Indomethacin farnesil (CHEM020837)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 07:29:03 UTC
Update Date2016-11-09 01:16:17 UTC
Accession NumberCHEM020837
Identification
Common NameIndomethacin farnesil
ClassSmall Molecule
DescriptionIndometacin farnesil (INN) is a prodrug of the nonsteroidal anti-inflammatory drug (NSAID) indometacin, designed to reduce the occurrence of side-effects by esterification of the carboxyl group on indometacin with farnesol. Indometacin farnesil was first approved in Japan in 1991, and is available in Japan and Indonesia, under the trade names Infree and Dialon, respectively.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
InfreeKegg
Indometacin farnesilMeSH
[(2E,6E)-3,7,11-Trimethyldodeca-2,6,10-trienyl] 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acidGenerator
Indomethacin farnesilMeSH
(2E,6E)-3,7,11-Trimethyldodeca-2,6,10-trien-1-yl 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetic acidGenerator
Chemical FormulaC34H40ClNO4
Average Molecular Mass562.150 g/mol
Monoisotopic Mass561.265 g/mol
CAS Registry Number85801-02-1
IUPAC Name(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetate
Traditional Nameinfree
SMILES[H]\C(CC\C(C)=C(/[H])COC(=O)CC1=C(C)N(C(=O)C2=CC=C(Cl)C=C2)C2=C1C=C(OC)C=C2)=C(\C)CCC=C(C)C
InChI IdentifierInChI=1S/C34H40ClNO4/c1-23(2)9-7-10-24(3)11-8-12-25(4)19-20-40-33(37)22-30-26(5)36(32-18-17-29(39-6)21-31(30)32)34(38)27-13-15-28(35)16-14-27/h9,11,13-19,21H,7-8,10,12,20,22H2,1-6H3/b24-11+,25-19+
InChI KeyCFIGYZZVJNJVDQ-LMJOQDENSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzoylindoles. These are organic compounds containing an indole attached to a benzoyl moiety through the acyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassBenzoylindoles
Direct ParentBenzoylindoles
Alternative Parents
Substituents
  • Benzoylindole
  • Sesquiterpenoid
  • Farsesane sesquiterpenoid
  • Indole-3-acetic acid derivative
  • Indolyl carboxylic acid derivative
  • Indolecarboxylic acid derivative
  • 4-halobenzoic acid or derivatives
  • Halobenzoic acid or derivatives
  • 3-alkylindole
  • Indole
  • Benzoic acid or derivatives
  • Benzoyl
  • Anisole
  • Halobenzene
  • Alkyl aryl ether
  • Chlorobenzene
  • Substituted pyrrole
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl chloride
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrole
  • Carboxylic acid ester
  • Azacycle
  • Carboxylic acid derivative
  • Ether
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organochloride
  • Organohalogen compound
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility4.3e-05 g/LALOGPS
logP7.61ALOGPS
logP8.36ChemAxon
logS-7.1ALOGPS
pKa (Strongest Basic)-2.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity166.3 m³·mol⁻¹ChemAxon
Polarizability64.97 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-0445090000-c8669287f99cbefc1babSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-4957000000-1ca221c59239c5360a6aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03xr-8926000000-556cc9fe1e219a7ea9f0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dr-0039070000-57889fc6cf51692f8ba6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0btl-0139010000-84c9ab98b11fc8ba35f6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000f-0569000000-284e8c4925a13caef0a2Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkIndometacin farnesil
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID5282183
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available