Rolapitant free base
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MedKoo CAT#: 206785

CAS#: 552292-08-7 (free base)

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).


Price and Availability

Size
Price

10mg
USD 190
100mg
USD 950
1g
USD 3450
Size
Price

25mg
USD 350
200mg
USD 1650
2g
USD 5450
Size
Price

50mg
USD 550
500mg
USD 2650
5g
USD 9750

Rolapitant free base, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received. Delivery time: overnight (USA/Canada); 3-5 days (worldwide). Shipping fee: from $30.00 (USA); from $45.00 (Canada); from $70.00 (international).


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 206785
Name: Rolapitant free base
CAS#: 552292-08-7 (free base)
Chemical Formula: C25H26F6N2O2
Exact Mass: 500.1898
Molecular Weight: 500.4854
Elemental Analysis: C, 60.00; H, 5.24; F, 22.78; N, 5.60; O, 6.39


Related CAS #: 914462-92-3 (HCl)   552292-08-7 (free base)    

Synonym: Rolapitant free base; SCH619734 SCH-619734; SCH 619734; 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

InChi Key: FIVSJYGQAIEMOC-ZGNKEGEESA-N

InChi Code: InChI=1S/C25H26F6N2O2/c1-16(17-11-19(24(26,27)28)13-20(12-17)25(29,30)31)35-15-23(18-5-3-2-4-6-18)10-9-22(14-32-23)8-7-21(34)33-22/h2-6,11-13,16,32H,7-10,14-15H2,1H3,(H,33,34)/t16-,22-,23-/m1/s1

SMILES Code: O=C1N[C@]2(CN[C@@](C3=CC=CC=C3)(CO[C@@H](C4=CC(C(F)(F)F)=CC(C(F)(F)F)=C4)C)CC2)CC1


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped 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 Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


References

1: Rapoport B, Schwartzberg L, Chasen M, Powers D, Arora S, Navari R, Schnadig I. Efficacy and safety of rolapitant for prevention of chemotherapy-induced nausea and vomiting over multiple cycles of moderately or highly emetogenic chemotherapy. Eur J Cancer. 2016 Apr;57:23-30. doi: 10.1016/j.ejca.2015.12.023. PubMed PMID: 26851398.

2: Rapoport B, Chua D, Poma A, Arora S, Wang Y, Fein LE. Study of rolapitant, a novel, long-acting, NK-1 receptor antagonist, for the prevention of chemotherapy-induced nausea and vomiting (CINV) due to highly emetogenic chemotherapy (HEC). Support Care Cancer. 2015 Nov;23(11):3281-8. doi: 10.1007/s00520-015-2738-1. PubMed PMID: 25940030.

3: Schwartzberg LS, Modiano MR, Rapoport BL, Chasen MR, Gridelli C, Urban L, Poma A, Arora S, Navari RM, Schnadig ID. Safety and efficacy of rolapitant for prevention of chemotherapy-induced nausea and vomiting after administration of moderately emetogenic chemotherapy or anthracycline and cyclophosphamide regimens in patients with cancer: a randomised, active-controlled, double-blind, phase 3 trial. Lancet Oncol. 2015 Sep;16(9):1071-8. doi: 10.1016/S1470-2045(15)00034-0. PubMed PMID: 26272768.

4: Rapoport BL, Chasen MR, Gridelli C, Urban L, Modiano MR, Schnadig ID, Poma A, Arora S, Kansra V, Schwartzberg LS, Navari RM. Safety and efficacy of rolapitant for prevention of chemotherapy-induced nausea and vomiting after administration of cisplatin-based highly emetogenic chemotherapy in patients with cancer: two randomised, active-controlled, double-blind, phase 3 trials. Lancet Oncol. 2015 Sep;16(9):1079-89. doi: 10.1016/S1470-2045(15)00035-2. PubMed PMID: 26272769.

5: Hesketh PJ, Schnadig ID, Schwartzberg LS, Modiano MR, Jordan K, Arora S, Powers D, Aapro M. Efficacy of the neurokinin-1 receptor antagonist rolapitant in preventing nausea and vomiting in patients receiving carboplatin-based chemotherapy. Cancer. 2016 Aug 1;122(15):2418-25. doi: 10.1002/cncr.30054. PubMed PMID: 27176138; PubMed Central PMCID: PMC5084806.

6: Chasen M, Urban L, Schnadig I, Rapoport B, Powers D, Arora S, Navari R, Schwartzberg L, Gridelli C. Rolapitant improves quality of life of patients receiving highly or moderately emetogenic chemotherapy. Support Care Cancer. 2017 Jan;25(1):85-92. PubMed PMID: 27557833; PubMed Central PMCID: PMC5127871.

7: Syed YY. Rolapitant: first global approval. Drugs. 2015 Nov;75(16):1941-5. doi: 10.1007/s40265-015-0485-8. Review. PubMed PMID: 26467681.

8: Abdel-Rahman O, Fouad M. Rolapitant: a pooled analysis of its efficacy and safety in the prophylaxis of chemotherapy-induced nausea and vomiting. Future Oncol. 2016 Mar;12(6):871-9. doi: 10.2217/fon.15.360. Review. PubMed PMID: 26806790.

9: 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. PubMed PMID: 22497992.

10: Chasen MR, Rapoport BL. Rolapitant for the treatment of chemotherapy-induced nausea and vomiting: a review of the clinical evidence. Future Oncol. 2016 Mar;12(6):763-78. doi: 10.2217/fon.16.11. Review. PubMed PMID: 26842387.

11: Navari R. Rolapitant hydrochloride: prophylactic treatment for chemotherapy-induced nausea and vomiting. Drugs Today (Barc). 2016 Aug;52(8):431-438. Review. PubMed PMID: 27722211.

12: 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. PubMed PMID: 21385988.

13: Rojas C, Slusher BS. Mechanisms and latest clinical studies of new NK1 receptor antagonists for chemotherapy-induced nausea and vomiting: Rolapitant and NEPA (netupitant/palonosetron). Cancer Treat Rev. 2015 Dec;41(10):904-13. doi: 10.1016/j.ctrv.2015.09.005. Review. PubMed PMID: 26442475.

14: Rapoport B, van Eeden R, Smit T. Rolapitant for the prevention of delayed nausea and vomiting over initial and repeat courses of emetogenic chemotherapy. Expert Rev Clin Pharmacol. 2017 Jan;10(1):17-29. doi: 10.1080/17512433.2017.1266251. PubMed PMID: 27894202.

15: Navari RM. Rolapitant for the treatment of chemotherapy-induced nausea and vomiting. Expert Rev Anticancer Ther. 2015;15(10):1127-33. doi: 10.1586/14737140.2015.1088787. PubMed PMID: 26366937.

16: Rolapitant (Varubi) for prevention and delayed chemotherapy-induced nausea and vomiting. Med Lett Drugs Ther. 2016 Feb 1;58(1487):17-8. Review. PubMed PMID: 26812124.

17: Traynor K. Rolapitant approved for chemotherapy-induced nausea and vomiting. Am J Health Syst Pharm. 2015 Nov 1;72(21):1838. doi: 10.2146/news150071. PubMed PMID: 26490812.

18: Olver I. Role of rolapitant in chemotherapy-induced emesis. Lancet Oncol. 2015 Sep;16(9):1006-7. doi: 10.1016/S1470-2045(15)00096-0. PubMed PMID: 26272772.

19: Romero D. Chemotherapy: Rolapitant—a new and safer antiemetic agent. Nat Rev Clin Oncol. 2015 Oct;12(10):562. doi: 10.1038/nrclinonc.2015.144. PubMed PMID: 26305036.

20: Bošnjak SM, Gralla RJ, Schwartzberg L. Prevention of chemotherapy-induced nausea: the role of neurokinin-1 (NK(1)) receptor antagonists. Support Care Cancer. 2017 Jan 20. doi: 10.1007/s00520-017-3585-z. [Epub ahead of print] PubMed PMID: 28108820.