ContaminantDB: Valaciclovir

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2009-07-30 17:59:13 UTC

Update Date

2026-03-31 17:38:51 UTC

Accession Number

CHEM002535

Identification

Common Name

Valaciclovir

Class

Small Molecule

Description

Valaciclovir (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]

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins

Contaminant Type

Amide
Amine
Antiviral Agent
Drug
Ester
Ether
Metabolite
Organic Compound
Prodrug
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
L-Valine ester with 9-((2-hydroxyethoxy)methyl)guanine	ChEBI
L-Valine, 2-((2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy)ethyl ester	ChEBI
Valacyclovir	Kegg
Valtrex	Kegg
Valacyclover hydrochloric	HMDB
Valacyclovir hydrochloride	HMDB
Valacyclovir, (D)-isomer	HMDB
Valacyclovir, (L)-isomer	HMDB
2-((2-Amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy)ethyl L-valinate	HMDB
Valacyclovir hydrochloride, (DL)-isomer	HMDB
Valacyclovir, X-hydrochloride, (D)-isomer	HMDB
Valacyclovir, X-hydrochloride, (DL)-isomer	HMDB
L-Valylacyclovir	HMDB
Acyclovir, L-valyl ester	HMDB
Valacyclovir, (DL)-isomer	HMDB
Valaciclovir	MeSH

Chemical Formula

C₁₃H₂₀N₆O₄

Average Molecular Mass

324.336 g/mol

Monoisotopic Mass

324.155 g/mol

CAS Registry Number

124832-26-4

IUPAC Name

2-[(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)methoxy]ethyl (2S)-2-amino-3-methylbutanoate

Traditional Name

valtrex

SMILES

CC(C)[C@H](N)C(=O)OCCOCN1C=NC2=C1NC(N)=NC2=O

InChI Identifier

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

InChI Key

HDOVUKNUBWVHOX-QMMMGPOBSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acid esters

Alternative Parents

Substituents

Alpha-amino acid ester
Valine or derivatives
6-oxopurine
Hypoxanthine
Imidazopyrimidine
Purine
Aminopyrimidine
Pyrimidone
Fatty acid ester
N-substituted imidazole
Pyrimidine
Fatty acyl
Azole
Heteroaromatic compound
Vinylogous amide
Imidazole
Carboxylic acid ester
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organooxygen compound
Primary amine
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organopnictogen compound
Primary aliphatic amine
Amine
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

L-valinyl ester (CHEBI:35854 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

The blue, film-coated caplets are printed with edible white ink.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	3.55e+00 g/L

Predicted Properties

Property	Value	Source
Water Solubility	3.55 g/L	ALOGPS
logP	-0.84	ALOGPS
logP	-0.45	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	8.1	ChemAxon
pKa (Strongest Basic)	7.36	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	146.85 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	80.63 m³·mol⁻¹	ChemAxon
Polarizability	31.96 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-9210000000-51af1895b69904867582	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0udi-1910000000-3db14f76ba496cea0d81	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0udi-2900000000-a3e92ac9125245cf5513	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-016r-0910000000-01375a23cf811e488a21	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-1913000000-e8d1da3daee2d7637783	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-2900000000-90825e6bac8b121f346e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zg0-2900000000-9ced6b2b253471425de0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00xs-5913000000-05fdd28b28d4365d3f85	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-106s-5922000000-36d450a0ce5422cc73d6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0pbc-5900000000-8eaf432e968b85e4cb9a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0fb9-0926000000-779dfd0f2b063ec5e6c4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0901000000-0d030c844b5ab6d9d46d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-2900000000-7c25463514f877a34043	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0359000000-0a84f61843d1db09c776	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-2920000000-8736ab32172119625d46	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0k9x-5900000000-21c409fb0971f216644d	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

After 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%.

Mechanism of Toxicity

Valaciclovir 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.

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. Acyclovir is converted to a small extent to inactive metabolites by aldehyde oxidase and by alcohol and aldehyde dehydrogenase. Plasma concentrations of unconverted valacyclovir are low and transient, generally becoming non-quantifiable by 3 hours after administration. Peak plasma valacyclovir concentrations are generally less than 0.5 mcg/mL at all doses. After single-dose administration of 1 gram of VALTREX, average plasma valacyclovir concentrations observed were 0.5, 0.4, and 0.8 mcg/mL in patients with hepatic dysfunction, renal insufficiency, and in healthy volunteers who received concomitant cimetidine and probenecid, respectively. Route of Elimination: Acyclovir accounted for 89% of the radioactivity excreted in the urine. Half Life: 2.5-3.3 hours

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For 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. Cold Sores (Herpes Labialis): VALTREX is indicated for treatment of cold sores (herpes labialis). The efficacy of VALTREX initiated after the development of clinical signs of a cold sore (e.g., papule, vesicle, or ulcer) has not been established. Genital Herpes: Initial Episode: VALTREX is indicated for treatment of the initial episode of genital herpes in immunocompetent adults. The efficacy of treatment with VALTREX when initiated more than 72 hours after the onset of signs and symptoms has not been established.

Minimum Risk Level

Not Available

Health Effects

General: Facial edema, hypertension, tachycardia. Allergic:Acute hypersensitivity reactions including anaphylaxis, angioedema, dyspnea, pruritus, rash, and urticaria. CNS Symptoms: Aggressive behavior; agitation; ataxia; coma; confusion; decreased consciousness; dysarthria; encephalopathy; mania; and psychosis, including auditory and visual hallucinations, seizures, tremors. Eye: Visual abnormalities. Gastrointestinal: Diarrhea. Hepatobiliary Tract and Pancreas: Liver enzyme abnormalities, hepatitis. Renal: Renal failure, renal pain (may be associated with renal failure). Hematologic: Thrombocytopenia, aplastic anemia, leukocytoclastic vasculitis, TTP/HUS. Skin: Erythema multiforme, rashes including photosensitivity, alopecia.

Symptoms

Adverse effects of overexposure might include headache and nausea.

Treatment

In the event of acute renal failure and anuria, the patient may benefit from hemodialysis until renal function is restored. (4)

Concentrations

Not Available

External Links

DrugBank ID

DB00577

HMDB ID

HMDB0014716

FooDB ID