(3-{[(2R,3S)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholin-4-yl]methyl}-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)phosphonic acid

• ChemBase ID: 169442
• Molecular Formular: C23H22F7N4O6P
• Molecular Mass: 614.4065634
• Monoisotopic Mass: 614.11651861
• SMILES: c1(cc(cc(c1)[C@H](O[C@@H]1[C@@H](N(CCO1)Cc1[nH]c(=O)n(n1)P(=O)(O)O)c1ccc(cc1)F)C)C(F)(F)F)C(F)(F)F
• Canonical SMILES: Fc1ccc(cc1)[C@H]1[C@H](OCCN1Cc1[nH]c(=O)n(n1)P(=O)(O)O)O[C@@H](c1cc(cc(c1)C(F)(F)F)C(F)(F)F)C
• InChI: InChI=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
• InChIKey: BARDROPHSZEBKC-OITMNORJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3-{[(2R,3S)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholin-4-yl]methyl}-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)phosphonic acid
• IUPAC Traditional name: fosaprepitant
• Synonyms: P-[3-[[(2R,3S)-2-[(1R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)-4-morpholinyl]methyl]-2,5-dihydro-5-oxo-1H-1,2,4-triazol-1-yl]phosphonic Acid; L 758298; Fosaprepitant

Database IDs

• CAS Number: 172673-20-0
• PubChem SID: 162263574
• PubChem CID: 219090

CALCULATED PROPERTIES

• Acid pKa: 0.361456
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -0.26704422
• LogD (pH = 7.4): -0.47184062
• Log P: 2.7154026
• Molar Refractivity: 128.2155 cm^3
• Polarizability: 48.026802 Å^3
• Polar Surface Area: 123.93 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 130-133°C

DETAILS

Toronto Research Chemicals - F727300

Fosaprepitant is a selective neurokinin-1 (NK-1) receptor antahonist. Fosaprepitant is an antiemetic drug, a Aprepitant (A729800) prodrug.

REFERENCES

• Tattersall, F., et al.: Neuropharmacol., 39, 652 (2000)
• Cocquyt, V., et al.: Eur. J. Canc., 37, 835 (2000)
• Lasseter, K., et al.: J. Clin. Pharmacol., 47, 834 (2000)
• Marbury, T., et al.: Anesthes., Analges., 109, 418 (2000)