pyrazinamide

Modify Date: 2024-01-02 10:41:32

pyrazinamide Structure
pyrazinamide structure
Common Name pyrazinamide
CAS Number 98-96-4 Molecular Weight 123.113
Density 1.4±0.1 g/cm3 Boiling Point 273.3±43.0 °C at 760 mmHg
Molecular Formula C5H5N3O Melting Point 189-191 °C(lit.)
MSDS Chinese USA Flash Point 119.1±28.2 °C

 Use of pyrazinamide


Pyrazinamide is a pyrazine that is used therapeutically as an antitubercular agent.Target: AntibacterialPyrazinamide is a prodrug that stops the growth of Mycobacterium tuberculosis. Pyrazinoic acid was thought to inhibit the enzyme fatty acid synthase (FAS) I, which is required by the bacterium to synthesise fatty acids although this has been discounted. It was also 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 binds to the ribosomal protein S1 (RpsA) and inhibits trans-translation. This may explain the ability of the drug to kill dormant mycobacteria [1-4].

 Names

Name pyrazinecarboxamide
Synonym More Synonyms

 pyrazinamide Biological Activity

Description Pyrazinamide is a pyrazine that is used therapeutically as an antitubercular agent.Target: AntibacterialPyrazinamide is a prodrug that stops the growth of Mycobacterium tuberculosis. Pyrazinoic acid was thought to inhibit the enzyme fatty acid synthase (FAS) I, which is required by the bacterium to synthesise fatty acids although this has been discounted. It was also 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 binds to the ribosomal protein S1 (RpsA) and inhibits trans-translation. This may explain the ability of the drug to kill dormant mycobacteria [1-4].
Related Catalog
References

[1]. Zhang, Y. and D. Mitchison, The curious characteristics of pyrazinamide: a review. Int J Tuberc Lung Dis, 2003. 7(1): p. 6-21.

[2]. Zimhony, O., et al., Pyrazinamide inhibits the eukaryotic-like fatty acid synthetase I (FASI) of Mycobacterium tuberculosis. Nat Med, 2000. 6(9): p. 1043-7.

[3]. Boshoff, H.I., V. Mizrahi, and C.E. Barry, 3rd, Effects of pyrazinamide on fatty acid synthesis by whole mycobacterial cells and purified fatty acid synthase I. J Bacteriol, 2002. 184(8): p. 2167-72.

[4]. Shi, W., et al., Pyrazinamide inhibits trans-translation in Mycobacterium tuberculosis. Science, 2011. 333(6049): p. 1630-2.

 Chemical & Physical Properties

Density 1.4±0.1 g/cm3
Boiling Point 273.3±43.0 °C at 760 mmHg
Melting Point 189-191 °C(lit.)
Molecular Formula C5H5N3O
Molecular Weight 123.113
Flash Point 119.1±28.2 °C
Exact Mass 123.043259
PSA 68.87000
LogP -0.83
Vapour Pressure 0.0±0.6 mmHg at 25°C
Index of Refraction 1.648
Storage condition -20°C Freezer
Water Solubility 15 mg/mL

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
UQ2275000
CHEMICAL NAME :
Pyrazinecarboxamide
CAS REGISTRY NUMBER :
98-96-4
BEILSTEIN REFERENCE NO. :
0112306
LAST UPDATED :
199806
DATA ITEMS CITED :
16
MOLECULAR FORMULA :
C5-H5-N3-O
MOLECULAR WEIGHT :
123.13
WISWESSER LINE NOTATION :
T6N DNJ BVZ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
10 mg/kg
TOXIC EFFECTS :
Vascular - BP elevation not characterized in autonomic section
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
3 gm/kg
TOXIC EFFECTS :
Behavioral - excitement Behavioral - ataxia
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
3 gm/kg
TOXIC EFFECTS :
Behavioral - excitement Behavioral - ataxia
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1680 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
2973 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
90 gm/kg/90D-I
TOXIC EFFECTS :
Liver - hepatitis (hepatocellular necrosis), zonal
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
328 gm/kg/78W-C
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Blood - lymphoma, including Hodgkin's disease
TYPE OF TEST :
TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
756 gm/kg/30W-C
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Lungs, Thorax, or Respiration - tumors
TYPE OF TEST :
Mutation test systems - not otherwise specified
TYPE OF TEST :
Cytogenetic analysis

MUTATION DATA

TEST SYSTEM :
Rodent - mouse
DOSE/DURATION :
500 mg/kg
REFERENCE :
MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 321,1,1994 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X6080 No. of Facilities: 7 (estimated) No. of Industries: 1 No. of Occupations: 2 No. of Employees: 307 (estimated) No. of Female Employees: 251 (estimated)

 Safety Information

Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes F: Flammable;C: Corrosive;
Risk Phrases R11
Safety Phrases S22-S24/25
RIDADR NONH for all modes of transport
WGK Germany 3
RTECS UQ2275000
HS Code 2933599090

 Synthetic Route

 Customs

HS Code 2934999090
Summary 2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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 Synonyms

5-25-04-00178 (Beilstein Handbook Reference)
Pyrafat
2-Pyrazinecarboxamide
2-(Aminocarbonyl)pyrazine
pyrazinamide
Aldinamide
Zinamide
a-Pyrazinamide
pyrazinoic acid amide
Tebrazid
Aldinamid
MFCD00006132
pyrazinecarboxylic acid amide
Pyrazinecarboxamide
EINECS 202-717-6
Rifater
Pyrazinamide (TN)
pyrazine-2-carboxamide
pyrazine-2-carboxylic acid amide
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