Allopurinol
Allopurinol
Systematic (IUPAC) name
3,5,7,8-tetrazabicyclo[4.3.0] nona-3,5,9-trien-2-one
Identifiers
CAS number
315-30-0
ATC code
M04AA01
PubChem
2094
DrugBank
APRD00435
ChemSpider
2010
Chemical data
Formula
C5H4N4O
Mol. mass
136.112 g/mol
Pharmacokinetic data
Bioavailability
78±20%
Protein binding
Negligible
Metabolism
hepatic (80% oxypurinol, 10% allopurinol ribosides)
Half life
2 hours (oxypurinol 18-30 hours)
Excretion
?
Therapeutic considerations
Pregnancy cat.
C(USA)
Legal status
Schedule 6 (USA)
Routes
tablet (100, 300 mg)
Allopurinol is a drug used primarily to treat conditions arising from excess uric acid in blood plasma. Most notable of these conditions is chronic gout. Allopurinol does not alleviate acute attacks of gout, but is useful in preventing recurrence. Allopurinol has been used in the United States since 1964.
Contents[hide]
1 Mechanism of action
2 Uses (other than in treatment of gout)
3 Metabolism
4 Side effects
5 Brand names
6 References
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[edit] Mechanism of action
Allopurinol is a structural isomer of hypoxanthine (a naturally occurring purine in the body) and is an enzyme inhibitor, inhibiting xanthine oxidase.[citation needed] Xanthine oxidase is responsible for the successive oxidation of hypoxanthine and xanthine resulting in the production of uric acid, the product of human purine metabolism.[1] In addition to blocking uric acid production, inhibition of xanthine oxidase causes an increase in hypoxanthine and xanthine, which are converted to closely related purine ribotides adenosine and guanosine monophosphates. Increased levels of these ribotides causes feedback inhibition of amidophosphoribosyl transferase, the first and rate-limiting enzyme of purine biosynthesis. Allopurinol therefore decreases...
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