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Identification
NameValaciclovir
Accession NumberDB00577  (APRD00697)
TypeSmall Molecule
GroupsApproved, Investigational
DescriptionValaciclovir (INN) or valacyclovir (USAN) is an antiviral drug used in the management of herpes simplex and herpes zoster (shingles). It is a prodrug, being converted in vivo to aciclovir. It is marketed by GlaxoSmithKline under the trade name Valtrex or Zelitrex. [Wikipedia]
Structure
Thumb
Synonyms
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
Valaciclovirum
Valacyclovir
External Identifiers
  • 256 U 87
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Auro-valacyclovirTablet500 mgOralAuro Pharma Inc2013-05-30Not applicableCanada
Bio-valacyclovirTablet500 mgOralBiomed PharmaNot applicableNot applicableCanada
Co ValacyclovirTablet1000 mgOralCobalt Pharmaceuticals CompanyNot applicableNot applicableCanada
Co ValacyclovirTablet500 mgOralCobalt Pharmaceuticals Company2010-07-27Not applicableCanada
Dom-valacyclovirTablet500 mgOralDominion Pharmacal2010-07-01Not applicableCanada
Ipg-valacyclovirTablet500 mgOralMarcan Pharmaceuticals IncNot applicableNot applicableCanada
Jamp-valacyclovirTablet500 mgOralJamp Pharma Corporation2015-10-14Not applicableCanada
Mar-valacyclovirTablet500 mgOralMarcan Pharmaceuticals Inc2015-10-20Not applicableCanada
Mylan-valacyclovirTablet1000 mgOralMylan Pharmaceuticals Ulc2010-05-25Not applicableCanada
Mylan-valacyclovirTablet500 mgOralMylan Pharmaceuticals Ulc2010-05-25Not applicableCanada
PHL-valacyclovirTablet500 mgOralPharmel Inc2010-02-192016-10-25Canada
PMS-valacyclovirTablet1000 mgOralPharmascience Inc2012-03-13Not applicableCanada
PMS-valacyclovirTablet500 mgOralPharmascience Inc2008-05-16Not applicableCanada
Priva-valacyclovirTablet500 mgOralPharmapar Inc2015-10-21Not applicableCanada
Pro-valacyclovirTablet500 mgOralPro Doc Limitee2009-02-10Not applicableCanada
Riva-valacyclovirTablet500 mgOralLaboratoire Riva Inc2008-10-27Not applicableCanada
Sandoz ValacyclovirTablet1000 mgOralSandoz Canada IncorporatedNot applicableNot applicableCanada
Sandoz ValacyclovirTablet500 mgOralSandoz Canada Incorporated2015-07-21Not applicableCanada
Teva-valacyclovirTablet500 mgOralTeva Canada Limited2010-10-01Not applicableCanada
Teva-valacyclovirTablet1000 mgOralTeva Canada LimitedNot applicableNot applicableCanada
ValacyclovirTablet1000 mgOralSivem Pharmaceuticals Ulc2015-10-14Not applicableCanada
ValacyclovirTablet500 mgOralSanis Health Inc2016-06-10Not applicableCanada
ValacyclovirTablet500 mgOralSorres Pharma IncNot applicableNot applicableCanada
ValacyclovirTablet500 mgOralSivem Pharmaceuticals Ulc2015-10-14Not applicableCanada
ValtrexTablet1 gOralGlaxosmithkline Inc2005-05-09Not applicableCanada
ValtrexTablet, film coated500 mg/1OralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2012-03-20Not applicableUs
ValtrexTablet, film coated500 mg/1OralA S Medication Solutions1995-08-01Not applicableUs
ValtrexTablet, film coated500 mg/1Oralbryant ranch prepack1995-08-01Not applicableUs
ValtrexTablet, film coated1 g/1OralPhysicians Total Care, Inc.2003-04-25Not applicableUs
ValtrexTablet, film coated1 g/1OralA S Medication Solutions2002-08-12Not applicableUs
ValtrexTablet, film coated1 g/1Oralbryant ranch prepack2002-08-12Not applicableUs
ValtrexTablet, film coated500 mg/1OralCardinal Health1995-08-01Not applicableUs
ValtrexTablet, film coated1 g/1OralGlaxo Smith Kline Llc2002-08-12Not applicableUs
ValtrexTablet500 mgOralGlaxosmithkline Inc1996-12-31Not applicableCanada
ValtrexTablet, film coated1 g/1OralREMEDYREPACK INC.2016-05-26Not applicableUs
ValtrexTablet, film coated500 mg/1OralPd Rx Pharmaceuticals, Inc.1995-08-01Not applicableUs
ValtrexTablet, film coated500 mg/1OralGlaxo Smith Kline Llc1995-08-01Not applicableUs
Van-valacyclovirTablet500 mgOralVanc Pharmaceuticals IncNot applicableNot applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-valacyclovirTablet500 mgOralApotex Inc2008-05-23Not applicableCanada
Apo-valacyclovirTablet1000 mgOralApotex Inc2011-10-21Not applicableCanada
ValacyclovirTablet, film coated500 mg/1OralTeva Pharmaceuticals USA Inc2010-05-24Not applicableUs
ValacyclovirTablet, film coated1 g/1OralA S Medication Solutions2007-01-31Not applicableUs
ValacyclovirTablet500 mg/1OralWest Ward Pharmaceuticals Corp.2010-05-24Not applicableUs
ValacyclovirTablet, film coated500 mg/1OralCamber Pharmaceuticals, Inc.2015-05-25Not applicableUs
ValacyclovirTablet, film coated500 mg/1OralLucid Pharma Llc2010-05-24Not applicableUs
ValacyclovirTablet, film coated1 g/1OralTeva Pharmaceuticals USA Inc2010-05-24Not applicableUs
ValacyclovirTablet, film coated500 mg/1OralAphena Pharma Solutions Tennessee, Llc2010-05-24Not applicableUs
ValacyclovirTablet500 mg/1OralDIRECT RX2015-01-01Not applicableUs
ValacyclovirTablet1 g/1OralWest Ward Pharmaceuticals Corp.2010-05-24Not applicableUs
ValacyclovirTablet, film coated1 g/1OralCamber Pharmaceuticals, Inc.2015-05-25Not applicableUs
ValacyclovirTablet, film coated1 g/1OralLucid Pharma Llc2010-05-24Not applicableUs
ValacyclovirTablet, film coated1 g/1Oralbryant ranch prepack2007-01-31Not applicableUs
ValacyclovirTablet500 mg/1OralOhm Laboratories Inc.2009-11-25Not applicableUs
ValacyclovirCapsule1 g/1OralDIRECT RX2015-01-01Not applicableUs
ValacyclovirTablet, film coated500 mg/1OralRanbaxy Pharmaceuticals Inc.2007-01-31Not applicableUs
ValacyclovirTablet1 g/1OralOhm Laboratories Inc.2009-11-25Not applicableUs
ValacyclovirTablet, film coated1 g/1OralRanbaxy Pharmaceuticals Inc.2007-01-31Not applicableUs
Valacyclovir HydrochlorideTablet1 g/1OralSandoz Inc2010-05-24Not applicableUs
Valacyclovir HydrochlorideTablet, film coated500 mg/1OralMylan Institutional Inc.2011-03-07Not applicableUs
Valacyclovir HydrochlorideTablet, film coated1 g/1OralPreferred Pharmaceuticals, Inc.2015-05-04Not applicableUs
Valacyclovir HydrochlorideTablet, film coated500 mg/1OralCardinal Health2011-05-23Not applicableUs
Valacyclovir HydrochlorideTablet, film coated1 g/1OralNorth Star Rx Llc2010-05-24Not applicableUs
Valacyclovir HydrochlorideTablet, film coated1 g/1OralMc Kesson Packaging Services A Business Unit Of Mc Kesson Corporation2012-02-24Not applicableUs
Valacyclovir HydrochlorideTablet, film coated1 g/1OralPd Rx Pharmaceuticals, Inc.2011-04-25Not applicableUs
Valacyclovir HydrochlorideTablet, film coated1 g/1OralJubilant Cadista Pharmaceuticals Inc.2012-04-05Not applicableUs
Valacyclovir HydrochlorideTablet, film coated500 mg/1OralState of Florida DOH Central Pharmacy2013-01-01Not applicableUs
Valacyclovir HydrochlorideTablet, film coated1 g/1OralA S Medication Solutions2010-05-24Not applicableUs
Valacyclovir HydrochlorideTablet, film coated500 mg/1OralProficient Rx LP2011-04-25Not applicableUs
Valacyclovir HydrochlorideTablet1000 mg/1OralCipla USA Inc.2010-05-24Not applicableUs
Valacyclovir HydrochlorideTablet, film coated500 mg/1OralCitron Pharma LLC2010-05-24Not applicableUs
Valacyclovir HydrochlorideTablet, film coated1 g/1OralAurobindo Pharma Limited2010-05-24Not applicableUs
Valacyclovir HydrochlorideTablet, film coated1 g/1OralAmerican Health Packaging2014-02-28Not applicableUs
Valacyclovir HydrochlorideTablet, film coated1 g/1OralDr. Reddys Laboratories Limited2010-12-06Not applicableUs
Valacyclovir HydrochlorideTablet, film coated1 g/1OralA S Medication Solutions2010-05-24Not applicableUs
Valacyclovir HydrochlorideTablet, film coated500 mg/1Oralbryant ranch prepack2010-05-24Not applicableUs
Valacyclovir HydrochlorideTablet, film coated1 g/1OralAmerican Health Packaging2012-11-292015-11-11Us
Valacyclovir HydrochlorideTablet, film coated500 mg/1OralWatson Laboratories, Inc.2010-05-24Not applicableUs
Valacyclovir HydrochlorideTablet, film coated1 g/1OralREMEDYREPACK INC.2013-04-092016-10-13Us
Valacyclovir HydrochlorideTablet, film coated1 g/1OralBlenheim Pharmacal, Inc.2012-04-05Not applicableUs
Valacyclovir HydrochlorideTablet, film coated500 mg/1OralNorthwind Pharmaceuticals2014-05-06Not applicableUs
Valacyclovir HydrochlorideTablet, film coated500 mg/1OralA S Medication Solutions2011-04-25Not applicableUs
Valacyclovir HydrochlorideTablet, film coated500 mg/1OralWockhardt Limited2010-05-24Not applicableUs
Valacyclovir HydrochlorideTablet, film coated500 mg/1OralNorth Star Rx Llc2010-05-24Not applicableUs
Valacyclovir HydrochlorideTablet, film coated500 mg/1OralWockhardt USA LLC.2010-05-24Not applicableUs
Valacyclovir HydrochlorideTablet1000 mg/1OralProficient Rx LP2010-05-24Not applicableUs
Valacyclovir HydrochlorideTablet, film coated1 g/1OralPhysicians Total Care, Inc.2010-06-11Not applicableUs
Valacyclovir HydrochlorideTablet500 mg/1OralREMEDYREPACK INC.2016-09-21Not applicableUs
Valacyclovir HydrochlorideTablet, film coated1 g/1OralProficient Rx LP2012-04-05Not applicableUs
Valacyclovir HydrochlorideTablet, coated500 mg/1OralLife Line Home Care Services, Inc.2010-05-24Not applicableUs
Valacyclovir HydrochlorideTablet500 mg/1OralA S Medication Solutions2010-05-24Not applicableUs
Valacyclovir HydrochlorideTablet, film coated1 g/1OralCitron Pharma LLC2010-05-24Not applicableUs
Valacyclovir HydrochlorideTablet, film coated1 g/1OralMed Vantx, Inc.2010-05-24Not applicableUs
Valacyclovir HydrochlorideTablet, film coated500 mg/1OralAv Pak2014-09-22Not applicableUs
Valacyclovir HydrochlorideTablet500 mg/1OralPreferred Pharmaceuticals, Inc.2014-09-12Not applicableUs
Valacyclovir HydrochlorideTablet, film coated500 mg/1OralCardinal Health2012-11-29Not applicableUs
Valacyclovir HydrochlorideTablet, film coated500 mg/1OralA S Medication Solutions2010-05-24Not applicableUs
Valacyclovir HydrochlorideTablet, film coated1 g/1OralAvera Mc Kennan Hospital2015-03-16Not applicableUs
Valacyclovir HydrochlorideTablet, film coated1 g/1OralWatson Laboratories, Inc.2010-05-24Not applicableUs
Valacyclovir HydrochlorideTablet, film coated500 mg/1OralRebel Distributors Corp2009-12-03Not applicableUs
Valacyclovir HydrochlorideTablet, film coated1 g/1OralA S Medication Solutions2010-05-24Not applicableUs
Valacyclovir HydrochlorideTablet, film coated1 g/1OralWockhardt Limited2010-05-24Not applicableUs
Valacyclovir HydrochlorideTablet, film coated1 g/1OralProficient Rx LP2010-05-24Not applicableUs
Valacyclovir HydrochlorideTablet, film coated1 g/1OralWockhardt USA LLC.2010-05-24Not applicableUs
Valacyclovir HydrochlorideTablet, film coated1 g/1OralLake Erie Medical DBA Quality Care Products LLC2012-04-05Not applicableUs
Valacyclovir HydrochlorideTablet, film coated500 mg/1OralMylan Pharmaceuticals Inc.2010-05-24Not applicableUs
Valacyclovir HydrochlorideTablet, film coated500 mg/1OralActavis Pharma, Inc.2011-04-25Not applicableUs
Valacyclovir HydrochlorideTablet, film coated500 mg/1OralPhysicians Total Care, Inc.2009-12-03Not applicableUs
Valacyclovir HydrochlorideTablet, film coated500 mg/1OralPreferred Pharmaceuticals Inc.2016-04-27Not applicableUs
Valacyclovir HydrochlorideTablet, film coated1 g/1OralAv Kare, Inc.2013-07-112015-12-29Us
Valacyclovir HydrochlorideTablet, film coated500 mg/1OralPd Rx Pharmaceuticals, Inc.2007-01-31Not applicableUs
Valacyclovir HydrochlorideTablet, film coated1 g/1OralH.J. Harkins Company, Inc.2010-05-24Not applicableUs
Valacyclovir HydrochlorideTablet, film coated500 mg/1OralA S Medication Solutions2010-05-24Not applicableUs
Valacyclovir HydrochlorideTablet1 g/1OralClinical Solutions Wholesale2010-05-24Not applicableUs
Valacyclovir HydrochlorideTablet, film coated1 g/1OralMed Vantx, Inc.2010-05-24Not applicableUs
Valacyclovir HydrochlorideTablet, film coated1 g/1OralREMEDYREPACK INC.2013-04-04Not applicableUs
Valacyclovir HydrochlorideTablet500 mg/1OralSandoz Inc2010-05-24Not applicableUs
Valacyclovir HydrochlorideTablet, film coated1 g/1OralAv Pak2014-09-22Not applicableUs
Valacyclovir HydrochlorideTablet, film coated1 g/1OralPreferred Pharmaceuticals, Inc.2013-10-03Not applicableUs
Valacyclovir HydrochlorideTablet, film coated500 mg/1OralCardinal Health2012-09-25Not applicableUs
Valacyclovir HydrochlorideTablet1000 mg/1OralPreferred Pharmaceuticals Inc.2016-10-24Not applicableUs
Valacyclovir HydrochlorideTablet, film coated500 mg/1OralMc Kesson Packaging Services A Business Unit Of Mc Kesson Corporation2011-05-23Not applicableUs
Valacyclovir HydrochlorideTablet, film coated500 mg/1OralREMEDYREPACK INC.2016-04-08Not applicableUs
Valacyclovir HydrochlorideTablet, film coated1 g/1OralRebel Distributors Corp2010-06-11Not applicableUs
Valacyclovir HydrochlorideTablet, film coated1 g/1OralA S Medication Solutions2011-04-25Not applicableUs
Valacyclovir HydrochlorideTablet, film coated1 g/1OralLake Erie Medical DBA Quality Care Products LLC2010-05-24Not applicableUs
Valacyclovir HydrochlorideTablet, film coated500 mg/1OralPd Rx Pharmaceuticals, Inc.2010-05-24Not applicableUs
Valacyclovir HydrochlorideTablet, film coated500 mg/1OralAurobindo Pharma Limited2010-05-24Not applicableUs
Valacyclovir HydrochlorideTablet1000 mg/1OralA S Medication Solutions2010-05-24Not applicableUs
Valacyclovir HydrochlorideTablet, film coated500 mg/1OralAmerican Health Packaging2012-11-292015-12-31Us
Valacyclovir HydrochlorideTablet, film coated1 g/1OralMylan Pharmaceuticals Inc.2010-05-24Not applicableUs
Valacyclovir HydrochlorideTablet, film coated1 g/1OralActavis Pharma, Inc.2011-04-25Not applicableUs
Valacyclovir HydrochlorideTablet, film coated500 mg/1OralAmerican Health Packaging2014-02-28Not applicableUs
Valacyclovir HydrochlorideTablet, film coated500 mg/1OralDr. Reddys Laboratories Limited2010-12-06Not applicableUs
Valacyclovir HydrochlorideTablet, film coated500 mg/1OralPd Rx Pharmaceuticals, Inc.2011-04-25Not applicableUs
Valacyclovir HydrochlorideTablet, film coated500 mg/1OralAidarex Pharmaceuticals LLC2010-05-24Not applicableUs
Valacyclovir HydrochlorideTablet, film coated1 g/1OralA S Medication Solutions2010-05-24Not applicableUs
Valacyclovir HydrochlorideTablet1000 mg/1OralREMEDYREPACK INC.2015-05-20Not applicableUs
Valacyclovir HydrochlorideTablet500 mg/1OralCipla USA Inc.2010-05-24Not applicableUs
Valacyclovir HydrochlorideTablet, film coated500 mg/1OralJubilant Cadista Pharmaceuticals Inc.2012-04-05Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
BagovirBago
CyclovalGMP
MitangaAversi
OvalacBeximco
PervioralRoyal Pharma
ReviraSquare
VacylessYung Shin
VadiralGynopharm
ValdacirActavis
ValotixRowex
ValvirSoho
ValztrexNorthia
ViramixalPanalab
ViropelPelpharma
VociflonPharmathen
ZelitrexGlaxoSmithKline
ZelivireRanbaxy
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Valaciclovir Hydrochloride
124832-27-5
Thumb
  • InChI Key: ZCDDBUOENGJMLV-QRPNPIFTSA-N
  • Monoisotopic Mass: 360.131280897
  • Average Mass: 360.797
DBSALT000289
Categories
UNIIMZ1IW7Q79D
CAS number124832-26-4
WeightAverage: 324.3357
Monoisotopic: 324.154603158
Chemical FormulaC13H20N6O4
InChI KeyHDOVUKNUBWVHOX-QMMMGPOBSA-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
IUPAC Name
2-[(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)methoxy]ethyl (2S)-2-amino-3-methylbutanoate
SMILES
CC(C)[[email protected]](N)C(=O)OCCOCN1C=NC2=C1NC(N)=NC2=O
Pharmacology
IndicationFor the treatment or suppression of cold sores (herpes labialis), herpes zoster (shingles), genital herpes in immunocompetent individuals, and recurrent genital herpes in HIV-infected individuals.
Structured Indications
PharmacodynamicsValaciclovir (INN) or Valacyclovir (USAN) is a prodrug and synthetic purine nucleoside analogue with inhibitory activity against herpes simplex virus types 1 (HSV-1), 2 (HSV-2), varicella-zoster virus (VZV), Epstein-Barr virus (EBV), and cytomegalovirus (CMV). Valaciclovir is almost completely converted to acyclovir and L-valine. The inhibitory activity of valaciclovir is highly selective due to its affinity for the enzyme thymidine kinase (TK) encoded by HSV and VZV. This viral enzyme converts acyclovir into acyclovir monophosphate, which is then converted into acyclovir diphosphate and triphosphate by cellular enzymes. Acyclovir is selectively converted to the active triphosphate form by cells infected with herpes viruses.
Mechanism of actionValaciclovir is phosphorylated by viral thymidine kinase to acyclovir triphosphate (the active metabolite) which then inhibits herpes viral DNA replication by competitive inhibition of viral DNA polymerase, and by incorporation into and termination of the growing viral DNA chain. When used as a substrate for viral DNA polymerase, acyclovir triphosphate competitively inhibits dATP leading to the formation of 'faulty' DNA. This is where acyclovir triphosphate is incorporated into the DNA strand replacing many of the adenosine bases. This results in the prevention of DNA synthesis, as phosphodiester bridges can longer to be built, destabilizing the strand.
TargetKindPharmacological actionActionsOrganismUniProt ID
Thymidine kinaseProteinyes
inducer
HHV-1Q9QNF7 details
DNA polymerase catalytic subunitProteinyes
inhibitor
HHV-1P04293 details
Related Articles
AbsorptionAfter oral administration, valaciclovir hydrochloride is rapidly absorbed from the gastrointestinal tract. The absolute bioavailability of acyclovir after administration of valaciclovir is 54.5% ± 9.1%.
Volume of distributionNot Available
Protein binding13-18%
Metabolism

Valaciclovir is rapidly and almost entirely (~99%) converted to the active compound, acyclovir, and L-valine by first-pass intestinal and hepatic metabolism by enzymatic hydrolysis. Neither valaciclovir nor acyclovir is metabolized by cytochrome P450 enzymes.

Route of eliminationAcyclovir accounted for 89% of the radioactivity excreted in the urine.
Half life2.5-3.3 hours
Clearance
  • Renal cl=255 +/-  86 mL/min [healthy]
  • apparent cl=86.3 +/- 21.3 mL/min/1.73 m2 [dialysis patients]
  • apparent cl=679.16 +/- 162.76 mL/min/1.73 m2 [healthy]
ToxicityAdverse effects of overexposure might include headache and nausea.
Affected organisms
  • Human Herpes Virus
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
FoscarnetFoscarnet may increase the nephrotoxic activities of Valaciclovir.Approved
Mycophenolic acidThe serum concentration of Mycophenolic acid can be increased when it is combined with Valaciclovir.Approved
TenofovirValaciclovir may decrease the excretion rate of Tenofovir which could result in a higher serum level.Approved, Investigational
TizanidineThe serum concentration of Tizanidine can be increased when it is combined with Valaciclovir.Approved
ZidovudineValaciclovir may increase the central nervous system depressant (CNS depressant) activities of Zidovudine.Approved
Food InteractionsNot Available
References
Synthesis Reference

Marina Etinger, “Synthesis and purification of valacyclovir.” U.S. Patent US20030153757, issued August 14, 2003.

US20030153757
General References
  1. O'Brien JJ, Campoli-Richards DM: Acyclovir. An updated review of its antiviral activity, pharmacokinetic properties and therapeutic efficacy. Drugs. 1989 Mar;37(3):233-309. [PubMed:2653790 ]
  2. Umapathy NS, Ganapathy V, Ganapathy ME: Transport of amino acid esters and the amino-acid-based prodrug valganciclovir by the amino acid transporter ATB(0,+). Pharm Res. 2004 Jul;21(7):1303-10. [PubMed:15290873 ]
External Links
ATC CodesJ05AB11
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSDownload (29.3 KB)
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9475
Blood Brain Barrier+0.9389
Caco-2 permeable-0.8957
P-glycoprotein substrateSubstrate0.7487
P-glycoprotein inhibitor INon-inhibitor0.7467
P-glycoprotein inhibitor IINon-inhibitor0.9586
Renal organic cation transporterNon-inhibitor0.8553
CYP450 2C9 substrateNon-substrate0.8941
CYP450 2D6 substrateNon-substrate0.8244
CYP450 3A4 substrateSubstrate0.5571
CYP450 1A2 substrateNon-inhibitor0.8155
CYP450 2C9 inhibitorNon-inhibitor0.8734
CYP450 2D6 inhibitorNon-inhibitor0.8797
CYP450 2C19 inhibitorNon-inhibitor0.7944
CYP450 3A4 inhibitorNon-inhibitor0.9351
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8373
Ames testNon AMES toxic0.6139
CarcinogenicityNon-carcinogens0.9345
BiodegradationNot ready biodegradable0.899
Rat acute toxicity2.2217 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9427
hERG inhibition (predictor II)Non-inhibitor0.7378
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Aurobindo pharma ltd
  • Dr reddys laboratories ltd
  • Matrix laboratories ltd
  • Mylan pharmaceuticals inc
  • Ranbaxy laboratories ltd
  • Roxane laboratories inc
  • Sandoz inc
  • Teva pharmaceuticals usa
  • Watson laboratories inc
  • Wockhardt ltd
  • Glaxosmithkline
Packagers
Dosage forms
FormRouteStrength
TabletOral1000 mg
CapsuleOral1 g/1
Tablet, film coatedOral1 g/1
Tablet, film coatedOral500 mg/1
TabletOral1 g/1
TabletOral1000 mg/1
TabletOral500 mg/1
Tablet, coatedOral500 mg/1
TabletOral1 g
TabletOral500 mg
Prices
Unit descriptionCostUnit
Valtrex 1 gm tablet14.62USD tablet
Valtrex 1 gm caplet14.06USD caplet
Valacyclovir HCl 1 gm tablet12.87USD tablet
Valtrex 500 mg tablet8.36USD tablet
Valacyclovir HCl 500 mg tablet7.35USD tablet
Valtrex (Caplet) 500 mg Tablet3.82USD tablet
Apo-Valacyclovir (Caplet) 500 mg Tablet2.14USD tablet
Pms-Valacyclovir (Caplet) 500 mg Tablet2.14USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA1340083 No1998-10-132015-10-13Canada
CA2243237 No2008-09-022017-01-17Canada
US4957924 No1992-12-232009-12-23Us
US5879706 Yes1996-07-192016-07-19Us
US6107302 Yes1996-07-192016-07-19Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
logP-0.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility3.55 mg/mLALOGPS
logP-0.84ALOGPS
logP-0.45ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)8.1ChemAxon
pKa (Strongest Basic)7.36ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area146.85 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity80.63 m3·mol-1ChemAxon
Polarizability31.96 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acid esters
Alternative Parents
Substituents
  • Alpha-amino acid ester
  • Hypoxanthine
  • 6-oxopurine
  • Purine
  • Imidazopyrimidine
  • Pyrimidone
  • Fatty acid ester
  • Fatty acyl
  • Pyrimidine
  • Primary aromatic amine
  • N-substituted imidazole
  • Heteroaromatic compound
  • Vinylogous amide
  • Imidazole
  • Azole
  • Carboxylic acid ester
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors

Targets

Kind
Protein
Organism
HHV-1
Pharmacological action
yes
Actions
inducer
General Function:
Thymidine kinase activity
Specific Function:
In latent infection, may allow the virus to be reactivated and to grow in cells lacking a high concentration of phosphorylated nucleic acid precursors, such as nerve cells that do not replicate their genome.
Gene Name:
TK
Uniprot ID:
Q9QNF7
Molecular Weight:
40896.475 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Teh BS, Ayala G, Aguilar L, Mai WY, Timme TL, Vlachaki MT, Miles B, Kadmon D, Wheeler T, Caillouet J, Davis M, Carpenter LS, Lu HH, Chiu JK, Woo SY, Thompson T, Aguilar-Cordova E, Butler EB: Phase I-II trial evaluating combined intensity-modulated radiotherapy and in situ gene therapy with or without hormonal therapy in treatment of prostate cancer-interim report on PSA response and biopsy data. Int J Radiat Oncol Biol Phys. 2004 Apr 1;58(5):1520-9. [PubMed:15050332 ]
  4. Satoh T, Teh BS, Timme TL, Mai WY, Gdor Y, Kusaka N, Fujita T, Pramudji CK, Vlachaki MT, Ayala G, Wheeler T, Amato R, Miles BJ, Kadmon D, Butler EB, Thompson TC: Enhanced systemic T-cell activation after in situ gene therapy with radiotherapy in prostate cancer patients. Int J Radiat Oncol Biol Phys. 2004 Jun 1;59(2):562-71. [PubMed:15145177 ]
  5. Hinata N, Shirakawa T, Terao S, Goda K, Tanaka K, Yamada Y, Hara I, Kamidono S, Fujisawa M, Gotoh A: Progress report on phase I/II clinical trial of Ad-OC-TK plus VAL therapy for metastatic or locally recurrent prostate cancer: Initial experience at Kobe University. Int J Urol. 2006 Jun;13(6):834-7. [PubMed:16834676 ]
Kind
Protein
Organism
HHV-1
Pharmacological action
yes
Actions
inhibitor
General Function:
Rna-dna hybrid ribonuclease activity
Specific Function:
Replicates viral genomic DNA. The replication complex is composed of six viral proteins: the DNA polymerase, processivity factor, primase, primase-associated factor, helicase, and ssDNA-binding protein. Additionally, the polymerase contains an intrinsic ribonuclease H (RNase H) activity that specifically degrades RNA/DNA heteroduplexes or duplex DNA substrates in the 5' to 3' direction. Therefo...
Gene Name:
Not Available
Uniprot ID:
P04293
Molecular Weight:
136419.66 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Scott GM, Ng HL, Morton CJ, Parker MW, Rawlinson WD: Murine cytomegalovirus resistant to antivirals has genetic correlates with human cytomegalovirus. J Gen Virol. 2005 Aug;86(Pt 8):2141-51. [PubMed:16033961 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Proton-dependent oligopeptide secondary active transmembrane transporter activity
Specific Function:
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products.
Gene Name:
SLC15A1
Uniprot ID:
P46059
Molecular Weight:
78805.265 Da
References
  1. Ganapathy ME, Huang W, Wang H, Ganapathy V, Leibach FH: Valacyclovir: a substrate for the intestinal and renal peptide transporters PEPT1 and PEPT2. Biochem Biophys Res Commun. 1998 May 19;246(2):470-5. [PubMed:9610386 ]
  2. Han H, de Vrueh RL, Rhie JK, Covitz KM, Smith PL, Lee CP, Oh DM, Sadee W, Amidon GL: 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. [PubMed:9706043 ]
  3. Balimane PV, Tamai I, Guo A, Nakanishi T, Kitada H, Leibach FH, Tsuji A, Sinko PJ: Direct evidence for peptide transporter (PepT1)-mediated uptake of a nonpeptide prodrug, valacyclovir. Biochem Biophys Res Commun. 1998 Sep 18;250(2):246-51. [PubMed:9753615 ]
  4. Sawada K, Terada T, Saito H, Hashimoto Y, Inui KI: Recognition of L-amino acid ester compounds by rat peptide transporters PEPT1 and PEPT2. J Pharmacol Exp Ther. 1999 Nov;291(2):705-9. [PubMed:10525090 ]
  5. Balimane P, Sinko P: 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. [PubMed:11180195 ]
  6. Guo A, Hu P, Balimane PV, Leibach FH, Sinko PJ: 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. [PubMed:10087037 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Peptide:proton symporter activity
Specific Function:
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides.
Gene Name:
SLC15A2
Uniprot ID:
Q16348
Molecular Weight:
81782.77 Da
References
  1. Ganapathy ME, Huang W, Wang H, Ganapathy V, Leibach FH: Valacyclovir: a substrate for the intestinal and renal peptide transporters PEPT1 and PEPT2. Biochem Biophys Res Commun. 1998 May 19;246(2):470-5. [PubMed:9610386 ]
  2. Sawada K, Terada T, Saito H, Hashimoto Y, Inui KI: Recognition of L-amino acid ester compounds by rat peptide transporters PEPT1 and PEPT2. J Pharmacol Exp Ther. 1999 Nov;291(2):705-9. [PubMed:10525090 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenadine. Transports benzylpenicillin (PCG), estrone-3-sulfate (E1S), cimetidine (CMD), 2,4-dichloro-phenoxyacetate (2,4-D), p-amino-hippurate (PAH), acyclovir (ACV) and ochratoxin (OTA).
Gene Name:
SLC22A8
Uniprot ID:
Q8TCC7
Molecular Weight:
59855.585 Da
References
  1. Takeda M, Khamdang S, Narikawa S, Kimura H, Kobayashi Y, Yamamoto T, Cha SH, Sekine T, Endou H: Human organic anion transporters and human organic cation transporters mediate renal antiviral transport. J Pharmacol Exp Ther. 2002 Mar;300(3):918-24. [PubMed:11861798 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS) (By similarity). Mediates the sodium-in...
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
Molecular Weight:
61815.78 Da
References
  1. Wada S, Tsuda M, Sekine T, Cha SH, Kimura M, Kanai Y, Endou H: Rat multispecific organic anion transporter 1 (rOAT1) transports zidovudine, acyclovir, and other antiviral nucleoside analogs. J Pharmacol Exp Ther. 2000 Sep;294(3):844-9. [PubMed:10945832 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Neurotransmitter:sodium symporter activity
Specific Function:
Mediates the uptake of a broad range of neutral and cationic amino acids (with the exception of proline) in a Na(+)/Cl(-)-dependent manner.
Gene Name:
SLC6A14
Uniprot ID:
Q9UN76
Molecular Weight:
72152.145 Da
References
  1. Umapathy NS, Ganapathy V, Ganapathy ME: Transport of amino acid esters and the amino-acid-based prodrug valganciclovir by the amino acid transporter ATB(0,+). Pharm Res. 2004 Jul;21(7):1303-10. [PubMed:15290873 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Bile acid:sodium symporter activity
Specific Function:
Plays a critical role in the sodium-dependent reabsorption of bile acids from the lumen of the small intestine. Plays a key role in cholesterol metabolism.
Gene Name:
SLC10A2
Uniprot ID:
Q12908
Molecular Weight:
37713.405 Da
References
  1. Tolle-Sander S, Lentz KA, Maeda DY, Coop A, Polli JE: Increased acyclovir oral bioavailability via a bile acid conjugate. Mol Pharm. 2004 Jan 12;1(1):40-8. [PubMed:15832499 ]
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Drug created on June 13, 2005 07:24 / Updated on December 02, 2016 03:58