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

• ChemBase编号: 555
• 分子式: C23H21F7N4O3
• 平均质量: 534.4266624
• 单一同位素质量: 534.15018809
• SMILES: Fc1ccc([C@H]2N(CCO[C@H]2O[C@@H](c2cc(cc(c2)C(F)(F)F)C(F)(F)F)C)Cc2[nH][nH]c(=O)n2)cc1
• Canonical SMILES: Fc1ccc(cc1)[C@@H]1[C@@H](OCCN1Cc1[nH][nH]c(=O)n1)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-BYYRLHKVSA-N

名称和登记号

名称

• IUPAC标准名: 5-{[(2S,3R)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholin-4-yl]methyl}-2,3-dihydro-1H-1,2,4-triazol-3-one
• IUPAC传统名: emend
• 商标名: Emend
• 别名: aprepitant; MK-869; MK-0517; Aprepitant

登记号

• CAS号: 170729-80-3
• PubChem SID: 160964018
• PubChem CID: 151165

理论计算性质

JChem

• Acid pKa: 2.269396
• 质子受体: 6
• 质子供体: 2
• LogD (pH = 5.5): 3.5673702
• LogD (pH = 7.4): 3.5806317
• Log P: 3.3180022
• 摩尔折射率: 127.3431 cm^3
• 极化性: 43.315456 Å^3
• 极化表面积: 75.19 Å^2
• 可自由旋转的化学键: 8
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: 3.37
• LOG S: -4.39
• 溶解度: 2.18e-02 g/l

分子性质

理化性质

• 溶解度: Practically insoluble
• 疏水性(logP): 4.5

详细说明

DrugBank - DB00673

• Drug Groups: approved; investigational
• Description: Aprepitant, an antiemetic, is 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).
• Indication: For the prevention of nausea and vomiting associated with highly emetogenic cancer chemotherapy, including high-dose cisplatin (in combination with other antiemetic agents).
• Pharmacology: Aprepitant, an antiemetic, is 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).
• Affected Organisms: Humans and other mammals
• 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.
• Absorption: The mean absolute oral bioavailability of aprepitant is approximately 60 to 65%.
• 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.
• Distribution: * 70 L
• Clearance: * Apparent plasma cl=62-90 mL/min
• External Links: Wikipedia; RxList; Drugs.com