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MedKoo Cat#: 464677 | Name: Allopurinol Riboside
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Description:

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

Allopurinol riboside is a ribonucleoside and a ribose-containing derivative of the xanthine oxidase inhibitor allopurinol. It inhibits the growth of Leishmania promastigotes and prevents amastigote maturation into the promastigote phase of the parasite life cycle in cell-free assays. Allopurinol riboside (239, 511, and 929 mg/kg per day) prevents mortality in mouse models of T. cruzi infection but does not eradicate the infection.

Chemical Structure

Allopurinol Riboside
CAS#16220-07-8 (ribonucleoside)

Theoretical Analysis

MedKoo Cat#: 464677

Name: Allopurinol Riboside

CAS#: 16220-07-8 (ribonucleoside)

Chemical Formula: C10H12N4O5

Exact Mass: 268.0808

Molecular Weight: 268.23

Elemental Analysis: C, 44.78; H, 4.51; N, 20.89; O, 29.82

Price and Availability

Size Price Availability Quantity
10mg USD 350.00 2 Weeks
25mg USD 600.00 2 Weeks
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Related CAS #
16220-07-8 (ribonucleoside) 315-30-0 (free)
Synonym
Allopurinol Riboside; Allopurinol Ribonucleoside; NSC 138437; NSC138437; NSC-138437; NSC 252629; NSC252629; NSC-252629;
IUPAC/Chemical Name
1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1,7-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one
InChi Key
KFQUAMTWOJHPEJ-DAGMQNCNSA-N
InChi Code
InChI=1S/C10H12N4O5/c15-2-5-6(16)7(17)10(19-5)14-8-4(1-13-14)9(18)12-3-11-8/h1,3,5-7,10,15-17H,2H2,(H,11,12,18)/t5-,6-,7-,10-/m1/s1
SMILES Code
OC[C@H]1O[C@@]([H])(N2N=CC3=C2NC=NC3=O)[C@H](O)[C@@H]1O
Appearance
Solid powder
Purity
>95% (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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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
Solvent mg/mL mM comments
Solubility
DMSO 5.0 18.64
PBS (pH 7.2) 5.0 18.64
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 268.23 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.

Recalculate based on batch purity %
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
1: 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. Epub 2015 Feb 18. PMID: 25753675. 2: Villabona-Monsalve JP, Islas RE, Rodríguez-Córdoba W, Matsika S, Peón J. Ultrafast excited state dynamics of allopurinol, a modified DNA base. J Phys Chem A. 2013 Feb 7;117(5):898-904. doi: 10.1021/jp3107815. Epub 2013 Jan 28. PMID: 23327654. 3: Kannangara DR, Roberts DM, Furlong TJ, Graham GG, Williams KM, Day RO. Oxypurinol, allopurinol and allopurinol-1-riboside in plasma following an acute overdose of allopurinol in a patient with advanced chronic kidney disease. Br J Clin Pharmacol. 2012 May;73(5):828-9. doi: 10.1111/j.1365-2125.2011.04147.x. PMID: 22098112; PMCID: PMC3403212. 4: Ramasamy KS, Amador RB, Habib Q, Rong F, Han X, Li DY, Huang J, Hong Z, An H. Solid-phase parallel synthesis of 4-beta-D- ribofuranosylpyrazolo[4,3-d]pyrimidine nucleosides. Nucleosides Nucleotides Nucleic Acids. 2005;24(10-12):1947-70. doi: 10.1080/15257770500269432. PMID: 16438059. 5: Detke S. Identification of a transcription factor like protein at the TOR locus in Leishmania mexicana amazonensis. Mol Biochem Parasitol. 1997 Dec 15;90(2):505-11. doi: 10.1016/s0166-6851(97)00201-6. PMID: 9476797. 6: Were JB, Shapiro TA. Effects of probenecid on the pharmacokinetics of allopurinol riboside. Antimicrob Agents Chemother. 1993 May;37(5):1193-6. doi: 10.1128/aac.37.5.1193. PMID: 8517715; PMCID: PMC187932. 7: Nègre E, Chance ML, Hanboula SY, Monsigny M, Roche AC, Mayer RM, Hommel M. Antileishmanial drug targeting through glycosylated polymers specifically internalized by macrophage membrane lectins. Antimicrob Agents Chemother. 1992 Oct;36(10):2228-32. doi: 10.1128/aac.36.10.2228. PMID: 1332591; PMCID: PMC245481. 8: Moorman AR, LaFon SW, Nelson DJ, Carter HH, Marr JJ, Berens RL. Antiprotozoal activity of 3'-deoxyinosine. Inverse correlation to cleavage of the glycosidic bond. Biochem Pharmacol. 1991 Jul 5;42(2):207-12. doi: 10.1016/0006-2952(91)90704-9. PMID: 1859443. 9: Guderian RH, Chico ME, Rogers MD, Pattishall KM, Grogl M, Berman JD. Placebo controlled treatment of Ecuadorian cutaneous leishmaniasis. Am J Trop Med Hyg. 1991 Jul;45(1):92-7. doi: 10.4269/ajtmh.1991.45.92. PMID: 1651060. 10: Shapiro TA, Were JB, Danso K, Nelson DJ, Desjardins RE, Pamplin CL 3rd. Pharmacokinetics and metabolism of allopurinol riboside. Clin Pharmacol Ther. 1991 May;49(5):506-14. doi: 10.1038/clpt.1991.61. PMID: 2029827. 11: Saenz RE, Paz HM, Johnson CM, Marr JJ, Nelson DJ, Pattishall KH, Rogers MD. Treatment of American cutaneous leishmaniasis with orally administered allopurinol riboside. J Infect Dis. 1989 Jul;160(1):153-8. doi: 10.1093/infdis/160.1.153. PMID: 2659681. 12: Ramalingaswami V. Perspectives on research and diseases of the Tropics: an Asian view. Ann N Y Acad Sci. 1989;569:25-35. doi: 10.1111/j.1749-6632.1989.tb27356.x. PMID: 2698093. 13: Dee Nord L, Willis RC, Smee DF, Riley TA, Revankar GR, Robins RK. Inhibition of orotidylate decarboxylase by 4(5H)-oxo-1-beta-D-ribofuranosylpyrazolo[3,4-d] pyrimidine-3-thiocarboxamide (APR-TC) in B lymphoblasts. Activation by adenosine kinase. Biochem Pharmacol. 1988 Dec 15;37(24):4697-705. doi: 10.1016/0006-2952(88)90340-1. PMID: 2849455. 14: Martinez S, Looker DL, Berens RL, Marr JJ. The synergistic action of pyrazolopyrimidines and pentavalent antimony against Leishmania donovani and L. braziliensis. Am J Trop Med Hyg. 1988 Sep;39(3):250-5. doi: 10.4269/ajtmh.1988.39.250. PMID: 2845824. 15: Martinez S, Looker DL, Marr JJ. A tissue culture system for the growth of several species of Leishmania: growth kinetics and drug sensitivities. Am J Trop Med Hyg. 1988 Mar;38(2):304-7. doi: 10.4269/ajtmh.1988.38.304. PMID: 2833127. 16: Berman JD, Gallalee JV. In vitro antileishmanial activity of inhibitors of steroid biosynthesis and combinations of antileishmanial agents. J Parasitol. 1987 Jun;73(3):671-3. PMID: 3037057. 17: Looker DL, Martinez S, Horton JM, Marr JJ. Growth of Leishmania donovani amastigotes in the continuous human macrophage cell line U937: studies of drug efficacy and metabolism. J Infect Dis. 1986 Aug;154(2):323-7. doi: 10.1093/infdis/154.2.323. PMID: 3014012. 18: Looker DL, Marr JJ, Berens RL. Mechanisms of action of pyrazolopyrimidines in Leishmania donovani. J Biol Chem. 1986 Jul 15;261(20):9412-5. PMID: 2424909. 19: Bartlett MS, Marr JJ, Queener SF, Klein RS, Smith JW. Activity of inosine analogs against Pneumocystis carinii in culture. Antimicrob Agents Chemother. 1986 Jul;30(1):181-3. doi: 10.1128/aac.30.1.181. PMID: 3489438; PMCID: PMC176462. 20: Reiter S, Löffler W, Gröbner W, Zöllner N. Urinary oxipurinol-1-riboside excretion and allopurinol-induced oroticaciduria. Adv Exp Med Biol. 1986;195 Pt A:453-60. doi: 10.1007/978-1-4684-5104-7_75. PMID: 3728178.