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pyrazinamide 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
	2328	98-96-4

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: pyrazinecarboxamide pyrazinamide 2-pyrazinecarboxamide pyramizade alpha-pyrazinamide zinamide	A pyrazine that is used therapeutically as an antitubercular agent. Molecular weight: 123.12 Formula: C5H5N3O CLOGP: -0.68 LIPINSKI: 0 HAC: 4 HDO: 1 TPSA: 68.87 ALOGS: -0.12 ROTB: 1 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

pyrazinecarboxamide
pyrazinamide
2-pyrazinecarboxamide
pyramizade
alpha-pyrazinamide
zinamide

A pyrazine that is used therapeutically as an antitubercular agent.

Molecular weight: 123.12
Formula: C5H5N3O
CLOGP: -0.68
LIPINSKI: 0
HAC: 4
HDO: 1
TPSA: 68.87
ALOGS: -0.12
ROTB: 1

Status: OFP

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

Dose	Unit	Route
1.50	g	O

ADMET properties:

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Property	Value	Reference
BA (Bioavailability)	90 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
MRTD (Maximum Recommended Therapeutic Daily Dose)	243.67 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
S (Water solubility)	15 mg/mL	Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine)	1.60 %	Benet LZ, Broccatelli F, Oprea TI
BDDCS (Biopharmaceutical Drug Disposition Classification System)	1	Benet LZ, Broccatelli F, Oprea TI

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Approvals:

Date	Agency	Company	Orphan
June 3, 1971	FDA	DAVA PHARMS INC

FDA Adverse Event Reporting System (Female)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Drug reaction with eosinophilia and systemic symptoms	774.94	24.33	260	9154	33576	63446032
Paradoxical drug reaction	519.37	24.33	121	9293	4031	63475577
Drug-induced liver injury	403.55	24.33	169	9245	40053	63439555
Acute hepatic failure	376.40	24.33	130	9284	18197	63461411
Drug resistance	340.63	24.33	128	9286	22805	63456803
Tuberculoma of central nervous system	273.58	24.33	47	9367	300	63479308
Hepatotoxicity	219.76	24.33	108	9306	36933	63442675
Immune reconstitution inflammatory syndrome	218.44	24.33	66	9348	6018	63473590
Hepatitis	206.62	24.33	106	9308	39682	63439926
Immune reconstitution inflammatory syndrome associated tuberculosis	204.14	24.33	37	9377	333	63479275

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FDA Adverse Event Reporting System (Male)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Paradoxical drug reaction	915.43	20.48	215	11631	3136	34941949
Immune reconstitution inflammatory syndrome	506.09	20.48	166	11680	8593	34936492
Drug-induced liver injury	442.62	20.48	209	11637	28623	34916462
Drug reaction with eosinophilia and systemic symptoms	424.57	20.48	212	11634	32800	34912285
Hepatotoxicity	327.23	20.48	155	11691	21330	34923755
Immune reconstitution inflammatory syndrome associated tuberculosis	268.15	20.48	55	11791	403	34944682
Drug resistance	243.30	20.48	135	11711	25792	34919293
Jaundice	217.38	20.48	135	11711	31747	34913338
Tuberculosis	171.92	20.48	75	11771	8502	34936583
Tuberculoma of central nervous system	168.11	20.48	34	11812	230	34944855

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FDA Adverse Event Reporting System (Geriatric)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Paradoxical drug reaction	1361.61	18.97	326	20383	6859	79716820
Drug reaction with eosinophilia and systemic symptoms	1134.15	18.97	474	20235	63770	79659909
Drug-induced liver injury	752.43	18.97	359	20350	65758	79657921
Immune reconstitution inflammatory syndrome	710.55	18.97	225	20484	13616	79710063
Hepatotoxicity	536.04	18.97	263	20446	51089	79672590
Drug resistance	528.45	18.97	245	20464	41968	79681711
Immune reconstitution inflammatory syndrome associated tuberculosis	471.00	18.97	93	20616	743	79722936
Acute hepatic failure	457.04	18.97	200	20509	29913	79693766
Tuberculoma of central nervous system	390.17	18.97	75	20634	512	79723167
Jaundice	367.51	18.97	207	20502	53142	79670537

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	J04AK01	ANTIINFECTIVES FOR SYSTEMIC USE ANTIMYCOBACTERIALS DRUGS FOR TREATMENT OF TUBERCULOSIS Other drugs for treatment of tuberculosis
ATC	J04AM05	ANTIINFECTIVES FOR SYSTEMIC USE ANTIMYCOBACTERIALS DRUGS FOR TREATMENT OF TUBERCULOSIS Combinations of drugs for treatment of tuberculosis
ATC	J04AM06	ANTIINFECTIVES FOR SYSTEMIC USE ANTIMYCOBACTERIALS DRUGS FOR TREATMENT OF TUBERCULOSIS Combinations of drugs for treatment of tuberculosis
CHEBI has role	CHEBI:33231	antitubercular agents
CHEBI has role	CHEBI:50266	Prodrugs
FDA EPC	N0000175483	Antimycobacterial
MeSH PA	D000900	Anti-Bacterial Agents
MeSH PA	D000890	Anti-Infective Agents
MeSH PA	D000995	Antitubercular Agents

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Drug Use | Suggest Off label Use Form| |View source of the data|

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Disease	Relation	SNOMED_ID	DOID
Acute tuberculosis	indication	25629007
Tuberculosis of meninges	indication	58437007
Pulmonary tuberculosis	indication	154283005	DOID:2957
Nutritional disorder	contraindication	2492009	DOID:374
Alcoholism	contraindication	7200002
Jaundice	contraindication	18165001
Acute hepatitis	contraindication	37871000
Acute nephropathy	contraindication	58574008
Hepatic failure	contraindication	59927004
Diabetes mellitus	contraindication	73211009	DOID:9351

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🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	11.39	acidic
pKa2	2.14	Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Cytochrome P450 3A4	Enzyme	P08684	CP3A4_HUMAN		IC50	6.89	WOMBAT-PK
Carbonic anhydrase 2	Enzyme	P00918	CAH2_HUMAN		IC50	5.77	WOMBAT-PK
Cytochrome P450 3A5	Enzyme	P20815	CP3A5_HUMAN		IC50	4.89	WOMBAT-PK
3-oxoacyl-ACP synthase; Fatty acid synthase Fas; Probable fatty acid synthase Fas (Fatty acid synthetase)	Enzyme		P95029_MYCTU	INHIBITOR			CHEMBL	CHEMBL
Cyclopropane mycolic acid synthase 1	Enzyme		CMAS1_MYCTO				WOMBAT-PK
Amidase; Nicotinamidase; Nicotinamidase/pyrazinamidase; Pyrazinamidase; Pyrazinamidase/nicotinamidase; Pyrazinamidase/nicotinamidase PncA	Enzyme		Q50575_MYCTX				WOMBAT-PK

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External reference:

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ID	Source
PZA	PDB_CHEM_ID
002849	NDDF
1046	PUBCHEM_CID
13592004	SNOMEDCT_US
2368	MMSL
2KNI5N06TI	UNII
387076005	SNOMEDCT_US
4017915	VUID
4017915	VANDF
5390	MMSL

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Pyrazinamide	HUMAN PRESCRIPTION DRUG LABEL	1	0904-6696	TABLET	500 mg	ORAL	ANDA	21 sections
PYRAZINAMIDE	HUMAN PRESCRIPTION DRUG LABEL	1	10135-735	TABLET	500 mg	ORAL	ANDA	22 sections
Pyrazinamide	Human Prescription Drug Label	1	33342-447	TABLET	500 mg	ORAL	ANDA	21 sections
Pyrazinamide	Human Prescription Drug Label	1	33342-447	TABLET	500 mg	ORAL	ANDA	21 sections
Pyrazinamide	HUMAN PRESCRIPTION DRUG LABEL	1	50090-0520	TABLET	500 mg	ORAL	ANDA	22 sections
Pyrazinamide	HUMAN PRESCRIPTION DRUG LABEL	1	50090-0520	TABLET	500 mg	ORAL	ANDA	22 sections
Pyrazinamide	HUMAN PRESCRIPTION DRUG LABEL	1	50090-0521	TABLET	500 mg	ORAL	ANDA	21 sections
Pyrazinamide	Human Prescription Drug Label	1	50090-5963	TABLET	500 mg	ORAL	ANDA	21 sections
Pyrazinamide	HUMAN PRESCRIPTION DRUG LABEL	1	55695-026	TABLET	500 mg	ORAL	ANDA	22 sections
Pyrazinamide	HUMAN PRESCRIPTION DRUG LABEL	1	61748-012	TABLET	500 mg	ORAL	ANDA	22 sections

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