Hmdb loader
Survey
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:40 UTC
HMDB IDHMDB0014570
Secondary Accession Numbers
  • HMDB14570
Metabolite Identification
Common NameFamciclovir
DescriptionFamciclovir, also known as famvir or BRL-42810, 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. Famciclovir is a drug which is used 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. Famciclovir is a very strong basic compound (based on its pKa).
Structure
Data?1582753194
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-aminopurineHMDB
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
Description 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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point102 - 104 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.32 g/LNot Available
LogP0.6Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available168.417http://allccs.zhulab.cn/database/detail?ID=AllCCS00001040
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+175.55531661259
DarkChem[M-H]-173.41931661259
DeepCCS[M-2H]-196.71430932474
DeepCCS[M+Na]+172.22130932474
AllCCS[M+H]+172.132859911
AllCCS[M+H-H2O]+169.232859911
AllCCS[M+NH4]+174.932859911
AllCCS[M+Na]+175.632859911
AllCCS[M-H]-174.232859911
AllCCS[M+Na-2H]-174.232859911
AllCCS[M+HCOO]-174.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
FamciclovirCC(=O)OCC(CCN1C=NC2=CN=C(N)N=C12)COC(C)=O3329.3Standard polar33892256
FamciclovirCC(=O)OCC(CCN1C=NC2=CN=C(N)N=C12)COC(C)=O2355.3Standard non polar33892256
FamciclovirCC(=O)OCC(CCN1C=NC2=CN=C(N)N=C12)COC(C)=O2704.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Famciclovir,1TMS,isomer #1CC(=O)OCC(CCN1C=NC2=CN=C(N[Si](C)(C)C)N=C21)COC(C)=O2706.3Semi standard non polar33892256
Famciclovir,1TMS,isomer #1CC(=O)OCC(CCN1C=NC2=CN=C(N[Si](C)(C)C)N=C21)COC(C)=O2697.2Standard non polar33892256
Famciclovir,1TMS,isomer #1CC(=O)OCC(CCN1C=NC2=CN=C(N[Si](C)(C)C)N=C21)COC(C)=O4556.9Standard polar33892256
Famciclovir,2TMS,isomer #1CC(=O)OCC(CCN1C=NC2=CN=C(N([Si](C)(C)C)[Si](C)(C)C)N=C21)COC(C)=O2696.7Semi standard non polar33892256
Famciclovir,2TMS,isomer #1CC(=O)OCC(CCN1C=NC2=CN=C(N([Si](C)(C)C)[Si](C)(C)C)N=C21)COC(C)=O2783.8Standard non polar33892256
Famciclovir,2TMS,isomer #1CC(=O)OCC(CCN1C=NC2=CN=C(N([Si](C)(C)C)[Si](C)(C)C)N=C21)COC(C)=O4020.5Standard polar33892256
Famciclovir,1TBDMS,isomer #1CC(=O)OCC(CCN1C=NC2=CN=C(N[Si](C)(C)C(C)(C)C)N=C21)COC(C)=O2850.5Semi standard non polar33892256
Famciclovir,1TBDMS,isomer #1CC(=O)OCC(CCN1C=NC2=CN=C(N[Si](C)(C)C(C)(C)C)N=C21)COC(C)=O2922.4Standard non polar33892256
Famciclovir,1TBDMS,isomer #1CC(=O)OCC(CCN1C=NC2=CN=C(N[Si](C)(C)C(C)(C)C)N=C21)COC(C)=O4426.2Standard polar33892256
Famciclovir,2TBDMS,isomer #1CC(=O)OCC(CCN1C=NC2=CN=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C21)COC(C)=O3092.0Semi standard non polar33892256
Famciclovir,2TBDMS,isomer #1CC(=O)OCC(CCN1C=NC2=CN=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C21)COC(C)=O3245.2Standard non polar33892256
Famciclovir,2TBDMS,isomer #1CC(=O)OCC(CCN1C=NC2=CN=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C21)COC(C)=O3978.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Famciclovir GC-MS (Non-derivatized) - 70eV, Positivesplash10-01ox-7790000000-b7591056c9a4a954cf542017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Famciclovir GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Famciclovir GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Famciclovir , positive-QTOFsplash10-00dr-1869000000-c198d52e11cc029a313c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Famciclovir , positive-QTOFsplash10-00di-0329000000-cfd0210d7c106403c4fe2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Famciclovir 35V, Positive-QTOFsplash10-0079-1983000000-d8ee07fbce9af629cd5c2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Famciclovir 10V, Positive-QTOFsplash10-0229-1298000000-d5136e5b9df2f19b790a2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Famciclovir 20V, Positive-QTOFsplash10-03dr-1971000000-e7d91146862aeb4cf1272016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Famciclovir 40V, Positive-QTOFsplash10-000l-2920000000-e3143ba32792194079092016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Famciclovir 10V, Negative-QTOFsplash10-00di-4029000000-2a4e705554c3ab16e50d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Famciclovir 20V, Negative-QTOFsplash10-053r-7922000000-ec9365fe5af199a1d4c02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Famciclovir 40V, Negative-QTOFsplash10-0536-9800000000-60c297c902469ee6f5fa2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Famciclovir 10V, Positive-QTOFsplash10-00di-0009000000-78f4f0994078633f8a0f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Famciclovir 20V, Positive-QTOFsplash10-0fk9-0479000000-e23c5d13aac6fbd2f27a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Famciclovir 40V, Positive-QTOFsplash10-000i-1930000000-7b8d2995ee0555d2ce2c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Famciclovir 10V, Negative-QTOFsplash10-0a4i-9200000000-44fb2fcb2578da21c7862021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Famciclovir 20V, Negative-QTOFsplash10-0a4i-9200000000-bed3b3a468bd2f1429872021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Famciclovir 40V, Negative-QTOFsplash10-0006-9400000000-a899d0ec1d4b27e6e9c72021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00426 details
UrineExpected but not QuantifiedNot QuantifiedNot 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
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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 ]