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.
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 CDK toolkit. 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
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.

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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
References
1. Vere Hodge RA, Sutton D, Boyd MR, Harnden MR, Jarvest RL. (1989)
Selection of an oral prodrug (BRL 42810; famciclovir) for the antiherpesvirus agent BRL 39123 [9-(4-hydroxy-3-hydroxymethylbut-l-yl)guanine; penciclovir].
Antimicrob Agents Chemother, 33 (10): 1765-73. [PMID:2589844]