PYRAZINOIC ACID

Details

Stereochemistry	ACHIRAL
Molecular Formula	C5H4N2O2
Molecular Weight	124.0975
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)C1=NC=CN=C1

InChI

InChIKey=NIPZZXUFJPQHNH-UHFFFAOYSA-N

InChI=1S/C5H4N2O2/c8-5(9)4-3-6-1-2-7-4/h1-3H,(H,8,9)

HIDE SMILES / InChI

Molecular Formula	C5H4N2O2
Molecular Weight	124.0975
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

PubMed

Title	Date	PubMed
Substituted pyrazinecarboxamides: synthesis and biological evaluation.	2006 Mar 29	17962755
Substituted N-phenylpyrazine-2-carboxamides, their synthesis and evaluation as herbicides and abiotic elicitors.	2007 Dec 20	18259145
Structural determination of hypnosin, a spore germination inhibitor of phytopathogenic Streptomyces sp. causing root tumor in melon (Cucumis sp.).	2007 Dec 26	18052243
2'-(3-Hydroxy-benzyl-idene)pyrazine-2-carbohydrazide monohydrate.	2007 Dec 6	21200959
Dibromidobis(pyrazine-2-carboxylic acid-κN)mercury(II) dihydrate.	2007 Dec 6	21200487
Magnetic properties and molecular structures of binuclear (2-pyrazinecarboxylate)-bridged complexes containing Re(IV) and M(II) (M = Co, Ni).	2007 Jan 21	17200754
Discovery of pyrazine carboxamide CB1 antagonists: the introduction of a hydroxyl group improves the pharmaceutical properties and in vivo efficacy of the series.	2007 Jul 15	17513109
Mechanistic implications of the active species involved in the oxidation of hydrocarbons by iron complexes of pyrazine-2-carboxylic acid.	2008 Apr 21	18382780
Characterization of Mycobacterium tuberculosis nicotinamidase/pyrazinamidase.	2008 Feb	18201201
Interpretation of the multiple vanadium-oxygen bonds in the central VO(eta2-O2)+ group. Synthesis, structure, supramolecular interactions and DFT studies for complexes with 2,2'-bipyridine, 1,10-phenanthroline, pyrazinato(1-) and pyrazinamide ligands.	2008 Jan 7	18399238
Medical management of genitourinary tuberculosis.	2008 Jul	19468470
4-Carboxy-pyridazin-1-ium chloride.	2008 Jul 19	21203256
Silymarin protects liver against toxic effects of anti-tuberculosis drugs in experimental animals.	2008 Jul 5	18601745
Identification of a new urate and high affinity nicotinate transporter, hOAT10 (SLC22A13).	2008 Jun 13	18411268
Diaqua-bis(pyrazine-2-carboxyl-ato-κN,O)manganese(II) dihydrate.	2008 Mar 14	21202014
Vibrational spectroscopic studies and ab initio calculations of a substituted amide of pyrazine-2-carboxylic acid--C12H10ClN3O.	2008 Nov 15	18353710
Metal and mixed-metal coordination polymers synthesized with pyrazine-2-carboxylate.	2008 Nov 21	19082035
Suppression of blood lipid concentrations by volatile Maillard reaction products.	2008 Nov-Dec	18586457
Plasma urate level is directly regulated by a voltage-driven urate efflux transporter URATv1 (SLC2A9) in humans.	2008 Oct 3	18701466
Synthesis and structures of a new series of silver-vanadate hybrid solids and their optical and photocatalytic properties.	2008 Sep 15	18698760
Poly[diaqua(μ(2)-oxalato-κO,O:O,O)(μ(2)-pyrazine-2-carboxyl-ato-κN,O:O')cerium(III)].	2008 Sep 20	21201029
Protective effects of coffee-derived compounds on lipopolysaccharide/D-galactosamine induced acute liver injury in rats.	2009 Apr	19298694
Interpreting expression data with metabolic flux models: predicting Mycobacterium tuberculosis mycolic acid production.	2009 Aug	19714220
Poly[diaqua-(μ(2)-oxalato-κO,O:O,O)(μ(2)-pyrazine-2-carboxyl-ato-κN,O:O,O')neodymium(III)].	2009 Aug 12	21577423
Poly[bis-(μ(2)-pyrazine-2-carboxyl-ato)-κN,O:O';κN,O:O-cadmium(II)].	2009 Dec 24	21579983
What lies behind serum urate concentration? Insights from genetic and genomic studies.	2009 Dec 29	20090896
Ligand-based modification of the structures and optical properties of new silver(I)-rhenate(VII) oxide/organic hybrid solids.	2009 Dec 7	19886642
Poly[hexa-aqua-bis(μ(3)-terephthalato)(μ(2)-terephthalato)diytterbium(III)].	2009 Dec 9	21579932
Genome-wide analysis of the PreA/PreB (QseB/QseC) regulon of Salmonella enterica serovar Typhimurium.	2009 Feb 23	19236707
Derivatives of pyrazinecarboxylic acid: 1H, 13C and 15N NMR spectroscopic investigations.	2009 Jul	19402051
Lipophilic pyrazinoic acid amide and ester prodrugs stability, activation and activity against M. tuberculosis.	2009 Jun 28	19491013
The identification of orally bioavailable thrombopoietin agonists.	2009 Mar 1	19186055
A polymorph of diaqua-bis(pyrazine-2-carboxyl-ato-κN,O)copper(II).	2009 Nov 4	21578560
Tetra-ethyl-ammonium tricarbonyl-chlorido-(pyrazine-2-carboxyl-ato-N,O)rhenate(I).	2009 Oct 17	21578139
Substituted N-Phenylpyrazine-2-carboxamides: synthesis and antimycobacterial evaluation.	2009 Oct 20	19924056
Combined Mössbauer spectral and density functional theory determination of the magnetic easy-axis in two high-spin iron(II) 2-pyrazinecarboxylate complexes.	2009 Sep 7	19630378
Mutations found in the pncA gene of Mycobacterium tuberculosis in clinical pyrazinamide-resistant isolates from a local region of China.	2009 Sep-Oct	19930847
Epidemiology of gout.	2010	21205285
Poly[aqua-(μ-pyrazine-2-carboxyl-ato-κN,O:O)(μ-pyrazine-2-carboxyl-ato-κN,O:O')lead(II)].	2010 Apr 17	21579020
Photoluminescent lanthanide-organic bilayer networks with 2,3-pyrazinedicarboxylate and oxalate.	2010 Apr 5	20225832
Synthesis and anti-mycobacterial evaluation of some pyrazine-2-carboxylic acid hydrazide derivatives.	2010 Aug	20488590
Surveillance of pyrazinamide susceptibility among multidrug-resistant Mycobacterium tuberculosis isolates from Siriraj Hospital, Thailand.	2010 Aug 20	20727143
A series of transition metal-azido extended complexes with various anionic and neutral co-ligands: synthesis, structure and their distinct magnetic behavior.	2010 Aug 28	20623057
Antimicrobial Susceptibility Testing of Mycobacterium bovis Isolates from Michigan White-Tailed Deer during the 2009 Hunting Season.	2010 Dec 2	21151656
Poly[di-μ-aqua-μ(4)-(pyrazine-2,5-dicarboxyl-ato)-dilithium(I)].	2010 Dec 8	21522570
QSAR modeling of a set of pyrazinoate esters as antituberculosis prodrugs.	2010 Feb	20099263
Xanthine oxidase inhibition by allopurinol increases in vitro pyrazinamide-induced hepatotoxicity in HepG2 cells.	2010 Jul	20429806
Peruvian and globally reported amino acid substitutions on the Mycobacterium tuberculosis pyrazinamidase suggest a conserved pattern of mutations associated to pyrazinamide resistance.	2010 Mar	19963078
The near future: improving the activity of rifamycins and pyrazinamide.	2010 May	20382083
Reductive degradation of pyrazine-2-carboxylate by a newly isolated Stenotrophomonas sp. HCU1.	2010 Sep	20217461

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:56:00 GMT 2025` Edited by `admin` on `Mon Mar 31 19:56:00 GMT 2025`
Record UNII	2WB23298SP
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PYRAZINOIC ACID

Systematic Name

English

NSC-13146

Preferred Name

English

2-PYRAZINECARBOXYLIC ACID

Systematic Name

English

PYRAZINOIC ACID [MI]

Common Name

English

PYRAZINAMIDE RELATED COMPOUND A [USP-RS]

Common Name

English

Code System Code Type Description

RS_ITEM_NUM

1585017