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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2018-05-20 20:50:58 UTC
HMDB IDHMDB0014570
Secondary Accession Numbers
  • HMDB14570
Metabolite Identification
Common NameFamciclovir
DescriptionFamciclovir 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
ValueSource
2-(2-(2-amino-9H-Purin-9-yl)ethyl)-1,3-propanediol diacetateChEBI
9-[4-Acetoxy-3-(acetoxymethyl)but-1-yl]-2-aminopurineChEBI
Acetic acid 2-acetoxymethyl-4-(2-amino-purin-9-yl)-butyl esterChEBI
BRL-42810ChEBI
FamciclovirumChEBI
FamvirChEBI
FCVChEBI
2-(2-(2-amino-9H-Purin-9-yl)ethyl)-1,3-propanediol diacetic acidGenerator
Acetate 2-acetoxymethyl-4-(2-amino-purin-9-yl)-butyl esterGenerator
9-(4-Acetoxy-3-(acetoxymethyl)but-1-yl)-2-aminopurineMeSH
Chemical FormulaC14H19N5O4
Average Molecular Weight321.3318
Monoisotopic Molecular Weight321.143704121
IUPAC Name2-[(acetyloxy)methyl]-4-(2-amino-9H-purin-9-yl)butyl acetate
Traditional Namefamciclovir
CAS Registry Number104227-87-4
SMILES
CC(=O)OCC(CCN1C=NC2=CN=C(N)N=C12)COC(C)=O
InChI Identifier
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 KeyGGXKWVWZWMLJEH-UHFFFAOYSA-N
Chemical 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
  • Aminopyrimidine
  • Pyrimidine
  • Dicarboxylic acid or derivatives
  • N-substituted imidazole
  • Azole
  • Heteroaromatic compound
  • Imidazole
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Azacycle
  • Amine
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point102 - 104 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.32 g/LNot Available
LogP0.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.32 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity81.54 m³·mol⁻¹ChemAxon
Polarizability32.83 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01ox-7790000000-b7591056c9a4a954cf54View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00dr-1869000000-c198d52e11cc029a313cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00di-0329000000-cfd0210d7c106403c4feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0229-1298000000-d5136e5b9df2f19b790aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dr-1971000000-e7d91146862aeb4cf127View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000l-2920000000-e3143ba3279219407909View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-4029000000-2a4e705554c3ab16e50dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-053r-7922000000-ec9365fe5af199a1d4c0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0536-9800000000-60c297c902469ee6f5faView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00426 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00426 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00426
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3207
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkFamciclovir
METLIN IDNot Available
PubChem Compound3324
PDB IDNot Available
ChEBI ID4974
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
AOX1
Uniprot ID:
Q06278
Molecular weight:
147916.735
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 ]
General function:
Involved in monooxygenase 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 xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
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 ]