172673-20-0

Basic information

• Product Name: Fosaprepitant
• Synonyms: [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-yl]phosphonic acid;[3-[[(2R,3S)-2-[(1R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)-4-morpholinyl]methyl]-2,5-dihydro-5-oxo-1H-1,2,4-triazol-1-yl]phosphonic acid;Fosaprepitant;L 758298;P-[3-[[(2R,3S)-2-[(1R)-1-[3,5-Bis(trifluoroMethyl)phenyl]ethoxy]-3-(4-fluorophenyl)-4-Morpholinyl]Methyl]-2,5-dihydro-5-oxo-1H-1,2,4-triazol-1-yl]phosphonic Acid;MK-0517 (Fosaprepitant);D-Glucitol, 1-deoxy-1-(MethylaMino)-, (3-(((2R,3S)-2-((1R)-1-(3,5-bis(trifluoroMethyl)phenyl)ethoxy)-3-(4-fluorophenyl)-4- Morpholinyl)Methyl)-2,5-dihydro-5-oxo-1H-1,2,4-triazol-1-yl)phosphonate (2:1);Fosaprepitant (See also F727305)
• CAS NO: 172673-20-0
• Molecular Formula: C₂₃H₂₂F₇N₄O₆P
• Molecular Weight: 614.41
• Product Categories: Aromatics;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 172673-20-0.mol
• Article Data: 0

Chemical Properties

• Boiling Point: 588.9 °C at 760 mmHg
• Flash Point: 310 °C
• Appearance: /
• Density: 1.65
• Vapor Pressure: 1.03E-14mmHg at 25°C
• Refractive Index: 1.589
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Solubility: DMSO, Methanol
• PKA: 2.45±0.20(Predicted)
• CAS DataBase Reference: Fosaprepitant(CAS DataBase Reference)
• NIST Chemistry Reference: Fosaprepitant(172673-20-0)
• EPA Substance Registry System: Fosaprepitant(172673-20-0)

Safety Data

• Hazardous Substances Data: 172673-20-0(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 172673-20-0 differently. You can refer to the following data:
1. Fosaprepitant is a selective neurokinin-1 (NK-1) receptor antahonist. Fosaprepitant is an antiemetic drug, a Aprepitant (A729800) prodrug.
2. An antiemetic drug, a Aprepitant prodrug.
3. Fosaprepitant is a selective neurokinin-1 (NK-1) receptor antagonist. Fosaprepitant is an antiemetic drug, a Aprepitant (A729800) prodrug.

Definition

ChEBI: A morpholine derivative that is the (1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl ether of (3-{[(2R,3S)-3-(4-fluorophenyl)-2-hydroxymorpholin-4-yl]methyl}-5-oxo-4,5-dihydro-1H-1,2,4-triaz l-1-yl)phosphonic acid.

Biological Activity

fosaprepitant (l-758,298 mk-0517) is an antagonist of neurokinin-1[1].fosaprepitant has shown the pharmacodynamic function by its active metabolite aprepitant. fosaprepitanot has been found to be a highly selective antagonist of the nk-1 receptor and inhibit the cation of substance p. in addition, fosaprepitant has been exhibited to have the effect on cisplatin induced emesis in the classical ferret model. besides, because of the brain penetrating of aprepitant, fosaprepitant has been revealed to have a very high affinity for the nk-1 receptor and increase the efficacy by dexamethasone, granisetron and so on. fosaprepitant has been evaluated to use in the prevention of chemotherapy-induced nausea and vomiting (cinv) by combination with a 5-ht3 antagonist and a steroid [1].

Clinical Use

#N/A

Drug interactions

Potentially hazardous interactions with other drugs Antidepressants: avoid with St John’s wort. Antipsychotics: avoid with pimozide. Cytotoxics: possibly increases bosutinib concentration - avoid or reduce bosutinib dose. Oestrogens and progestogens: may cause contraceptive failure.

Metabolism

Fosaprepitant is a prodrug and is rapidly metabolised to aprepitant. Aprepitant undergoes extensive hepatic metabolism, mainly via oxidation by the cytochrome P450 isoenzyme CYP3A4; the isoenzymes CYP1A2 and CYP2C19 mediate minor metabolic pathways. The resultant metabolites have weak activity and are excreted in the urine and in the faeces.

references

[1] van belle sj1, cocquyt v. fosaprepitant dimeglumine (mk-0517 or l-785,298), an intravenous neurokinin-1 antagonist for the prevention of chemotherapy induced nausea and vomiting.expert opin pharmacother. 2008 dec; 9(18):3261-70.

InChI:InChI=1/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