Valopicitabine HCl

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

MedKoo CAT#: 328049

CAS#: 640725-71-9

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


Price and Availability

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Valopicitabine dihydrochloride is not in stock, but 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#: 328049
Name: Valopicitabine HCl
CAS#: 640725-71-9
Chemical Formula: C15H26Cl2N4O6
Exact Mass: 356.1696
Molecular Weight: 429.295
Elemental Analysis: C, 41.97; H, 6.10; Cl, 16.52; N, 13.05; O, 22.36


Related CAS #: 640725-71-9 (HCl)   640281-90-9 (free base)  

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, dihydrochloride

InChi Key: XENHXZMAOSTXGD-DSMKLBDQSA-N

InChi Code: InChI=1S/C15H24N4O6.2ClH/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);2*1H/t8-,10+,11-,13-,15-;;/m1../s1

SMILES Code: N[C@@H](C(C)C)C(O[C@@H]1[C@@H](CO)O[C@@H](N2C=CC(N)=NC2=O)[C@@]1(O)C)=O.[H]Cl.[H]Cl


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).

Harmonized System Code:
293490


Additional Information

Related CAS#
640725-71-9 (Valopicitabine dihydrochloride)
640281-90-9 (Valopicitabine free base)


References

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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.