VALACYCLOVIR HYDROCHLORIDE DIHYDRATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C13H20N6O4.ClH.2H2O
Molecular Weight	396.827
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of VALACYCLOVIR HYDROCHLORIDE DIHYDRATE

Structure Search

SMILES

O.O.Cl.CC(C)[C@H](N)C(=O)OCCOCN1C=NC2=C1N=C(N)NC2=O

InChI

InChIKey=QMVFKSCLPIIINF-CZDIJEQGSA-N

InChI=1S/C13H20N6O4.ClH.2H2O/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);1H;2*1H2/t8-;;;/m0.../s1

HIDE SMILES / InChI

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C13H20N6O4
Molecular Weight	324.3357
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020487s016lbl.pdfhttps://www.ncbi.nlm.nih.gov/pubmed/3680558 | https://www.ncbi.nlm.nih.gov/pubmed/3790156 | https://www.ncbi.nlm.nih.gov/pubmed/2159990 | Leoung, G.S. (1989) Opportunistic Infections in Patients with the Acquired Immunodeficiency Syndrome, page 207, retrieved from: https://books.google.ru/books?id=As56gGv7E_YChttps://www.accessdata.fda.gov/drugsatfda_docs/label/2005/018828s030,020089s019,019909s020lbl.pdf
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/6313598 | https://www.ncbi.nlm.nih.gov/pubmed/2828440 | https://www.ncbi.nlm.nih.gov/pubmed/202961

Acyclovir is a synthetic antiviral nucleoside analogue. A screening program for antiviral drugs begun at Burroughs Wellcome in the 1960s resulted in the discovery of acyclovir in 1974. Preclinical investigation brought the drug to clinical trials in 1977 and the first form of the drug (topical) was available to physicians in 1982. Activity of acyclovir is greatest against herpes 1 and herpes 2, less against varicella zoster, still less against Epstein-Barr, and very little against cytomegalovirus. Acyclovir is an antiviral agent only after it is phosphorylated in infected cells by a viral-induced thymidine kinase. Acyclovir monophosphate is phosphorylated to diphosphate and triphosphate forms by cellular enzymes in the infected host cell where the drug is concentrated. Acyclovir triphosphate inactivates viral deoxyribonucleic acid polymerase.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Thymidine kinase 17 Target ID: CHEMBL1820 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020487s016lbl.pdf	Inhibitor 8504
Human herpesvirus 1 DNA polymerase 24 Target ID: CHEMBL1872 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/018828s030,020089s019,019909s020lbl.pdf	Inhibitor 8504		0.08 µM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Herpes zoster infections 15 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/18603slr027_zovirax_lbl.pdf https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/018828s030,020089s019,019909s020lbl.pdf	Primary	Approved 8583	ZOVIRAX Approved Use Oral ZOVIRAX® (acyclovir) is indicated for the treatment: Herpes Zoster Infections: ZOVIRAX is indicated for the acute treatment of herpes zoster (shingles). Genital Herpes: ZOVIRAX is indicated for the treatment of initial episodes and the management of recurrent episodes of genital herpes. Chickenpox: ZOVIRAX is indicated for the treatment of chickenpox (varicella). Injectable ZOVIRAX® (acyclovir) is indicated for the treatment: Herpes Simplex Infections in Immunocompromised Patients: ZOVIRAX for Injection is indicated for the treatment of initial and recurrent mucosal and cutaneous herpes simplex (HSV-1 and HSV-2) in immunocompromised patients. Initial Episodes of Herpes Genitalis: ZOVIRAX for Injection is indicated for the treatment of severe initial clinical episodes of herpes genitalis in immunocompetent patients. Herpes Simplex Encephalitis: ZOVIRAX for Injection is indicated for the treatment of herpessimplex encephalitis. Neonatal Herpes Simplex Virus Infection: ZOVIRAX for Injection is indicated for the treatmentof neonatal herpes infections. Varicella-Zoster Infections in Immunocompromised Patients: ZOVIRAX for Injection is indicated for the treatment of varicella-zoster (shingles) infections in immunocompromised patients. Launch Date 1982
Herpes simplex infection 28 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/18603slr027_zovirax_lbl.pdf https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/018828s030,020089s019,019909s020lbl.pdf	Primary	Approved 8583	ZOVIRAX Approved Use Oral ZOVIRAX® (acyclovir) is indicated for the treatment: Herpes Zoster Infections: ZOVIRAX is indicated for the acute treatment of herpes zoster (shingles). Genital Herpes: ZOVIRAX is indicated for the treatment of initial episodes and the management of recurrent episodes of genital herpes. Chickenpox: ZOVIRAX is indicated for the treatment of chickenpox (varicella). Injectable ZOVIRAX® (acyclovir) is indicated for the treatment: Herpes Simplex Infections in Immunocompromised Patients: ZOVIRAX for Injection is indicated for the treatment of initial and recurrent mucosal and cutaneous herpes simplex (HSV-1 and HSV-2) in immunocompromised patients. Initial Episodes of Herpes Genitalis: ZOVIRAX for Injection is indicated for the treatment of severe initial clinical episodes of herpes genitalis in immunocompetent patients. Herpes Simplex Encephalitis: ZOVIRAX for Injection is indicated for the treatment of herpessimplex encephalitis. Neonatal Herpes Simplex Virus Infection: ZOVIRAX for Injection is indicated for the treatmentof neonatal herpes infections. Varicella-Zoster Infections in Immunocompromised Patients: ZOVIRAX for Injection is indicated for the treatment of varicella-zoster (shingles) infections in immunocompromised patients. Launch Date 1982
Cold sores 11 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020487s016lbl.pdf	Primary	Approved 8583	VALTREX Approved Use INDICATIONS AND USAGE. VALTREX is a nucleoside analogue DNA polymerase inhibitor indicated for: Adult Patients Cold Sores (Herpes Labialis), Genital Herpes, Treatment in immunocompetent patients (initial or recurrent episode), Suppression in immunocompetent or HIV-infected patients, Reduction of transmission, Herpes Zoster. Pediatric Patients Cold Sores (Herpes Labialis), Chickenpox Limitations of Use. The efficacy and safety of VALTREX have not been established in immunocompromised patients other than for the suppression of genital herpes in HIV-infected patients. Launch Date 2004
Genital herpes 13 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020487s016lbl.pdf	Primary	Approved 8583	VALTREX Approved Use INDICATIONS AND USAGE. VALTREX is a nucleoside analogue DNA polymerase inhibitor indicated for: Adult Patients Cold Sores (Herpes Labialis), Genital Herpes, Treatment in immunocompetent patients (initial or recurrent episode), Suppression in immunocompetent or HIV-infected patients, Reduction of transmission, Herpes Zoster. Pediatric Patients Cold Sores (Herpes Labialis), Chickenpox Limitations of Use. The efficacy and safety of VALTREX have not been established in immunocompromised patients other than for the suppression of genital herpes in HIV-infected patients. Launch Date 2004
Herpes zoster infections 15 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020487s016lbl.pdf	Primary	Approved 8583	VALTRE Approved Use INDICATIONS AND USAGE. VALTREX is a nucleoside analogue DNA polymerase inhibitor indicated for: Adult Patients Cold Sores (Herpes Labialis), Genital Herpes, Treatment in immunocompetent patients (initial or recurrent episode), Suppression in immunocompetent or HIV-infected patients, Reduction of transmission, Herpes Zoster. Pediatric Patients Cold Sores (Herpes Labialis), Chickenpox Limitations of Use. The efficacy and safety of VALTREX have not been established in immunocompromised patients other than for the suppression of genital herpes in HIV-infected patients. Launch Date 2004

C_max

Value	Dose	Co-administered	Analyte	Population
599.2 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/17692728	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:		ACYCLOVIR plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
3015.7 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/17692728	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:		ACYCLOVIR plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
3.9 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/17692728	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:		ACYCLOVIR plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
79% EXPERIMENT https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/018828s030,020089s019,019909s020lbl.pdf			ACYCLOVIR plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OAT1 725 OAT2 153 OAT3 747 OAT4 150 OCT1 620 OCT2 779 OATP1B1 1079 OATP1B3 961 OATP2B1 157 CYP1A2 2153	OAT1 395 OAT2 125 OAT3 391 OAT4 93 OCT1 393 OCT2 434 MRP2 252 MATE1 182 MATE2 98 BCRP 697

Drug as perpetrator

Target	Modality	Activity
OAT2 155	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/11861798/	no
OAT4 150	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/11861798/	no
OATP1B1 1095	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/22541068/	no
OATP1B3 970	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/22541068/	no
OATP2B1 162	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/22541068/	no
OCT2 782	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/11861798/	no
CYP1A2 2333	inhibitor 4027 Sources: https://www.fda.gov/drugs/drug-interactions-labeling/drug-development-and-drug-interactions-table-substrates-inhibitors-and-inducers	weak
OAT1 730	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/11861798/	yes
OAT3 749	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/11861798/	yes
OCT1 656	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/11861798/	yes

Drug as victim

Target	Modality	Activity
OAT2 125	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11861798/	no
OAT3 391	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11861798/	no
OAT4 93	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11861798/	no
OCT2 434	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11861798/	no
BCRP 697	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21859328/	yes
MATE1 182	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/17509534/	yes
MATE2 98	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/17509534/	yes
MRP2 252	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/31341258/	yes
OAT1 395	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11861798/\|https://pubmed.ncbi.nlm.nih.gov/31341258/	yes
OCT1 393	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11861798/	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:2453	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:2453
ChemicalBook	CB7126677	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB7126677
eMolecules	29702921	https://www.emolecules.com/cgi-bin/more?vid=29702921
eMolecules	768732	https://www.emolecules.com/cgi-bin/more?vid=768732
eMolecules	901331	https://www.emolecules.com/cgi-bin/more?vid=901331
MolPort	MolPort-000-768-994	https://www.molport.com/shop/molecule-link/MolPort-000-768-994
MolPort	MolPort-001-889-834	https://www.molport.com/shop/molecule-link/MolPort-001-889-834
MolPort	MolPort-003-940-063	https://www.molport.com/shop/molecule-link/MolPort-003-940-063
Selleck Chemicals	Acyclovir(Aciclovir)	http://www.selleckchem.com/products/Acyclovir(Aciclovir).html
ZINC	ZINC000001530555	http://zinc15.docking.org/substances/ZINC000001530555

PubMed

Title	Date	PubMed
FV-100 versus valacyclovir for the prevention of post-herpetic neuralgia and the treatment of acute herpes zoster-associated pain: A randomized-controlled trial.	2017-07	27943311
Diagnosis and Treatment of Acute Retinal Necrosis: A Report by the American Academy of Ophthalmology.	2017-03	28094044
Selection and characterization of varicella-zoster virus variants resistant to (R)-9-[4-hydroxy-2-(hydroxymethy)butyl]guanine.	2001-06	11353604
Synthesis and biological evaluation of purine-containing butenolides.	2001-05-24	11356110
Neurotoxicity of valacyclovir in peritoneal dialysis: a pharmacokinetic study.	2001-05-19	11359026
Enhancement of the anti-herpetic effect of trichosanthin by acyclovir and interferon.	2001-05-11	11356198
Coexpression of guanylate kinase with thymidine kinase enhances prodrug cell killing in vitro and suppresses vascular smooth muscle cell proliferation in vivo.	2001-05	11356082
Oral recurrent human herpes virus infection and bone marrow transplantation survival.	2001-05	11346734
Famciclovir for ophthalmic zoster: a randomised aciclovir controlled study.	2001-05	11316720
Acyclovir prophylaxis in late pregnancy prevents recurrent genital herpes and viral shedding.	2001-05	11311761
Contact dermatitis from topical antiviral drugs.	2001-05	11298689
Chemical stability, enzymatic hydrolysis, and nasal uptake of amino acid ester prodrugs of acyclovir.	2001-05	11288106
[Intrauterine herpes simplex virus infection].	2001-04-18	11305194
Novel synthesis of seco type of acyclo C-nucleosides of 1,2,4-triazole and 1,2,4-triazol.	2001-04-17	11303556
Hydrophilic interaction chromatography using amino and silica columns for the determination of polar pharmaceuticals and impurities.	2001-04-13	11355803
Practice parameter: Steroids, acyclovir, and surgery for Bell's palsy (an evidence-based review): report of the Quality Standards Subcommittee of the American Academy of Neurology.	2001-04-10	11294918
Postherpetic neuralgia. Treatment with amitriptyline is cheaper than with aciclovir.	2001-04-07	11290647
Postherpetic neuralgia. Pathogenesis of postherpetic neuralgia should be determined.	2001-04-07	11290628
Herpes simplex virus-1 thymidine kinase mutants created by semi-random sequence mutagenesis improve prodrug-mediated tumor cell killing.	2001-04-01	11306482
Cough syncope with herpetic tracheobronchitis.	2001-04	11344844
Rotavirus encephalopathy: pathogenesis reviewed.	2001-04	11328483
Heart transplantation and the Batista operation for children with refractory heart failure.	2001-04	11316125
Treatment of EBV driven lymphoproliferation with erythrophagocytosis: 12 year follow up.	2001-04	11304854
Famciclovir vs. aciclovir in immunocompetent patients with recurrent genital herpes infections: a parallel-groups, randomized, double-blind clinical trial.	2001-04	11298543
[Peptide transporter family].	2001-04	11296359
Acyclovir treatment in 2 patients with benign trigeminal sensory neuropathy.	2001-04	11289180
Meta-analysis of prophylaxis of CMV disease in solid organ transplantation: is Ganciclovir a superior agent to Acyclovir?	2001-03-27	11267547
Prophylactic antiviral therapy in CMV high-risk liver transplant recipients.	2001-03-27	11267523
Antiviral drugs can inhibit lymphocyte apoptosis induced by cytomegalovirus antigens.	2001-03-27	11267517
The management of varicella-zoster virus exposure and infection in pregnancy and the newborn period. Australasian Subgroup in Paediatric Infectious Diseases of the Australasian Society for Infectious Diseases.	2001-03-19	11297117
Mild herpes simplex encephalitis worsening despite acyclovir treatment.	2001-03	11355162
[Highly active antiviral and immunosuppressive combination therapy with acyclovir and mycophenolate mofetil following keratoplasty in patients with herpetic eye disease].	2001-03	11322055
[Benign acute ataxia in an adult with VZV infection].	2001-03	11319497
A pilot study of treatment of herpes labialis with 1072 nm narrow waveband light.	2001-03	11298104
[Neurologic toxicity caused by zelitrex (valaciclovir) in 3 patients with renal failure. Is overdose associated with improvement of product bioavailability improvement?].	2001-03	11270274
A 35-year-old man with recurrent aseptic meningitis.	2001-03	11263848
[Photoallergy to Zovirax cream].	2001-02	11275608
Painful skin erosions and fever in an infant. Eczema herpeticum.	2001-02	11272689
Prophylaxis of intravenous immunoglobulin and acyclovir in perinatal varicella.	2001-02	11271397
Pretransplant varicella vaccination is cost-effective in pediatric renal transplantation.	2001-02	11260488
Recurrent herpes labialis: efficacy of topical therapy with penciclovir compared with acyclovir (aciclovir).	2001-01	11354919
Topical treatment of recurrent herpes labialis.	2001-01	11354913
Aerobic bacterial and fungal infections in peripheral blood stem cell transplants.	2001-01	11281391
Flow cytometric evaluation of antiviral agents against human herpesvirus 6.	2001	11345533
Atypical Herpes simplex keratitis (HSK) presenting as a perforated corneal ulcer with a large infiltrate in a contact lens wearer: multinucleated giant cells in the Giemsa smear offered a clue to the diagnosis.	2001	11325340
A randomized, double-blind trial of famciclovir versus acyclovir for the treatment of localized dermatomal herpes zoster in immunocompromised patients.	2001	11291551
Interventions for herpes simplex virus epithelial keratitis.	2001	11279774
Prophylaxis against herpesvirus infections in transplant recipients.	2001	11270937
Management of neonatal herpes simplex virus infection.	2001	11269641
Selection of an oral prodrug (BRL 42810; famciclovir) for the antiherpesvirus agent BRL 39123 [9-(4-hydroxy-3-hydroxymethylbut-l-yl)guanine; penciclovir].	1989-10	2589844

Patents

Sample Use Guides

In Vivo Use Guide

Valacyclovir may be given without regard to meals. Cold Sores (Herpes Labialis): The recommended dosage of Valacyclovir for treatment of cold sores is 2 grams twice daily for 1 day taken 12 hours apart. Therapy should be initiated at the earliest symptom of a cold sore. Genital Herpes: Initial Episode: The recommended dosage of Valacyclovir for treatment of initial genital herpes is 1 gram twice daily for 10 days. Therapy was most effective when administered within 48 hours of the onset of signs and symptoms. Recurrent Episodes: The recommended dosage of Valacyclovir for treatment of recurrent genital herpes is 500 mg twice daily for 3 days. Initiate treatment at the first sign or symptom of an episode.

Route of Administration: Oral

In Vitro Use Guide

In uptake studies using valacyclovir, the extraction solution (water/methanol, 50:50) was added to the Caco-2 cells after the uptake period. After standing for 1 h at room temperature, the solutions were centrifuged and the supernatants were filtered. The filtrate was analyzed by highperformance liquid chromatography (HPLC). Valacyclovir showed a marked inhibitory effect (K=440 +/- 29mkM) on [14C]glycylsarcosine uptake via the apical PEPT1.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:08:56 GMT 2025` Edited by `admin` on `Mon Mar 31 18:08:56 GMT 2025`
Record UNII	A7JO128919
Record Status	`Validated (UNII)`
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Name

Type

Language

VALACYCLOVIR HYDROCHLORIDE DIHYDRATE

Common Name

English

L-VALINE, 2-((2-AMINO-1,6-DIHYDRO-6-OXO-9H-PURIN-9-YL)METHOXY)ETHYL ESTER, HYDROCHLORIDE, HYDRATE (1:1:2)

Preferred Name

English

L-VALINE, 2-((2-AMINO-1,6-DIHYDRO-6-OXO-9H-PURIN-9-YL)METHOXY)ETHYL ESTER, MONOHYDROCHLORIDE, DIHYDRATE

Common Name

English

L-VALINE, 2-((2-AMINO-1,6-DIHYDRO-6-OXO-9H-PURIN-9-YL)METHOXY)ETHYL ESTER, MONOHYDROCHLORIDE DIHYDRATE

Common Name

English

Code System Code Type Description

EPA CompTox

DTXSID90198248