PYRAZINAMIDE

First approved in 1955

Details

Stereochemistry	ACHIRAL
Molecular Formula	C5H5N3O
Molecular Weight	123.1127
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC(=O)C1=CN=CC=N1

InChI

InChIKey=IPEHBUMCGVEMRF-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C5H5N3O
Molecular Weight	123.1127
Charge	0
Count

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

Description
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=257bd8cf-74d7-45db-bf25-354a8d26634e
Curator's Comment: description was created based on several sources, including: http://www.drugbank.ca/drugs/DB00339 https://en.wikipedia.org/wiki/Pyrazinamide

Pyrazinamide is indicated for the initial treatment of active tuberculosis in adults and children when combined with other antituberculous agents. (The current recommendation of the CDC for drug-susceptible disease is to use a six-month regimen for initial treatment of active tuberculosis, consisting of isoniazid, rifampin and pyrazinamide given for 2 months, followed by isoniazid and rifampin for 4 months. Pyrazinamide should only be used in conjunction with other effective antituberculous agents. Pyrazinamide diffuses into M. tuberculosis, where the enzyme pyrazinamidase converts pyrazinamide to the active form pyrazinoic acid. Under acidic conditions, the pyrazinoic acid that slowly leaks out converts to the protonated conjugate acid, which is thought to diffuse easily back into the bacilli and accumulate. 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. 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 . 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. 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

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Fatty acid synthase 6 Target ID: CHEMBL2011 Sources: http://www.drugbank.ca/drugs/DB00339	Inhibitor 8504
70S ribosome 16 Target ID: CHEMBL2363965 Sources: http://www.ncbi.nlm.nih.gov/pubmed/?term=21835980	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Tuberculosis 83 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=257bd8cf-74d7-45db-bf25-354a8d26634e	Curative		Approved 8583	PYRAZINAMIDE Approved Use Pyrazinamide Launch Date 1971

C_max

Value	Dose	Co-administered	Analyte	Population
38.2 mg/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/23629715	27.8 mg/kg bw 3 times / day steady-state, oral dose: 27.8 mg/kg bw route of administration: Oral experiment type: STEADY-STATE co-administered: Isoniazid \| Rifampicin \| Ethambutol	Isoniazid \| Rifampicin \| Ethambutol	PYRAZINAMIDE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
38.7 mg/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2737233	27 mg/kg bw single, oral dose: 27 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered:		PYRAZINAMIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
344 mg × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/23629715	27.8 mg/kg bw 3 times / day steady-state, oral dose: 27.8 mg/kg bw route of administration: Oral experiment type: STEADY-STATE co-administered: Isoniazid \| Rifampicin \| Ethambutol	Isoniazid \| Rifampicin \| Ethambutol	PYRAZINAMIDE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
520 mg × h/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2737233	27 mg/kg bw single, oral dose: 27 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered:		PYRAZINAMIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
5.5 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/23629715	27.8 mg/kg bw 3 times / day steady-state, oral dose: 27.8 mg/kg bw route of administration: Oral experiment type: STEADY-STATE co-administered: Isoniazid \| Rifampicin \| Ethambutol	Isoniazid \| Rifampicin \| Ethambutol	PYRAZINAMIDE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
1500 mg 1 times / day multiple, oral Recommended Dose: 1500 mg, 1 times / day Route: oral Route: multiple Dose: 1500 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8139647	healthy Health Status: healthy Sources: https://pubmed.ncbi.nlm.nih.gov/8139647	Disc. AE: Arthralgia, Distress gastrointestinal... AEs leading to discontinuation/dose reduction: Arthralgia (43.75%) Distress gastrointestinal (37.5%) Pruritus (25%) Fatigue (25%) Generalized maculopapular rash (18.8%) Insomnia (18.8%) Vertigo (12.5%) Sources: https://pubmed.ncbi.nlm.nih.gov/8139647
20 mg/kg 1 times / day multiple, oral Recommended Dose: 20 mg/kg, 1 times / day Route: oral Route: multiple Dose: 20 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12379063	unhealthy Health Status: unhealthy Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/12379063	Disc. AE: Hepatotoxicity... AEs leading to discontinuation/dose reduction: Hepatotoxicity (5.8%) Sources: https://pubmed.ncbi.nlm.nih.gov/12379063
30 mg/kg 1 times / day multiple, oral Recommended Dose: 30 mg/kg, 1 times / day Route: oral Route: multiple Dose: 30 mg/kg, 1 times / day Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=257bd8cf-74d7-45db-bf25-354a8d26634e&type=display#LINK_5b1b9b20-2ad0-4c1c-b6cb-e086db370aff	unhealthy Health Status: unhealthy Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=257bd8cf-74d7-45db-bf25-354a8d26634e&type=display#LINK_5b1b9b20-2ad0-4c1c-b6cb-e086db370aff	Disc. AE: Hepatotoxicity... AEs leading to discontinuation/dose reduction: Hepatotoxicity Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=257bd8cf-74d7-45db-bf25-354a8d26634e&type=display#LINK_5b1b9b20-2ad0-4c1c-b6cb-e086db370aff

AEs

AE	Significance	Dose	Population
Vertigo	12.5% Disc. AE	1500 mg 1 times / day multiple, oral Recommended Dose: 1500 mg, 1 times / day Route: oral Route: multiple Dose: 1500 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8139647	healthy Health Status: healthy Sources: https://pubmed.ncbi.nlm.nih.gov/8139647
Generalized maculopapular rash	18.8% Disc. AE	1500 mg 1 times / day multiple, oral Recommended Dose: 1500 mg, 1 times / day Route: oral Route: multiple Dose: 1500 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8139647	healthy Health Status: healthy Sources: https://pubmed.ncbi.nlm.nih.gov/8139647
Insomnia	18.8% Disc. AE	1500 mg 1 times / day multiple, oral Recommended Dose: 1500 mg, 1 times / day Route: oral Route: multiple Dose: 1500 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8139647	healthy Health Status: healthy Sources: https://pubmed.ncbi.nlm.nih.gov/8139647
Fatigue	25% Disc. AE	1500 mg 1 times / day multiple, oral Recommended Dose: 1500 mg, 1 times / day Route: oral Route: multiple Dose: 1500 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8139647	healthy Health Status: healthy Sources: https://pubmed.ncbi.nlm.nih.gov/8139647
Pruritus	25% Disc. AE	1500 mg 1 times / day multiple, oral Recommended Dose: 1500 mg, 1 times / day Route: oral Route: multiple Dose: 1500 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8139647	healthy Health Status: healthy Sources: https://pubmed.ncbi.nlm.nih.gov/8139647
Distress gastrointestinal	37.5% Disc. AE	1500 mg 1 times / day multiple, oral Recommended Dose: 1500 mg, 1 times / day Route: oral Route: multiple Dose: 1500 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8139647	healthy Health Status: healthy Sources: https://pubmed.ncbi.nlm.nih.gov/8139647
Arthralgia	43.75% Disc. AE	1500 mg 1 times / day multiple, oral Recommended Dose: 1500 mg, 1 times / day Route: oral Route: multiple Dose: 1500 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8139647	healthy Health Status: healthy Sources: https://pubmed.ncbi.nlm.nih.gov/8139647
Hepatotoxicity	5.8% Disc. AE	20 mg/kg 1 times / day multiple, oral Recommended Dose: 20 mg/kg, 1 times / day Route: oral Route: multiple Dose: 20 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12379063	unhealthy Health Status: unhealthy Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/12379063
Hepatotoxicity	Disc. AE	30 mg/kg 1 times / day multiple, oral Recommended Dose: 30 mg/kg, 1 times / day Route: oral Route: multiple Dose: 30 mg/kg, 1 times / day Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=257bd8cf-74d7-45db-bf25-354a8d26634e&type=display#LINK_5b1b9b20-2ad0-4c1c-b6cb-e086db370aff	unhealthy Health Status: unhealthy Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=257bd8cf-74d7-45db-bf25-354a8d26634e&type=display#LINK_5b1b9b20-2ad0-4c1c-b6cb-e086db370aff

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
	inhibitor 2438	inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP3A 227 CYP2B6 926 CYP2C8 1057 CYP2C19 2057 CYP2E1 1060

Drug as perpetrator

Target	Modality	Activity
CYP1A2 2333	inhibitor 4027 Sources: https://dmd.aspetjournals.org/content/early/2017/06/26/dmd.117.076034	no
CYP2B6 1160	inhibitor 4027 Sources: https://dmd.aspetjournals.org/content/early/2017/06/26/dmd.117.076034	no
CYP2C19 2141	inhibitor 4027 Sources: https://dmd.aspetjournals.org/content/early/2017/06/26/dmd.117.076034	no
CYP2C8 1117	inhibitor 4027 Sources: https://dmd.aspetjournals.org/content/early/2017/06/26/dmd.117.076034	no
CYP2C9 2497	inhibitor 4027 Sources: https://dmd.aspetjournals.org/content/early/2017/06/26/dmd.117.076034	no
CYP2D6 2546	inhibitor 4027 Sources: https://dmd.aspetjournals.org/content/early/2017/06/26/dmd.117.076034	no
CYP2E1 1146	inhibitor 4027 Sources: https://dmd.aspetjournals.org/content/early/2017/06/26/dmd.117.076034	no
CYP3A 317	inhibitor 4027 Sources: https://dmd.aspetjournals.org/content/early/2017/06/26/dmd.117.076034	no

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY427375	https://www.001chemical.com/chem/4238-71-5
001 Chemical	NO13379	https://www.001chemical.com/chem/98-96-4
3B Scientific (Wuhan) Corp	3B1-00092	http://www.3bsc.com/index/pro_info.php?id=20304
AA Blocks	AA003TZ0	https://www.aablocks.com/goods/Goods/detail?id=AA003TZ0
Aaron Chemicals	AR003UQS	http://www.aaronchem.com/98-96-4
abcr GmbH	AB251460	http://www.abcr.com/shop/en/AB251460
AbMole Bioscience	M3299	http://www.abmole.com/products/pyrazinamide.html
Acadechem	ACDS-028210	http://www.acadechemical.com/product/102909
Accela ChemBio Inc	SY013550	http://www.accelachem.com/cn/search.html?keyword=SY013550&attname=GoodsCode
Achemica	ACMC-20aive	http://www.achemica.com/prodinfo/?id=132042
Achemo Scientific Limited	AC-76823	http://www.achemo.com/search/?Keyword= 98-96-4
Achemtek	0104-015515	http://www.achemtek.com/98-96-4
Acorn PharmaTech	ACN-038145	http://www.acornpharmatech.com/
Acros Organics	AC157640100	https://www.fishersci.com/shop/products/pyrazinamide-99-acros-organics/AC157640100
Acros Organics	AC157640250	https://www.fishersci.com/shop/products/pyrazinamide-99-acros-organics/AC157640250
Acros Organics	AC157641000	https://www.fishersci.com/shop/products/pyrazinamide-99-acros-organics/AC157641000
AK Scientific, Inc. (AKSCI)	265049	http://www.aksci.com/item_detail.php?cat=265049
AK Scientific, Inc. (AKSCI)	J10111	http://www.aksci.com/item_detail.php?cat=J10111
Alfa Chemistry	AP98964	https://reagents.alfa-chemistry.com/product/pyrazinamide-cas-98-96-4-19142.html
Alichem	99001189	http://www.alichem.com/en/products/98-96-4.html
Alsachim	2529	http://www.alsachim.com/product-C3602-glo.bal-view.html
Ambinter	Amb22166847	http://www.ambinter.com/reference/22166847
Angene	AGN-PC-07Q1HT	http://www.angenechemical.com/productshow/AGN-PC-07Q1HT.html
Anward	ANW-75384	http://www.anward.com/pro_result/61835
ApexBio Technology	B2122	http://www.apexbt.com/pyrazinamide.html
Ark Pharm	AK-94813	http://www.arkpharminc.com/products/98-96-4.html
Aurora Fine Chemicals LLC	A00.157.180	http://online.aurorafinechemicals.com/info?ID=A00.157.180
Aurora Fine Chemicals LLC	K01.795.399	http://online.aurorafinechemicals.com/info?ID=K01.795.399
Aurum Pharmatech LLC	M-7421	http://www.Aurumpharmatech.com/Product/ProductDetails/M_7421
BioChemPartner	BCP30257	http://www.biochempartner.com/98-96-4-BCP30257
BioCrick	BCC4932	http://www.biocrick.com/Pyrazinamide-BCC4932.html
BioSynth	W-100059	https://www.biosynth.com/en/products/chemical-intermediates/basic-intermediates/products/W-100059.html
BLD Pharm	BD17175	http://www.bldpharm.com/products/98-96-4.html
BOC Sciences	1246817-81-1	https://isotope.bocsci.com/product/pyrazine-d3-carboxamide-15n-cas-1246817-81-1-345056.html
Chem Scene	CS-2260	http://www.chemscene.com/98-96-4.html
Chemenu	CM110203	http://www.chemenu.com/products/CM110203
ChemMol	44010831	http://www.chemmol.com/chemmol/44010831.html
Chemspace	CSSB00000162229	https://chem-space.com/CSSB00000162229
Clearsynth	CS-O-00733	https://www.clearsynth.com/en/CSO00733.html
CSNpharm	CSN12465	https://www.csnpharm.com/products/pyrazinamide.html
DC Chemicals	DCAPI1405	http://www.dcchemicals.com//product_show-Pyrazinamide_Pyrazinoic_acid_amide_.html
Debye Scientific	DB-002866	http://www.debyesci.com/DB-002866.html
Enamine	Z33546644	https://www.enaminestore.com/catalog/Z33546644
Finetech	FT-0659757	http://www.finetechnology-ind.com/prod/detail/pub/98-96-4.html
Glentham Life Sciences	GA1140	http://www.glentham.com/products/product/GA1140/
Hairui	HR134410	http://www.hairuichem.com/en/product/98-96-4.html
Huateng Pharma	F80006455	http://en.huatengsci.com/product/Pyrazinamide.html
iChemical	EBD430	http://www.ichemical.com/products/98-96-4.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
Lab Network	LN00185010	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00185010
LGC Standards	DRE-C16608000	https://www.lgcstandards.com/US/en/p/DRE-C16608000
LGC Standards	LGCFOR0385.00	https://www.lgcstandards.com/US/en/p/LGCFOR0385.00
LGC Standards	MM0385.00	https://www.lgcstandards.com/US/en/p/MM0385.00
Matrix Scientific	85417	https://www.matrixscientific.com/085417.html
mcule	MCULE-6846697749	https://mcule.com/MCULE-6846697749/
MedChem Express	HY-B0271	https://www.medchemexpress.com/pyrazinamide.html
Molcore	CS13379	https://www.molcore.com/product/98-96-4
Molcore	MC427375	https://www.molcore.com/product/4238-71-5
MuseChem	A000469	https://www.musechem.com/product/A000469.html
Oakwood	68696	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=58015&ExtHyperLink=1
Otava	1375193	https://search.otavachemicals.com/#!/search?query=1375193&type=code&base=dbb
Sigma-Aldrich	1585006_USP	https://www.sigmaaldrich.com/catalog/product/usp/1585006?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	40751_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/40751?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	BP906_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/bp906?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	P4050000_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/p4050000?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	P7136_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/p7136?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sinfoo Biotech	S012553	http://www.sinfoobiotech.com/product/1015951
Smolecule	S540690	http://www.smolecule.com/products/s540690
Smolecule	S793272	https://www.smolecule.com/products/s793272
TCI (Tokyo Chemical Industry)	P0633	http://www.tcichemicals.com/eshop/en/us/commodity/P0633/index.html
THE BioTek	bt-280889	https://www.thebiotek.com/product/inhibitors/bt-280889
Vitas-M Laboratory	BBL010592	http://www.request.vitasmlab.biz/index.php?option=com_search_stk&Itemid=22&stk=BBL010592&?utm_source=pubchem&utm_medium=p_search_link&utm_campaign=pubchem_search&utm_content=pubchem_slink
VladaChem	VL120458	https://www.vladachem.com/product.php?products=98-96-4
VladaChem	VL276551-100G	https://www.vladachem.com/product.php?products=98-96-4

PubMed

Title	Date	PubMed
Tuberculoma of the conus medullaris: case report.	2002-03	11841737
Treatment of childhood tuberculosis with a six month directly observed regimen of only two weeks of daily therapy.	2002-02	11840073
Tuberculosis presenting as immune thrombocytopenic purpura.	2002-02	11836186
Liquid chromatographic determination of isoniazid, pyrazinamide and rifampicin from pharmaceutical preparations and blood.	2002-01-25	11829003
Therapeutic isoniazid monitoring using a simple high-performance liquid chromatographic method with ultraviolet detection.	2002-01-05	11820293
Pulmonary tuberculosis in Kumasi, Ghana: presentation, drug resistance, molecular epidemiology and outcome of treatment.	2002-01-05	11768026
Conditions that may affect the results of susceptibility testing of Mycobacterium tuberculosis to pyrazinamide.	2002-01	11800471
Susceptibility testing of Mycobacterium tuberculosis to pyrazinamide.	2002-01	11800467
High rates of tuberculosis in end-stage renal failure: the impact of international migration.	2002-01	11749753
Surveillance for antimicrobial resistance in Croatia.	2002-01	11749742
Rapidly progressive glomerulonephritis due to rifampicin therapy.	2002-01	11744817
Can serial qualitative polymerase chain reaction monitoring predict outcome of pulmonary tuberculosis treatment?	2001-12	11844121
[Treatment outcomes of multidrug-resistant tuberculosis--comparison between success and failure cases].	2001-12	11806128
Isonicotinic acid hydrazide induced anagen effluvium and associated lichenoid eruption.	2001-12	11804071
Pyrazinamide use as a method of estimating under-reporting of tuberculosis.	2001-12	11769775
Side effects of antituberculosis treatment.	2001-12	11758512
Postantibiotic effects of antituberculosis agents alone and in combination.	2001-12	11709357
Crystal structure and mechanism of catalysis of a pyrazinamidase from Pyrococcus horikoshii.	2001-11-27	11714269
Pattern of some haematological indices in newly diagnosed pulmonary tuberculosis cases in Iwo, Nigeria: diagnostic and therapeutic implications.	2001-11-14	11705048
Duration of efficacy of treatment of latent tuberculosis infection in HIV-infected adults.	2001-11-09	11684933
Antimycobacterial plant terpenoids.	2001-11	11731906
Pyrazinamide induced photoallergy.	2001-11	11716347
Tuberculous meningitis: is a 6-month treatment regimen sufficient?	2001-11	11716339
Tuberculosis infection in Chinese patients undergoing continuous ambulatory peritoneal dialysis.	2001-11	11684559
Rapamycin and less immunosuppressive analogs are toxic to Candida albicans and Cryptococcus neoformans via FKBP12-dependent inhibition of TOR.	2001-11	11600372
Tuberculosis and HIV infection: epidemiology, immunology, and treatment.	2001-10-09	11590540
Antitubercular drugs (isoniazid, rifampin and pyrazinamide): hepatobiliary reactions.	2001-10-02	11599338
Hepatotoxicity from rifampin plus pyrazinamide: lessons for policymakers and messages for care providers.	2001-10-01	11673194
[Orchiectomy for tuberculous epididymitis: a report of two cases with intractable to antituberculosis treatment].	2001-10	11712389
Characterization of pncA mutations of pyrazinamide-resistant Mycobacterium tuberculosis in Korea.	2001-10	11641519
Characterisation of the pncA gene in Mycobacterium tuberculosis isolates from Gauteng, South Africa.	2001-10	11605890
Treatment of tuberculosis in Haiti.	2001-10	11574298
From the Centers for Disease Control and Prevention. Update: Fatal and severe liver injuries associated with Rifampin and Pyrazinamide for latent tuberculosis infection, and revisions in American Thoracic Society/CDC recommendations--United States, 2001.	2001-09-26	11596606
Tuberculosis: guidelines changed for latent TB treatment.	2001-09-21	11668976
[Multiple intracranial tuberculomas in infancy].	2001-09-20	11562860
[Functional role of the red nucleus in the cerebral cortex-cerebellum-spinal cord communication system].	2001-09-11	11548591
US guidelines for treatment of latent tuberculosis revised.	2001-09-08	11564495
[Vesical uric acid lithiasis in a child with renal hypouricemia].	2001-09	11676906
Safety of an ofloxacin-based antitubercular regimen for the treatment of tuberculosis in patients with underlying chronic liver disease: a preliminary report.	2001-09	11595068
Intramedullary tuberculoma of the conus medullaris: case report and review of the literature.	2001-09	11571663
Modulating effect of Liv.100, an ayurvedic formulation on antituberculosis drug-induced alterations in rat liver microsomes.	2001-09	11536379
Update: Fatal and severe liver injuries associated with rifampin and pyrazinamide for latent tuberculosis infection, and revisions in American Thoracic Society/CDC recommendations--United States, 2001.	2001-08-31	11787580
Renal handling of uric acid assessed by means of pharmacological tests in obese women.	2001-08	11716287
Rifampicin allergy confirmed by an intradermal test, but with a negative patch test.	2001-08	11553123
Reintroducing antituberculosis therapy after Stevens-Johnson syndrome in human immunodeficiency virus-infected patients with tuberculosis: role of desensitization.	2001-07	11679013
Pancreatic mass caused by Mycobacterium tuberculosis with reduced drug sensitivity.	2001-04	11545552
New mutations in pncA of in vitro selected pyrazinamide-resistant strains of Mycobacterium tuberculosis.	2001	11759083
Serial counts of Mycobacterium tuberculosis in sputum as surrogate markers of the sterilising activity of rifampicin and pyrazinamide in treating pulmonary tuberculosis.	2001	11737875
The molecular basis of resistance to isoniazid, rifampin, and pyrazinamide in Mycobacterium tuberculosis.	2001	11686881
[Effectiveness of chemotherapy of intrathoracic tuberculosis in children: late follow-up data].	2001	11588952

Patents

Sample Use Guides

In Vivo Use Guide

15 to 30 mg/kg once daily

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:55:42 GMT 2025` Edited by `admin` on `Mon Mar 31 17:55:42 GMT 2025`
Record UNII	2KNI5N06TI
Record Status	`Validated (UNII)`
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Name

Type

Language

PYRAZINAMIDE

Official Name

English

RIFATER COMPONENT PYRAZINAMIDE

Preferred Name

English

PYRAZINAMIDE [USP-RS]

Common Name

English

D-50

Code

English

PYRAZIDE

Common Name

English

PYRAZINAMIDE [MART.]

Common Name

English

PYRAZINAMIDE [HSDB]

Common Name

English

PYRAZINAMIDE [USP MONOGRAPH]

Common Name

English

PYRAFAT

Common Name

English

PYRAMIZADE

Common Name

English

PIRAZINAMID

Common Name

English

PYRAZINAMIDE [MI]

Common Name

English

Pyrazinecarboxamide

Systematic Name

English

PYRAZINAMIDE [JAN]

Common Name

English

ZINAMIDE

Common Name

English

ALDINAMID

Common Name

English

NOVAMID

Common Name

English

PYRAZINAMIDE [VANDF]

Common Name

English

ALDINAMIDE

Common Name

English

PYRAZINAMIDE [USP IMPURITY]

Common Name

English

FARMIZINA

Common Name

English

NSC-14911

Code

English

pyrazinamide [INN]

Common Name

English

PYRAZINAMIDE [ORANGE BOOK]

Common Name

English

UNIPYRANAMIDE

Common Name

English

PIRAZIMIDA

Common Name

English

PYRAZINAMIDUM [WHO-IP LATIN]

Common Name

English

PYRAZINAMIDE [EP MONOGRAPH]

Common Name

English

MK-56

Code

English

PYRAZINE CARBOXYLAMIDE

Common Name

English

.ALPHA.-PYRAZINAMIDE

Common Name

English

ISOPAS

Common Name

English

PYRAZINAMIDE [WHO-IP]

Common Name

English

ROZIDE

Common Name

English

TEBRAZID

Common Name

English

Pyrazinamide [WHO-DD]

Common Name

English

EPRAZIN

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C280