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/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. FDA (1994)  |  UK (1995)
IUPAC Name Click here for help
[2-(acetyloxymethyl)-4-(2-aminopurin-9-yl)butyl] acetate
International Nonproprietary Names Click here for help
INN number INN
6438 famciclovir
Synonyms Click here for help
BRL-42810 | BRL42810 | Famvir® | FCV
Database Links Click here for help
CAS Registry No. 104227-87-4 (source: PubChem)
ChEMBL Ligand CHEMBL880
DrugBank Ligand DB00426
GtoPdb PubChem SID 442878663
PubChem CID 3324
Search Google for chemical match using the InChIKey GGXKWVWZWMLJEH-UHFFFAOYSA-N
Search Google for chemicals with the same backbone GGXKWVWZWMLJEH
Search PubMed clinical trials famciclovir
Search PubMed titles famciclovir
Search PubMed titles/abstracts famciclovir
UniChem Compound Search for chemical match using the InChIKey GGXKWVWZWMLJEH-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey GGXKWVWZWMLJEH-UHFFFAOYSA-N

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MedChemExpress
Famciclovir (links to external site)
Cat. No. HY-17426