested that the accumulation of pyrazinoic acid disrupts membrane potential and interferes with energy production, necessary for survival of M. tuberculosis at an acidic site of infection. Pyrazinoic acid has also been shown to bind to the ribosomal protein S1 (RpsA) and inhibit trans-translation. This may explain the ability of the drug to kill dormant mycobacteria (PMID: 21835980). (en)
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| http://linked.open...drugbank/packager
| |
| http://linked.open...outeOfElimination
| - Approximately 70% of an oral dose is excreted in the urine, mainly by glomerular filtration within 24 hours (en)
|
| http://linked.open.../drugbank/synonym
| - Pyrazinamide (en)
- Aldinamide (en)
- Pyrazineamide (en)
- Pyrazinecarboxamide (en)
- Pyrazinoic acid amide (en)
- 2-carbamylpyrazine (en)
- 2-pyrazinecarboxamide (en)
- Pirazinamida (en)
- Pirazinamide (en)
- Pyrazinamid (en)
- Pyrazinamida (en)
- Pyrazinamidum (en)
- Pyrazine carboxamide (en)
- Pyrizinamide (en)
- pyrazine-2-carboxamide (en)
|
| http://linked.open...drugbank/toxicity
| - Side effects include liver injury, arthralgias, anorexia, nausea and vomiting, dysuria,malaise and fever, sideroblastic anemia, adverse effects on the blood clotting mechanism or vascular integrity, and hypersensitivity reactions such as urticaria, pruritis and skin rashes. (en)
|
| http://linked.open.../drug/hasAHFSCode
| |
| http://linked.open...k/foodInteraction
| - Take without regard to meals. (en)
|
| http://linked.open.../drugbank/mixture
| |
| http://linked.open...nk/proteinBinding
| - ~10% (bound to plasma proteins) (en)
|
| http://linked.open...y/mesh/hasConcept
| |
| foaf:page
| |
| http://linked.open...ugbank/IUPAC-Name
| |
| http://linked.open...gy/drugbank/InChI
| |
| http://linked.open...Molecular-Formula
| |
| http://linked.open.../Molecular-Weight
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| http://linked.open...noisotopic-Weight
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| http://linked.open...y/drugbank/SMILES
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| http://linked.open.../Water-Solubility
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| http://linked.open...ogy/drugbank/logP
| |
| http://linked.open...ogy/drugbank/logS
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| http://linked.open...logy/drugbank/pKa
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| http://linked.open...l/drug/hasATCCode
| |
| http://linked.open...nd-Acceptor-Count
| |
| http://linked.open...-Bond-Donor-Count
| |
| http://linked.open...drugbank/InChIKey
| |
| http://linked.open...urface-Area--PSA-
| |
| http://linked.open...nk/Polarizability
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| http://linked.open...bank/Refractivity
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| http://linked.open...atable-Bond-Count
| |
| http://linked.open...ugbank/absorption
| - Rapidly and well absorbed from the gastrointestinal tract. (en)
|
| http://linked.open.../affectedOrganism
| - Mycobacterium tuberculosis (en)
|
| http://linked.open...casRegistryNumber
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| http://linked.open...drugbank/category
| |
| http://linked.open...gbank/containedIn
| |
| http://linked.open...k/Bioavailability
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| http://linked.open...bank/Ghose-Filter
| |
| http://linked.open...nk/MDDR-Like-Rule
| |
| http://linked.open...ank/Melting-Point
| |
| http://linked.open...k/Number-of-Rings
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| http://linked.open...siological-Charge
| |
| http://linked.open...bank/Rule-of-Five
| |
| http://linked.open...tional-IUPAC-Name
| |
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