Pyrazinamide

Identification

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Name

Pyrazinamide

Accession Number

DB00339  (APRD01206)

Type

Small Molecule

Groups

Approved, Investigational

Description

A pyrazine that is used therapeutically as an antitubercular agent.

Structure

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Pyrazinamide (DB00339)

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Synonyms

• 2-carbamylpyrazine
• 2-pyrazinecarboxamide
• Aldinamide
• Pirazinamida
• Pirazinamide
• Pyrazinamid
• Pyrazinamida
• Pyrazinamide
• Pyrazinamidum
• Pyrazine carboxamide
• pyrazine-2-carboxamide
• Pyrazineamide
• Pyrazinecarboxamide
• Pyrazinoic acid amide
• Pyrizinamide

External IDs

D-50 / MK-56 / NSC-14911 / PZA

Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
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Tebrazid Tab 500mg	Tablet	500 mg	Oral	Valeant Canada Lp Valeant Canada S.E.C.	1973-12-31	Not applicable

Additional Data Available

Application Number
Application Number
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Product Code
Product Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
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Pdp-pyrazinamide	Tablet	500 mg	Oral	Pendopharm Division Of De Pharmascience Inc	1984-12-31	Not applicable
Pyrazinamide	Tablet	500 mg/1	Oral	VersaPharm Inc. - an Akorn Company	1995-04-01	Not applicable
Pyrazinamide	Tablet	500 mg/1	Oral	Mikart, Inc.	1992-06-30	2016-08-26
Pyrazinamide	Tablet	500 mg/1	Oral	Effcon Laboratories, Inc.	1992-06-30	1995-12-29
Pyrazinamide	Tablet	500 mg/1	Oral	American Health Packaging	2016-10-24	Not applicable
Pyrazinamide	Tablet	500 mg/1	Oral	Clinical Solutions Wholsesale	1971-06-03	2017-06-15
Pyrazinamide	Tablet	500 mg/1	Oral	Department Of State Health Services, Pharmacy Branch	1995-04-01	Not applicable
Pyrazinamide	Tablet	500 mg/1	Oral	DAVA Pharmaceuticals, Inc.	1971-06-03	Not applicable
Pyrazinamide	Tablet	500 mg/1	Oral	Major Pharmaceuticals	1971-06-03	Not applicable
Pyrazinamide	Tablet	500 mg/1	Oral	A-S Medication Solutions	1971-06-03	Not applicable

Additional Data Available

Application Number
Application Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
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Product Code
Product Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Rifater	Pyrazinamide (300 mg/1) + Isoniazid (50 mg/1) + Rifampicin (120 mg/1)	Tablet, sugar coated	Oral	sanofi-aventis U.S. LLC	1994-05-31	Not applicable
Rifater	Pyrazinamide (300 mg/1) + Isoniazid (50 mg/1) + Rifampicin (120 mg/1)	Tablet, sugar coated	Oral	Remedy Repack	2010-09-15	2010-09-16
Rifater	Pyrazinamide (300 mg) + Isoniazid (50 mg) + Rifampicin (120 mg)	Tablet	Oral	Sanofi Aventis	1995-12-31	2017-03-29

International/Other Brands

Piraldina (Bracco) / Prazina (Armoxindo) / Pyrafat (Riemser) / Pyrazide (Sanofi-Aventis) / Tebrazid (Valeant) / Tisamid (Orion)

Categories

• Anti-Bacterial Agents
• Anti-Infective Agents
• Antiinfectives for Systemic Use
• Antimycobacterials
• Antituberculosis Agents
• Cytochrome P-450 CYP3A Substrates
• Cytochrome P-450 CYP3A4 Substrates
• Cytochrome P-450 CYP3A4 Substrates (strength unknown)
• Drugs for Treatment of Tuberculosis
• Drugs that are Mainly Renally Excreted
• Pyrazines

UNII

2KNI5N06TI

CAS number

98-96-4

Weight

Average: 123.1127
Monoisotopic: 123.043261797

Chemical Formula

C₅H₅N₃O

InChI Key

IPEHBUMCGVEMRF-UHFFFAOYSA-N

InChI

InChI=1S/C5H5N3O/c6-5(9)4-3-7-1-2-8-4/h1-3H,(H2,6,9)

IUPAC Name

pyrazine-2-carboxamide

SMILES

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

Pharmacology

Indication

For the initial treatment of active tuberculosis in adults and children when combined with other antituberculous agents.

Associated Conditions

• Active Tuberculosis
• Pulmonary Tuberculosis (TB)

Pharmacodynamics

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.

Mechanism of action

Pyrazinamide diffuses into active M. tuberculosis that express pyrazinamidase enzyme that converts pyrazinamide to the active form pyrazinoic acid. Pyrazinoic acid can leak out under acidic conditions to be converted to the protonated conjugate acid, which is readily diffused back into the bacilli and accumulate intracellularly. The net effect is that more pyrazinoic acid accumulates inside the bacillus at acid pH than at neutral pH. Pyrazinoic acid was thought to inhibit the enzyme fatty acid synthase (FAS) I, which is required by the bacterium to synthesise fatty acids. However, this theory was thought to have been discounted (PMID: 11914348). However, further studies reproduced the results of FAS I inhibition as the putative mechanism first in whole cell assay of replicating M. tuberculosis bacilli which have shown that pyrazinoic acid and its ester inhibit the synthesis of fatty acids (PMID: 17101678). This study was followed by in vitro assay of tuberculous FAS I enzyme that tested the activity with pyrazinamide, pyrazinoic acid and several classes of pyrazinamide analogs. Pyrazinamide and its analogs inhibited the activity of purified FAS I (PMID: 17485499).

It has also been 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 has also been shown to bind to the ribosomal protein S1 (RpsA) and inhibit trans-translation. This may explain the ability of the drug to kill dormant mycobacteria (PMID: 21835980).

Target	Actions	Organism
AFatty acid synthetase I (FASI)	inhibitor	Mycobacterium tuberculosis

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Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

Rapidly and well absorbed from the gastrointestinal tract.

Volume of distribution

Not Available

Protein binding

~10% (bound to plasma proteins)

Metabolism

Hepatic.

• Pyrazinamide
  5-hydroxypyrazinamide

Route of elimination

Approximately 70% of an oral dose is excreted in the urine, mainly by glomerular filtration within 24 hours

Half life

9-10 hours (normal conditions)

Clearance

Not Available

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

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

• All Drugs
• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental

Drug	Interaction
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(R)-warfarin	The risk or severity of bleeding can be increased when Pyrazinamide is combined with (R)-warfarin.
(S)-Warfarin	The risk or severity of bleeding can be increased when Pyrazinamide is combined with (S)-Warfarin.
3,5-diiodothyropropionic acid	The metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Pyrazinamide.
4-hydroxycoumarin	The metabolism of 4-hydroxycoumarin can be decreased when combined with Pyrazinamide.
5-androstenedione	The metabolism of 5-androstenedione can be decreased when combined with Pyrazinamide.
6-Deoxyerythronolide B	The metabolism of Pyrazinamide can be decreased when combined with 6-Deoxyerythronolide B.
6-O-benzylguanine	The metabolism of 6-O-benzylguanine can be decreased when combined with Pyrazinamide.
7-ethyl-10-hydroxycamptothecin	The metabolism of Pyrazinamide can be decreased when combined with 7-ethyl-10-hydroxycamptothecin.
9-aminocamptothecin	The metabolism of 9-aminocamptothecin can be decreased when combined with Pyrazinamide.
Abacavir	Pyrazinamide may decrease the excretion rate of Abacavir which could result in a higher serum level.

Additional Data Available

Extended Description
Extended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
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Severity
Severity
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Evidence Level
Evidence Level
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Food Interactions

• Take without regard to meals.

References

General References

1. Authors unspecified: 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:6109855]
2. Authors unspecified: 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:6356538]
3. Authors unspecified: 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:6386028]
4. 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:12569078]
5. Boshoff HI, Mizrahi V, Barry CE 3rd: Effects of pyrazinamide on fatty acid synthesis by whole mycobacterial cells and purified fatty acid synthase I. J Bacteriol. 2002 Apr;184(8):2167-72. [PubMed:11914348]
6. Zimhony O, Vilcheze C, Arai M, Welch JT, Jacobs WR Jr: Pyrazinoic acid and its n-propyl ester inhibit fatty acid synthase type I in replicating tubercle bacilli. Antimicrob Agents Chemother. 2007 Feb;51(2):752-4. Epub 2006 Nov 13. [PubMed:17101678]
7. Ngo SC, Zimhony O, Chung WJ, Sayahi H, Jacobs WR Jr, Welch JT: Inhibition of isolated Mycobacterium tuberculosis fatty acid synthase I by pyrazinamide analogs. Antimicrob Agents Chemother. 2007 Jul;51(7):2430-5. Epub 2007 May 7. [PubMed:17485499]
8. Shi W, Zhang X, Jiang X, Yuan H, Lee JS, Barry CE 3rd, Wang H, Zhang W, Zhang Y: Pyrazinamide inhibits trans-translation in Mycobacterium tuberculosis. Science. 2011 Sep 16;333(6049):1630-2. doi: 10.1126/science.1208813. Epub 2011 Aug 11. [PubMed:21835980]

External Links

Human Metabolome Database

HMDB0014483

KEGG Drug

D00144

KEGG Compound

C01956

PubChem Compound

1046

PubChem Substance

46507478

ChemSpider

1017

BindingDB

228814

ChEBI

45285

ChEMBL

CHEMBL614

Therapeutic Targets Database

DAP000660

PharmGKB

PA451182

HET

PZA

RxList

RxList Drug Page

Drugs.com

Drugs.com Drug Page

Wikipedia

Pyrazinamide

ATC Codes

J04AK01 — Pyrazinamide

• J04AK — Other drugs for treatment of tuberculosis
• J04A — DRUGS FOR TREATMENT OF TUBERCULOSIS
• J04 — ANTIMYCOBACTERIALS
• J — ANTIINFECTIVES FOR SYSTEMIC USE

J04AM06 — Rifampicin, pyrazinamide, ethambutol and isoniazid

• J04AM — Combinations of drugs for treatment of tuberculosis
• J04A — DRUGS FOR TREATMENT OF TUBERCULOSIS
• J04 — ANTIMYCOBACTERIALS
• J — ANTIINFECTIVES FOR SYSTEMIC USE

J04AM05 — Rifampicin, pyrazinamide and isoniazid

• J04AM — Combinations of drugs for treatment of tuberculosis
• J04A — DRUGS FOR TREATMENT OF TUBERCULOSIS
• J04 — ANTIMYCOBACTERIALS
• J — ANTIINFECTIVES FOR SYSTEMIC USE

AHFS Codes

• 08:16.04 — Antituberculosis Agents

PDB Entries

3r4x / 3r55 / 5fpd

MSDS

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Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
0	Recruiting	Treatment	Osteomyelitis	1
1	Completed	Other	Tuberculosis Infection	1
1	Completed	Treatment	Healthy Volunteers	1
1	Completed	Treatment	Human Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection	1
1	Completed	Treatment	Tuberculosis Infection	3
1	Terminated	Treatment	Disseminated Neuroblastoma / Recurrent Neuroblastoma	1
1, 2	Not Yet Recruiting	Treatment	Other Specified Pulmonary Tuberculosis / Pulmonary Tuberculoses	1
1, 2	Recruiting	Treatment	Tuberculous Meningitis	1
2	Active Not Recruiting	Prevention	Cancer, Breast / Osteoporosis	1
2	Completed	Treatment	Pulmonary Tuberculosis (TB)	5
2	Completed	Treatment	Tuberculosis Infection	4
2	Recruiting	Treatment	Pulmonary Tuberculosis (TB)	1
2	Recruiting	Treatment	Tuberculosis, Multidrug Resistant	1
2	Terminated	Treatment	Human Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection	1
2	Unknown Status	Treatment	Tuberculosis Infection	1
2	Withdrawn	Treatment	Liver Cancer / Metastatic Cancers	1
2, 3	Recruiting	Treatment	Drug-resistant Tuberculosis / Extensively Drug Resistant Tuberculosis / Multi-Drug Resistant Tuberculosis / Pulmonary Tuberculosis (TB) / Tuberculosis Infection / Tuberculosis, Multidrug Resistant	1
2, 3	Recruiting	Treatment	Extensively Drug Resistant Tuberculosis / Tuberculosis Infection / Tuberculosis, Multidrug Resistant	1
2, 3	Recruiting	Treatment	Pulmonary Tuberculosis (TB)	2
3	Completed	Treatment	Acquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection	1
3	Completed	Treatment	Human Immunodeficiency Virus (HIV) Infections / Pulmonary Tuberculosis (TB)	1
3	Completed	Treatment	Human Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection	1
3	Completed	Treatment	Pulmonary Multi-Drug Resistant Tuberculosis (MDR-TB) / Tuberculosis, Pulmonary, Drug Sensitive	1
3	Completed	Treatment	Tuberculosis Infection	2
3	Recruiting	Treatment	Multi-Drug Resistant Tuberculosis	1
3	Recruiting	Treatment	Tuberculosis Infection	1
3	Recruiting	Treatment	Tuberculosis, Multidrug Resistant	1
3	Terminated	Treatment	Multiple System Atrophy (MSA)	1
3	Unknown Status	Treatment	Human Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection	1
3	Withdrawn	Treatment	Tuberculosis Multi Drug Resistant Active	1
4	Active Not Recruiting	Prevention	Human Immunodeficiency Virus Type 1 (HIV-1) Infection	1
4	Completed	Treatment	Drug Induced Hepatotoxicity / Tuberculosis Infection	1
4	Completed	Treatment	Obstructive Sleep Apnea Syndrome (OSAS)	1
4	Recruiting	Treatment	AIDS With Tuberculosis	1
4	Recruiting	Treatment	Human Immunodeficiency Virus (HIV) Infections	1
4	Recruiting	Treatment	Pulmonary Tuberculosis (TB)	1
4	Recruiting	Treatment	Tuberculosis, Spinal	1
4	Unknown Status	Treatment	Hepatitis / Pulmonary Tuberculosis (TB)	1
4	Unknown Status	Treatment	Reinfection Pulmonary Tuberculosis	1
Not Available	Completed	Prevention	Human Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection	1
Not Available	Completed	Supportive Care	Body Weight Changes / Motor Activities / Pulmonary Tuberculosis (TB)	1
Not Available	Completed	Treatment	Human Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection	3
Not Available	Completed	Treatment	Tuberculosis Infection	1
Not Available	Recruiting	Not Available	Tuberculosis Infection	1
Not Available	Recruiting	Treatment	Acquired Immune Deficiency Syndrome (AIDS) / Pulmonary Tuberculosis (TB)	1
Not Available	Unknown Status	Not Available	Pulmonary Tuberculosis (TB)	1

Pharmacoeconomics

Manufacturers

• Dava pharmaceuticals inc
• Mikart inc

Packagers

• Amerisource Health Services Corp.
• A-S Medication Solutions LLC
• Belgomex Sprl
• Cardinal Health
• Comprehensive Consultant Services Inc.
• DAVA Pharmaceuticals
• Dept Health Central Pharmacy
• Mikart Inc.
• Murfreesboro Pharmaceutical Nursing Supply
• PCA LLC
• PD-Rx Pharmaceuticals Inc.
• Physicians Total Care Inc.
• Prescript Pharmaceuticals
• Remedy Repack
• Sanofi-Aventis Inc.
• Versapharm Inc.
• West-Ward Pharmaceuticals

Dosage forms

Form	Route	Strength
Tablet	Oral	500 mg
Tablet	Oral	500 mg/1
Tablet	Oral
Tablet, sugar coated	Oral

Prices

Unit description	Cost	Unit
Rifater tablet	3.1USD	tablet
Pyrazinamide 500 mg tablet	1.26USD	tablet

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	192 °C	PhysProp
water solubility	1.5E+004 mg/L (at 25 °C)	MERCK INDEX (1996)
logP	-0.60	HANSCH,C ET AL. (1995)
logS	-0.91	ADME Research, USCD
pKa	-0.5	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	93.7 mg/mL	ALOGPS
logP	-0.71	ALOGPS
logP	-1.2	ChemAxon
logS	-0.12	ALOGPS
pKa (Strongest Acidic)	13.06	ChemAxon
pKa (Strongest Basic)	-0.68	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	68.87 Å2	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	30.45 m3·mol-1	ChemAxon
Polarizability	11.13 Å3	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET features

Property	Value	Probability
Human Intestinal Absorption	+	0.9813
Blood Brain Barrier	+	0.9745
Caco-2 permeable	+	0.7222
P-glycoprotein substrate	Non-substrate	0.8219
P-glycoprotein inhibitor I	Non-inhibitor	0.9709
P-glycoprotein inhibitor II	Non-inhibitor	0.9971
Renal organic cation transporter	Non-inhibitor	0.8985
CYP450 2C9 substrate	Non-substrate	0.8861
CYP450 2D6 substrate	Non-substrate	0.876
CYP450 3A4 substrate	Non-substrate	0.7754
CYP450 1A2 substrate	Non-inhibitor	0.8791
CYP450 2C9 inhibitor	Non-inhibitor	0.9545
CYP450 2D6 inhibitor	Non-inhibitor	0.9731
CYP450 2C19 inhibitor	Non-inhibitor	0.9547
CYP450 3A4 inhibitor	Non-inhibitor	0.9697
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.9353
Ames test	Non AMES toxic	0.9133
Carcinogenicity	Non-carcinogens	0.9321
Biodegradation	Not ready biodegradable	0.9602
Rat acute toxicity	1.8145 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9939
hERG inhibition (predictor II)	Non-inhibitor	0.9617

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

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Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash10-0ab9-1900000000-d29284f74cafc89d62ad
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash10-001i-9200000000-f1f9853e24fa676ffa99
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash10-001j-9000000000-7be5ab1fa895dc272521
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash10-000t-9000000000-9c4235602fdfd2d2cdeb
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash10-014i-3009000000-ab4d0160c375af6d52ee
1H NMR Spectrum	1D NMR	Not Applicable
13C NMR Spectrum	1D NMR	Not Applicable

Taxonomy

Description

This compound belongs to the class of organic compounds known as pyrazines. These are compounds containing a pyrazine ring, which is a six-member aromatic heterocycle, that consists of two nitrogen atoms (at positions 1 and 4) and four carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrazines

Direct Parent

Pyrazines

Alternative Parents

Heteroaromatic compounds / Carboximidic acids / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds / Hydrocarbon derivatives

Substituents

Pyrazine / Heteroaromatic compound / Azacycle / Carboximidic acid derivative / Carboximidic acid / Organic nitrogen compound / Organic oxygen compound / Organopnictogen compound / Hydrocarbon derivative / Organooxygen compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyrazines, monocarboxylic acid amide (CHEBI:45285) / a carboxamide (PYRAZINAMIDE)

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Drug created on June 13, 2005 07:24 / Updated on August 24, 2019 06:27