ContaminantDB: Famciclovir

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 03:41:02 UTC

Update Date

2016-11-09 01:15:27 UTC

Accession Number

CHEM016705

Identification

Common Name

Famciclovir

Class

Small Molecule

Description

Famciclovir, marketed as Famciclovir 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.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-(2-(2-Amino-9H-purin-9-yl)ethyl)-1,3-propanediol diacetate	ChEBI
9-[4-Acetoxy-3-(acetoxymethyl)but-1-yl]-2-aminopurine	ChEBI
Acetic acid 2-acetoxymethyl-4-(2-amino-purin-9-yl)-butyl ester	ChEBI
BRL-42810	ChEBI
Famciclovirum	ChEBI
Famvir	ChEBI
FCV	ChEBI
2-(2-(2-Amino-9H-purin-9-yl)ethyl)-1,3-propanediol diacetic acid	Generator
Acetate 2-acetoxymethyl-4-(2-amino-purin-9-yl)-butyl ester	Generator
9-(4-Acetoxy-3-(acetoxymethyl)but-1-yl)-2-aminopurine	HMDB

Chemical Formula

C₁₄H₁₉N₅O₄

Average Molecular Mass

321.332 g/mol

Monoisotopic Mass

321.144 g/mol

CAS Registry Number

104227-87-4

IUPAC Name

2-[(acetyloxy)methyl]-4-(2-amino-9H-purin-9-yl)butyl acetate

Traditional Name

famciclovir

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 Key

GGXKWVWZWMLJEH-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Imidazopyrimidines

Sub Class

Purines and purine derivatives

Direct Parent

Purines 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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

acetate ester (CHEBI:4974 )
2-aminopurines (CHEBI:4974 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	1.32 g/L	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

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-01ox-7790000000-b7591056c9a4a954cf54	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-00dr-1869000000-c198d52e11cc029a313c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-00di-0329000000-cfd0210d7c106403c4fe	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0079-1983000000-d8ee07fbce9af629cd5c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0229-1298000000-d5136e5b9df2f19b790a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03dr-1971000000-e7d91146862aeb4cf127	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000l-2920000000-e3143ba3279219407909	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-4029000000-2a4e705554c3ab16e50d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-053r-7922000000-ec9365fe5af199a1d4c0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0536-9800000000-60c297c902469ee6f5fa	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0009000000-78f4f0994078633f8a0f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fk9-0479000000-e23c5d13aac6fbd2f27a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1930000000-7b8d2995ee0555d2ce2c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-9200000000-44fb2fcb2578da21c786	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9200000000-bed3b3a468bd2f142987	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9400000000-a899d0ec1d4b27e6e9c7	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00426

HMDB ID

HMDB0014570

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=17870541

2. https://www.ncbi.nlm.nih.gov/pubmed/?term=2754699

3. https://www.ncbi.nlm.nih.gov/pubmed/?term=9719596

Famciclovir (CHEM016705)

Structure for CHEM016705: Famciclovir