Product Name

Valaciclovir

CAS Number

124832-27-5

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Product Name:
Valaciclovir
CAS Number:
124832-27-5
Indication:
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.
Mode of Action:

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.

Pharmacodynamics:

Valaciclovir (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.

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.

Toxicity:

Adverse effects of overexposure might include headache and nausea.

IUPAC:
2-[(2-amino-6-oxo-6, 9-dihydro-3H-purin-9-yl)methoxy]ethyl (2S)-2-amino-3-methylbutanoate
ATC:
J05AB11
PubChem:
60773
DrugBank:
DB00577 (APRD00697)
Formula:
C34H36F3NO13
Molecular Mass:
324.3357
Synonyms:
Valaciclovir Hcl Valaciclovir Hydrochloride Valacyclover Hydrochloric Valacyclover Hydrochloride Valacyclovir Valacyclovir Hydrochloride
SMILES:
CC(C)[C@H](N)C(=O)OCCOCN1C=NC2=C1NC(N)=NC2=O
InChi:
HDOVUKNUBWVHOX-QMMMGPOBSA-N
General Reference:
General Reference:

  1. OêBrien 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

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