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Compound Detail

CHEMBL1542

AZATHIOPRINE
💊 Approved Drug
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💊 Approved Drug
Cn1cnc([N+](=O)[O-])c1Sc1ncnc2[nH]cnc12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1542
Name AZATHIOPRINE
Phase Approved
Structure Type MOL
InChI Key LMEKQMALGUDUQG-UHFFFAOYSA-N
Therapeutic ✓ Yes
Active Moiety CHEMBL1237125

Known Names

Azamune Azapress Azasan Azathioprine Azathioprinum Azatioprina Berkaprine BW-57-322 Immunoprin 50 Imuran Jayempi Kentaprine +2 more
4
Targets
15
Activities
2
Assay Types
30
PK Parameters
20
Publications
14
Known Names
20
Indications
2
Mechanisms

Molecular Properties

277.3
MW (Da)
1.15
ALogP
8
HBA
1
HBD
115.4
PSA (Ų)
0.43
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1968
Availability Prescription
Chirality Achiral

Routes of Administration

Oral Parenteral

Flags

Black Box Warning Natural Product Prodrug
USAN Year 1962

Extended Properties

Molecular Formula C9H7N7O2S
MW 277.27
Aromatic Rings 3
Heavy Atoms 19
NP-Likeness -1.16

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Amidophosphoribosyltransferase inhibitor INHIBITOR Amidophosphoribosyltransferase ✓ ✓
DNA inhibitor INHIBITOR DNA ✓ ✓

Indications

Arthritis, Rheumatoid Delayed Graft Function Immune System Diseases Anti-Neutrophil Cytoplasmic Antibody-Associated Vasculitis Carcinoma, Hepatocellular Cardiomyopathies Churg-Strauss Syndrome Colitis, Ulcerative Crohn Disease Eczema Encephalomyelitis Glomerulonephritis, IGA Granulomatosis with Polyangiitis Kidney Diseases Lupus Erythematosus, Systemic Lupus Nephritis Microscopic Polyangiitis Myasthenia Gravis Neuromyelitis Optica Pulmonary Fibrosis

ATC Classification

L04AX01
azathioprine
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: IMMUNOSUPPRESSANTS

Drug Warnings

Black Box Warning
carcinogenicity
Country: United States
Black Box Warning
hematological toxicity
Country: United States
Black Box Warning
immune system toxicity
Country: United States
Black Box Warning
teratogenicity
Country: United States

Activity Summary

IC50 13 meas. best 6.68
EC50 2 meas. best 5.54

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 IC50 6.68 5.8217 207.4 6
PBMC
CHEMBL613107
 IC50 6.64 6.64 230.4 1
Unchecked
CHEMBL612545
 EC50 5.54 5.54 2897.0 1
BJ
CHEMBL614358
 EC50 5.3 5.3 5039.0 1
Plasmodium falciparum
CHEMBL364
 IC50 5.1 4.96 7943.3 5

Pharmacokinetic Data

Parameter Value Units Species
AUC 2.133 ng.hr.mL-1 Homo sapiens
AUC 1.8 ng.hr.mL-1 Homo sapiens
AUC 5.9 ng.hr.mL-1 Homo sapiens
AUC 9.6 ng.hr.mL-1 Homo sapiens
AUC 41.6 ng.hr.mL-1 Homo sapiens
AUC 137.7 ng.hr.mL-1 Homo sapiens
AUC 34.2 ng.hr.mL-1 Homo sapiens
AUC 72.4 ng.hr.mL-1 Homo sapiens
AUC 74.4 ng.hr.mL-1 Homo sapiens
AUC 150.64 ng.hr.mL-1 Homo sapiens
AUC 45.33 ng.hr.mL-1 Homo sapiens
AUC 591.42 ng.hr.mL-1 Homo sapiens
AUC 297.23 ng.hr.mL-1 Homo sapiens
AUC 289.75 ng.hr.mL-1 Homo sapiens
CL 103.33 mL.min-1.kg-1 Homo sapiens
CL 57.0 mL.min-1.kg-1 Homo sapiens
CL 7.97 L/min Homo sapiens
CL 6.92 L/min Homo sapiens
CL 57.0 mL.min-1.kg-1 Homo sapiens
Cmax 79.35 nM Homo sapiens
Cmax 8.475 nM Homo sapiens
Cmax 8.656 nM Homo sapiens
Cmax 13.34 nM Homo sapiens
Cmax 60.95 nM Homo sapiens
Cmax 233.71 nM Homo sapiens
Cmax 37.87 nM Homo sapiens
Cmax 85.12 nM Homo sapiens
Cmax 68.89 nM Homo sapiens
Cmax 162.3 nM Homo sapiens
Cmax 180.0 nM Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 207.39 nM 6.68 PubChem BioAssay. HCT116 viability from Cell TiterGlo-IC50. (Class of assay: c... -
PBMC IC50 = 230.4 nM 6.64 Inhibition of T cell mitogen-induced blastogenesis in human PBMC after 4 days 18467007
Unchecked IC50 = 363.53 nM 6.44 PubChem BioAssay. DLD-1 viability from Cell TiterGlo-IC50. (Class of assay: co... -
Unchecked IC50 = 623.22 nM 6.21 PubChem BioAssay. GSK3B-pretreated HCT116 viability from Cell TiterGlo-IC50. (... -
Unchecked IC50 = 2661.36 nM 5.58 PubChem BioAssay. RKO viability from Cell TiterGlo-IC50. (Class of assay: conf... -
Unchecked EC50 = 2897.0 nM 5.54 PUBCHEM_BIOASSAY: Luminescence Cell-Based Dose Response HTS to Identify Compound... -
BJ EC50 = 5039.0 nM 5.3 PUBCHEM_BIOASSAY: Luminescence Cell-Based Dose Confirmation HTS to Identify Comp... -
Plasmodium falciparum IC50 = 7943.28 nM 5.1 Antiplasmodial activity against Plasmodium falciparum 7G8 after 72 hrs by SYBR g... 19734910
Unchecked IC50 = 9435.3 nM 5.03 PubChem BioAssay. SW480 viability from Cell TiterGlo-IC50. (Class of assay: co... -
Plasmodium falciparum IC50 = 10000.0 nM 5.0 Antiplasmodial activity against Plasmodium falciparum GB4 after 72 hrs by SYBR g... 19734910
Unchecked IC50 = 10340.2 nM 4.99 PubChem BioAssay. Colo320 viability from Cell TiterGlo-IC50. (Class of assay: ... -
Plasmodium falciparum IC50 = 12589.25 nM 4.9 Antiplasmodial activity against Plasmodium falciparum 3D7 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 12589.25 nM 4.9 Antiplasmodial activity against Plasmodium falciparum HB3 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 12589.25 nM 4.9 Antiplasmodial activity against Plasmodium falciparum W2 after 72 hrs by SYBR gr... 19734910

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885861 Rattus norvegicus 1387
- 10.6019/CHEMBL3885881 Rattus norvegicus 935
- 10.1101/2024.03.28.586928 ADMET 100
8881811 10.1136/gut.39.1.63 Homo sapiens 26
3957504 10.1016/0192-0561(86)90067-6 Homo sapiens 20
18070971 10.1128/aac.00678-07 Mycobacterium avium subsp. paratuberculosis 19
9048271 10.1177/009127009703700107 Homo sapiens 18
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
18070971 10.1128/aac.00678-07 Mycobacterium avium 13
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
3957504 10.1016/0192-0561(86)90067-6 Plasma 9
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
3957504 10.1016/0192-0561(86)90067-6 ADMET 6
7265110 10.1021/jm00135a003 Rattus norvegicus 5
19734910 10.1038/nchembio.215 Plasmodium falciparum 5
18070971 10.1128/aac.00678-07 Mycolicibacterium smegmatis 4
3373220 10.1021/np50055a001 Lymphocyte 3
20014752 10.1021/tx900326k Hepatotoxicity 3
2738881 10.1021/jm00127a013 Rattus norvegicus 3

Data from ChEMBL 36 via Core Engine