Oxipurinol | CAS#2465-59-0 | xanthine oxidase inhibitor

MedKoo Cat#: 529402 | Name: Oxipurinol

Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Chemical Structure

Oxipurinol

CAS#2465-59-0

Theoretical Analysis

MedKoo Cat#: 529402

Name: Oxipurinol

CAS#: 2465-59-0

Chemical Formula: C5H4N4O2

Exact Mass: 152.0334

Molecular Weight: 152.11

Elemental Analysis: C, 39.48; H, 2.65; N, 36.83; O, 21.04

Price and Availability

Size	Price	Availability	Quantity
250mg	USD 450.00
500mg	USD 600.00
1g	USD 800.00

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Related CAS #

No Data

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

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

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Oxipurinol (Oxipurinol), the major active metabolite of Allopurinol, is an inhibitor of xanthine oxidase.

In vitro activity:

As shown in Fig. 1A excess glucose (10 mM) significantly increased trophoblast secretion of IL-1β to 135.2 ± 10.6 pg/mL) when compared to glucose at 5 mM (34.0 ± 4.4 pg/mL). This was significantly inhibited by allopurinol at 200 µM (allo 200) to 109.7 ± 9.7 pg/mL and by allopurinol at 400 µM (allo 400) to 87.3 ± 10.2 pg/mL. To determine whether the inhibition of excess glucose-induced trophoblast IL-1β was a result of allopurinol inhibiting inflammasome function, caspase-1 activity was measured. As shown in Fig. 1B, excess glucose significantly increased trophoblast caspase-1 activity to 78.0 ± 3.7 RLU when compared to glucose at 5 mM (54.9 ± 3.7 RLU), and this was significantly inhibited by allopurinol at 400 µM to 53.9 ± 3.1 RLU. Allopurinol at 200 µM had no effect on trophoblast caspase-1 activity under excess glucose conditions. However, both doses of allopurinol significantly reduced trophoblast caspase-1 activity under 5 mM glucose conditions (Fig. 1B). Reference: Reproduction. 2020 Jan;159(1):73-80. https://pubmed.ncbi.nlm.nih.gov/31705795/

In vivo activity:

To investigate the therapeutic potential and underlying mechanism of oxypurinol in ischemic AKI, C57BL/6 male mice were intraperitoneally injected with oxypurinol and subjected to renal I/R or sham surgery. This study found that oxypurinol-treated mice had lower plasma creatinine and blood urea nitrogen levels and tubular damage (hematoxylin-and-eosin staining) compared to vehicle-treated mice after renal I/R injury. Furthermore, oxypurinol treatment reduced kidney inflammation (i.e., neutrophil infiltration and MIP-2 mRNA induction), oxidative stress (i.e., 4-HNE, heme oxygenase-1 [HO-1], 8-OHdG expression, and Catalase mRNA induction), and apoptosis (i.e., TUNEL or cleaved caspase-3-positive renal tubular cells), compared to vehicle-treated mice. Reference: Front Med (Lausanne). 2023 Mar 9;10:1030577. https://pubmed.ncbi.nlm.nih.gov/36968831/

	Solvent	mg/mL	mM
Solubility
	DMSO	7.8	50.95
	DMSO:PBS (pH 7.2) (1:10)	0.1	0.66

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 152.11 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Negi M, Mulla MJ, Han CS, Abrahams VM. Allopurinol inhibits excess glucose-induced trophoblast IL-1β and ROS production. Reproduction. 2020 Jan;159(1):73-80. doi: 10.1530/REP-19-0422. PMID: 31705795. 2. Eleftheriadis T, Pissas G, Antoniadi G, Liakopoulos V, Stefanidis I. Allopurinol protects human glomerular endothelial cells from high glucose-induced reactive oxygen species generation, p53 overexpression and endothelial dysfunction. Int Urol Nephrol. 2018 Jan;50(1):179-186. doi: 10.1007/s11255-017-1733-5. Epub 2017 Nov 1. PMID: 29094329. 3. Kang HB, Lim CK, Kim J, Han SJ. Oxypurinol protects renal ischemia/reperfusion injury via heme oxygenase-1 induction. Front Med (Lausanne). 2023 Mar 9;10:1030577. doi: 10.3389/fmed.2023.1030577. PMID: 36968831; PMCID: PMC10033620. 4. Zeng F, Luo J, Han H, Xie W, Wang L, Han R, Chen H, Cai Y, Huang H, Xia Z. Allopurinol ameliorates liver injury in type 1 diabetic rats through activating Nrf2. Int J Immunopathol Pharmacol. 2021 Jan-Dec;35:20587384211031417. doi: 10.1177/20587384211031417. PMID: 34240649.

In vitro protocol:

In vivo protocol:

1. Kang HB, Lim CK, Kim J, Han SJ. Oxypurinol protects renal ischemia/reperfusion injury via heme oxygenase-1 induction. Front Med (Lausanne). 2023 Mar 9;10:1030577. doi: 10.3389/fmed.2023.1030577. PMID: 36968831; PMCID: PMC10033620. 2. Zeng F, Luo J, Han H, Xie W, Wang L, Han R, Chen H, Cai Y, Huang H, Xia Z. Allopurinol ameliorates liver injury in type 1 diabetic rats through activating Nrf2. Int J Immunopathol Pharmacol. 2021 Jan-Dec;35:20587384211031417. doi: 10.1177/20587384211031417. PMID: 34240649.

1: Fanning NC, Cadzow M, Topless RK, Frampton C, Dalbeth N, Merriman TR, Stamp LK. Association of rare and common genetic variants in MOCOS with inadequate response to allopurinol. Rheumatology (Oxford). 2024 Aug 13:keae420. doi: 10.1093/rheumatology/keae420. Epub ahead of print. PMID: 39137147. 2: Chepchirchir R, Mwalimu R, Tanui I, Kiprop A, Krauss M, Brack W, Kandie F. Occurrence, removal and risk assessment of chemicals of emerging concern in selected rivers and wastewater treatment plants in western Kenya. Sci Total Environ. 2024 Oct 20;948:174982. doi: 10.1016/j.scitotenv.2024.174982. Epub 2024 Jul 23. PMID: 39053549. 3: Meloche M, Pilon MO, Provost S, Leclair G, Oussaïd E, St-Jean I, Jutras M, Gaulin MJ, Lemieux Perreault LP, Valois D, Mongrain I, Busseuil D, Rouleau JL, Tardif JC, Dubé MP, de Denus S. A Genome-Wide Association Study of Oxypurinol Concentrations in Patients Treated with Allopurinol. J Pers Med. 2024 Jun 18;14(6):649. doi: 10.3390/jpm14060649. PMID: 38929870; PMCID: PMC11204675. 4: Zhou B, Liu X, Lan Q, Wan F, Yang Z, Nie X, Cai Z, Hu B, Tang J, Zhu C, Laghi L. Comparison of Aroma and Taste Profiles of Kiwi Wine Fermented with/without Peel by Combining Intelligent Sensory, Gas Chromatography-Mass Spectrometry, and Proton Nuclear Magnetic Resonance. Foods. 2024 May 31;13(11):1729. doi: 10.3390/foods13111729. PMID: 38890957; PMCID: PMC11172059. 5: Hao J, Zhang X, Hu R, Lu X, Wang H, Li Y, Cheng K, Li Q. Metabolomics combined with network pharmacology reveals a role for astragaloside IV in inhibiting enterovirus 71 replication via PI3K-AKT signaling. J Transl Med. 2024 Jun 10;22(1):555. doi: 10.1186/s12967-024-05355-9. PMID: 38858642; PMCID: PMC11163744. 6: Morningstar J, Lee J, Mahon S, Brenner M, Nath AK. Mass Spectrometric Analysis of Purine Intermediary Metabolism Indicates Cyanide Induces Purine Catabolism in Rabbits. Metabolites. 2024 May 10;14(5):279. doi: 10.3390/metabo14050279. PMID: 38786756; PMCID: PMC11123099. 7: Lai Y, Tang W, Luo X, Zheng H, Zhang Y, Wang M, Yu G, Yang M. Gut microbiome and metabolome to discover pathogenic bacteria and probiotics in ankylosing spondylitis. Front Immunol. 2024 Apr 22;15:1369116. doi: 10.3389/fimmu.2024.1369116. PMID: 38711505; PMCID: PMC11070502. 8: Chaudhary A, He Z, Atwood DJ, Miyazaki M, Oto OA, Davidoff A, Edelstein CL. Raising serum uric acid with a uricase inhibitor worsens PKD in rat and mouse models. Am J Physiol Renal Physiol. 2024 Jun 1;326(6):F1004-F1015. doi: 10.1152/ajprenal.00372.2023. Epub 2024 Apr 18. PMID: 38634129. 9: Wilson LC, Ward J, Wright DFB, Green SC, Stocker SL, Putt TL, Schollum JBW, Walker RJ. The impact of peritoneal dialysis on oxypurinol and urate elimination in people with gout. Nephrology (Carlton). 2024 Aug;29(8):547-550. doi: 10.1111/nep.14306. Epub 2024 Apr 16. PMID: 38626950. 10: Sittiwattanawong P, Kantikosum K, Charoenchaipiyakul K, Pootongkam S, Asawanonda P, Kerr SJ, Thantiworasit P, Sodsai P, Hirankarn N, Klaewsongkram J, Rerknimitr P. In-vivo and ex-vivo tests for culprit drugs identification in severe cutaneous adverse drugs reactions. J Dermatol. 2024 Apr 11. doi: 10.1111/1346-8138.17207. Epub ahead of print. PMID: 38605448. 11: Thorsteinsdottir UA, Runolfsdottir HL, Eiriksson FF, Agustsdottir IMS, Edvardsson VO, Palsson R, Thorsteinsdottir M. Optimization and validation of a UPLC-MS/MS assay for simultaneous quantification of 2,8-dihydroxyadenine, adenine, allopurinol, oxypurinol and febuxostat in human plasma. J Chromatogr B Analyt Technol Biomed Life Sci. 2024 Mar 1;1235:124041. doi: 10.1016/j.jchromb.2024.124041. Epub 2024 Feb 5. PMID: 38359644. 12: Hasikova L, Bartl J, Stiburkova B. Urinary oxypurinol is a useful tool to assess adherence to allopurinol in clinical practice. Rheumatology (Oxford). 2024 May 3;63(6):e174-e176. doi: 10.1093/rheumatology/keae009. PMID: 38197578. 13: Zhu Z, Yi B, Tang Z, Chen X, Li M, Xu T, Zhao Z, Tang C. Lactobacillus casei combined with Lactobacillus reuteri alleviate pancreatic cancer by inhibiting TLR4 to promote macrophage M1 polarization and regulate gut microbial homeostasis. BMC Cancer. 2023 Oct 30;23(1):1044. doi: 10.1186/s12885-023-11557-z. PMID: 37904102; PMCID: PMC10614400. 14: Sekine M, Okamoto K, Pai EF, Nagata K, Ichida K, Hille R, Nishino T. Allopurinol and oxypurinol differ in their strength and mechanisms of inhibition of xanthine oxidoreductase. J Biol Chem. 2023 Sep;299(9):105189. doi: 10.1016/j.jbc.2023.105189. Epub 2023 Aug 23. PMID: 37625592; PMCID: PMC10511816. 15: Wardecki D, Dołowy M, Bober-Majnusz K. Evaluation of the Usefulness of Topological Indices for Predicting Selected Physicochemical Properties of Bioactive Substances with Anti-Androgenic and Hypouricemic Activity. Molecules. 2023 Aug 2;28(15):5822. doi: 10.3390/molecules28155822. PMID: 37570792; PMCID: PMC10420683. 16: Vanden Heuvel JP, Zhou S, Patel AB, Kamerow HN, Baran P, Ford JP. Preclinical Demonstration of a Novel Treatment with High Efficacy and No Detectable Toxicity for Inflammatory Skin Conditions including Psoriasis. Biomed Res Int. 2023 Jul 11;2023:4878774. doi: 10.1155/2023/4878774. PMID: 37469991; PMCID: PMC10353900. 17: Mifsud NA, Illing PT, Ho R, Tuomisto JE, Fettke H, Mullan KA, McCluskey J, Rossjohn J, Vivian J, Reantragoon R, Purcell AW. The allopurinol metabolite, oxypurinol, drives oligoclonal expansions of drug-reactive T cells in resolved hypersensitivity cases and drug-naïve healthy donors. Allergy. 2023 Nov;78(11):2980-2993. doi: 10.1111/all.15814. Epub 2023 Jul 14. PMID: 37452515; PMCID: PMC10952278. 18: Maghsoud Y, Dong C, Cisneros GA. Investigation of the Inhibition Mechanism of Xanthine Oxidoreductase by Oxipurinol: A Computational Study. J Chem Inf Model. 2023 Jul 10;63(13):4190-4206. doi: 10.1021/acs.jcim.3c00624. Epub 2023 Jun 15. PMID: 37319436; PMCID: PMC10405278. 19: Huan X, Zhuo N, Lee HY, Ren EC. Allopurinol non-covalently facilitates binding of unconventional peptides to HLA-B*58:01. Sci Rep. 2023 Jun 9;13(1):9373. doi: 10.1038/s41598-023-36293-z. PMID: 37296297; PMCID: PMC10256732. 20: Wen YF, Brundage RC, Roman YM, Culhane-Pera KA, Straka RJ. Population pharmacokinetics, pharmacodynamics and pharmacogenetics modelling of oxypurinol in Hmong adults with gout and/or hyperuricemia. Br J Clin Pharmacol. 2023 Oct;89(10):2964-2976. doi: 10.1111/bcp.15792. Epub 2023 Jun 4. PMID: 37202871; PMCID: PMC10527451.