P7136
Pyrazinecarboxamide
Synonym(s):
Pyrazinamide, Pyrazinoic acid amide
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About This Item
Empirical Formula (Hill Notation):
C5H5N3O
CAS Number:
Molecular Weight:
123.11
UNSPSC Code:
41116107
NACRES:
NA.85
PubChem Substance ID:
EC Number:
202-717-6
Beilstein/REAXYS Number:
112306
MDL number:
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InChI key
IPEHBUMCGVEMRF-UHFFFAOYSA-N
InChI
1S/C5H5N3O/c6-5(9)4-3-7-1-2-8-4/h1-3H,(H2,6,9)
SMILES string
NC(=O)c1cnccn1
form
powder
mp
189-191 °C (lit.)
antibiotic activity spectrum
mycobacteria
mode of action
cell membrane | interferes
Quality Level
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1 of 4
This Item | A76958 | P56100 | PHR1576 |
|---|---|---|---|
| antibiotic activity spectrum mycobacteria | antibiotic activity spectrum - | antibiotic activity spectrum - | antibiotic activity spectrum - |
| mode of action cell membrane | interferes | mode of action - | mode of action - | mode of action - |
| Quality Level 200 | Quality Level 200 | Quality Level 200 | Quality Level 300 |
| form powder | form crystals | form powder | form - |
| mp 189-191 °C (lit.) | mp 118-120 °C (lit.) | mp 222-225 °C (dec.) (lit.) | mp 189-191 °C (lit.) |
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].
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.
Other Notes
Keep container tightly closed in a dry and well-ventilated place.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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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
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
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
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