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Identification
NameFamciclovir
Accession NumberDB00426  (APRD00600)
TypeSmall Molecule
GroupsApproved
Description

Famciclovir is a guanine analogue antiviral drug used for the treatment of various herpes virus infections, most commonly for herpes zoster (shingles). It is a prodrug form of penciclovir with improved oral bioavailability. Famciclovir is marketed under the trade name Famvir (Novartis).

Structure
Thumb
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
BRL-42810
Famciclovir
Famciclovirum
Famvir
FCV
External Identifiers
  • AV 42810
  • BRL 42810
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act Famciclovirtablet500 mgoralActavis Pharma Company2008-10-29Not applicableCanada
Act Famciclovirtablet250 mgoralActavis Pharma Company2008-10-29Not applicableCanada
Act Famciclovirtablet125 mgoralActavis Pharma Company2008-10-29Not applicableCanada
Auro-famciclovirtablet500 mgoralAuro Pharma IncNot applicableNot applicableCanada
Auro-famciclovirtablet250 mgoralAuro Pharma IncNot applicableNot applicableCanada
Auro-famciclovirtablet125 mgoralAuro Pharma IncNot applicableNot applicableCanada
Ava-famciclovirtablet500 mgoralAvanstra Inc2011-09-192014-08-21Canada
Ava-famciclovirtablet250 mgoralAvanstra Inc2011-09-192014-08-21Canada
Ava-famciclovirtablet125 mgoralAvanstra Inc2011-09-192014-08-21Canada
Dom-famciclovirtablet500 mgoralDominion PharmacalNot applicableNot applicableCanada
Dom-famciclovirtablet250 mgoralDominion PharmacalNot applicableNot applicableCanada
Dom-famciclovirtablet125 mgoralDominion PharmacalNot applicableNot applicableCanada
Famciclovirtablet500 mgoralPro Doc Limitee2009-10-16Not applicableCanada
Famciclovirtablet250 mgoralPro Doc Limitee2009-10-16Not applicableCanada
Famciclovirtablet125 mgoralPro Doc Limitee2009-10-16Not applicableCanada
Famciclovirtablet500 mgoralCobalt Pharmaceuticals CompanyNot applicableNot applicableCanada
Famciclovirtablet250 mgoralCobalt Pharmaceuticals CompanyNot applicableNot applicableCanada
Famciclovirtablet125 mgoralCobalt Pharmaceuticals CompanyNot applicableNot applicableCanada
Famvirtablet, film coated125 mg/1oralNovartis Pharmaceuticals Corporation1994-06-29Not applicableUs
Famvirtablet, film coated500 mg/1oralNovartis Pharmaceuticals Corporation1994-06-29Not applicableUs
Famvirtablet, film coated250 mg/1oralNovartis Pharmaceuticals Corporation1994-06-29Not applicableUs
Famvir Tablets 125mgtablet125 mgoralNovartis Pharmaceuticals Canada Inc1996-09-11Not applicableCanada
Famvir Tablets 250mgtablet250 mgoralNovartis Pharmaceuticals Canada Inc1996-09-11Not applicableCanada
Famvir Tablets 500mgtablet500 mgoralNovartis Pharmaceuticals Canada Inc1995-12-31Not applicableCanada
Novo-famciclovirtablet125 mgoralNovopharm LimitedNot applicableNot applicableCanada
Novo-famciclovirtablet250 mgoralNovopharm LimitedNot applicableNot applicableCanada
Novo-famciclovirtablet500 mgoralNovopharm LimitedNot applicableNot applicableCanada
PHL-famciclovirtablet250 mgoralPharmel IncNot applicableNot applicableCanada
PHL-famciclovirtablet125 mgoralPharmel IncNot applicableNot applicableCanada
PHL-famciclovirtablet500 mgoralPharmel IncNot applicableNot applicableCanada
PMS-famciclovirtablet500 mgoralPharmascience Inc2006-11-17Not applicableCanada
PMS-famciclovirtablet250 mgoralPharmascience Inc2006-11-17Not applicableCanada
PMS-famciclovirtablet125 mgoralPharmascience Inc2006-11-17Not applicableCanada
Sandoz Famciclovirtablet500 mgoralSandoz Canada Incorporated2006-08-15Not applicableCanada
Sandoz Famciclovirtablet250 mgoralSandoz Canada Incorporated2006-08-15Not applicableCanada
Sandoz Famciclovirtablet125 mgoralSandoz Canada Incorporated2006-08-15Not applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-famciclovirtablet125 mgoralApotex Inc2007-02-22Not applicableCanada
Apo-famciclovirtablet500 mgoralApotex Inc2007-02-22Not applicableCanada
Apo-famciclovirtablet250 mgoralApotex Inc2007-02-22Not applicableCanada
Famciclovirtablet, film coated250 mg/1oralApotex Corp.2011-12-20Not applicableUs
Famciclovirtablet, film coated250 mg/1oralAv Pak2013-05-16Not applicableUs
Famciclovirtablet, film coated500 mg/1oralCamber Pharmaceuticals, Inc.2014-09-10Not applicableUs
Famciclovirtablet, film coated500 mg/1oralApotex Corp.2011-12-20Not applicableUs
Famciclovirtablet, film coated250 mg/1oralCamber Pharmaceuticals, Inc.2014-09-10Not applicableUs
Famciclovirtablet, film coated500 mg/1oralMylan Pharmaceuticals Inc.2011-04-18Not applicableUs
Famciclovirtablet125 mg/1oralRoxane Laboratories, Inc.2011-01-03Not applicableUs
Famciclovirtablet, film coated125 mg/1oralApotex Corp.2011-12-20Not applicableUs
Famciclovirtablet, film coated125 mg/1oralAv Pak2013-05-16Not applicableUs
Famciclovirtablet500 mg/1oralCipla USA Inc.2011-03-21Not applicableUs
Famciclovirtablet, film coated125 mg/1oralCamber Pharmaceuticals, Inc.2014-09-10Not applicableUs
Famciclovirtablet, film coated250 mg/1oralMylan Pharmaceuticals Inc.2011-04-18Not applicableUs
Famciclovirtablet, film coated500 mg/1oralGolden State Medical Supply, Inc.2011-12-20Not applicableUs
Famciclovirtablet, film coated500 mg/1oralAv Kare, Inc.2012-01-04Not applicableUs
Famciclovirtablet250 mg/1oralCipla USA Inc.2011-03-21Not applicableUs
Famciclovirtablet, film coated500 mg/1oralNorth Star Rx Llc2011-03-21Not applicableUs
Famciclovirtablet, film coated125 mg/1oralMylan Pharmaceuticals Inc.2011-04-18Not applicableUs
Famciclovirtablet125 mg/1oralCipla USA Inc.2011-03-21Not applicableUs
Famciclovirtablet, film coated250 mg/1oralNorth Star Rx Llc2011-03-21Not applicableUs
Famciclovirtablet, film coated500 mg/1oralTeva Pharmaceuticals USA Inc2007-09-05Not applicableUs
Famciclovirtablet, film coated250 mg/1oralGolden State Medical Supply, Inc.2011-12-20Not applicableUs
Famciclovirtablet, film coated250 mg/1oralAv Kare, Inc.2012-01-04Not applicableUs
Famciclovirtablet, film coated125 mg/1oralNorth Star Rx Llc2011-03-21Not applicableUs
Famciclovirtablet, film coated250 mg/1oralTeva Pharmaceuticals USA Inc2007-09-05Not applicableUs
Famciclovirtablet, film coated125 mg/1oralGolden State Medical Supply, Inc.2011-12-20Not applicableUs
Famciclovirtablet, film coated125 mg/1oralAv Kare, Inc.2012-01-04Not applicableUs
Famciclovirtablet, film coated500 mg/1oralAurobindo Pharma Limited2011-03-21Not applicableUs
Famciclovirtablet, film coated500 mg/1oralActavis Pharma, Inc.2011-03-21Not applicableUs
Famciclovirtablet, film coated125 mg/1oralTeva Pharmaceuticals USA Inc2007-09-05Not applicableUs
Famciclovirtablet, film coated500 mg/1oralPd Rx Pharmaceuticals, Inc.2011-04-01Not applicableUs
Famciclovirtablet, film coated500 mg/1oralMacleods Pharmaceuticals Limited2011-12-17Not applicableUs
Famciclovirtablet, film coated250 mg/1oralAurobindo Pharma Limited2011-03-21Not applicableUs
Famciclovirtablet, film coated250 mg/1oralActavis Pharma, Inc.2011-03-21Not applicableUs
Famciclovirtablet500 mg/1oralRoxane Laboratories, Inc.2011-01-03Not applicableUs
Famciclovirtablet, film coated500 mg/1oralPhysicians Total Care, Inc.2008-06-16Not applicableUs
Famciclovirtablet, film coated250 mg/1oralMacleods Pharmaceuticals Limited2011-12-17Not applicableUs
Famciclovirtablet, film coated125 mg/1oralAurobindo Pharma Limited2011-03-21Not applicableUs
Famciclovirtablet, film coated500 mg/1oralAv Pak2013-05-16Not applicableUs
Famciclovirtablet, film coated125 mg/1oralMacleods Pharmaceuticals Limited2011-12-17Not applicableUs
Famciclovirtablet, film coated500 mg/1oralAmerican Health Packaging2015-03-31Not applicableUs
Famciclovirtablet, film coated125 mg/1oralActavis Pharma, Inc.2011-03-21Not applicableUs
Famciclovirtablet250 mg/1oralRoxane Laboratories, Inc.2011-01-03Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
EzovirAlphapharm
FambirIl Hwa
FamcinoDaewoong
FamcirKwang Dong
Famvir OnceNovartis
FanclomaxBlausiegel
FanleJialin
MicrovirMicro Gratia
OravirNovartis
PentavirFortbenton
PenvirHetero
PixinPidi Pharmaceutical
VirovirFDC
Wan QiRenfu Pharmaceutical
WeikeHisun
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIQIC03ANI02
CAS number104227-87-4
WeightAverage: 321.3318
Monoisotopic: 321.143704121
Chemical FormulaC14H19N5O4
InChI KeyInChIKey=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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct ParentPurines and purine derivatives
Alternative Parents
Substituents
  • Purine
  • Pyrimidine
  • Primary aromatic amine
  • N-substituted imidazole
  • Heteroaromatic compound
  • Acetate salt
  • Imidazole
  • Azole
  • Carboxylic acid ester
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationFor 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.
PharmacodynamicsFamciclovir 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 actionFamciclovir 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.
Related Articles
Absorption77 %
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 binding20-25%
Metabolism

Hepatic

SubstrateEnzymesProduct
Famciclovir
6-oxo-famciclovirDetails
Route of eliminationActive tubular secretion contributes to the renal elimination of penciclovir.
Half life10 hours
Clearance
  • 36.6 +/- 6.3 L/hr [healthy male]
  • 0.48 +/- 0.09 L/hr/kg [healthy male]
ToxicitySymptoms of overdose include constipation, diarrhea, dizziness, fatigue, fever, headache, nausea, and vomiting.
Affected organisms
  • Human Herpes Virus
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
Manufacturers
  • Teva pharmaceuticals usa
  • Novartis pharmaceuticals corp
Packagers
Dosage forms
FormRouteStrength
Tabletoral125 mg/1
Tabletoral250 mg/1
Tabletoral500 mg/1
Tablet, film coatedoral125 mg/1
Tablet, film coatedoral250 mg/1
Tablet, film coatedoral500 mg/1
Tabletoral125 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)
CA2086756 No2003-04-082011-07-03Canada
CA2176392 No2005-11-082014-11-11Canada
US5246937 No1993-09-212010-09-21Us
US5840763 Yes1996-03-012016-03-01Us
US5916893 Yes1996-03-012016-03-01Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point102-104 °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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

DrugSyn.org

US5246937
General ReferencesNot Available
External Links
ATC CodesJ05AB09S01AD07
AHFS Codes
  • 08:18.32
PDB EntriesNot Available
FDA labelDownload (227 KB)
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

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 protein. Additionally, the polymerase contains an intrinsic ribonuclease H (RNase H) activity that specifically degrades RNA/DNA heteroduplexes or duplex DNA substrates in the 5' to 3' direction. Therefo...
Gene Name:
Not Available
Uniprot ID:
P04293
Molecular Weight:
136419.66 Da
References
  1. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  2. Schmid-Wendtner MH, Korting HC: Penciclovir cream--improved topical treatment for herpes simplex infections. Skin Pharmacol Physiol. 2004 Sep-Oct;17(5):214-8. [PubMed:15452407 ]
Kind
Protein
Organism
HHV-3
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 protein. Additionally, the polymerase contains an intrinsic ribonuclease H (RNase H) activity that specifically degrades RNA/DNA heteroduplexes or duplex DNA substrates in the 5' to 3' direction. Therefo...
Gene Name:
Not Available
Uniprot ID:
P09252
Molecular Weight:
134046.615 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Enzymes

Kind
Protein
Organism
Human
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, and vanillin. Plays a key role in the metabolism of xenobiotics and drugs containing aromatic azaheterocyclic substituents. Participates in the bioactivation of prodrugs such as famciclovir, catalyz...
Gene Name:
AOX1
Uniprot ID:
Q06278
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. [PubMed:9224775 ]
  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. [PubMed:12161167 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on May 31, 2016 03:27