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

• ChemBase ID: 160770
• Molecular Formular: C23H21F7N4O3
• Molecular Mass: 534.4266624
• Monoisotopic Mass: 534.15018809
• SMILES: N1(CCO[C@H]([C@H]1c1ccc(cc1)F)O[C@H](c1cc(cc(c1)C(F)(F)F)C(F)(F)F)C)Cc1[nH]c(=O)[nH]n1
• Canonical SMILES: Fc1ccc(cc1)[C@@H]1[C@@H](OCCN1Cc1n[nH]c(=O)[nH]1)O[C@H](c1cc(cc(c1)C(F)(F)F)C(F)(F)F)C
• InChI: InChI=1S/C23H21F7N4O3/c1-12(14-8-15(22(25,26)27)10-16(9-14)23(28,29)30)37-20-19(13-2-4-17(24)5-3-13)34(6-7-36-20)11-18-31-21(35)33-32-18/h2-5,8-10,12,19-20H,6-7,11H2,1H3,(H2,31,32,33,35)/t12-,19+,20-/m0/s1
• InChIKey: ATALOFNDEOCMKK-KNMUDHKVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{[(2S,3R)-2-[(1S)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholin-4-yl]methyl}-4,5-dihydro-1H-1,2,4-triazol-5-one
• IUPAC Traditional name: 5-{[(2S,3R)-2-[(1S)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholin-4-yl]methyl}-2,4-dihydro-1,2,4-triazol-3-one
• Synonyms: 5-[[(2S,3R)-2-[(1S)-1-[3,5-Bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)-4-morpholinyl]methyl]-1,2-dihydro-3H-1,2,4-triazol-3-one; [2S-[2α(R*),3α]]-5-[[2-[1-[3,5-Bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)-4-morpholinyl]methyl]-1,2-dihydro-3H-1,2,4-triazol-3-one; ent-Aprepitant

Database IDs

• CAS Number: 172822-29-6
• PubChem SID: 162254905
• PubChem CID: 15341300

CALCULATED PROPERTIES

• Acid pKa: 9.646593
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 5.211254
• LogD (pH = 7.4): 5.2134037
• Log P: 5.215729
• Molar Refractivity: 116.9282 cm^3
• Polarizability: 43.315456 Å^3
• Polar Surface Area: 75.19 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A729790

The (S,R,S)-enantiomer of Aprepitant (A729800), an unwanted enantiomer of Aprepitant in bulk drug and formulation samples of Aprepitant.

REFERENCES

• Chawla, S., et al.: Cancer, 97, 2290 (2003)
• Huskey, S., et al.: Drug Metab. Dispos., 31, 785 (2003)
• Warr, D., et al.: Eur. J. Cancer, 41, 1278 (2003)