Fosaprepitant (CHEM022363)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:29:58 UTC
Update Date2016-11-09 01:17:28 UTC
Accession NumberCHEM022363
Identification
Common NameFosaprepitant
ClassSmall Molecule
DescriptionA morpholine derivative that is the (1R)-1-ethyl ether of (3-{methyl}-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)phosphonic acid.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
FosaprepitantumChEBI
L-758,298ChEBI
L-758298ChEBI
Emend for injectionHMDB
Fosaprepitant dimeglumineHMDB
Chemical FormulaC23H22F7N4O6P
Average Molecular Mass614.407 g/mol
Monoisotopic Mass614.117 g/mol
CAS Registry Number172673-20-0
IUPAC Name(3-{[(2R,3S)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholin-4-yl]methyl}-5-oxo-2,5-dihydro-1H-1,2,4-triazol-1-yl)phosphonic acid
Traditional Namefosaprepitant
SMILESC[C@@H](O[C@H]1OCCN(CC2=NC(=O)N(N2)P(O)(O)=O)[C@H]1C1=CC=C(F)C=C1)C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F
InChI IdentifierInChI=1S/C23H22F7N4O6P/c1-12(14-8-15(22(25,26)27)10-16(9-14)23(28,29)30)40-20-19(13-2-4-17(24)5-3-13)33(6-7-39-20)11-18-31-21(35)34(32-18)41(36,37)38/h2-5,8-10,12,19-20H,6-7,11H2,1H3,(H,31,32,35)(H2,36,37,38)/t12-,19+,20-/m1/s1
InChI KeyBARDROPHSZEBKC-OITMNORJSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenylmorpholines. These are aromatic compounds containing a morpholine ring and a benzene ring linked to each other through a CC or a CN bond.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassOxazinanes
Sub ClassMorpholines
Direct ParentPhenylmorpholines
Alternative Parents
Substituents
  • Phenylmorpholine
  • Trifluoromethylbenzene
  • Fluorobenzene
  • Halobenzene
  • Aralkylamine
  • Aryl fluoride
  • Aryl halide
  • Monocyclic benzene moiety
  • Benzenoid
  • Azole
  • Heteroaromatic compound
  • 1,2,4-triazole
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Oxacycle
  • Acetal
  • Alkyl fluoride
  • Organofluoride
  • Organohalogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Alkyl halide
  • Organooxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
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 Solubility0.0063 g/LALOGPS
logP2.89ALOGPS
logP2.4ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)1.02ChemAxon
pKa (Strongest Basic)5.69ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area123.93 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity138.63 m³·mol⁻¹ChemAxon
Polarizability49.92 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-0469020000-a9d53cff50121f0ac397Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014l-1291148000-89d7ce5293bc9b67d05cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-0090120000-90a954db621c91e2b6b9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01pk-9640000000-5e645105fbd967a5973fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9320110000-e5a11eb20cb539f51093Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-2091220000-cdeb0047166d8b481ca8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9130000000-4475aa8dcea01509b8ccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05mo-0098017000-b3c70a835cf33fa90790Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05mx-0092033000-6371fe9f0667b041c9a2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ffx-0791000000-0e95b35ac4fd4a5233e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0001019000-0dac5bd74f2a8ef931e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bvi-8696383000-679567e6c5615842e08cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000t-6310910000-d9ef03984b10377db0ebSpectrum
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 IDDB06717
HMDB IDHMDB0015662
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkFosaprepitant_dimeglumine
Chemspider ID189912
ChEBI ID64321
PubChem Compound ID219090
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=19608812
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=20795794
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21042544
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=21209230
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=21270665
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=21383291
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=21711119
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=21947834
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=22228030
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=22316362