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Valopicitabine

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Chemical compound

Pharmaceutical compound

Valopicitabine
Clinical data

ATC code	None
Legal status
Legal status	US: Investigational drug
Identifiers
IUPAC name [(2R,3R,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-4-hydroxy-2-(hydroxymethyl)-4-methyloxolan-3-yl] (2S)-2-amino-3-methylbutanoate
CAS Number	640281-90-9
PubChemCID	6918726
DrugBank	DB13920
ChemSpider	5293918
UNII	I2T0B5G94M
KEGG	D09028
ChEMBL	ChEMBL1743757
CompTox Dashboard(EPA)	DTXSID70214011
Chemical and physical data
Formula	C₁₅H₂₄N₄O₆
Molar mass	356.379 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CC(C)[C@@H](C(=O)O[C@@H]1[C@H](O[C@H]([C@]1(C)O)N2C=CC(=NC2=O)N)CO)N
InChI 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 Key:TVRCRTJYMVTEFS-ICGCPXGVSA-N

Valopicitabine (NM-283) is anantiviral drug which was developed as a treatment forhepatitis C, though only progressed as far as Phase IIIclinical trials. It acts as an RNA-dependentRNA polymerase inhibitor. It is aprodrug which is converted inside the body to the active form, 2'-C-methylcytidine triphosphate.^[1]^[2]^[3]^[4]^[5]

References

[edit]

^Pierra C, Benzaria S, Amador A, Moussa A, Mathieu S, Storer R, Gosselin G (2005). "Nm 283, an efficient prodrug of the potent anti-HCV agent 2'-C-methylcytidine".Nucleosides, Nucleotides & Nucleic Acids.24 (5–7):767–70.doi:10.1081/ncn-200060112.PMID 16248033.S2CID 23883085.
^Toniutto P, Fabris C, Bitetto D, Fornasiere E, Rapetti R, Pirisi M (February 2007). "Valopicitabine dihydrochloride:a specific polymerase inhibitor of hepatitis C virus".Current Opinion in Investigational Drugs.8 (2):150–8.PMID 17328231.
^Liu-Young G, Kozal MJ (June 2008)."Hepatitis C protease and polymerase inhibitors in development".AIDS Patient Care and STDs.22 (6):449–57.doi:10.1089/apc.2007.0199.PMC 2928549.PMID 18479202.
^Carroll SS, Koeplinger K, Vavrek M, Zhang NR, Handt L, MacCoss M, et al. (August 2011)."Antiviral efficacy upon administration of a HepDirect prodrug of 2'-C-methylcytidine to hepatitis C virus-infected chimpanzees".Antimicrobial Agents and Chemotherapy.55 (8):3854–60.doi:10.1128/AAC.01152-10.PMC 3147631.PMID 21628542.
^Krecmerova M (2017). "Amino Acid Ester Prodrugs of Nucleoside and Nucleotide Antivirals".Mini Reviews in Medicinal Chemistry.17 (10):818–833.doi:10.2174/1389557517666170216151601.PMID 28215138.

RNA virus antivirals (primarilyJ05, alsoS01AD andD06BB)

Hepatitis C

NS3/4A protease inhibitors (–previr)	Asunaprevir Boceprevir^‡ Ciluprevir^§ Danoprevir^† Faldaprevir^‡ Glecaprevir Grazoprevir Narlaprevir Paritaprevir Simeprevir Sovaprevir^† Telaprevir^‡ Vaniprevir Vedroprevir^§ Voxilaprevir
NS5A inhibitors (–asvir)	Coblopasvir Daclatasvir^# Elbasvir Ledipasvir Odalasvir^† Ombitasvir Pibrentasvir Ravidasvir^† Ruzasvir^† Samatasvir^† Velpatasvir
NS5B RNA polymerase inhibitors (–buvir)	Beclabuvir^† Bemnifosbuvir^† Dasabuvir^# Deleobuvir^§ Filibuvir^§ GS-6620^§ IDX-184^§ Setrobuvir^§ Sofosbuvir^# Tegobuvir^§ TMC-647055^§ Radalbuvir^† Uprifosbuvir^†
Combination drugs	Elbasvir/grazoprevir Glecaprevir/pibrentasvir Ledipasvir/sofosbuvir^# Ombitasvir/paritaprevir/ritonavir^# Sofosbuvir/daclatasvir Sofosbuvir/velpatasvir^# Sofosbuvir/velpatasvir/voxilaprevir

Hepatitis D

Bulevirtide

Picornavirus

viral entry:Pleconaril^†

Anti-influenza agents

neuraminidase inhibitors/release phase (Oseltamivir^#
Zanamivir
Peramivir,Laninamivir^†)

Multiple/general

Interferon	Interferon alfa 2b Peginterferon alfa-2a^# Peginterferon alfa-2b^#
3CL protease inhibitors (–trelvir)	Atilotrelvir Ensitrelvir^† Ibuzatrelvir Leritrelvir Lufotrelvir Nirmatrelvir^† (+ritonavir)^† Rupintrivir Simnotrelvir (+ritonavir^†)
RNA pol inhibitors	CMX521^§ Deuremidevir^† Favipiravir Galidesivir^† GS-441524^§ Remdesivir MK-608^§ Mericitabine^† Molnupiravir NITD008^§ Ribavirin^# Taribavirin^† Triazavirin Valopicitabine^†
Multiple/Unknown/Other	EICAR^§ Merimepodib^§ Moroxydine Presatovir^†

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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