P7136

Sigma-Aldrich

Pyrazinecarboxamide

Synonym(s):
Pyrazinamide, Pyrazinoic acid amide
Empirical Formula (Hill Notation):
C5H5N3O
CAS Number:
Molecular Weight:
123.11
Beilstein/REAXYS Number:
112306
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.85

Quality Level

mp

189-191 °C (lit.)

Mode of action

cell membrane | interferes

antibiotic activity spectrum

mycobacteria

SMILES string

NC(=O)c1cnccn1

InChI

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

InChI key

IPEHBUMCGVEMRF-UHFFFAOYSA-N

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Related Categories

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 .

Packaging

10, 25, 100 g in poly bottle

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

Other Notes

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

storage_class_code

13 - Non Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Emmanuel Chigutsa et al.
Antimicrobial agents and chemotherapy, 57(2), 789-795 (2012-11-28)
Days to positivity in automated liquid mycobacterial culture have been shown to correlate with mycobacterial load and have been proposed as a useful biomarker for treatment responses in tuberculosis. However, there is currently no quantitative method or model to analyze...
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...
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...
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...
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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