Drug/Small Molecule:
aciclovir

2D structure

Overview

Generic Names: 9-Hyroxyethoxymethylguanine; AC2; Aciclovier; Aciclovir Sodium; Acycloguanosine; Acyclovir; Acyclovir Sodium; Wellcome-248u
Trade Names: Alti-Acyclovir; Avirax; Vipral; Virorax; Zovir; Zovirax; Zovirax Injection (Zovirax sodium)
PharmGKB Accession Id: PA448045

Description

A guanosine analog that acts as an antimetabolite. Viruses are especially susceptible. Used especially against herpes. PubChem (source: Drug Bank)

Indication

For the treatment and management of herpes zoster (shingles), genital herpes, and chickenpox (source: Drug Bank)

ATC Therapeutic Categories

  • D06BB:Antivirals
  • J05AB:Nucleosides and nucleotides excl. reverse transcriptase inhibitors
  • S01AD:Antivirals

Pharmacology, Interactions, and Contraindications

Mechanism Of Action

Viral (HSV-1, HSV-2 and VZV) thymidine kinase converts aciclovir to the aciclovir monophosphate, which is then converted to the diphosphate by cellular guanylate kinase, and finally to the triphosphate by phosphoglycerate kinase, phosphoenolpyruvate carboxykinase, and pyruvate kinase. Aciclovir triphosphate competitively inhibits viral DNA polymerase and competes with the natural deoxyguanosine triphosphate, for incorporation into viral DNA. Once incorporated, aciclovir triphosphate inhibits DNA synthesis by acting as a chain terminator. (source: Drug Bank)

Pharmacology

Aciclovir (INN) or acyclovir (USAN, former BAN) is a synthetic deoxyguanosine analog and it is the prototype antiviral agent that is activated by viral thymidine kinase. The selective activity of aciclovir is due to its affinity for the thymidine kinase enzyme encoded by HSV and VZV. (source: Drug Bank)

Food Interactions

Increase liquid intake.
Take without regard to meals. (source: Drug Bank)

Absorption, Distribution, Metabolism, Elimination & Toxicity

Biotransformation

Hepatic, the only major urinary metabolite that has been detected is 9-carboxymethoxymethylguanine. (source: Drug Bank)

Protein Binding

9%-33% (source: Drug Bank)

Absorption

Oral: bioavailability 10 to 20% (source: Drug Bank)

Toxicity

Aciclovir may cause nephrotoxicity (crystallization of aciclovir within renal tubules, elevation of serum creatinine, transient), and neurotoxicity (coma, hallucinations, lethargy, seizures, tremors). Nephrotoxicity and neurotoxicity usually resolve after cessation of aciclovir therapy. However, there is no well-defined relationship between aciclovir concentrations in the blood and these adverse effects. (source: Drug Bank)

Isomeric SMILES Code:

c1nc2c(=O)[nH]c(nc2n1COCCO)N (source: Drug Bank)

The following genes are in curated knowledge about this drug.

  Gene Relationship Evidence
Phenotype data available Genotype Data Available Literature annotations available Not annotated
SLC22A1
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  • PK
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Publications

A list of non-curated publications that mention this drug along with other genes is available.

Drug Targets

Gene Description
NP Uncurated Annotation (source: Drug Bank)

A list of non-curated publications that mention this drug along with other drugs is available.

Drug Interactions

Drug Description
theophylline Uncurated Annotation Increases the effect and toxicity of theophylline (source: Drug Bank)

Non-Curated Information

A list of non-curated publications that mention this drug along with other diseases is available.

LinkOuts

Web Resource:
Wikipedia
DrugBank:
DB00787
KEGG Compound ID:
C06810
KEGG Drug ID:
D00222
PubChem Compound ID:
2022
PubChem Substance ID:
7847289

Common Searches

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Non-Curated Publications

A list of non-curated publications that mention this drug is available.

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