Drug Information

General Information
Drug ID
DR00078
Drug Name
Valacyclovir
Synonyms
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; Acyclovir-valine; BW-256U; BW256U87; 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; TBB067866; Talavir; VACV; ValACV; Valaciclovir (INN); Valaciclovir Hcl; Valaciclovir [INN:BAN]; Valaciclovir, Valtrex; Valacyclover Hydrochloric; Valacyclover Hydrochloride; Valacyclovir; Valacyclovir, (L)-isomer; Valtrex; Valtrex (TN); Virval; Zelitrex; Zelitrex (TN)
Drug Type
Small molecular drug
Indication Herpes simplex virus infection [ICD11:1F00] Approved [1]
Shingles [ICD11:1.00E+91] Approved [1]
Therapeutic Class
Antiviral Agents
Structure
3D MOL 2D MOL
Formula
C13H20N6O4
Canonical SMILES
CC(C)C(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
CAS Number
CAS 124832-27-5
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
XLogP
-0.9
PubChem CID
135398742
PubChem SID
103440109 ,104048282 ,104178841 ,104321602 ,117583422 ,118313436 ,12014356 ,124800881 ,126631789 ,126658129 ,126682447 ,128045545 ,131905333 ,134213320 ,134221757 ,134337933 ,135030189 ,135659820 ,137005923 ,137005924 ,142590832 ,14718342 ,14777186 ,14801572 ,14850688 ,14850689 ,14874889 ,15940044 ,160963922 ,162782405 ,163231563 ,163621098 ,29215498 ,43118121 ,46508197 ,47589092 ,48416691 ,50062212 ,56422581 ,57314102 ,626316 ,78076275 ,7980871 ,85279714 ,85789653 ,89736139 ,92309076 ,92710527 ,96025347 ,99775325
ChEBI ID
CHEBI:35854
TTD Drug ID
D04QJD
DT(s) Transporting This Drug ASCT2 Transporter Info Alanine/serine/cysteine/threonine transporter 2 Substrate [2]
OAT3 Transporter Info Organic anion transporter 3 Substrate [3]
PEPT1 Transporter Info Peptide transporter 1 Substrate [4]
PEPT2 Transporter Info Peptide transporter 2 Substrate [4]
Drug-Transporter Activity Data
Drug-Transporter Activity Data OAT3 Transporter Info Km =57.9 microM Proximal tubule (S2) cells-OAT3 [3]
PEPT1 Transporter Info Km =1640 microM Chinese hamster ovary (CHO) cells-PEPT1 [5]
PEPT1 Transporter Info Km =2200 microM Chinese hamster ovary (CHO) cells-PEPT1 [6]
PEPT1 Transporter Info Km =2700 microM Chinese hamster ovary (CHO) cells-PEPT1 [6]
PEPT1 Transporter Info Km =5400 microM Chinese hamster ovary (CHO) cells-PEPT1 [6]
PEPT1 Transporter Info Km =6600 microM Chinese hamster ovary (CHO) cells-PEPT1 [6]
PEPT1 Transporter Info Km =7400 microM Chinese hamster ovary (CHO) cells-PEPT1 [6]
PEPT1 Transporter Info Km =2.2 microM Chinese hamster ovary (CHO) cells-PEPT1 [7]
PEPT1 Transporter Info Km =7.4 microM Chinese hamster ovary (CHO) cells-PEPT1 [7]
PEPT1 Transporter Info Km =292 microM Human enterocyte-like 2 cells (Caco-2)-PEPT1 [8]
PEPT1 Transporter Info Km =3.8 microM Madin-Darby canine kidney (MDCK) cells-PEPT1 [7]
PEPT1 Transporter Info Km =5940 microM Oocytes-PEPT1 [9]
PEPT1 Transporter Info Km =5.9 microM Xenopus oocytes-PEPT1 [7]
References
1 Acyclovir was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 Transport of amino acid-based prodrugs by the Na+- and Cl(-) -coupled amino acid transporter ATB0,+ and expression of the transporter in tissues amenable for drug delivery. J Pharmacol Exp Ther. 2004 Mar;308(3):1138-47.
3 Human organic anion transporters and human organic cation transporters mediate renal antiviral transport. J Pharmacol Exp Ther. 2002 Mar;300(3):918-24.
4 Valacyclovir: a substrate for the intestinal and renal peptide transporters PEPT1 and PEPT2. Biochem Biophys Res Commun. 1998 May 19;246(2):470-5.
5 Interactions of a nonpeptidic drug, valacyclovir, with the human intestinal peptide transporter (hPEPT1) expressed in a mammalian cell line. J Pharmacol Exp Ther. 1999 Apr;289(1):448-54.
6 Effect of ionization on the variable uptake of valacyclovir via the human intestinal peptide transporter (hPepT1) in CHO cells. Biopharm Drug Dispos. 2000 Jul;21(5):165-74.
7 Significance of peptide transporter 1 in the intestinal permeability of valacyclovir in wild-type and PepT1 knockout mice. Drug Metab Dispos. 2013 Mar;41(3):608-14.
8 5'-Amino acid esters of antiviral nucleosides, acyclovir, and AZT are absorbed by the intestinal PEPT1 peptide transporter. Pharm Res. 1998 Aug;15(8):1154-9.
9 Direct evidence for peptide transporter (PepT1)-mediated uptake of a nonpeptide prodrug, valacyclovir. Biochem Biophys Res Commun. 1998 Sep 18;250(2):246-51.

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