Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR5446)
Drug Name
Valaciclovir
Prodrug Info Valaciclovir is the prodrug of Acyclovir
Synonyms
Talavir; VACV; ValACV; Valacyclovir; Virval; Zelitrex; Valaciclovir Hcl; Valacyclover Hydrochloric; Valacyclover Hydrochloride; BW256U87; TBB067866; Acyclovir-valine; BW-256U; Valaciclovir (INN); Valaciclovir [INN:BAN]; Valaciclovir, Valtrex; Valtrex (TN); Zelitrex (TN); Valacyclovir, (L)-isomer; 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; L-valine, 2-[(2-amino-1,6-dihydro-6-oxo-9 H-purin-9-yl)methoxy]ethyl ester, monohydrochloride; 2-[(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)methoxy]ethyl L-valinate; 2-[(2-amino-6-oxo-3H-purin-9-yl)methoxy]ethyl (2S)-2-amino-3-methylbutanoate; 2-{[(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)methyl]oxy}ethyl L-valinate
Indication Virus infection [ICD11: 1A24-1D9Z] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 324.34 Topological Polar Surface Area 147
Heavy Atom Count 23 Rotatable Bond Count 8
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 7
Cross-matching ID
PubChem CID
135398742
ChEBI ID
CHEBI:35854
CAS Number
124832-26-4
TTD Drug ID
D04QJD
Formula
C13H20N6O4
Canonical SMILES
CC(C)[C@@H](C(=O)OCCOCN1C=NC2=C1N=C(NC2=O)N)N
InChI
InChI=1S/C13H20N6O4/c1-7(2)8(14)12(21)23-4-3-22-6-19-5-16-9-10(19)17-13(15)18-11(9)20/h5,7-8H,3-4,6,14H2,1-2H3,(H3,15,17,18,20)/t8-/m0/s1
InChIKey
HDOVUKNUBWVHOX-QMMMGPOBSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Acyclovir DM016608
135398513
Unclear 1 [6] , [5]
L-valine DM014899
6287
Unclear 1 [6] , [5]
Acyclovir monophosphate DM016622
135422933
Conjugation - Phosphorylation 2 [7]
Acyclovir diphosphate DM016627
135434163
Conjugation - Phosphorylation 3 [7]
Acyclovir triphosphate DM016613
135405018
Conjugation - Phosphorylation 4 [7]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Aldehyde dehydrogenase (ALDH) DMEN076 . Not Available Not Available [2]
Aldehyde oxidase (AOX1) DME0052 Homo sapiens
AOXA_HUMAN
1.2.3.1
[2]
Guanylate kinase (GUK1) DMEN721 Homo sapiens
KGUA_HUMAN
2.7.4.8
[3]
Putative hydrolase RBBP9 (Rbbp9) DMEN860 Mus musculus
RBBP9_MOUSE
3.-.-.-
[4]
Thymidine kinase (TK1) DMEN825 Homo sapiens
KITH_HUMAN
2.7.1.21
[3]
Valacyclovir hydrolase (BPHL) DMEN738 Homo sapiens
BPHL_HUMAN
3.1.-.-
[5]
⏷ Show the Full List of 6  DME(s)
References
1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 4824).
2 Absolute bioavailability and metabolic disposition of valaciclovir, the L-valyl ester of acyclovir, following oral administration to humans
3 DrugBank(Pharmacology-Metabolism):Valaciclovir
4 Chemoproteomic Identification of Serine Hydrolase RBBP9 as a Valacyclovir-Activating Enzyme
5 Human valacyclovir hydrolase/biphenyl hydrolase-like protein is a highly efficient homocysteine thiolactonase
6 Valacyclovir: a review of its antiviral activity, pharmacokinetic properties, and clinical efficacy
7 DrugBank(Pharmacology-Metabolism):Valacyclovir Hydrochloride

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