Valopicitabine

Chemical compound

None

Legal statusLegal 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

PubChem CID

6918726

DrugBank

DB13920

ChemSpider

5293918

UNII

I2T0B5G94M

KEGG

D09028

ChEMBL

ChEMBL1743757

CompTox Dashboard (EPA)

DTXSID70214011

Chemical and physical dataFormulaC₁₅H₂₄N₄O₆Molar mass356.379 g·mol⁻¹3D 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 an antiviral drug which was developed as a treatment for hepatitis C, though only progressed as far as Phase III clinical trials. It acts as an RNA-dependent RNA polymerase inhibitor. It is a prodrug which is converted inside the body to the active form, 2'-C-methylcytidine triphosphate.^[1]^[2]^[3]^[4]^[5]

References

^ 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 (primarily J05, also S01AD and D06BB)

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)	Ensitrelvir^† 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^†