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famciclovir   Click here for help

GtoPdb Ligand ID: 11629

Synonyms: BRL-42810 | BRL42810 | Famvir® | FCV
Approved drug
famciclovir is an approved drug (FDA (1994), UK (1995))
Compound class: Synthetic organic
Comment: Famciclovir is an orally-delivered, prodrug of the antiviral agent penciclovir [1]. The active metabolite, penciclovir triphosphate, has activity against Herpes viruses and varicella-zoster. Penciclovir triphosphate is a nucleoside analogue that inhibits viral DNA replication by interfering competitively with DNA polymerase.

famciclovir is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 8
Hydrogen bond donors 1
Rotatable bonds 9
Topological polar surface area 122.22
Molecular weight 321.14
XLogP 0.62
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CC(=O)OCC(CCn1cnc2c1nc(N)nc2)COC(=O)C
Isomeric SMILES CC(=O)OCC(CCn1cnc2c1nc(N)nc2)COC(=O)C
InChI InChI=1S/C14H19N5O4/c1-9(20)22-6-11(7-23-10(2)21)3-4-19-8-17-12-5-16-14(15)18-13(12)19/h5,8,11H,3-4,6-7H2,1-2H3,(H2,15,16,18)
InChI Key GGXKWVWZWMLJEH-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
No information available.
Summary of Clinical Use Click here for help
Famciclovir is used to treat herpes zoster and simplex virus infections.
Pharmacokinetics Click here for help
Biotransformation/Metabolism
After oral dosing more than half the dose of famciclovir is absorbed and rapidly converted to penciclovir [1].
External links Click here for help
For extended ADME data see the following:

Drugs.com