Aprepitant

"Emend" redirects here. For Emend for injection, see Fosaprepitant.

Aprepitant
Structural formula of aprepitant
Ball-and-stick model of the aprepitant molecule
Clinical data
Trade namesEmend, Cinvanti, Aponvie, others
AHFS/Drugs.comMonograph
MedlinePlusa604003
License data
Pregnancy
category
  • AU: B1
Routes of
administration		By mouth
Drug classNK1 receptor antagonist, antiemetic
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability60–65%
Protein binding>95%
MetabolismLiver (mostly CYP3A4- mediated; some contributions by CYP2C19 & CYP1A2)
Elimination half-life9–13 hours
ExcretionKidney (57%), feces (45%)
Identifiers
  • 5-([(2R,3S)-2-((R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethoxy)-3-(4-fluorophenyl)morpholino]methyl)-1H-1,2,4-triazol-3(2H)-one
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.202.762 Edit this at Wikidata
Chemical and physical data
FormulaC23H21F7N4O3
Molar mass534.435 g·mol−1
3D model (JSmol)
  • FC(F)(F)c1cc(cc(c1)C(F)(F)F)[C@H](O[C@H]4OCCN(CC/2=N/C(=O)NN\2)[C@H]4c3ccc(F)cc3)C
  • 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 checkY
  • Key:ATALOFNDEOCMKK-OITMNORJSA-N checkY
  (verify)

Aprepitant, sold under the brand name Emend among others, is a medication used to prevent chemotherapy-induced nausea and vomiting and to prevent postoperative nausea and vomiting.[5] It may be used together with ondansetron and dexamethasone.[5] It is taken by mouth[5] or administered by intravenous injection.[3]

Common side effects include tiredness, loss of appetite, diarrhea, abdominal pain, hiccups, itchiness, pneumonia, and blood pressure changes.[5] Other severe side effects may include anaphylaxis.[5] While use in pregnancy does not appear to be harmful, such use has not been well studied.[6] Aprepitant belongs to the class of neurokinin-1 receptor antagonists.[5] It works by blocking substance P from attaching to the NK1 receptors.[4]

Aprepitant was approved for medical use in the European Union and the United States in 2003.[5][4] It is made by Merck & Co.[5] It is on the World Health Organization's List of Essential Medicines.[7][8]

  1. ^ "Emend- aprepitant capsule Emend- aprepitant kit Emend- aprepitant powder, for suspension". DailyMed. 6 May 2022. Archived from the original on 9 March 2022. Retrieved 27 September 2022.
  2. ^ "Cinvanti- aprepitant injection, emulsion". DailyMed. 24 March 2022. Archived from the original on 31 August 2022. Retrieved 27 September 2022.
  3. ^ a b "Aponvie (aprepitant) injectable emulsion, for intravenous use Initial U.S. Approval: 2003" (PDF). Archived (PDF) from the original on 28 September 2022. Retrieved 28 September 2022.
  4. ^ a b c "Emend EPAR". European Medicines Agency. 17 September 2018. Archived from the original on 12 November 2020. Retrieved 13 October 2019.
  5. ^ a b c d e f g h "Aprepitant/Fosaprepitant Dimeglumine Monograph for Professionals". Drugs.com. Archived from the original on 13 August 2020. Retrieved 13 October 2019.
  6. ^ "Aprepitant Use During Pregnancy". Drugs.com. Archived from the original on 28 October 2020. Retrieved 13 October 2019.
  7. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  8. ^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.