4,6-Dihydroxypyrazolo[3,4-d]pyrimidine

For research use only. Not for therapeutic Use.

  • CAT Number: R000087
  • CAS Number: 2465-59-0
  • Molecular Formula: C5H4N4O2
  • Molecular Weight: 152.113
  • Purity: ≥95%
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Oxipurinol is a xanthine oxidase inhibitor potentially for the treatment of heart failure and gout.


Catalog Number R000087
CAS Number 2465-59-0
Synonyms

1H-Pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione; 1,7-Dihydro-4H-pyrazolo[3,4-d]?pyrimidine-4,6(5H)-dione; Alloxanthine; BW 55-5; NSC 76239; Oxipurinol; Oxoallopurinol; Oxyprim; Oxypurinol

Molecular Formula C5H4N4O2
Purity ≥95%
Target XAO
Solubility Soluble in DMSO
Storage Store at -20°C
IUPAC Name 1,2-dihydropyrazolo[3,4-d]pyrimidine-4,6-dione
InChI InChI=1S/C5H4N4O2/c10-4-2-1-6-9-3(2)7-5(11)8-4/h1H,(H3,6,7,8,9,10,11)
InChIKey HXNFUBHNUDHIGC-UHFFFAOYSA-N
SMILES C1=C2C(=NC(=O)NC2=O)NN1
Reference

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Allopurinol and oxypurinol promote osteoblast differentiation and increase bone formation. Exp Cell Res. 2016 Mar 15;342(2):166-74. doi: 10.1016/j.yexcr.2016.03.004. PubMed PMID: 26968635; PubMed Central PMCID: PMC4829071.</br>5: Funke J, Prasse C, Lütke Eversloh C, Ternes TA. Oxypurinol – A novel marker for wastewater contamination of the aquatic environment. Water Res. 2015 May 1;74:257-65. doi: 10.1016/j.watres.2015.02.007. PubMed PMID: 25753675.</br>6: Yun J, Mattsson J, Schnyder K, Fontana S, Largiadèr CR, Pichler WJ, Yerly D. Allopurinol hypersensitivity is primarily mediated by dose-dependent oxypurinol-specific T cell response. Clin Exp Allergy. 2013 Nov;43(11):1246-55. doi: 10.1111/cea.12184. PubMed PMID: 24152157.</br>7: Springer J, Tschirner A, Hartman K, von Haehling S, Anker SD, Doehner W. The xanthine oxidase inhibitor oxypurinol reduces cancer cachexia-induced cardiomyopathy. Int J Cardiol. 2013 Oct 9;168(4):3527-31. doi: 10.1016/j.ijcard.2013.05.063. 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Furosemide increases plasma oxypurinol without lowering serum urate–a complex drug interaction: implications for clinical practice. Rheumatology (Oxford). 2012 Sep;51(9):1670-6. doi: 10.1093/rheumatology/kes091. PubMed PMID: 22539486.</br>12: Stocker SL, McLachlan AJ, Savic RM, Kirkpatrick CM, Graham GG, Williams KM, Day RO. The pharmacokinetics of oxypurinol in people with gout. Br J Clin Pharmacol. 2012 Sep;74(3):477-89. doi: 10.1111/j.1365-2125.2012.04207.x. PubMed PMID: 22300439; PubMed Central PMCID: PMC3477349.</br>13: Okamoto K, Eger BT, Nishino T, Pai EF, Nishino T. Mechanism of inhibition of xanthine oxidoreductase by allopurinol: crystal structure of reduced bovine milk xanthine oxidoreductase bound with oxipurinol. Nucleosides Nucleotides Nucleic Acids. 2008 Jun;27(6):888-93. doi: 10.1080/15257770802146577. PubMed PMID: 18600558.</br>14: Vaughan VC, Sullivan-Gunn M, Hinch E, Martin P, Lewandowski PA. Eicosapentaenoic acid and oxypurinol in the treatment of muscle wasting in a mouse model of cancer cachexia. PLoS One. 2012;7(9):e45900. doi: 10.1371/journal.pone.0045900. PubMed PMID: 23029301; PubMed Central PMCID: PMC3447801.</br>15: Escobar J, Pereda J, Arduini A, Sandoval J, Moreno ML, Pérez S, Sabater L, Aparisi L, Cassinello N, Hidalgo J, Joosten LA, Vento M, López-Rodas G, Sastre J. Oxidative and nitrosative stress in acute pancreatitis. Modulation by pentoxifylline and oxypurinol. Biochem Pharmacol. 2012 Jan 1;83(1):122-30. doi: 10.1016/j.bcp.2011.09.028. PubMed PMID: 22000995.</br>16: Stamp LK, Barclay ML, O/’Donnell JL, Zhang M, Drake J, Frampton C, Chapman PT. Relationship between serum urate and plasma oxypurinol in the management of gout: determination of minimum plasma oxypurinol concentration to achieve a target serum urate level. Clin Pharmacol Ther. 2011 Sep;90(3):392-8. doi: 10.1038/clpt.2011.113. 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Clinical pharmacokinetics and pharmacodynamics of allopurinol and oxypurinol. Clin Pharmacokinet. 2007;46(8):623-44. Review. PubMed PMID: 17655371.</br></br>

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