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98-96-4 molecular structure
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pyrazine-2-carboxamide

ChemBase ID: 223
Molecular Formular: C5H5N3O
Molecular Mass: 123.1127
Monoisotopic Mass: 123.0432618
SMILES and InChIs

SMILES:
O=C(N)c1nccnc1
Canonical SMILES:
NC(=O)c1cnccn1
InChI:
InChI=1S/C5H5N3O/c6-5(9)4-3-7-1-2-8-4/h1-3H,(H2,6,9)
InChIKey:
IPEHBUMCGVEMRF-UHFFFAOYSA-N

Cite this record

CBID:223 http://www.chembase.cn/molecule-223.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
pyrazine-2-carboxamide
IUPAC Traditional name
pyrazinamide
Brand Name
Aldinamid
Aldinamide
Braccopiral
Corsazinmid
Dipimide
Eprazin
Farmizina
Isopas
Lynamide
Novamid
Pezetamid
Piraldina
Pirilene
Prazina
Pyrafat
Pyramide
Pyrazide
Pyrazinamide BP 2000
Rifater
Rozide
Tebrazid
Tebrazio
Unipyranamide
Zinamide
Zinastat
pms-Pyrazinamide
Synonyms
Pirazinecarboxamide
D-50
Piraldina
Tebrazid
Zinamide
Pyrazinamide
Pyrazinecarboxamide
pyrazine-2-carboxamide
Pezetamid
Pyrafat
2-Carbamoylpyrazine
Pyrazine-2-carboxamide 99%
Pyrazinecarboxylic acid amide
Pyrazinecarboxamide
Pyrazinoic acid amide
PZA
Pyrazineamide
Pyrazine carboxylamide
Pyrazinamdie
Pirazinamid
Pirazimida
Pyrazinamide
CAS Number
98-96-4
EC Number
202-717-6
MDL Number
MFCD00006132
Beilstein Number
112306
PubChem SID
160963686
46507478
24887930
24278648
PubChem CID
1046
CHEBI ID
45285
ATC CODE
J04AK01
CHEMBL
614
Chemspider ID
1017
DrugBank ID
DB00339
KEGG ID
D00144
Unique Ingredient Identifier
2KNI5N06TI
Wikipedia Title
Pyrazinamide
Medline Plus
a682402

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 13.059009  H Acceptors
H Donor LogD (pH = 5.5) -1.2256087 
LogD (pH = 7.4) -1.2256075  Log P -1.2256085 
Molar Refractivity 30.4506 cm3 Polarizability 11.437884 Å3
Polar Surface Area 68.87 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P -0.71  LOG S -0.12 
Solubility (Water) 9.37e+01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
1.5E+004 mg/L expand Show data source
DMSO expand Show data source
Apperance
White Solid expand Show data source
Melting Point
189°C expand Show data source
189-191 °C expand Show data source
189-191 °C(lit.) expand Show data source
189-191°C expand Show data source
189-191°C expand Show data source
Hydrophobicity(logP)
-1 expand Show data source
Storage Condition
-20°C expand Show data source
-20°C Freezer expand Show data source
Storage Warning
Irritant expand Show data source
RTECS
UQ2275000 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Admin Routes
Oral expand Show data source
Bioavailability
>90% expand Show data source
Excretion
Renal expand Show data source
Half Life
9 to 10 hours expand Show data source
Metabolism
Hepatic expand Show data source
Pregnancy Category
C expand Show data source
Purity
≥99.0% (N) expand Show data source
95+% expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Empirical Formula (Hill Notation)
C5H5N3O expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Selleck Chemicals Selleck Chemicals Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals - 05217986 external link
MP Biomedicals Rare Chemical collection
DrugBank - DB00339 external link
Item Information
Drug Groups approved
Description A pyrazine that is used therapeutically as an antitubercular agent.
Indication For the initial treatment of active tuberculosis in adults and children when combined with other antituberculous agents.
Pharmacology Pyrazinamide kills or stops the growth of certain bacteria that cause tuberculosis (TB). It is used with other drugs to treat tuberculosis. It is a highly specific agent and is active only against Mycobacterium tuberculosis. In vitro and in vivo, the drug is active only at a slightly acid pH. Pyrazinamie gets activated to Pyrazinoic acid in the bacilli where it interferes with fatty acid synthase FAS I. This interferes with the bacteriums ability to synthesize new fatty acids, required for growth and replication.
Toxicity Side effects include liver injury, arthralgias, anorexia, nausea and vomiting, dysuria,malaise and fever, sideroblastic anemia, adverse effects on the blood clotting mechanism or vascular integrity, and hypersensitivity reactions such as urticaria, pruritis and skin rashes.
Affected Organisms
Mycobacterium tuberculosis
Biotransformation Hepatic.
Absorption Rapidly and well absorbed from the gastrointestinal tract.
Half Life 9-10 hours (normal conditions)
Protein Binding ~10% (bound to plasma proteins)
Elimination Approximately 70% of an oral dose is excreted in the urine, mainly by glomerular filtration within 24 hours
References
Controlled trial of four thrice-weekly regimens and a daily regimen all given for 6 months for pulmonary tuberculosis. Lancet. 1981 Jan 24;1(8213):171-4. [Pubmed]
Controlled clinical trial of 4 short-couse regimens of chemotherapy (three 6-month and one 8-month) for pulmonary tuberculosis. Tubercle. 1983 Sep;64(3):153-66. [Pubmed]
A controlled trial of 6 months' chemotherapy in pulmonary tuberculosis. Final report: results during the 36 months after the end of chemotherapy and beyond. British Thoracic Society. Br J Dis Chest. 1984 Oct;78(4):330-6. [Pubmed]
Yee D, Valiquette C, Pelletier M, Parisien I, Rocher I, Menzies D: Incidence of serious side effects from first-line antituberculosis drugs among patients treated for active tuberculosis. Am J Respir Crit Care Med. 2003 Jun 1;167(11):1472-7. Epub 2003 Jan 31. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com
Selleck Chemicals - S1762 external link
Research Area: Infection
Biological Activity:
Pyrazinamide (Pyrazinoic acid amide) is an agent used to treat tuberculosis. M. tuberculosis has the enzyme pyrazinamidase which is only active in acidic conditions. Pyrazinamidase converts pyrazinamide (Pyrazinoic acid amide) to the active form, pyrazinoic acid which accumulates in the bacilli. Pyrazinoic acid inhibits the enzyme fatty acid synthase (FAS) I, which is required by the bacterium to synthesise fatty acids although this has been discounted. [1]
Sigma Aldrich - P7136 external link
包装
10, 25, 100 g in poly bottle
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.
Pyrazinamide is used to form polymeric copper complexes, create pyrazine carboxamide scaffolds useful as FXs inhibitors, and as a component of mycobacteria identification kits.
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.
Toronto Research Chemicals - P840600 external link
Antibacterial (tuberculostatic).

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Controlled trial of four thrice-weekly regimens and a daily regimen all given for 6 months for pulmonary tuberculosis. Lancet. 1981 Jan 24;1(8213):171-4. Pubmed
  • • Controlled clinical trial of 4 short-couse regimens of chemotherapy (three 6-month and one 8-month) for pulmonary tuberculosis. Tubercle. 1983 Sep;64(3):153-66. Pubmed
  • • A controlled trial of 6 months' chemotherapy in pulmonary tuberculosis. Final report: results during the 36 months after the end of chemotherapy and beyond. British Thoracic Society. Br J Dis Chest. 1984 Oct;78(4):330-6. Pubmed
  • • Yee D, Valiquette C, Pelletier M, Parisien I, Rocher I, Menzies D: Incidence of serious side effects from first-line antituberculosis drugs among patients treated for active tuberculosis. Am J Respir Crit Care Med. 2003 Jun 1;167(11):1472-7. Epub 2003 Jan 31. Pubmed
  • •  http://en.wikipedia.org/wiki/Pyrazinamide
  • • Weiner, I.M., et al.: J. Pharmacol. Exp. Ther., 180, 411 (1972)
  • • Feldner, E., et al.: Anal. Profiles Drug Subs., 12, 433 (1983)
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PATENTS

PATENTS

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INTERNET

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