Aprepitant

Aprepitant
Clinical data
Trade names	Emend, Cinvanti, Aponvie, others
AHFS/Drugs.com	Monograph
MedlinePlus	a604003
License data	US DailyMed: Aprepitant;
Pregnancy; category	AU: B1;
Routes of; administration	By mouth
Drug class	NK1 receptor antagonist, antiemetic
ATC code	A04AD12 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); UK: POM (Prescription only); US: ℞-only; EU: Rx-only;
Pharmacokinetic data
Bioavailability	60–65%
Protein binding	>95%
Metabolism	Liver (mostly CYP3A4- mediated; some contributions by CYP2C19 & CYP1A2)
Elimination half-life	9–13 hours
Excretion	Kidney (57%), feces (45%)
Identifiers
	IUPAC name 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	170729-80-3 ;
PubChem CID	6918365;
IUPHAR/BPS	3490;
DrugBank	DB00673 ;
ChemSpider	5293568 ;
UNII	1NF15YR6UY;
ChEBI	CHEBI:499361 ;
ChEMBL	ChEMBL1471 ;
CompTox Dashboard (EPA)	DTXSID3049047 ;
ECHA InfoCard	100.202.762
Chemical and physical data
Formula	C23H21F7N4O3
Molar mass	534.435 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES 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 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 ; Key:ATALOFNDEOCMKK-OITMNORJSA-N ;
	(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. It may be used together with ondansetron and dexamethasone. It is taken by mouth or administered by intravenous injection. A prodrug, fosaprepitant, is also available for intravenous administration.

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. 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.