pyrazine-2-carboxamide

• ChemBase ID: 223
• Molecular Formular: C5H5N3O
• Molecular Mass: 123.1127
• Monoisotopic Mass: 123.0432618
• SMILES: O=C(N)c1nccnc1
• Canonical SMILES: NC(=O)c1cnccn1
• InChI: InChI=1S/C5H5N3O/c6-5(9)4-3-7-1-2-8-4/h1-3H,(H2,6,9)
• InChIKey: IPEHBUMCGVEMRF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: pyrazine-2-carboxamide
• IUPAC Traditional name: pyrazinamide
• Brand Name: Aldinamid; Aldinamide; Braccopiral; Corsazinmid; Dipimide; Eprazin; Farmizina; Isopas; Lynamide; Novamid; Pezetamid; Piraldina; Pirilene; Prazina; Pyrafat; Pyramide; Pyrazide; Pyrazinamide BP 2000; Rifater; Rozide; Tebrazid; Tebrazio; Unipyranamide; Zinamide; Zinastat; pms-Pyrazinamide
• Synonyms: Pirazinecarboxamide; D-50; Piraldina; Tebrazid; Zinamide; Pyrazinamide; Pyrazinecarboxamide; pyrazine-2-carboxamide; Pezetamid; Pyrafat; 2-Carbamoylpyrazine; Pyrazine-2-carboxamide 99%; Pyrazinecarboxylic acid amide; Pyrazinecarboxamide; Pyrazinoic acid amide; PZA; Pyrazineamide; Pyrazine carboxylamide; Pyrazinamdie; Pirazinamid; Pirazimida; Pyrazinamide

Database IDs

• CAS Number: 98-96-4
• EC Number: 202-717-6
• MDL Number: MFCD00006132
• Beilstein Number: 112306
• PubChem SID: 160963686; 24278648; 24887930; 46507478
• PubChem CID: 1046
• CHEBI ID: 45285
• ATC CODE: J04AK01
• CHEMBL: 614
• Chemspider ID: 1017
• DrugBank ID: DB00339
• KEGG ID: D00144
• Unique Ingredient Identifier: 2KNI5N06TI
• Wikipedia Title: Pyrazinamide
• Medline Plus: a682402

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.059009
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -1.2256087
• LogD (pH = 7.4): -1.2256075
• Log P: -1.2256085
• Molar Refractivity: 30.4506 cm^3
• Polarizability: 11.437884 Å^3
• Polar Surface Area: 68.87 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.71
• LOG S: -0.12
• Solubility (Water): 9.37e+01 g/l

PROPERTIES

Physical Property

• Solubility: 1.5E+004 mg/L; DMSO
• Apperance: White Solid
• Melting Point: 189°C; 189-191 °C; 189-191 °C(lit.); 189-191°C; 189-191°C
• Hydrophobicity(logP): -1

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• Storage Warning: Irritant
• RTECS: UQ2275000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Admin Routes: Oral
• Bioavailability: >90%
• Excretion: Renal
• Half Life: 9 to 10 hours
• Metabolism: Hepatic
• Pregnancy Category: C

Product Information

• Purity: ≥99.0% (N); 95+%
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C5H5N3O

DETAILS

MP Biomedicals - 05217986

MP Biomedicals Rare Chemical collection

DrugBank - DB00339

• Drug Groups: approved
• Description: A pyrazine that is used therapeutically as an antitubercular agent.
• Indication: For the initial treatment of active tuberculosis in adults and children when combined with other antituberculous agents.
• Pharmacology: Pyrazinamide kills or stops the growth of certain bacteria that cause tuberculosis (TB). It is used with other drugs to treat tuberculosis. It is a highly specific agent and is active only against Mycobacterium tuberculosis. In vitro and in vivo, the drug is active only at a slightly acid pH. Pyrazinamie gets activated to Pyrazinoic acid in the bacilli where it interferes with fatty acid synthase FAS I. This interferes with the bacteriums ability to synthesize new fatty acids, required for growth and replication.
• 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.
• Affected Organisms: Mycobacterium tuberculosis
• Biotransformation: Hepatic.
• Absorption: Rapidly and well absorbed from the gastrointestinal tract.
• Half Life: 9-10 hours (normal conditions)
• Protein Binding: ~10% (bound to plasma proteins)
• Elimination: Approximately 70% of an oral dose is excreted in the urine, mainly by glomerular filtration within 24 hours
• References: 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] ; 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] ; 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] ; 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]
• External Links: Wikipedia; RxList; Drugs.com

Selleck Chemicals - S1762

Research Area: Infection
Biological Activity:
Pyrazinamide (Pyrazinoic acid amide) is an agent used to treat tuberculosis. M. tuberculosis has the enzyme pyrazinamidase which is only active in acidic conditions. Pyrazinamidase converts pyrazinamide (Pyrazinoic acid amide) to the active form, pyrazinoic acid which accumulates in the bacilli. Pyrazinoic acid inhibits the enzyme fatty acid synthase (FAS) I, which is required by the bacterium to synthesise fatty acids although this has been discounted. [1]

Sigma Aldrich - P7136

包装
10, 25, 100 g in poly bottle
Application
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.
Biochem/physiol Actions
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.

Toronto Research Chemicals - P840600

Antibacterial (tuberculostatic).

REFERENCES

• 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
• 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
• 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
• 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://en.wikipedia.org/wiki/Pyrazinamide
• Weiner, I.M., et al.: J. Pharmacol. Exp. Ther., 180, 411 (1972)
• Feldner, E., et al.: Anal. Profiles Drug Subs., 12, 433 (1983)