MedKoo Cat#: 127433 | Name: Valopicitabine

Description:

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

Valopicitabine (NM-283; NMC-283; val-mCyd; valmCyd) is a NS5B inhibitor potentially for the treatment of HCV infection.

Chemical Structure

Valopicitabine
Valopicitabine
CAS#640281-90-9 (free base)

Theoretical Analysis

MedKoo Cat#: 127433

Name: Valopicitabine

CAS#: 640281-90-9 (free base)

Chemical Formula: C15H24N4O6

Exact Mass: 356.1696

Molecular Weight: 356.38

Elemental Analysis: C, 50.55; H, 6.79; N, 15.72; O, 26.94

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
Bulk Inquiry
Synonym
Valopicitabine; Valopicitabine dihydrochloride, Valopicitabine HCl; NM-283; NMC-283; NM283; NMC283; val-mCyd; valmCyd.
IUPAC/Chemical Name
(2R,3R,4R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-4-hydroxy-2-(hydroxymethyl)-4-methyltetrahydrofuran-3-yl L-valinate
InChi Key
TVRCRTJYMVTEFS-ICGCPXGVSA-N
InChi Code
InChI=1S/C15H24N4O6/c1-7(2)10(17)12(21)25-11-8(6-20)24-13(15(11,3)23)19-5-4-9(16)18-14(19)22/h4-5,7-8,10-11,13,20,23H,6,17H2,1-3H3,(H2,16,18,22)/t8-,10+,11-,13-,15-/m1/s1
SMILES Code
CC(C)[C@H](N)C(=O)O[C@@H]1[C@@H](CO)O[C@@H](N2C=CC(N)=NC2=O)[C@]1(C)O
Appearance
To be determined
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
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

Preparing Stock Solutions

The following data is based on the product molecular weight 356.38 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: Carroll SS, Koeplinger K, Vavrek M, Zhang NR, Handt L, MacCoss M, Olsen DB, Reddy KR, Sun Z, van Poelje PD, Fujitaki JM, Boyer SH, Linemeyer DL, Hecker SJ, Erion MD. Antiviral efficacy upon administration of a HepDirect prodrug of 2'-C-methylcytidine to hepatitis C virus-infected chimpanzees. Antimicrob Agents Chemother. 2011 Aug;55(8):3854-60. doi: 10.1128/AAC.01152-10. PubMed PMID: 21628542; PubMed Central PMCID: PMC3147631. 2: Hrstić I, Ostojić R, Vucelić B. [Retreatment options for patients with chronic hepatitis C]. Acta Med Croatica. 2009 Dec;63(5):417-22. . PubMed PMID: 20198901. 3: Takehara T. [Antiviral therapy for chronic hepatitis C: current status and perspectives]. Yakugaku Zasshi. 2010 Feb;130(2):143-56. Review. Japanese. PubMed PMID: 20118636. 4: Pucci V, Giuliano C, Zhang R, Koeplinger KA, Leone JF, Monteagudo E, Bonelli F. HILIC LC-MS for the determination of 2'-C-methyl-cytidine-triphosphate in rat liver. J Sep Sci. 2009 May;32(9):1275-83. doi: 10.1002/jssc.200800722. PubMed PMID: 19347863. 5: Kronenberger B, Zeuzem S. Future treatment options for HCV: double, triple, what is the optimal combination? Best Pract Res Clin Gastroenterol. 2008;22(6):1123-36. doi: 10.1016/j.bpg.2008.12.002. Review. PubMed PMID: 19187871. 6: Tedaldi EM. Emerging therapies for hepatitis C and HIV in drug abusers: drugs and strategies. J Addict Dis. 2008;27(2):83-91. doi: 10.1300/J069v27n02_10. Review. PubMed PMID: 18681195. 7: Liu-Young G, Kozal MJ. Hepatitis C protease and polymerase inhibitors in development. AIDS Patient Care STDS. 2008 Jun;22(6):449-57. doi: 10.1089/apc.2007.0199. Review. PubMed PMID: 18479202; PubMed Central PMCID: PMC2928549. 8: Le Pogam S, Seshaadri A, Kosaka A, Chiu S, Kang H, Hu S, Rajyaguru S, Symons J, Cammack N, Nájera I. Existence of hepatitis C virus NS5B variants naturally resistant to non-nucleoside, but not to nucleoside, polymerase inhibitors among untreated patients. J Antimicrob Chemother. 2008 Jun;61(6):1205-16. doi: 10.1093/jac/dkn085. PubMed PMID: 18343801. 9: Toniutto P, Fabris C, Bitetto D, Fornasiere E, Rapetti R, Pirisi M. Valopicitabine dihydrochloride:a specific polymerase inhibitor of hepatitis C virus. Curr Opin Investig Drugs. 2007 Feb;8(2):150-8. Review. PubMed PMID: 17328231. 10: Sigal S, Jacobson I. Future therapies for hepatitis C: where do we go from here? Nat Clin Pract Gastroenterol Hepatol. 2007 Feb;4(2):60-1. PubMed PMID: 17268539. 11: Davis GL. New therapies: oral inhibitors and immune modulators. Clin Liver Dis. 2006 Nov;10(4):867-80. Review. PubMed PMID: 17164122. 12: Pierra C, Amador A, Benzaria S, Cretton-Scott E, D'Amours M, Mao J, Mathieu S, Moussa A, Bridges EG, Standring DN, Sommadossi JP, Storer R, Gosselin G. Synthesis and pharmacokinetics of valopicitabine (NM283), an efficient prodrug of the potent anti-HCV agent 2'-C-methylcytidine. J Med Chem. 2006 Nov 2;49(22):6614-20. PubMed PMID: 17064080. 13: Coelmont L, Paeshuyse J, Windisch MP, De Clercq E, Bartenschlager R, Neyts J. Ribavirin antagonizes the in vitro anti-hepatitis C virus activity of 2'-C-methylcytidine, the active component of valopicitabine. Antimicrob Agents Chemother. 2006 Oct;50(10):3444-6. PubMed PMID: 17005827; PubMed Central PMCID: PMC1610077. 14: Stauber RE, Stadlbauer V. Novel approaches for therapy of chronic hepatitis C. J Clin Virol. 2006 Jun;36(2):87-94. Review. PubMed PMID: 16546442. 15: Pierra C, Benzaria S, Amador A, Moussa A, Mathieu S, Storer R, Gosselin G. Nm 283, an efficient prodrug of the potent anti-HCV agent 2'-C-methylcytidine. Nucleosides Nucleotides Nucleic Acids. 2005;24(5-7):767-70. PubMed PMID: 16248033. 16: Bayes M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2005 Jul-Aug;27(6):411-61. PubMed PMID: 16179960.