Fosaprepitant

Fosaprepitant

Clinical data
Trade names	Emend, Ivemend
AHFS/Drugs.com	Micromedex Detailed Consumer Information
MedlinePlus	a604003
License data	EU EMA: by INN US DailyMed: Fosaprepitant US FDA: Fosaprepitant
Pregnancy category	AU: B2[1]
Routes of administration	Intravenous
ATC code	A04AD12 (WHO)
Legal status
Legal status	AU: S4 (Prescription only)[2][3] UK: POM (Prescription only) US: ℞-only[4] EU: Rx-only[5]
Pharmacokinetic data
Bioavailability	n/a
Protein binding	>95% (aprepitant)
Metabolism	To aprepitant
Elimination half-life	9 to 13 hours (aprepitant)
Identifiers
IUPAC 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-yl]phosphonic acid
CAS Number	172673-20-0^Y 265121-04-8 (dimeglumine)
PubChem CID	219090
IUPHAR/BPS	7623
DrugBank	DB06717^N
ChemSpider	189912^N
UNII	6L8OF9XRDC
KEGG	D06597^N
ChEBI	CHEBI:64321^N
ChEMBL	ChEMBL1199324^N
CompTox Dashboard (EPA)	DTXSID801021651
Chemical and physical data
Formula	C23H22F7N4O6P
Molar mass	614.414 g·mol^−1
3D model (JSmol)	Interactive image
SMILES C[C@H](c1cc(cc(c1)C(F)(F)F)C(F)(F)F)O[C@@H]2[C@@H](N(CCO2)Cc3[nH]c(=O)n(n3)P(=O)(O)O)c4ccc(cc4)F
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^N Key:BARDROPHSZEBKC-OITMNORJSA-N^N
^NY (what is this?)  (verify)

Fosaprepitant, sold under the brand names Emend (US) and Ivemend (EU) among others, is an antiemetic medication,^[6] administered intravenously. It is a prodrug of aprepitant.

Fosaprepitant was developed by Merck & Co. and was approved for medical use in the United States,^[7] and in the European Union in January 2008.^[5]

References

1. "Prescribing medicines in pregnancy database". Therapeutic Goods Administration (TGA). 21 June 2022. Archived from the original on 2 March 2023. Retrieved 28 April 2023.
2. "Emend IV fosaprepitant 150mg (as fosaprepitant dimeglumine) powder for injection vial (167061)". Therapeutic Goods Administration (TGA). 27 May 2022. Retrieved 28 April 2023.
3. "Fosaprepitant MSN (Accelagen Pty Ltd)". Therapeutic Goods Administration (TGA). 11 November 2022. Archived from the original on 18 March 2023. Retrieved 28 April 2023.
4. "Emend- fosaprepitant dimeglumine injection, powder, lyophilized, for solution". DailyMed. 2 May 2022. Archived from the original on 1 December 2021. Retrieved 27 September 2022.
5. "Ivemend EPAR". European Medicines Agency. 17 September 2018. Archived from the original on 31 December 2021. Retrieved 27 September 2022.
6. Garnock-Jones KP (September 2016). "Fosaprepitant Dimeglumine: A Review in the Prevention of Nausea and Vomiting Associated with Chemotherapy". Drugs. 76 (14): 1365–72. doi:10.1007/s40265-016-0627-7. PMID 27510503. S2CID 30018182.
7. "Drugs.com, FDA Approves Emend (fosaprepitant dimeglumine) for Injection, Merck's New Intravenous Therapy, for Use in Combination with Other Antiemetics for Prevention of Nausea and Vomiting Caused by Chemotherapy". Archived from the original on 2008-04-09. Retrieved 2008-03-15.