Structure via PubChem · Public domain (PubChem)
aprepitant
Sign in to saveAlso known as 3-(((2R,3S)-3-(p-fluorophenyl)-2-(((alphaR)-alpha-methyl-3,5-bis(trifluoromethyl)benzyl)oxy)morpholino)methyl)-Delta(2)-1,2,4-triazolin-5-one, 3-(((2R,3S)-3-(p-fluorophenyl)-2-(((alphar)-alpha-methyl-3,5-bis(trifluoromethyl)benzyl)oxy)morpholino)methyl)-delta(2)-1,2,4-triazolin-5-one
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.
Chemical data
- Formula
- C23H21F7N4O3
- Molecular weight
- 534.4 g/mol
- IUPAC name
- 3-[[(2R,3S)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholin-4-yl]methyl]-1,4-dihydro-1,2,4-triazol-5-one
- SMILES
- C[C@H](C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)O[C@@H]2[C@@H](N(CCO2)CC3=NNC(=O)N3)C4=CC=C(C=C4)F
- InChIKey
- ATALOFNDEOCMKK-OITMNORJSA-N
- XLogP
- 4.2
- Polar surface area
- 75.2 Ų
- H-bond donors
- 2
- H-bond acceptors
- 12
- Formal charge
- 0
via PubChem
Research
1,461 papers- Aprepitant, fosaprepitant and risk of ifosfamide-induced neurotoxicity: a systematic review.Cancer chemotherapy and pharmacology · 2022
- The efficacy of aprepitant for the prevention of postoperative nausea and vomiting: A meta-analysis.Medicine · 2023
- Aprepitant--a novel NK1-receptor antagonist.Expert opinion on pharmacotherapy · 2003
- Aprepitant and fosaprepitant drug interactions: a systematic review.British journal of clinical pharmacology · 2017
- Aprepitant for the Treatment of Chronic Refractory Pruritus.BioMed research international · 2017
via PubMed
~9 min read
Encyclopedic overview
10 sectionsContents
- Medical uses
- Mechanism of action
- Pharmacokinetics
- Structure and properties
- Synthesis
- History
- Research
- Major depression
- Cannabinoid Hyperemesis Syndrome
- References
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.
Excerpted from Wikipedia’s “aprepitant” article, available under the CC BY-SA 4.0 licence.