3-{[(2R,3S)-2-[(1R)-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: 72569
• Molecular Formular: C23H21F7N4O3
• Molecular Mass: 534.4266624
• Monoisotopic Mass: 534.15018809
• SMILES: n1[nH]c(=O)[nH]c1CN1[C@H]([C@H](OCC1)O[C@H](C)c1cc(cc(c1)C(F)(F)F)C(F)(F)F)c1ccc(cc1)F
• 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-/m1/s1
• InChIKey: ATALOFNDEOCMKK-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}-4,5-dihydro-1H-1,2,4-triazol-5-one
• IUPAC Traditional name: aprepitant; @aprepitant
• Synonyms: 5-[[(2R,3S)-2-[(1R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)-4-morpholinyl]methyl]-1,2-dihydro-3H-1,2,4-triazol-3-one; L 754030; MK 0869; MK 869; ONO 7436; MK-869; L-754030; Emend; ); Aprepitant

Database IDs

• CAS Number: 170729-80-3
• PubChem SID: 162037494
• PubChem CID: 6918365

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

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 244-246°C

Safety Information

• Storage Condition: -20°C; -20°C Freezer

Pharmacology Properties

• Target: substance P

Product Information

• Salt Data: Free Base

DETAILS

Selleck Chemicals - S1189

Research Area: Neurological Disease
Biological Activity:
Aprepitant is an antiemetic chemical compound that belongs to a class of drugs called substance P antagonists (SPA). It mediates its effect by blocking the neurokinin 1 (NK1) receptor. Aprepitant is used for prevention of acute and delayed chemotherapy-induced nausea and vomiting (CINV) and for prevention of postoperative nausea and vomiting.[1]References on Aprepitant (MK-0869)[1] http://en.wikipedia.org/wiki/Aprepitant, ,

Toronto Research Chemicals - A729800

A novel selective neurokinin-1 (NK-1) receptor antagonist. In vitro studies using human liver microsomes indicate that Aprepitant is metabolised primarily by CYP3A4 with minor metabolism by CYP1A2 and CYP2C19, and no metabolism by CYP2D6, CYP2C9, or CYP2E

REFERENCES

• http://www.search.com/reference/Aprepitant
• Hale, J.J., et al.: J. Med. Chem., 41, 4607 (1998)
• Campos, D., et al.: J. Clin. Oncol., 19, 1759 (1998)
• Van Belle, S., et al.: Cancer, 94, 3032 (1998)
• Majumdar, A.K., et al.: J. Clin. Pharmacol., 46, 291 (1998)