Valopicitabine

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;
PubChem CID	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 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.

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[1] 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.

[2] 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.

[3] 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.

[4] 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.

[5] 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.

[1]

[2]

[3]

[4]

[5]

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
PubChem CID	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