Famciclovir
Identification
- Summary
Famciclovir is a nucleoside analog DNA polymerase inhibitor used for the treatment of recurrent cold sores and genital herpes in healthy patients and patients with HIV, and to manage herpes zoster.
- Brand Names
- Famvir
- Generic Name
- Famciclovir
- DrugBank Accession Number
- DB00426
- Background
Famciclovir, marketed as Famvir by Novartis, is a guanine analogue used to treat herpes virus infections. It is most commonly used to treat herpes zoster (shingles). Famciclovir is a prodrug of penciclovir with higher oral bioavailability.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Famciclovir (DB00426)
- Weight
- Average: 321.3318
Monoisotopic: 321.143704121 - Chemical Formula
- C14H19N5O4
- Synonyms
- 2-(2-(2-amino-9H-purin-9-yl)ethyl)-1,3-propanediol diacetate
- 9-[4-acetoxy-3-(acetoxymethyl)but-1-yl]-2-aminopurine
- acetic acid 2-acetoxymethyl-4-(2-amino-purin-9-yl)-butyl ester
- Famciclovir
- Famciclovirum
- FCV
- External IDs
- AV 42810
- BRL 42810
- BRL-42810
Pharmacology
- Indication
For the treatment of acute herpes zoster (shingles). Also for the treatment or suppression of recurrent genital herpes in immunocompetent patients and treatment of recurrent mucocutaneous herpes simplex infections in HIV infected patients.
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- Contraindications & Blackbox Warnings
Contraindications & Blackbox WarningsWith our commercial data, access important information on dangerous risks, contraindications, and adverse effects.Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects- Pharmacodynamics
Famciclovir is a prodrug that undergoes rapid biotransformation to the active antiviral compound penciclovir. Penciclovir is an anti-viral drug which has inhibitory activity against herpes simplex virus types 1 (HSV-1) and 2 (HSV-2) and varicella zoster virus (VZV). Therefore, herpes viral DNA synthesis and replication are selectively inhibited.
- Mechanism of action
Famciclovir undergoes rapid biotransformation to the active antiviral compound penciclovir, which has inhibitory activity against herpes simplex virus types 1 (HSV-1) and 2 (HSV-2) and varicella zoster virus (VZV). In cells infected with HSV-1, HSV-2 or VZV, viral thymidine kinase phosphorylates penciclovir to a monophosphate form that, in turn, is converted to penciclovir triphosphate by cellular kinases. In vitro studies demonstrate that penciclovir triphosphate inhibits HSV-2 DNA polymerase competitively with deoxyguanosine triphosphate. Consequently, herpes viral DNA synthesis and, therefore, replication are selectively inhibited.
Target Actions Organism ADNA polymerase catalytic subunit inhibitorHHV-1 - Absorption
77 %
- Volume of distribution
- 1.08±0.17 L/kg [healthy male subjects following a single intravenous dose of penciclovir at 400 mg administered as a 1-hour intravenous infusion]
- Protein binding
20-25%
- Metabolism
Hepatic
Hover over products below to view reaction partners
- Route of elimination
Active tubular secretion contributes to the renal elimination of penciclovir.
- Half-life
10 hours
- Clearance
- 36.6 +/- 6.3 L/hr [healthy male]
- 0.48 +/- 0.09 L/hr/kg [healthy male]
- Adverse Effects
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Symptoms of overdose include constipation, diarrhea, dizziness, fatigue, fever, headache, nausea, and vomiting.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAdenovirus 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. BCG vaccine The therapeutic efficacy of BCG vaccine can be decreased when used in combination with Famciclovir. Human adenovirus e serotype 4 strain cl-68578 antigen The therapeutic efficacy of Human adenovirus e serotype 4 strain cl-68578 antigen can be decreased when used in combination with Famciclovir. Rubella virus vaccine The therapeutic efficacy of Rubella virus vaccine can be decreased when used in combination with Famciclovir. Typhoid Vaccine Live The therapeutic efficacy of Typhoid Vaccine Live can be decreased when used in combination with Famciclovir. Varicella zoster vaccine (live/attenuated) The therapeutic efficacy of Varicella zoster vaccine (live/attenuated) can be decreased when used in combination with Famciclovir. 
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- Take with or without food. The absorption is unaffected by food.
Products
Comprehensive & structured drug product infoFrom application numbers to product codes, connect different identifiers through our commercial datasets.Easily connect various identifiers back to our datasets- Active Moieties
Name Kind UNII CAS InChI Key Penciclovir prodrug 359HUE8FJC 39809-25-1 JNTOCHDNEULJHD-UHFFFAOYSA-N - Product Images
- International/Other Brands
- Ezovir (Alphapharm) / Fambir (Il Hwa) / Famcino (Daewoong) / Famcir (Kwang Dong) / Famvir Once (Novartis) / Fanclomax (Blausiegel) / Fanle (Jialin) / Microvir (Micro Gratia) / Oravir (Novartis) / Pentavir (Fortbenton) / Penvir (Hetero) / Pixin (Pidi Pharmaceutical) / Virovir (FDC) / Wan Qi (Renfu Pharmaceutical) / Weike (Hisun)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Act Famciclovir Tablet 500 mg Oral TEVA Canada Limited 2008-10-29 Not applicable Canada 
Act Famciclovir Tablet 250 mg Oral TEVA Canada Limited 2008-10-29 Not applicable Canada Act Famciclovir Tablet 125 mg Oral TEVA Canada Limited 2008-10-29 Not applicable Canada Famciclovir Tablet 250 mg Oral Cobalt Laboratories Not applicable Not applicable Canada Famciclovir Tablet 250 mg Oral Pro Doc Limitee 2009-10-16 2018-03-27 Canada Famciclovir Tablet 125 mg Oral Cobalt Laboratories Not applicable Not applicable Canada Famciclovir Tablet 500 mg Oral Pro Doc Limitee 2009-10-16 2017-11-13 Canada Famciclovir Tablet 500 mg Oral Cobalt Laboratories Not applicable Not applicable Canada Famciclovir Tablet 125 mg Oral Pro Doc Limitee 2009-10-16 2018-04-13 Canada Famvir Tablet, film coated 125 mg/1 Oral Physicians Total Care, Inc. 1994-06-29 2011-05-31 US 
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Apo-famciclovir Tablet 125 mg Oral Apotex Corporation 2007-02-22 Not applicable Canada Apo-famciclovir Tablet 500 mg Oral Apotex Corporation 2007-02-22 Not applicable Canada Apo-famciclovir Tablet 250 mg Oral Apotex Corporation 2007-02-22 Not applicable Canada Auro-famciclovir Tablet 500 mg Oral Auro Pharma Inc Not applicable Not applicable Canada Auro-famciclovir Tablet 250 mg Oral Auro Pharma Inc Not applicable Not applicable Canada Auro-famciclovir Tablet 125 mg Oral Auro Pharma Inc Not applicable Not applicable Canada Ava-famciclovir Tablet 500 mg Oral Avanstra Inc 2011-09-19 2014-08-21 Canada Ava-famciclovir Tablet 250 mg Oral Avanstra Inc 2011-09-19 2014-08-21 Canada Ava-famciclovir Tablet 125 mg Oral Avanstra Inc 2011-09-19 2014-08-21 Canada Dom-famciclovir Tablet 500 mg Oral Dominion Pharmacal Not applicable Not applicable Canada
Categories
- ATC Codes
- J05AB09 — Famciclovir
- J05AB — Nucleosides and nucleotides excl. reverse transcriptase inhibitors
- J05A — DIRECT ACTING ANTIVIRALS
- J05 — ANTIVIRALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- 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
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as purines and purine derivatives. These are aromatic heterocyclic compounds containing a purine moiety, which is formed a pyrimidine-ring ring fused to an imidazole ring.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Imidazopyrimidines
- Sub Class
- Purines and purine derivatives
- Direct Parent
- Purines and purine derivatives
- Alternative Parents
- Aminopyrimidines and derivatives / N-substituted imidazoles / Dicarboxylic acids and derivatives / Heteroaromatic compounds / Carboxylic acid esters / Amino acids and derivatives / Azacyclic compounds / Primary amines / Organopnictogen compounds / Organic oxides show 2 more
- Substituents
- Amine / Amino acid or derivatives / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Azole / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Dicarboxylic acid or derivatives show 13 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- acetate ester, 2-aminopurines (CHEBI:4974)
- Affected organisms
- Human Herpes Virus
Chemical Identifiers
- UNII
- QIC03ANI02
- CAS number
- 104227-87-4
- InChI Key
- GGXKWVWZWMLJEH-UHFFFAOYSA-N
- 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)
- IUPAC Name
- 2-[(acetyloxy)methyl]-4-(2-amino-9H-purin-9-yl)butyl acetate
- SMILES
- CC(=O)OCC(CCN1C=NC2=CN=C(N)N=C12)COC(C)=O
References
- Synthesis Reference
- US5246937
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014570
- KEGG Drug
- D00317
- PubChem Compound
- 3324
- PubChem Substance
- 46507561
- ChemSpider
- 3207
- BindingDB
- 50248001
- 68099
- ChEBI
- 4974
- ChEMBL
- CHEMBL880
- ZINC
- ZINC000001530635
- Therapeutic Targets Database
- DAP000489
- PharmGKB
- PA449585
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Famciclovir
- AHFS Codes
- 08:18.32 — Nucleosides and Nucleotides
- FDA label
- Download (227 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Treatment Genital Herpes 2 4 Completed Treatment Recurrent Genital Herpes (RGH) 1 4 Completed Treatment Recurrent Herpes Labialis 1 3 Completed Treatment Chickenpox / Herpes Zoster 1 3 Completed Treatment Genital Herpes 2 3 Completed Treatment Herpes Simplex 1 3 Completed Treatment Herpes Zoster 1 3 Completed Treatment Recurrent Genital Herpes (RGH) 1 3 Terminated Treatment Menière's Disease 1 2 Completed Treatment Herpes Simplex 1
Pharmacoeconomics
- Manufacturers
- Teva pharmaceuticals usa
- Novartis pharmaceuticals corp
- Packagers
- Apotheca Inc.
- Murfreesboro Pharmaceutical Nursing Supply
- Novartis AG
- Novopharm Ltd.
- Nucare Pharmaceuticals Inc.
- Pharmaceutical Utilization Management Program VA Inc.
- Physicians Total Care Inc.
- Redpharm Drug
- Resource Optimization and Innovation LLC
- Southwood Pharmaceuticals
- Teva Pharmaceutical Industries Ltd.
- Dosage Forms
Form Route Strength Tablet Oral 125 mg/1 Tablet Oral 250 mg/1 Tablet Oral 500 mg/1 Tablet, film coated Oral 500 mg/1 Tablet, film coated Oral Tablet Oral Tablet Oral 250 mg Tablet Oral 500 mg Tablet, film coated Oral 125 mg/1 Tablet, film coated Oral 250 mg/1 Tablet, coated Oral 250 mg Tablet Oral 125 mg Tablet, film coated Oral 250 mg - Prices
Unit description Cost Unit Famvir 500 mg tablet 14.39USD tablet Famciclovir 500 mg tablet 11.67USD tablet Famvir 250 mg tablet 7.16USD tablet Famvir 125 mg tablet 6.59USD tablet Famciclovir 250 mg tablet 5.81USD tablet Famciclovir 125 mg tablet 5.34USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5246937 No 1993-09-21 2010-09-21 US CA2176392 No 2005-11-08 2014-11-11 Canada CA2086756 No 2003-04-08 2011-07-03 Canada US5840763 Yes 1998-11-24 2016-03-01 US US5916893 Yes 1999-06-29 2016-03-01 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 102-104 °C Not Available logP 0.6 Not Available - Predicted Properties
Property Value Source Water Solubility 1.32 mg/mL ALOGPS logP 0.13 ALOGPS logP -0.48 ChemAxon logS -2.4 ALOGPS pKa (Strongest Acidic) 16.7 ChemAxon pKa (Strongest Basic) 5.05 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 6 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 122.22 Å2 ChemAxon Rotatable Bond Count 9 ChemAxon Refractivity 81.54 m3·mol-1 ChemAxon Polarizability 32.83 Å3 ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.988 Blood Brain Barrier + 0.9429 Caco-2 permeable - 0.603 P-glycoprotein substrate Substrate 0.6719 P-glycoprotein inhibitor I Non-inhibitor 0.9305 P-glycoprotein inhibitor II Non-inhibitor 0.9213 Renal organic cation transporter Non-inhibitor 0.6392 CYP450 2C9 substrate Non-substrate 0.9156 CYP450 2D6 substrate Non-substrate 0.8345 CYP450 3A4 substrate Non-substrate 0.6545 CYP450 1A2 substrate Non-inhibitor 0.5863 CYP450 2C9 inhibitor Non-inhibitor 0.7961 CYP450 2D6 inhibitor Non-inhibitor 0.8068 CYP450 2C19 inhibitor Non-inhibitor 0.8151 CYP450 3A4 inhibitor Non-inhibitor 0.8987 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8661 Ames test Non AMES toxic 0.5887 Carcinogenicity Non-carcinogens 0.9257 Biodegradation Not ready biodegradable 0.9495 Rat acute toxicity 2.3203 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.797 hERG inhibition (predictor II) Non-inhibitor 0.9071
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available MS/MS Spectrum - , positive LC-MS/MS splash10-00dr-1869000000-c198d52e11cc029a313c MS/MS Spectrum - , positive LC-MS/MS splash10-00di-0329000000-cfd0210d7c106403c4fe
Targets
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- Kind
- Protein
- Organism
- HHV-1
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Rna-dna hybrid ribonuclease activity
- Specific Function
- Replicates viral genomic DNA. The replication complex is composed of six viral proteins: the DNA polymerase, processivity factor, primase, primase-associated factor, helicase, and ssDNA-binding pro...
- Gene Name
- Not Available
- Uniprot ID
- P04293
- Uniprot Name
- DNA polymerase catalytic subunit
- Molecular Weight
- 136419.66 Da
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Xanthine dehydrogenase activity
- Specific Function
- Oxidase with broad substrate specificity, oxidizing aromatic azaheterocycles, such as N1-methylnicotinamide and N-methylphthalazinium, as well as aldehydes, such as benzaldehyde, retinal, pyridoxal...
- Gene Name
- AOX1
- Uniprot ID
- Q06278
- Uniprot Name
- Aldehyde oxidase
- Molecular Weight
- 147916.735 Da
References
- Rashidi MR, Smith JA, Clarke SE, Beedham C: In vitro oxidation of famciclovir and 6-deoxypenciclovir by aldehyde oxidase from human, guinea pig, rabbit, and rat liver. Drug Metab Dispos. 1997 Jul;25(7):805-13. [Article]
- Al-Salmy HS: Inter-strain variability in aldehyde oxidase activity in the mouse. Comp Biochem Physiol C Toxicol Pharmacol. 2002 Jul;132(3):341-7. [Article]
Drug created on June 13, 2005 13:24 / Updated on June 18, 2021 14:15