Aprepitant

  • CAT# 100065
  • CAS# 170729-80-3
  • Purity >98%

Price and availability

Structure

Structure of Aprepitant

CAS# 170729-80-3

Pricing updated 2019-09-04 . Prices are subject to change without notice
Description:

Aprepitant is a small molecule, high-affinity substance P antagonist (SPA) with antiemetic activity. Crossing the blood brain barrier, aprepitant binds selectively to the human substance P/neurokinin 1 receptor in the central nervous system (CNS), thereby inhibiting receptor binding of endogenous substance P and substance P-induced emesis. This agent has little or no affinity for serotonin type 3 (5-HT3), dopamine, and corticosteroid receptors.

Technical data

IUPAC/Chemnical Name5-(((2R,3S)-2-((R)-1-(3,5-bis(trifluoromethyl)phenyl)ethoxy)-3-(4-fluorophenyl)morpholino)methyl)-1H-1,2,4-triazol-3(2H)-one
Synonym nameMK0869; MK 0869; MK-0869; ONO7436; ONO-7436; ONO 7436; L754030; L-754030; L 754030; Aprepitant; US brand name: Emend
CAS#170729-80-3
Molecule FormlaC23H21F7N4O3
Molecule Weight534.43
AppearanceSolid powder
Purity>98% (or refer to the Certificate of Analysis)
Shipping ConditionShipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage ConditionDry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Stability>2 years if stored properly
Harmonized System (HS) Code 2934.99.90.01
SMILES code O=C1NNC(CN2[C@@H](C3=CC=C(F)C=C3)[C@@H](O[C@@H](C4=CC(C(F)(F)F)=CC(C(F)(F)F)=C4)C)OCC2)=N1
InChi code 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
InChi keyATALOFNDEOCMKK-OITMNORJSA-N

References

1: Aapro MS, Schmoll HJ, Jahn F, Carides AD, Webb RT. Review of the efficacy of aprepitant for the prevention of chemotherapy-induced nausea and vomiting in a range of tumor types. Cancer Treat Rev. 2013 Feb;39(1):113-7. doi: 10.1016/j.ctrv.2012.09.002. Epub 2012 Oct 11. Review. PubMed PMID: 23062719. 2: Furukawa N, Kawaguchi R, Kobayashi H. Use of high-dose cisplatin with aprepitant in an outpatient setting. Eur J Cancer Care (Engl). 2012 Jul;21(4):436-41. doi: 10.1111/j.1365-2354.2011.01284.x. Epub 2011 Aug 25. Review. PubMed PMID: 21883567. 3: Hargreaves R, Ferreira JC, Hughes D, Brands J, Hale J, Mattson B, Mills S. Development of aprepitant, the first neurokinin-1 receptor antagonist for the prevention of chemotherapy-induced nausea and vomiting. Ann N Y Acad Sci. 2011 Mar;1222:40-8. doi: 10.1111/j.1749-6632.2011.05961.x. Review. PubMed PMID: 21434941. 4: Ruhlmann CH, Herrstedt J. Safety evaluation of aprepitant for the prevention of chemotherapy-induced nausea and vomiting. Expert Opin Drug Saf. 2011 May;10(3):449-62. doi: 10.1517/14740338.2011.563235. Epub 2011 Mar 21. Review. PubMed PMID: 21417835. 5: Kast RE. Glioblastoma: synergy of growth promotion between CCL5 and NK-1R can be thwarted by blocking CCL5 with miraviroc, an FDA approved anti-HIV drug and blocking NK-1R with aprepitant, an FDA approved anti-nausea drug. J Clin Pharm Ther. 2010 Dec;35(6):657-63. doi: 10.1111/j.1365-2710.2009.01148.x. Review. PubMed PMID: 21054456. 6: Aapro MS, Walko CM. Aprepitant: drug-drug interactions in perspective. Ann Oncol. 2010 Dec;21(12):2316-23. doi: 10.1093/annonc/mdq149. Epub 2010 May 20. Review. PubMed PMID: 20488873. 7: Sankhala KK, Pandya DM, Sarantopoulos J, Soefje SA, Giles FJ, Chawla SP. Prevention of chemotherapy induced nausea and vomiting: a focus on aprepitant. Expert Opin Drug Metab Toxicol. 2009 Dec;5(12):1607-14. doi: 10.1517/17425250903451675. Review. PubMed PMID: 19929449. 8: Curran MP, Robinson DM. Aprepitant: a review of its use in the prevention of nausea and vomiting. Drugs. 2009;69(13):1853-78. doi: 10.2165/11203680-000000000-00000. Review. PubMed PMID: 19719336. 9: Sarcev T, Secen N, Zaric B, Milovancev A. Aprepitant--where do we stand in the control of chemotherapy-induced nausea and vomiting? J BUON. 2008 Jul-Sep;13(3):333-9. Review. PubMed PMID: 18979546. 10: Olver I, Shelukar S, Thompson KC. Nanomedicines in the treatment of emesis during chemotherapy: focus on aprepitant. Int J Nanomedicine. 2007;2(1):13-8. Review. PubMed PMID: 17722507; PubMed Central PMCID: PMC2673828.