Aprepitant

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

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

Aprepitant
Clinical data
Trade namesEmend, Cinvanti, Aponvie
AHFS/Drugs.comMonograph
MedlinePlusa604003
License data
Pregnancy
category
  • AU: B1
Routes of
administration		By mouth
Drug classNK1 receptor antagonists, antiemetics
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only)
  • US: ℞-only
Pharmacokinetic data
Bioavailability60–65%
Protein binding>95%
MetabolismLiver (mostly CYP3A4- mediated; some contributions by CYP2C19 & CYP1A2)
Elimination half-life9–13 hours
ExcretionUrine (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
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 Y
  • Key:ATALOFNDEOCMKK-OITMNORJSA-N Y
  (verify)

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

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

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