CAS#: 914462-92-3 (HCl salt)
Description: Rolapitant, also known as SCH-619734, is an orally bioavailable, centrally-acting, selective, neurokinin 1 receptor (NK1-receptor) antagonist with potential antiemetic activity. Upon oral administration, rolapitant competitively binds to and blocks the activity of the NK1-receptor in the central nervous system, thereby inhibiting the binding of the endogenous ligand, substance P (SP). This may prevent both SP-induced emesis and chemotherapy-induced nausea and vomiting (CINV). The interaction of SP with the NK1-receptor plays a key role in the induction of nausea and vomiting caused by emetogenic cancer chemotherapy. Compared to other NK1-receptor antagonists, rolapitant has both a more rapid onset of action and a much longer half-life. Rolapitant was approved in 2015. Rolapitant hydrochloride is approved to be used with other drugs to prevent: Nausea and vomiting caused by chemotherapy.
Synonym: SCH619734 SCH-619734; SCH 619734; Rolapitant, brand name: Varubi.
IUPAC/Chemical Name: (5S,8S)-8-(((R)-1-(3,5-bis(trifluoromethyl)phenyl)ethoxy)methyl)-8-phenyl-1,7-diazaspiro[4.5]decan-2-one hydrochloride.
PRICE AND AVAILABILITY
Name: Rolapitant HCl
CAS#: 914462-92-3 (HCl salt)
Chemical Formula: C25H27ClF6N2O2
Molecular Weight: 536.94
Elemental Analysis: C, 55.92; H, 5.07; Cl, 6.60; F, 21.23; N, 5.22; O, 5.96
CAS#914462-92-3 (Rolapitant HCl salt);
CAS#552292-08-7 (Rolapitant free base).
1: Melton MS, Nielsen KC, Tucker M, Klein SM, Gan TJ. Long-acting serotonin antagonist (Palonosetron) and the NK-1 receptor antagonists: does extended duration of action improve efficacy? Anesthesiol Clin. 2014 Jun;32(2):505-16. doi: 10.1016/j.anclin.2014.02.004. Epub 2014 Apr 18. PubMed PMID: 24882134.
2: Morrow GR, Navari RM, Rugo HS. Clinical roundtable monograph: New data in emerging treatment options for chemotherapy-induced nausea and vomiting. Clin Adv Hematol Oncol. 2014 Mar;12(3 Suppl 9):1-14; quiz 15. PubMed PMID: 24874107.
3: Navari RM. Management of chemotherapy-induced nausea and vomiting : focus on newer agents and new uses for older agents. Drugs. 2013 Mar;73(3):249-62. doi: 10.1007/s40265-013-0019-1. Review. PubMed PMID: 23404093.
4: Duffy RA, Morgan C, Naylor R, Higgins GA, Varty GB, Lachowicz JE, Parker EM. Rolapitant (SCH 619734): a potent, selective and orally active neurokinin NK1 receptor antagonist with centrally-mediated antiemetic effects in ferrets. Pharmacol Biochem Behav. 2012 Jul;102(1):95-100. doi: 10.1016/j.pbb.2012.03.021. Epub 2012 Mar 31. PubMed PMID: 22497992.
5: Gan TJ, Gu J, Singla N, Chung F, Pearman MH, Bergese SD, Habib AS, Candiotti KA, Mo Y, Huyck S, Creed MR, Cantillon M; Rolapitant Investigation Group. Rolapitant for the prevention of postoperative nausea and vomiting: a prospective, double-blinded, placebo-controlled randomized trial. Anesth Analg. 2011 Apr;112(4):804-12. doi: 10.1213/ANE.0b013e31820886c3. Epub 2011 Mar 8. PubMed PMID: 21385988.