(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

• ChemBase ID: 4454
• Molecular Formular: C23H22F7N4O6P
• Molecular Mass: 614.4065634
• Monoisotopic Mass: 614.11651861
• SMILES: P(=O)(O)(O)n1[nH]c(nc1=O)CN1[C@H]([C@H](OCC1)O[C@@H](c1cc(cc(c1)C(F)(F)F)C(F)(F)F)C)c1ccc(F)cc1
• Canonical SMILES: Fc1ccc(cc1)[C@H]1[C@H](OCCN1Cc1nc(=O)n([nH]1)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-2,5-dihydro-1H-1,2,4-triazol-1-yl)phosphonic acid
• IUPAC Traditional name: 3-{[(2R,3S)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholin-4-yl]methyl}-5-oxo-2H-1,2,4-triazol-1-ylphosphonic acid
• Brand Name: EMEND® IV
• Synonyms: Fosaprepitant

Database IDs

• CAS Number: 172673-20-0
• PubChem SID: 160967886; 99443269
• PubChem CID: 219090

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.0232137
• H Acceptors: 9
• H Donor: 3
• LogD (pH = 5.5): -0.3152205
• LogD (pH = 7.4): -0.79554963
• Log P: 2.426249
• Molar Refractivity: 138.6304 cm^3
• Polarizability: 48.026802 Å^3
• Polar Surface Area: 123.93 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 2.89
• LOG S: -4.99
• Solubility (Water): 6.32e-03 g/l

DETAILS

DrugBank - DB06717

• Drug Groups: approved
• Description: Fosaprepitant is an intravenously administered antiemetic drug. It is a prodrug of Aprepitant. It aids in the prevention of acute and delayed nausea and vomiting associated with chemotherapy treatment.
• Indication: For the prevention of nausea and vomiting associated with highly emetogenic cancer chemotherapy.
• Pharmacology: Fosaprepitant is a prodrug of Aprepitant. Once biologically activated, the drug acts as a substance P/neurokinin 1 (NK1) receptor antagonist which, in combination with other antiemetic agents, is indicated for the prevention of acute and delayed nausea and vomiting associated with initial and repeat courses of highly emetogenic cancer chemotherapy. Aprepitant is a selective high-affinity antagonist of human substance P/neurokinin 1 (NK1) receptors. Aprepitant has little or no affinity for serotonin (5-HT₃), dopamine, and corticosteroid receptors, the targets of existing therapies for chemotherapy-induced nausea and vomiting (CI NV).
• Biotransformation: Aprepitant is metabolized primarily by CYP3A4 with minor metabolism by CYP1A2 and CYP2C19. Seven metabolites of aprepitant, which are only weakly active, have been identified in human plasma.
• Half Life: 9-13 hours
• Protein Binding: 95% +
• Elimination: Aprepitant is eliminated primarily by metabolism; aprepitant is not renally excreted. Aprepitant is excreted in the milk of rats. It is not known whether this drug is excreted in human milk.
• External Links: Wikipedia