279. Allopurinol

Nomenclature

CAS number: 315-30-0
1,5-Dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one; 1H-pyrazolo[3,4-d]pyrimidin-4-ol; 4-hydroxypyrazolo[3,4-d]pyrimidine; HPP; BW-56158; 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).
C5H4N4O; mol wt 136.11.
C 44.12%, H 2.96%, N 41.16%, O 11.75%.

Description and 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).

Chemical structure

Properties

Crystals, mp above 350°. uv max (0.1N NaOH): 257 nm (ε 7200); (0.1N HCl): 250 nm (ε 7600); (methanol): 252 nm (ε 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.

Derivative

Sodium salt.

Nomenclature

CAS number: 17795-21-0
Aloprim (Nabi).
C5H3N4NaO; mol wt 158.09.
C 37.99%, H 1.91%, N 35.44%, Na 14.54%, O 10.12%.

Properties

White amorphous mass. pKa 9.31.

Therapeutic Category

Treatment of hyperuricemia and chronic gout. Antiurolithic.

Keywords

Antigout; Antiurolithic; Xanthine Oxidase Inhibitor