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P7136

Sigma-Aldrich

Pyrazinecarboxamide

Synonyme(s) :

Pyrazinamide, Pyrazinoic acid amide

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About This Item

Formule empirique (notation de Hill):
C5H5N3O
Numéro CAS:
98-96-4
Poids moléculaire :
123.11
Numéro Beilstein :
112306
Numéro CE :
202-717-6
Numéro MDL:
MFCD00006132
Code UNSPSC :
41116107
ID de substance PubChem :
24278648
Nomenclature NACRES :
NA.85

Forme

powder

Niveau de qualité

200

Pf

189-191 °C (lit.)

Spectre d'activité de l'antibiotique

mycobacteria

Mode d’action

cell membrane | interferes

Chaîne SMILES 

NC(=O)c1cnccn1

InChI

1S/C5H5N3O/c6-5(9)4-3-7-1-2-8-4/h1-3H,(H2,6,9)

Clé InChI

IPEHBUMCGVEMRF-UHFFFAOYSA-N

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Catégories apparentées

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 and mechanisms of resistance .

Actions biochimiques/physiologiques

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 . Pyrazinamide and its analogs have been shown to inhibit the activity of purified FAS I.

Autres remarques

Keep container tightly closed in a dry and well-ventilated place.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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Pontus Juréen et al.
Antimicrobial agents and chemotherapy, 52(5), 1852-1854 (2008-03-05)
Thirty-four pyrazinamide-resistant and 37 pyrazinamide-susceptible Mycobacterium tuberculosis complex strains were analyzed for pncA gene mutations. None of the sensitive strains had any mutations, apart from silent mutations, whereas all but one resistant strain showed pncA mutations. By using sequencing as
C Raynaud et al.
Microbiology (Reading, England), 145 ( Pt 6), 1359-1367 (1999-07-20)
Mycobacteria are known to acquire resistance to the antituberculous drug pyrazinamide (PZA) through mutations in the gene encoding pyrazinamidase (PZase), an enzyme that converts PZA into pyrazinoic acid, the presumed active form of PZA against bacteria. Additional mechanisms of resistance
S A Tasduq et al.
Human & experimental toxicology, 25(3), 111-118 (2006-04-26)
Terminalia chebula Gertn. (Combetraceae) is an important herbal drug in Ayurvedic pharmacopea. In the present study, a 95% ethanolic extract of T. chebula (fruit) (TC extract), which was chemically characterized on the basis of chebuloside II as a marker, was
Akos Somoskovi et al.
The Journal of antimicrobial chemotherapy, 53(2), 192-196 (2004-01-20)
Pyrazinamide is a paradoxical frontline tuberculosis drug characterized by high in vivo sterilizing activity but poor in vitro activity. This separation in pyrazinamide activity reflects differences between the in vivo tissue environment and in vitro culture conditions. The well-known acid
Martin J Boeree et al.
American journal of respiratory and critical care medicine, 191(9), 1058-1065 (2015-02-06)
Rifampin at a dose of 10 mg/kg was introduced in 1971 based on pharmacokinetic, toxicity, and cost considerations. Available data in mice and humans showed that an increase in dose may shorten the duration of tuberculosis treatment. To evaluate the
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