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Fosaprepitant

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Fosaprepitant
Skeletal formula of fosaprepitant
Space-filling model of the fosaprepitant molecule
Clinical data
Trade namesEmend, Ivemend, others
Other namesFosaprepitant meglumine (JAN JP), Fosaprepitant dimeglumine (USAN US)
AHFS/Drugs.comMicromedex Detailed Consumer Information
MedlinePlusa604003
License data
Pregnancy
category
Routes of
administration		Intravenous
Drug classAntiemetic agent
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailabilityn/a
Protein binding>95% (aprepitant)
MetabolismTo aprepitant
Elimination half-life9 to 13 hours (aprepitant)
Identifiers
  • [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
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC23H22F7N4O6P
Molar mass614.414 g·mol−1
3D model (JSmol)
  • 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

  • C[C@H](C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)O[C@@H]2[C@@H](N(CCO2)CC3=NN(C(=O)N3)P(=O)(O)O)C4=CC=C(C=C4)F.CNC[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.CNC[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O
  • 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
  • Key:BARDROPHSZEBKC-OITMNORJSA-N

  • InChI=1S/C23H22F7N4O6P.2C7H17NO5/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;2*1-8-2-4(10)6(12)7(13)5(11)3-9/h2-5,8-10,12,19-20H,6-7,11H2,1H3,(H,31,32,35)(H2,36,37,38);2*4-13H,2-3H2,1H3/t12-,19+,20-;2*4-,5+,6+,7+/m100/s1
  • Key:VRQHBYGYXDWZDL-OOZCZQCLSA-N

Fosaprepitant, sold under the brand names Emend (US) and Ivemend (EU) among others, is an antiemetic medication,[11] administered intravenously.[6] Fosaprepitant is a substance P/neurokinin-1 (NK1) receptor antagonist.[6] It is a prodrug of aprepitant.[6]

Fosaprepitant was developed by Merck & Co. and was approved for medical use in the United States,[12] and in the European Union in January 2008.[10]

Medical uses

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Fosaprepitant is indicated for people aged six months of age and older, in combination with other antiemetic agents, for the prevention of acute and delayed nausea and vomiting associated with initial and repeat courses of highly emetogenic cancer chemotherapy including high-dose cisplatin;[6] and for delayed nausea and vomiting associated with initial and repeat courses of moderately emetogenic cancer chemotherapy.[6]

References

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  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. ↑ "Product information". Health-prodcuts.canada.ca. Retrieved 15 July 2026.
  5. ↑ "IVEMEND 150 mg powder for solution for infusion - Summary of Product Characteristics (SmPC) - (emc) | 5947". Medicines.org.uk. Retrieved 15 July 2026.
  6. 1 2 3 4 5 6 "Emend- fosaprepitant dimeglumine injection, powder, lyophilized, for solution". DailyMed. 2 May 2022. Archived from the original on 1 December 2021. Retrieved 27 September 2022.
  7. ↑ "DailyMed - FOCINVEZ- fosaprepitant dimeglumine injection". Dailymed.nlm.nih.gov. Retrieved 15 July 2026.
  8. ↑ "DailyMed - FOCINVEZ- fosaprepitant dimeglumine injection". Dailymed.nlm.nih.gov. Retrieved 15 July 2026.
  9. ↑ "DailyMed - NAVITRUX- fosaprepitant injection, powder, lyophilized, for solution". Dailymed.nlm.nih.gov. Retrieved 15 July 2026.
  10. 1 2 "Ivemend EPAR". European Medicines Agency (EMA). Archived from the original on 31 December 2021. Retrieved 27 September 2022.
  11. ↑ 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.
  12. ↑ "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 9 April 2008. Retrieved 15 March 2008.
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