ALLOPURINOL

Search structure
Trade Names:
Synonyms:
Status: Approved (1966)
Entry Type: Small molecule
Molecule Category: Parent
ATC: M04AA01
UNII: 63CZ7GJN5I

Structure
InChI Key OFCNXPDARWKPPY-UHFFFAOYSA-N
Smile O=c1ncnc2[nH][nH]cc1-2
InChI
InChI=1S/C5H4N4O/c10-5-3-1-8-9-4(3)6-2-7-5/h1-2H,(H2,6,7,8,9,10)

Physicochemical Descriptors

Property Name Value
Molecular Formula C5H4N4O
Molecular Weight 136.11
AlogP -0.4
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 0.0
Polar Surface Area 74.43
Molecular species NEUTRAL
Aromatic Rings 0.0
Heavy Atoms 10.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Xanthine dehydrogenase inhibitor FDA
Primary Target
xanthine dehydrogenase
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Hydrolase
- 23900 - - 76
Enzyme Oxidoreductase
- 4-50150 1 100-7300 95-100
Secreted protein
- 23900 - - 76
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 11-84
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- - - - 8

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Bipolar Disorder 3 D001714 ClinicalTrials
Hypertension 3 D006973 ClinicalTrials
Cardiovascular Diseases 3 D002318 ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-Lymphoma 3 D054198 ClinicalTrials
Sprains and Strains 3 D013180 ClinicalTrials
Hernias, Diaphragmatic, Congenital 3 D065630 ClinicalTrials
Hyperuricemia 3 D033461 ClinicalTrials
Obesity 3 D009765 ClinicalTrials
Colitis, Ulcerative 3 D003093 ClinicalTrials
Heart Diseases 3 D006331 ClinicalTrials
Diabetes Mellitus, Type 2 3 D003924 ClinicalTrials
Lymphoma, Non-Hodgkin 3 D008228 ClinicalTrials
Tumor Lysis Syndrome 3 D015275 ClinicalTrials
Peritoneal Neoplasms 2 D010534 ClinicalTrials
Ovarian Neoplasms 2 D010051 ClinicalTrials
Kidney Calculi 2 D007669 ClinicalTrials
Metabolic Syndrome 2 D024821 ClinicalTrials
Heart Failure 2 D006333 ClinicalTrials
Heart Failure 2 D006333 ClinicalTrials
Leukemia, Lymphocytic, Chronic, B-Cell 2 D015451 ClinicalTrials
Myelodysplastic Syndromes 2 D009190 ClinicalTrials
Leukemia, Myeloid, Acute 2 D015470 ClinicalTrials
Diabetes Mellitus 2 D003920 ClinicalTrials
Multiple Myeloma 2 D009101 ClinicalTrials
Leishmaniasis 2 D007896 ClinicalTrials
Hand-Foot Syndrome 2 D060831 ClinicalTrials
Essential Hypertension 2 D000075222 ClinicalTrials
Renal Insufficiency, Chronic 2 D051436 ClinicalTrials
Myeloproliferative Disorders 2 D009196 ClinicalTrials
Angina, Stable 2 D060050 ClinicalTrials
Fallopian Tube Neoplasms 2 D005185 ClinicalTrials
Leukemia, Biphenotypic, Acute 1 D015456 ClinicalTrials
Inflammatory Bowel Diseases 1 D015212 ClinicalTrials
Tuberculosis 1 D014376 ClinicalTrials
Osteoarthritis 1 D010003 ClinicalTrials

Related Entries

Salt
Mixture

Side Effects from Label

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Skin and subcutaneous tissue disorders
21.06
Immune system disorders
15.17
General disorders and administration site conditions
7.43
Injury, poisoning and procedural complications
5.85
Infections and infestations
5.64
Gastrointestinal disorders
4.76
Vascular disorders
4.64
Blood and lymphatic system disorders
4.45
Renal and urinary disorders
3.79
Respiratory, thoracic and mediastinal disorders
3.77
Cardiac disorders
3.66
Metabolism and nutrition disorders
3.28
Investigations
3.28
Nervous system disorders
2.75
Hepatobiliary disorders
2.7

Cross References

Resources Reference
CAS NUMBER 315-30-0
ChEBI 40279
ChEMBL CHEMBL1467
DrugBank DB00437
DrugCentral 124
EPA CompTox DTXSID4022573
FDA SRS 63CZ7GJN5I
Human Metabolome Database HMDB0014581
Guide to Pharmacology 6795
PharmGKB PA448320
PubChem 135401907
SureChEMBL SCHEMBL4627
ZINC ZINC000013298313
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