VALACYCLOVIR HYDROCHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C13H20N6O4.ClH
Molecular Weight	360.797
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

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

InChI

InChIKey=ZCDDBUOENGJMLV-QRPNPIFTSA-N

InChI=1S/C13H20N6O4.ClH/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/t8-;/m0./s1

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

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	MOL RATIO 1 MOL RATIO (average)

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

Description

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	Inhibitor 8,297
Human herpesvirus 1 DNA polymerase 19	Inhibitor 8,297		0.08 µM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Herpes zoster infections 15	Primary	Approved 8,429	ZOVIRAX
Herpes simplex infection 28	Primary	Approved 8,429	ZOVIRAX
Cold sores 11	Primary	Approved 8,429	VALTREX
Genital herpes 13	Primary	Approved 8,429	VALTREX
Herpes zoster infections 15	Primary	Approved 8,429	VALTRE

C_max

Value	Dose	Co-administered	Analyte	Population
599.2 ng/mL	400 mg single, oral		ACYCLOVIR plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
3015.7 ng × h/mL	400 mg single, oral		ACYCLOVIR plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
3.9 h	400 mg single, oral		ACYCLOVIR plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
79%			ACYCLOVIR plasma	Homo sapiens

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OAT1 599 OAT2 145 OAT3 642 OAT4 146 OCT1 512 OCT2 647 OATP1B1 788 OATP1B3 706 OATP2B1 123 CYP1A2 1,524	OAT1 326 OAT2 115 OAT3 339 OAT4 78 OCT1 327 OCT2 355 MRP2 205 MATE1 135 MATE2 96 BCRP 561

Drug as perpetrator

Show entries

Target	Modality	Activity
OAT2 147	inhibitor 3,277	no
OAT4 146	inhibitor 3,277	no
OATP1B1 803	inhibitor 3,277	no
OATP1B3 715	inhibitor 3,277	no
OATP2B1 126	inhibitor 3,277	no

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Drug as victim

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Target	Modality	Activity
OAT2 115	substrate 3,367	no
OAT3 339	substrate 3,367	no
OAT4 78	substrate 3,367	no
OCT2 355	substrate 3,367	no
BCRP 561	substrate 3,367	yes

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Sourcing

Sourcing

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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

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PubMed

Show entries

Title	Date	PubMed
Hepatic and renal effects of azidothymidine and acyclovir on pregnant rats.	2000	11214960
Acyclovir induced coma in the intensive care unit.	2000 Jun	10853214
Antiviral activity of ganciclovir elaidic acid ester against herpesviruses.	2000 Mar	10771080
Guanosine analogues as anti-herpesvirus agents.	2000 Oct-Dec	11200257
A randomized, double-blind trial of famciclovir versus acyclovir for the treatment of localized dermatomal herpes zoster in immunocompromised patients.	2001	11291551

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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.