Skip to main content
Free research Free research Free compound review with research home and workspace preview
Quick search ChEMBL 36
Compound Detail

CHEMBL614

PYRAZINAMIDE
💊 Approved Drug
Enter ChEMBL ID:
Free Research Context This compound will appear in recent viewed items on the research home for this browser.
Research home View demo workspace
💊 Approved Drug
NC(=O)c1cnccn1

Basic Information

ChEMBL ID CHEMBL614
Name PYRAZINAMIDE
Phase Approved
Structure Type MOL
InChI Key IPEHBUMCGVEMRF-UHFFFAOYSA-N
Therapeutic ✓ Yes
Active Moiety CHEMBL613

Known Names

.alpha.-pyrazinamide Aldinamid Aldinamide D-50 Eprazin Farmizina Isopas MK-56 Novamid NSC-14911 Pirazimida Pirazinamid +13 more
1
Targets
9
Activities
3
Assay Types
30
PK Parameters
20
Publications
25
Known Names
8
Indications
2
Mechanisms

Molecular Properties

123.1
MW (Da)
-0.42
ALogP
3
HBA
1
HBD
68.9
PSA (Ų)
0.55
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1971
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Natural Product Prodrug

Extended Properties

Molecular Formula C5H5N3O
MW 123.11
Aromatic Rings 1
Heavy Atoms 9
NP-Likeness -1.41

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Fatty acid synthase inhibitor INHIBITOR Fatty acid synthase
70S ribosome inhibitor INHIBITOR 70S ribosome

Indications

Tuberculosis Tuberculosis, Pulmonary Meningitis Tuberculosis, Multidrug-Resistant Tuberculosis, Multidrug-Resistant Acquired Immunodeficiency Syndrome HIV Infections Osteomyelitis

ATC Classification

J04AK01
pyrazinamide
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIMYCOBACTERIALS

Activity Summary

IC50 6 meas.
Ki 2 meas. best 4.39
Kd 1 meas. best 4.16

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
Ki 4.39 4.39 41000.0 1
Unchecked
CHEMBL612545
Kd 4.16 4.16 70000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 514500.0 ng.hr.mL-1 Homo sapiens
AUC 472800.0 ng.hr.mL-1 Homo sapiens
AUC 0.5 hr Mus musculus
AUC 409000.0 ng.hr.mL-1 Homo sapiens
AUC 468000.0 ng.hr.mL-1 Homo sapiens
AUC 31.82 - Cavia porcellus
AUC 2189200.0 ng.hr.mL-1 Homo sapiens
AUC 2267000.0 ng.hr.mL-1 Homo sapiens
AUC 2162000.0 ng.hr.mL-1 Homo sapiens
CL 4.11 L/hr Homo sapiens
CL 3.97 L/hr Homo sapiens
CL 4.16 L/hr Homo sapiens
CL 1.667 mL.min-1.kg-1 Mycobacterium tuberculosis H37Rv
Cmax 373649.58 nM Homo sapiens
Cmax 355779.38 nM Homo sapiens
Cmax 513362.03 nM Mus musculus
Cmax 481926.73 nM Homo sapiens
Cmax 369588.17 nM Homo sapiens
Cmax 381772.4 nM Homo sapiens
Cmax 164080.9 nM Homo sapiens
Cmax 274551.21 nM Homo sapiens
Cmax 548290.15 nM Homo sapiens
Ka 3.45 /hr Mycobacterium tuberculosis H37Rv
T1/2 6.6 hr Homo sapiens
T1/2 6.9 hr Homo sapiens
T1/2 1.1 hr Mus musculus
Tmax 2.5 hr Homo sapiens
Tmax 2.75 hr Homo sapiens
Tmax 197.0 ug.hr/ml Mus musculus
Tmax 1.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 270
18316515 10.1128/aac.00110-08 Mycobacterium tuberculosis 31
33826327 10.1021/acs.jmedchem.0c01833 Mycobacterium tuberculosis 27
1560435 10.1021/jm00085a007 Mycobacterium tuberculosis 19
20439617 10.1128/aac.01567-09 Homo sapiens 18
20876380 10.1128/aac.00529-10 Mycolicibacterium smegmatis 17
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
20876380 10.1128/aac.00529-10 Nicotinamidase/pyrazinamidase 13
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
17132069 10.1371/journal.pmed.0030466 Mus musculus 11
20439617 10.1128/aac.01567-09 Serum 9
17452486 10.1128/aac.01550-06 Homo sapiens 8
25740159 10.1016/j.bmcl.2015.02.013 No relevant target 8
20038625 10.1128/aac.00447-09 Homo sapiens 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
19704125 10.1128/aac.00643-09 Mycobacterium tuberculosis 7
19765866 10.1016/j.ejmech.2009.08.009 J774 6
21855181 10.1016/j.ejmech.2011.07.052 Mycobacterium kansasii 6
- 10.1007/s00044-010-9405-3 HepG2 6
20713679 10.1128/aac.00661-10 Mycobacterium tuberculosis 6

Data from ChEMBL 36 via Core Engine