pyrazinamide

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

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].

Name	pyrazinecarboxamide
Synonym	More Synonyms

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	Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> Anti-infection >> Bacterial Research Areas >> Infection
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.

Description

Related Catalog

Signaling Pathways >> Autophagy >> Autophagy

Signaling Pathways >> Anti-infection >> Bacterial

Research Areas >> Infection

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.

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

pyrazinamide MSDS(Chinese)

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)

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

Precursor 10
CAS#:19847-12-2 Pyrazinecarbonitrile CAS#:19847-10-0 2-pyrazinecarbo... CAS#:306990-94-3 (1H-benzo[d][1,... CAS#:109-08-0 methylpyrazine
CAS#:64-17-5 Ethanol CAS#:123-32-0 2,5-Dimethylpyrazine CAS#:98-97-5 Pyrazine-2-carb... CAS#:6164-79-0 Methyl 2-pyrazi...
CAS#:290-37-9 Pyrazine CAS#:77287-34-4 (Z)-Methanimidi...
DownStream 10
CAS#:100828-16-8 (+/-)-2-HYDROXY... CAS#:4604-72-2 2-Pyrazinecarbo... CAS#:31321-68-3 2-Piperazinecar... CAS#:6863-74-7 6-chloropyrazin...
CAS#:36070-75-4 5-Chloro-2-pyra... CAS#:55557-52-3 3-Chlorpyrazin-... CAS#:59489-39-3 2-Amino-6-cyano... CAS#:147425-80-7 5-benzoylpyrazi...
CAS#:5049-61-6 Aminopyrazine CAS#:98-97-5 Pyrazine-2-carb...

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

Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.

Chem. Res. Toxicol. 23 , 171-83, (2010)

Drug-induced liver injury is one of the main causes of drug attrition. The ability to predict the liver effects of drug candidates from their chemical structures is critical to help guide experimental...

Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).

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Drug-induced liver injury (DILI) is a significant concern in drug development due to the poor concordance between preclinical and clinical findings of liver toxicity. We hypothesized that the DILI typ...

Developing structure-activity relationships for the prediction of hepatotoxicity.

Chem. Res. Toxicol. 23 , 1215-22, (2010)

Drug-induced liver injury is a major issue of concern and has led to the withdrawal of a significant number of marketed drugs. An understanding of structure-activity relationships (SARs) of chemicals ...

5-25-04-00178 (Beilstein Handbook Reference)

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pyrazinamide

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