Compound: valacyclovir
SMILES: O=c1nc([nH]c2c1ncn2COCCOC(=O)[C@@H](N)C(C)C)N
InChIKey: HDOVUKNUBWVHOX-QMMMGPOBSA-N
Synonyms: valacyclovir, Valaciclovir, 124832-26-4, ValACV, Zelitrex, Val-ACV, L-Valine ester with 9-((2-hydroxyethoxy)methyl)guanine, L-Valine, 2-((2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy)ethyl ester, MZ1IW7Q79D, L-Valine, 2-[(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]ethyl ester, DTXSID1023732, CHEBI:35854, 2-[(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)methoxy]ethyl (2S)-2-amino-3-methylbutanoate, Valaciclovirum, L-valylacyclovir, L Valylacyclovir, 2-((2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)methoxy)ethyl (2S)-2-amino-3-methylbutanoate, L-valyl Ester Acyclovir, RefChem:56196, acyclovir, L-valyl ester, Acyclovir, L valyl Ester, DTXCID403732, J05AB11, 2-((2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy)ethyl L-valinate, 603-015-6, 658-047-3, Valtrex, Valcyclovir, Valaciclovir (INN), Valtrex (TN), CHEMBL1349, 2-[(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)methoxy]ethyl L-valinate, 256U87 HCl, Valcivir, VALACICLOVIR [INN], 2-[(2-amino-6-oxo-1H-purin-9-yl)methoxy]ethyl (2S)-2-amino-3-methylbutanoate, (S)-2-[(2-Amino-6-oxo-6,9-dihydro-3H-purin-9-yl)methoxy]ethyl-2-amino-3-methylbutanoate, 2-[(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)methoxy]ethyl (2S)-2-amino-3-methylbutanoate, Valaciclovir [INN:BAN], Talavir, Virval, Valacyclover Hydrochloric, Acyclovir-valine, CHEBI:9919, Valaciclovir, Valtrex, NCGC00159520-02, UNII-MZ1IW7Q79D, HSDB 8084, BW-256U, BW256U87, TXC, Valtrex (TM), Valcyclovir [INN:BAN], VALACYCLOVIR [MI], VALACYCLOVIR [VANDF], SCHEMBL28644, SCHEMBL34375, BSPBio_002474, MLS001304747, MLS006011776, VALACICLOVIR [WHO-DD], GTPL4824, orb1709988, HMS2090D20, HMS2234I15, BBL033701, BDBM50162073, BDBM50248296, EBC-46269, STK802272, STL535579, T1087L, ZB0748, 2-{[(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)methyl]oxy}ethyl L-valinate, AKOS005622706, AKOS007930693, AKOS025149468, AKOS037496964, CS-1356, DB00577, valacyclovir hydrochloride (monohydrate), NCGC00178638-04, NCGC00178638-05, NCGC00178638-15, AC-11128, HY-17425, SMR000752514, SMR004703478, SBI-0206711.P001, NS00009305, 256U87, D08664, EN300-150220, G78316, AB00698497-11, AB01275525-01, AB01275525_02, AB01275525_03, Q418594, BRD-K46435977-003-01-2, BRD-K46435977-003-03-8, BRD-K46435977-003-11-1, BRD-K46435977-003-12-9, 2-[(2-amino-6-hydroxy-9H-purin-9-yl)methoxy]ethyl L-valinate, L-VALINE, ESTER WITH 9-((2-HYDROXYETHOXY)METHYL)GUANINE, 2-[(2-amino-1,6-dihydro-6-oxo-9h-purin-9-yl)methoxy]ethyl-l-valinate, 2-[(2-amino-6-oxo-3,6-dihydro-9H-purin-9-yl)methoxy]ethyl L-valinate, (S)-2-((2-Amino-6-oxo-1H-purin-9(6H)-yl)methoxy)ethyl 2-amino-3-methylbutanoate, (S)-2-((2-amino-6-oxo-3H-purin-9(6H)-yl)methoxy)ethyl 2-amino-3-methylbutanoate, 2-[(2-amino-6-oxo-1H-purin-9-yl)methoxy]ethyl (2S)-2-amino-3-methyl-butanoate, L-VALINE 2-((2-AMINO-1,6-DIHYDRO-6-OXO-9H-PURIN-9-YL)METHOXY)ETHYL ESTER, (S)-2-[(2-Amino-6-oxo-6,9-dihydro-3H-purin-9-yl)methoxy]ethyl-2-amino-3-methylbutanoate_x000D_, (S)-2-Amino-3-methyl-butyric acid 2-(2-amino-6-oxo-1,6-dihydro-purin-9-ylmethoxy)-ethyl ester
Theoretical properties:
molecular_formula: C13H20N6O4
molecular_weight: 324.34 g/mol
exact_mass: 324.15460314 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 3
hydrogen_bond_acceptor_count: 7
rotatable_bond_count: 8
heavy_atom_count: 23
topological_polar_surface_area: 147 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: 170-172
Descriptions:
pubchem: Valacyclovir is a L-valyl ester. It has a role as an antiviral drug. It is functionally related to a guanine. It is a conjugate base of a valacyclovir(1+).
chembl: VALACYCLOVIR is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Valaciclovir, also spelled valacyclovir, is an antiviral medication used to treat outbreaks of herpes simplex or herpes zoster (shingles). It is also used to prevent cytomegalovirus following a kidney transplant in high risk cases. It is taken by mouth.
Common side effects include headache and vomiting. Severe side effects may include kidney problems. Use in pregnancy appears to be safe. It is a prodrug, which works after being converted to aciclovir in a person's body.
Valaciclovir was patented in 1987 and came into medical use in 1995. Valaciclovir is a therapeutic alternative on the World Health Organization's List of Essential Medicines. It is available as a generic medication. In 2023, it was the 98th most commonly prescribed medication in the United States, with more than 7 million prescriptions.