Allopurinol

Title: Allopurinol
CAS Registry Number: 315-30-0
CAS Name: 1,5-Dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one
Additional Names: 1H-pyrazolo[3,4-d]pyrimidin-4-ol; 4-hydroxypyrazolo[3,4-d]pyrimidine; HPP
Manufacturers' Codes: BW-56158
Trademarks: Adenock (Mitsubishi); Allurit (Aventis); Aloral (Lagap); Alositol (Tanabe); Allo-Puren (Isis); Allozym (Sawai); Allural (Rovi); Anoprolin (Azwell); Anzief (Nippon Chemiphar); Apulonga (Dorsch); Apurol (Siegfried); Apurin (GEA); Bleminol (Gepepharm); Caplenal (Teva); Cellidrin (Hennig); Cosuric (DDSA); Dabroson (Hoyer); Embarin (Merckle); Epidropal (Teofarma); Foligan (DESMA); Gichtex (Gerot); Hamarin (Roche); Hexanurat (Durascan); Ketanrift (Ohta); Lopurin (Abbott); Lysuron (Roche); Miniplanor (Galen); Monarch (SS Pharm.); Remid (TAD); Riball (Schering AG); Sigapurol (Siegfried); Suspendol (Merckle); Takanarumin (Takata); Uricemil (Molteni); Uripurinol (Azupharma); Urosin (Roche); Urtias (Novartis); Zyloprim (GSK); Zyloric (GSK)
Molecular Formula: C5H4N4O
Molecular Weight: 136.11
Percent Composition: C 44.12%, H 2.96%, N 41.16%, O 11.75%
Literature References: Xanthine oxidase inhibitor; decreases uric acid production. Prepn: Robins, J. Am. Chem. Soc. 78, 784 (1956); Schmidt, Druey, Helv. Chim. Acta 39, 986 (1956); Druey, Schmidt, US 2868803 (1959 to Ciba); GB 798646 (1958 to Wellcome Found.); Hitchings, Falco, US 3474098 (1969 to Burroughs Wellcome). Physiological and biochemical studies: Hitchings, in Biochem. Aspects Antimetab. Drug Hydroxylation, D. Shugar, Ed. (Academic Press, London, 1969) pp 11-22, C.A. 75, 3531h (1971). Clinical trial in treatment of renal calculi: M. J. V. Smith, J. Urol. 117, 690 (1977); B. Ettinger et al., N. Engl. J. Med. 315, 1386 (1986). Use in hyperuricemia and gout: G. R. Boss, J. E. Seegmiller, ibid. 300, 1459 (1977). Effect on renal function in treatment of gout: T. Gibson, Ann. Rheum. Dis. 41, 59 (1982). Comprehensive description: S. A. Benezra, T. R. Bennett, Anal. Profiles Drug Subs. 7, 1-17 (1978).
Properties: Crystals, mp above 350°. uv max (0.1N NaOH): 257 nm (e 7200); (0.1N HCl): 250 nm (e 7600); (methanol): 252 nm (e 7600). Soly in mg/ml at 25°: water 0.48; n-octanol <0.01; chloroform 0.60; ethanol 0.30; DMSO 4.6. pKa 10.2.
Melting point: mp above 350°
pKa: pKa 10.2
Absorption maximum: uv max (0.1N NaOH): 257 nm (e 7200); (0.1N HCl): 250 nm (e 7600); (methanol): 252 nm (e 7600)
Derivative Type: Sodium salt
CAS Registry Number: 17795-21-0
Trademarks: Aloprim (Nabi)
Molecular Formula: C5H3N4NaO
Molecular Weight: 158.09
Percent Composition: C 37.99%, H 1.91%, N 35.44%, Na 14.54%, O 10.12%
Properties: White amorphous mass. pKa 9.31.
pKa: pKa 9.31
Therap-Cat: Treatment of hyperuricemia and chronic gout. Antiurolithic.
Keywords: Antigout; Antiurolithic; Xanthine Oxidase Inhibitor.
Allotetrahydrocortisone Alloxan Alloxantin allo-Yohimbine Allura Red AC

Allopurinol
Allopurinol V.1.svg
Allopurinol 3d structure.png
Systematic (IUPAC) name
1H-pyrazolo[3,4-d]pyrimidin-4(2H)-one
Clinical data
Trade names Zyloprim
AHFS/Drugs.com monograph
MedlinePlus a682673
Pregnancy cat. C(USA)
Legal status -only (US)
Routes tablet (100, 300 mg)
Pharmacokinetic data
Bioavailability 78±20%
Protein binding Negligible
Metabolism hepatic (80% oxypurinol, 10% allopurinol ribosides)
Half-life 2 h (oxypurinol 18-30 h)
Identifiers
CAS number 315-30-0 YesY
ATC code M04AA01
PubChem CID 2094
DrugBank DB00437
ChemSpider 2010 YesY
UNII 63CZ7GJN5I YesY
KEGG D00224 YesY
ChEBI CHEBI:40279 YesY
ChEMBL CHEMBL1467 YesY
Chemical data
Formula C5H4N4O 
Mol. mass 136.112 g/mol
 YesY (what is this?)  (verify)

Allopurinol (Zyloprim, and generics) is a drug used primarily to treat hyperuricemia (excess uric acid in blood plasma) and its complications, including chronic gout.[1] It is a xanthine oxidase inhibitor which is administered orally.