Oxipurinol
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MedKoo CAT#: 529402

CAS#: 2465-59-0

Description: Oxipurinol is a xanthine oxidase inhibitor potentially for the treatment of heart failure and gout.


Price and Availability

Size Price Shipping out time Quantity
250mg USD 175 2 Weeks
500mg USD 300 2 Weeks
1g USD 510 2 Weeks
Inquire bulk and customized quantity

Pricing updated 2020-10-22. Prices are subject to change without notice.

Oxipurinol is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 529402
Name: Oxipurinol
CAS#: 2465-59-0
Chemical Formula: C5H4N4O2
Exact Mass: 152.0334
Molecular Weight: 152.113
Elemental Analysis: C, 39.48; H, 2.65; N, 36.83; O, 21.04


Synonym: NSC-76239; NSC76239; NSC 76239

IUPAC/Chemical Name: 1,7-dihydro-4H-pyrazolo[3,4-d]pyrimidine-4,6(5H)-dione

InChi Key: HXNFUBHNUDHIGC-UHFFFAOYSA-N

InChi Code: InChI=1S/C5H4N4O2/c10-4-2-1-6-9-3(2)7-5(11)8-4/h1H,(H3,6,7,8,9,10,11)

SMILES Code: O=C(N1)C2=C(NN=C2)NC1=O


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code:
2934.99.9001


References

1: Oxipurinol: alloxanthine, Oxyprim, oxypurinol. Drugs R D. 2004;5(3):171-5. Review. PubMed PMID: 15139781.

2: Chung WH, Chang WC, Stocker SL, Juo CG, Graham GG, Lee MH, Williams KM, Tian YC, Juan KC, Jan Wu YJ, Yang CH, Chang CJ, Lin YJ, Day RO, Hung SI. Insights into the poor prognosis of allopurinol-induced severe cutaneous adverse reactions: the impact of renal insufficiency, high plasma levels of oxypurinol and granulysin. Ann Rheum Dis. 2015 Dec;74(12):2157-64. doi: 10.1136/annrheumdis-2014-205577. PubMed PMID: 25115449.

3: Chung WH, Pan RY, Chu MT, Chin SW, Huang YL, Wang WC, Chang JY, Hung SI. Oxypurinol-Specific T Cells Possess Preferential TCR Clonotypes and Express Granulysin in Allopurinol-Induced Severe Cutaneous Adverse Reactions. J Invest Dermatol. 2015 Sep;135(9):2237-48. doi: 10.1038/jid.2015.165. PubMed PMID: 25946710.

4: Orriss IR, Arnett TR, George J, Witham MD. 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.

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.

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.

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. PubMed PMID: 23751350.

8: Reinders MK, Nijdam LC, van Roon EN, Movig KL, Jansen TL, van de Laar MA, Brouwers JR. A simple method for quantification of allopurinol and oxipurinol in human serum by high-performance liquid chromatography with UV-detection. J Pharm Biomed Anal. 2007 Oct 18;45(2):312-7. PubMed PMID: 17890037.

9: Liu X, Ni XJ, Shang DW, Zhang M, Hu JQ, Qiu C, Luo FT, Wen YG. Determination of allopurinol and oxypurinol in human plasma and urine by liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2013 Dec 15;941:10-6. doi: 10.1016/j.jchromb.2013.09.028. PubMed PMID: 24184830.

10: Wright DF, Stamp LK, Merriman TR, Barclay ML, Duffull SB, Holford NH. The population pharmacokinetics of allopurinol and oxypurinol in patients with gout. Eur J Clin Pharmacol. 2013 Jul;69(7):1411-21. doi: 10.1007/s00228-013-1478-8. PubMed PMID: 23475133.

11: Stamp LK, Barclay ML, O'Donnell JL, Zhang M, Drake J, Frampton C, Chapman PT. 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.

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.

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.

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.

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.

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. PubMed PMID: 21796116.

17: Yun J, Marcaida MJ, Eriksson KK, Jamin H, Fontana S, Pichler WJ, Yerly D. Oxypurinol directly and immediately activates the drug-specific T cells via the preferential use of HLA-B*58:01. J Immunol. 2014 Apr 1;192(7):2984-93. doi: 10.4049/jimmunol.1302306. PubMed PMID: 24591375.

18: Kurajoh M, Ka T, Okuda C, Yamamoto A, Tsutsumi Z, Koyama H, Moriwaki Y, Yamamoto T. Effects of bovine milk ingestion on urinary excretion of oxypurinol and uric acid. Int J Clin Pharmacol Ther. 2011 Jun;49(6):366-70. PubMed PMID: 21612743.

19: Stocker SL, Franklin ME, Anderson JM, Pillans PI, Williams KM, McLachlan AJ, Day RO, Taylor PJ. Measurement of urinary oxypurinol by high performance liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2010 Sep 1;878(25):2363-8. doi: 10.1016/j.jchromb.2010.07.017. PubMed PMID: 20702150.

20: Day RO, Graham GG, Hicks M, McLachlan AJ, Stocker SL, Williams KM. Clinical pharmacokinetics and pharmacodynamics of allopurinol and oxypurinol. Clin Pharmacokinet. 2007;46(8):623-44. Review. PubMed PMID: 17655371.