Famciclovir
Famciclovir
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Famciclovir

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Catalog Number PR104227874
CAS 104227-87-4
Description Famciclovir is 2-Amino-9H-purine in which the hydrogen at position 9 is substituted by a 4-acetoxy-3-(acetoxymethyl)but-1-yl group. A prodrug of the antiviral penciclovir, it is used for the treatment of acute herpes zoster (shingles), for the treatment or suppression of recurrent genital herpes in immunocompetent patients and for the treatment of recurrent mucocutaneous herpes simplex infections in HIV infected patients.
Synonyms Famciclovirum; 2-(2-(2-Amino-9H-purin-9-yl)ethyl)propane-1,3-diyl diacetate
IUPAC Name [2-(acetyloxymethyl)-4-(2-aminopurin-9-yl)butyl] acetate
Molecular Weight 321.33
Molecular Formula C14H19N5O4
InChI GGXKWVWZWMLJEH-UHFFFAOYSA-N
InChI Key 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)
Drug Categories Anti-Infective Agents; Antiinfectives for Systemic Use; Antiviral Agents; Antivirals for Systemic Use; Direct Acting Antivirals; Enzyme Inhibitors; Herpes Simplex Virus Nucleoside Analog DNA Polymerase Inhibitor; Herpesvirus Nucleoside Analog DNA Polymerase Inhibitor; Heterocyclic Compounds, Fused-Ring; Nucleic Acid Synthesis Inhibitors; Nucleosides and Nucleotides; Nucleosides and Nucleotides Excl. Reverse Transcriptase Inhibitors; Ophthalmologicals; Purines; Sensory Organs
Drug Interactions Adenovirus type 7 vaccine live-The therapeutic efficacy of Adenovirus type 7 vaccine live can be decreased when used in combination with Famciclovir.
Anthrax vaccine-The therapeutic efficacy of Anthrax vaccine can be decreased when used in combination with Famciclovir.
Bacillus calmette-guerin substrain connaught live antigen-The therapeutic efficacy of Bacillus calmette-guerin substrain connaught live antigen can be decreased when used in combination with Famciclovir.
Bacillus calmette-guerin substrain russian BCG-I live antigen-The therapeutic efficacy of Bacillus calmette-guerin substrain russian BCG-I live antigen can be decreased when used in combination with Famciclovir.
Bacillus calmette-guerin substrain tice live antigen-The therapeutic efficacy of Bacillus calmette-guerin substrain tice live antigen can be decreased when used in combination with Famciclovir.
Half-Life 10 hours
Isomeric SMILES CC(=O)OCC(CCN1C=NC2=CN=C(N=C21)N)COC(=O)C
Type Small Molecule
Therapeutic Category Antivirals
Pharmacology

Indications

Famciclovir is primarily indicated for the treatment of acute herpes zoster, commonly known as shingles. Additionally, it is used for both treatment and suppression of recurrent genital herpes in patients with a competent immune system. It also serves as a treatment option for recurrent mucocutaneous herpes simplex infections in individuals living with HIV.

Pharmacodynamics

Famciclovir functions as a prodrug, which means that it undergoes rapid conversion into its active form, penciclovir, once inside the body. Penciclovir is an antiviral agent that demonstrates inhibitory effects on herpes simplex virus types 1 (HSV-1) and 2 (HSV-2), as well as the varicella zoster virus (VZV). This activity effectively inhibits the synthesis and replication of herpes viral DNA.

Absorption

Upon administration, famciclovir exhibits an absorption rate of approximately 77%.

Metabolism

Famciclovir undergoes metabolic processing within the liver, where it is transformed into its active metabolite, penciclovir. This hepatic metabolism is a key step in activating famciclovir's antiviral properties and enables it to combat viral infections effectively.

Mechanism of Action

Famciclovir, following oral administration, is swiftly converted into its active form, penciclovir. This active metabolite exhibits potent antiviral properties, particularly against herpes simplex virus types 1 and 2 (HSV-1 and HSV-2), as well as varicella-zoster virus (VZV). Within cells infected by these viruses, viral thymidine kinase catalyzes the phosphorylation of penciclovir to its monophosphate form. Subsequently, cellular kinases further phosphorylate it to form penciclovir triphosphate. In vitro studies have shown that penciclovir triphosphate effectively inhibits HSV-2 DNA polymerase through competitive interaction with deoxyguanosine triphosphate. As a result, the synthesis and replication of viral DNA are selectively hindered, curtailing the proliferation of the herpesvirus.

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