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
The molecular basis of resistance to isoniazid, rifampin, and pyrazinamide in Mycobacterium tuberculosis.	2001	11686881
pncA mutations in clinical Mycobacterium tuberculosis isolates from Korea.	2001	11429043
Anion-directed crystallization of coordination polymers: syntheses and characterization of Cu(4)(2-pzc)(4)(H(2)O)(8)(Mo(8)O(26)).2H(2)O and Cu(3)(2-pzc)(4)(H(2)O)(2)(V(10)O(28)H(4)).6.5H(2)O (2-pzc = 2-pyrazinecarboxylate).	2001 Mar 12	11300846
Growth-promoting activity of pyrazinoic acid, a putative active compound of antituberculosis drug pyrazinamide, in niacin-deficient rats through the inhibition of ACMSD activity.	2002 Jul	12224625
Escherichia coli genes involved in resistance to pyrazinoic acid, the active component of the tuberculosis drug pyrazinamide.	2002 Jun 4	12076823
Augmentation of H2 photoproduction in Rhodopseudomonas palustris by N-heterocyclic aromatic compounds.	2003 Jan	12882311
Mode of action of pyrazinamide: disruption of Mycobacterium tuberculosis membrane transport and energetics by pyrazinoic acid.	2003 Nov	14563891
Self-assembly of diorganotin(IV) moieties and 2-pyrazinecarboxylic acid: syntheses, characterizations and crystal structures of monomeric, polymeric or trinuclear macrocyclic compounds.	2004 Jun 21	15381988
Hydrothermal syntheses and structures of two mixed-valence copper(I,II) 2-pyrazinecarboxylate coordination polymers.	2005 May 30	15907123
Structural origin of chirality and properties of a remarkable helically pillared solid.	2005 Sep 19	16156604
A density functional theory study of the mechanism of free radical generation in the system vanadate/PCA/H2O2.	2005 Sep 29	16853308
Renal urate transport.	2006 May	16716882
pncA mutations in pyrazinamide-resistant Mycobacterium tuberculosis clinical isolates from the southeast region of Brazil.	2006 Nov	16971417
Dibromidobis(pyrazine-2-carboxylic acid-κN)mercury(II) dihydrate.	2007 Dec 6	21200487
Pyrazinoic acid and its n-propyl ester inhibit fatty acid synthase type I in replicating tubercle bacilli.	2007 Feb	17101678
Concentration-dependent mode of interaction of angiotensin II receptor blockers with uric acid transporter.	2007 Jan	17043154
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
Characterization of Mycobacterium tuberculosis nicotinamidase/pyrazinamidase.	2008 Feb	18201201
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
Suppression of blood lipid concentrations by volatile Maillard reaction products.	2008 Nov-Dec	18586457
Interpreting expression data with metabolic flux models: predicting Mycobacterium tuberculosis mycolic acid production.	2009 Aug	19714220
Ligand-based modification of the structures and optical properties of new silver(I)-rhenate(VII) oxide/organic hybrid solids.	2009 Dec 7	19886642
Genome-wide analysis of the PreA/PreB (QseB/QseC) regulon of Salmonella enterica serovar Typhimurium.	2009 Feb 23	19236707
Epidemiology of gout.	2010	21205285
Photoluminescent lanthanide-organic bilayer networks with 2,3-pyrazinedicarboxylate and oxalate.	2010 Apr 5	20225832
Surveillance of pyrazinamide susceptibility among multidrug-resistant Mycobacterium tuberculosis isolates from Siriraj Hospital, Thailand.	2010 Aug 20	20727143
Poly[di-μ-aqua-μ(4)-(pyrazine-2,5-dicarboxyl-ato)-dilithium(I)].	2010 Dec 8	21522570
Molecular epidemiological study of pyrazinamide-resistance in clinical isolates of mycobacterium tuberculosis from South India.	2010 Jul 7	20717529
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 `Fri Dec 15 19:45:27 GMT 2023` Edited by `admin` on `Fri Dec 15 19:45:27 GMT 2023`
Record UNII	2WB23298SP
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PYRAZINOIC ACID

Systematic Name

English

2-PYRAZINECARBOXYLIC ACID

Systematic Name

English

NSC-13146

Code

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