fosaprepitant   Click here for help

GtoPdb Ligand ID: 7623

Synonyms: Ivemend® | MK-0517
Approved drug
fosaprepitant is an approved drug (FDA and EMA (2008))
Compound class: Synthetic organic
Comment: Marketed formulations contain fosaprepitant dimeglumine.
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: fosaprepitant

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 8
Hydrogen bond donors 3
Rotatable bonds 9
Topological polar surface area 139.72
Molecular weight 614.12
XLogP 4.31
No. Lipinski's rules broken 0
Click here for help
Canonical SMILES Fc1ccc(cc1)C1C(OCCN1Cc1nc(=O)n([nH]1)P(=O)(O)O)OC(c1cc(cc(c1)C(F)(F)F)C(F)(F)F)C
Isomeric 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
No information available.
Summary of Clinical Use Click here for help
Fosaprepitant is an intravenously administered prodrug of aprepitant, used to prevent nausea and vomiting induced by chemotherapy.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
The active metabolite of fosaprepitant, aprepitant, is a substance P analogue and acts as an antagonist of the neurokinin 1 receptor (NKR1). This prevents activation of NKR1 in the area of the medulla known as the vomiting center [2], and thereby reduces nausea and vomiting.
External links Click here for help