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Compound Detail

CHEMBL1467

ALLOPURINOL
💊 Approved Drug
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💊 Approved Drug
Oc1ncnc2[nH]ncc12

Basic Information

ChEMBL ID CHEMBL1467
Name ALLOPURINOL
Phase Approved
Structure Type MOL
InChI Key OFCNXPDARWKPPY-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Allopurinol Allopurinol component of duzallo Allopurinolum Alopurinol Aloral Aluline 100 Aluline 300 BW 56-158 BW-56-158 Caplenal Cosuric Hamarin 100 +13 more
12
Targets
134
Activities
4
Assay Types
14
PK Parameters
20
Publications
25
Known Names
20
Indications
1
Mechanisms

Molecular Properties

136.1
MW (Da)
0.06
ALogP
4
HBA
2
HBD
74.7
PSA (Ų)
0.54
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1966
Availability Prescription
Chirality Achiral

Routes of Administration

Oral Parenteral

Flags

Black Box Warning Natural Product
USAN Year 1964

Extended Properties

Molecular Formula C5H4N4O
MW 136.11
Aromatic Rings 2
Heavy Atoms 10
NP-Likeness -1.78

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Xanthine dehydrogenase inhibitor INHIBITOR Xanthine dehydrogenase/oxidase

Indications

Gout Leukemia Lymphoma Neoplasms Response Evaluation Criteria in Solid Tumors Bipolar Disorder Brain Diseases Cardiovascular Diseases Colitis, Ulcerative Diabetes Mellitus, Type 2 Heart Diseases Hernias, Diaphragmatic, Congenital Hypertension Hyperuricemia Lymphoma, Non-Hodgkin Obesity Precursor Cell Lymphoblastic Leukemia-Lymphoma Sprains and Strains Tumor Lysis Syndrome Wounds and Injuries

ATC Classification

M04AA01
allopurinol
Level 1: MUSCULO-SKELETAL SYSTEM
Level 2: ANTIGOUT PREPARATIONS
M04AA51
allopurinol, combinations
Level 1: MUSCULO-SKELETAL SYSTEM
Level 2: ANTIGOUT PREPARATIONS

Drug Warnings

Black Box Warning
General Warning
Country: United States

Activity Summary

IC50 122 meas. best 8.46
Ki 8 meas. best 7.0
Kd 3 meas. best 9.27
EC50 1 meas. best 5.46

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Xanthine dehydrogenase/oxidase
CHEMBL3649
Kd 9.27 9.27 0.5 1
Xanthine dehydrogenase/oxidase
CHEMBL1929
IC50 8.46 5.5838 3.5 56
Xanthine dehydrogenase/oxidase
CHEMBL1929
Ki 7.0 5.905 100.0 6
NON-PROTEIN TARGET
CHEMBL3879801
IC50 6.64 6.08 230.0 2
Xanthine dehydrogenase/oxidase
CHEMBL3649
IC50 6.6 5.3398 250.0 45
Xanthine dehydrogenase/oxidase
CHEMBL5465298
IC50 6.52 6.52 300.0 1
Unchecked
CHEMBL612545
IC50 6.14 5.2957 730.0 7
Xanthine dehydrogenase/oxidase
CHEMBL1075246
IC50 6.12 5.3367 753.0 3
Xanthine dehydrogenase/oxidase
CHEMBL3649
Ki 6.0 5.79 1000.0 2
Leishmania infantum
CHEMBL612848
EC50 5.46 5.46 3500.0 1
Leishmania infantum
CHEMBL612848
IC50 5.46 5.46 3510.0 1
Replicase polyprotein 1ab
CHEMBL4523582
IC50 5.42 5.42 3770.0 1
No relevant target
CHEMBL2362975
IC50 5.41 5.255 3900.0 2
Trypanosoma cruzi
CHEMBL368
IC50 5.02 5.015 9620.0 2
Shiga toxin subunit A
CHEMBL3879822
IC50 4.62 4.62 23900.0 1
Adenosine receptor A2a
CHEMBL251
Kd 4.11 4.11 77000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 11.0 mL.min-1.kg-1 Homo sapiens
CL 9.3 mL.min-1.kg-1 Homo sapiens
CL 11.0 mL.min-1.kg-1 Homo sapiens
CL 11.0 mL.min-1.kg-1 Homo sapiens
F 80.0 % Homo sapiens
Fu 0.95 - -
Fu 0.881 - -
Fu 0.95 - Homo sapiens
Fu 0.97 - Homo sapiens
Fu 0.97 - Homo sapiens
MRT 0.88 hr Homo sapiens
T1/2 0.8 hr Homo sapiens
T1/2 0.7 hr Homo sapiens
Tmax 1.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Xanthine dehydrogenase/oxidase Kd = 0.54 nM 9.27 Binding affinity to bovine milk xanthine oxidase assessed as reduction in conver... 28478180
Xanthine dehydrogenase/oxidase IC50 = 3.5 nM 8.46 xanthine oxidase activity assay: Xanthine oxidase inhibition was determined usin... -
Xanthine dehydrogenase/oxidase IC50 = 3.5 nM 8.46 xanthine oxidase activity assay: Xanthine oxidase inhibition was determined usin... -
Xanthine dehydrogenase/oxidase IC50 = 3.6 nM 8.44 Inhibition of xanthine oxidase (unknown origin) assessed as reduction in uric ac... 28340987
Xanthine dehydrogenase/oxidase IC50 = 50.0 nM 7.3 Inhibition of XO (unknown origin) using xanthine as substrate 37974965
Xanthine dehydrogenase/oxidase Ki = 100.0 nM 7.0 Inhibition of human xanthine oxidase 25060641
Xanthine dehydrogenase/oxidase IC50 = 100.0 nM 7.0 Inhibition of xanthine oxidase (unknown origin) assessed as reduction in uric ac... 28478180
Xanthine dehydrogenase/oxidase IC50 = 180.0 nM 6.75 Inhibition of XOD 19476336
Xanthine dehydrogenase/oxidase IC50 = 200.0 nM 6.7 Inhibition of xanthine oxidase (unknown origin) 26762836
NON-PROTEIN TARGET IC50 = 230.0 nM 6.64 Antioxidant activity assessed as superoxide-scavenging activity by nitrite metho... 9461655
Xanthine dehydrogenase/oxidase IC50 = 240.0 nM 6.62 Inhibition of xanthine oxidase assessed as decrease in uric acid production by s... 9461655
Xanthine dehydrogenase/oxidase IC50 = 250.0 nM 6.6 Inhibition of bovine milk xanthine oxidase using xanthine as substrate preincuba... 29207340
Xanthine dehydrogenase/oxidase IC50 = 260.0 nM 6.58 In vitro inhibitory concentration against Xanthine oxidase 11294382
Xanthine dehydrogenase/oxidase IC50 = 260.0 nM 6.58 Inhibition of bovine milk xanthine-oxygen reductase using xanthine as substrate ... 28478180
Xanthine dehydrogenase/oxidase IC50 = 300.0 nM 6.52 Inhibition of mouse serum XO 37974965
Xanthine dehydrogenase/oxidase IC50 = 600.0 nM 6.22 Inhibition of xanthine oxidase (unknown origin) at 10 uM using xanthine as subst... 34923389
Xanthine dehydrogenase/oxidase Ki = 700.0 nM 6.16 Inhibition of xanthine oxidase (unknown origin) 30769179
Xanthine dehydrogenase/oxidase Ki = 700.0 nM 6.16 Competitive inhibition of xanthine oxidase (unknown origin) assessed as inhibito... 34992040
Unchecked IC50 = 730.0 nM 6.14 Inhibition of microbial xanthine oxidase by spectrophotometry 21163661
Xanthine dehydrogenase/oxidase IC50 = 730.0 nM 6.14 Inhibition of bovine milk xanthine oxidase by spectrophotometry 21163661

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885861 Rattus norvegicus 1432
- 10.6019/CHEMBL3885881 Rattus norvegicus 508
16472241 10.2174/1570163043334794 Hepatotoxicity 18
19388706 10.1021/np8007123 Xanthine dehydrogenase/oxidase 16
35468514 10.1016/j.ejmech.2022.114379 Mus musculus 15
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
24090917 10.1016/j.ejmech.2013.08.045 No relevant target 13
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
28478180 10.1016/j.ejmech.2017.04.031 Xanthine dehydrogenase/oxidase 11
37974965 10.1039/d3md00316g Xanthine dehydrogenase/oxidase 10
20070106 10.1021/jm901371v Homo sapiens 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
2778 10.1021/jm00224a017 Xanthine dehydrogenase/oxidase 8
3351858 10.1021/jm00399a019 Rattus norvegicus 7
27933947 10.1021/acs.jmedchem.6b01517 Shiga toxin subunit A 6
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 6
28340987 10.1016/j.bmc.2016.10.022 NON-PROTEIN TARGET 5
35902063 10.1016/j.bmcl.2022.128907 Mus musculus 5
27933947 10.1021/acs.jmedchem.6b01517 Mus musculus 5
12061889 10.1021/jm0200409 ADMET 5

Data from ChEMBL 36 via Core Engine