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
Thumb
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.

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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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.

TargetActionsOrganism
ADNA polymerase catalytic subunit
inhibitor
HHV-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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Toxicity

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.
DrugInteraction
Adenovirus type 7 vaccine liveThe therapeutic efficacy of Adenovirus type 7 vaccine live can be decreased when used in combination with Famciclovir.
Anthrax vaccineThe therapeutic efficacy of Anthrax vaccine can be decreased when used in combination with Famciclovir.
Bacillus calmette-guerin substrain connaught live antigenThe 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 antigenThe 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 antigenThe therapeutic efficacy of Bacillus calmette-guerin substrain tice live antigen can be decreased when used in combination with Famciclovir.
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Famciclovir.
Human adenovirus e serotype 4 strain cl-68578 antigenThe therapeutic efficacy of Human adenovirus e serotype 4 strain cl-68578 antigen can be decreased when used in combination with Famciclovir.
Rubella virus vaccineThe therapeutic efficacy of Rubella virus vaccine can be decreased when used in combination with Famciclovir.
Typhoid Vaccine LiveThe 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.
Interactions
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Food Interactions
  • Take with or without food. The absorption is unaffected by food.

Products

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Active Moieties
NameKindUNIICASInChI Key
Penciclovirprodrug359HUE8FJC39809-25-1JNTOCHDNEULJHD-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
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Act FamciclovirTablet250 mgOralTEVA Canada Limited2008-10-29Not applicableCanada flag
Act FamciclovirTablet125 mgOralTEVA Canada Limited2008-10-29Not applicableCanada flag
Act FamciclovirTablet500 mgOralTEVA Canada Limited2008-10-29Not applicableCanada flag
FamciclovirTablet250 mgOralCobalt LaboratoriesNot applicableNot applicableCanada flag
FamciclovirTablet500 mgOralPro Doc Limitee2009-10-162017-11-13Canada flag
FamciclovirTablet125 mgOralCobalt LaboratoriesNot applicableNot applicableCanada flag
FamciclovirTablet125 mgOralPro Doc Limitee2009-10-162018-04-13Canada flag
FamciclovirTablet500 mgOralCobalt LaboratoriesNot applicableNot applicableCanada flag
FamciclovirTablet250 mgOralPro Doc Limitee2009-10-162018-03-27Canada flag
FamvirTablet, film coated250 mg/1OralNovartis Pharmaceuticals Corporation1994-06-292017-08-31US flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Apo-famciclovirTablet125 mgOralApotex Corporation2007-02-22Not applicableCanada flag
Apo-famciclovirTablet500 mgOralApotex Corporation2007-02-22Not applicableCanada flag
Apo-famciclovirTablet250 mgOralApotex Corporation2007-02-22Not applicableCanada flag
Auro-famciclovirTablet500 mgOralAuro Pharma IncNot applicableNot applicableCanada flag
Auro-famciclovirTablet250 mgOralAuro Pharma IncNot applicableNot applicableCanada flag
Auro-famciclovirTablet125 mgOralAuro Pharma IncNot applicableNot applicableCanada flag
Ava-famciclovirTablet125 mgOralAvanstra Inc2011-09-192014-08-21Canada flag
Ava-famciclovirTablet500 mgOralAvanstra Inc2011-09-192014-08-21Canada flag
Ava-famciclovirTablet250 mgOralAvanstra Inc2011-09-192014-08-21Canada flag
Dom-famciclovirTablet125 mgOralDominion PharmacalNot applicableNot applicableCanada flag

Categories

ATC Codes
J05AB09 — FamciclovirS01AD07 — Famciclovir
Drug Categories
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
Human Metabolome Database
HMDB0014570
KEGG Drug
D00317
PubChem Compound
3324
PubChem Substance
46507561
ChemSpider
3207
BindingDB
50248001
RxNav
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
FDA label
Download (227 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentGenital Herpes2
4CompletedTreatmentRecurrent Genital Herpes (RGH)1
4CompletedTreatmentRecurrent Herpes Labialis1
3CompletedTreatmentChickenpox / Herpes Zoster1
3CompletedTreatmentGenital Herpes2
3CompletedTreatmentHerpes Simplex1
3CompletedTreatmentHerpes Zoster1
3CompletedTreatmentRecurrent Genital Herpes (RGH)1
3TerminatedTreatmentMenière's Disease1
2CompletedTreatmentHerpes Simplex1

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
FormRouteStrength
TabletOral125 mg/1
TabletOral250 mg/1
TabletOral500 mg/1
Tablet, film coatedOral500 mg/1
Tablet, film coatedOral
TabletOral
Tablet, film coatedOral125 mg/1
Tablet, film coatedOral250 mg/1
Tablet, coatedOral250 mg
TabletOral125 mg
Tablet, film coatedOral250 mg
TabletOral250 mg
TabletOral500 mg
Prices
Unit descriptionCostUnit
Famvir 500 mg tablet14.39USD tablet
Famciclovir 500 mg tablet11.67USD tablet
Famvir 250 mg tablet7.16USD tablet
Famvir 125 mg tablet6.59USD tablet
Famciclovir 250 mg tablet5.81USD tablet
Famciclovir 125 mg tablet5.34USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5246937No1993-09-212010-09-21US flag
CA2176392No2005-11-082014-11-11Canada flag
CA2086756No2003-04-082011-07-03Canada flag
US5840763Yes1998-11-242016-03-01US flag
US5916893Yes1999-06-292016-03-01US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)102-104 °CNot Available
logP0.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.32 mg/mLALOGPS
logP0.13ALOGPS
logP-0.48ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)16.7ChemAxon
pKa (Strongest Basic)5.05ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area122.22 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity81.54 m3·mol-1ChemAxon
Polarizability32.83 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.988
Blood Brain Barrier+0.9429
Caco-2 permeable-0.603
P-glycoprotein substrateSubstrate0.6719
P-glycoprotein inhibitor INon-inhibitor0.9305
P-glycoprotein inhibitor IINon-inhibitor0.9213
Renal organic cation transporterNon-inhibitor0.6392
CYP450 2C9 substrateNon-substrate0.9156
CYP450 2D6 substrateNon-substrate0.8345
CYP450 3A4 substrateNon-substrate0.6545
CYP450 1A2 substrateNon-inhibitor0.5863
CYP450 2C9 inhibitorNon-inhibitor0.7961
CYP450 2D6 inhibitorNon-inhibitor0.8068
CYP450 2C19 inhibitorNon-inhibitor0.8151
CYP450 3A4 inhibitorNon-inhibitor0.8987
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8661
Ames testNon AMES toxic0.5887
CarcinogenicityNon-carcinogens0.9257
BiodegradationNot ready biodegradable0.9495
Rat acute toxicity2.3203 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.797
hERG inhibition (predictor II)Non-inhibitor0.9071
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00dr-1869000000-c198d52e11cc029a313c
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00di-0329000000-cfd0210d7c106403c4fe

Targets

Drugtargets
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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
  1. 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]
  2. 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 July 23, 2021 16:02