(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编号: 4454
• 分子式: C23H22F7N4O6P
• 平均质量: 614.4065634
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (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传统名: 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
• 商标名: EMEND® IV
• 别名: Fosaprepitant

登记号

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

理论计算性质

JChem

• Acid pKa: 1.0232137
• 质子受体: 9
• 质子供体: 3
• LogD (pH = 5.5): -0.3152205
• LogD (pH = 7.4): -0.79554963
• Log P: 2.426249
• 摩尔折射率: 138.6304 cm^3
• 极化性: 48.026802 Å^3
• 极化表面积: 123.93 Å^2
• 可自由旋转的化学键: 9
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: 2.89
• LOG S: -4.99
• 溶解度: 6.32e-03 g/l

详细说明

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