Aprepitant
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| Clinical data | |
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| Trade names | Emend |
| AHFS/Drugs.com | Monograph |
| MedlinePlus | a604003 |
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| Routes of administration |
Oral (capsules) |
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| Pharmacokinetic data | |
| Bioavailability | 60–65% |
| Protein binding | >95% |
| Metabolism | Hepatic (mostly CYP3A4- mediated; some contributions by CYP2C19 & CYP1A2) |
| Biological half-life | 9–13 hours |
| Excretion | Urine (5%), faeces (86%) |
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| ChEMBL | |
| ECHA InfoCard | 100.202.762 |
| Chemical and physical data | |
| Formula | C23H21F7N4O3 |
| Molar mass | 534.43 g·mol−1 |
| 3D model (Jmol) | |
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Aprepitant (brand name: Emend (the brand name used in all English-speaking countries)) is an antiemetic chemical compound that belongs to a class of drugs called substance P antagonists (SPA). It mediates its effect by blocking the neurokinin 1 (NK1) receptor.
Aprepitant is manufactured by Merck & Co. under the brand name Emend for prevention of acute and delayed chemotherapy-induced nausea and vomiting (CINV) and for prevention of postoperative nausea and vomiting. It was approved by the FDA in 2003.
Aprepitant may also be useful in the treatment of cyclic vomiting syndrome and late-stage chemotherapy induced vomiting, but there are few studies to date.
On January 2008, the FDA approved fosaprepitant, an intravenous form of aprepitant, which is to be sold under the tradename Emend Injection in the US and as Ivemend in some other countries.
Aprepitant is made up of a morpholine core with two substituents attached to adjacent ring carbons. These substitute groups are trifluoromethylated phenyl ethanol and group. Aprepitant also has a third substituent (triazolinone), which is joined to the morpholine ring nitrogen. It has three chiral centres very close together, which combine to produce an amino acetal arrangement. Its empirical formula is C23H21F7N4O3.
Aprepitant is an off-white crystalline solid that has a molecular weight of around 534.53. It has a very limited solubility in water. It does have a reasonably high solubility in non-polar molecules such as oils. This would, therefore, suggest that aprepitant as a whole, despite having components that are polar, is a non-polar substance.
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Wikipedia