Rolapitant HCl | SCH619734 | CAS#914462-92-3 | 552292-08-7 | NK1 receptor antagonist

Rolapitant HCl
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 202470

CAS#: 858102-79-1 (HCl)

Description: Rolapitant, also known as SCH-619734, is an orally bioavailable, centrally-acting, selective, neurokinin 1 receptor (NK1-receptor) antagonist with potential antiemetic activity.

Chemical Structure

Rolapitant HCl

CAS# 858102-79-1 (HCl)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 202470
Name: Rolapitant HCl
CAS#: 858102-79-1 (HCl)
Chemical Formula: C25H27ClF6N2O2
Exact Mass: 0.00
Molecular Weight: 536.940
Elemental Analysis: C, 55.92; H, 5.07; Cl, 6.60; F, 21.23; N, 5.22; O, 5.96

Price and Availability

Size	Price	Availability
10mg	USD 190
25mg	USD 350
50mg	USD 550
100mg	USD 950
200mg	USD 1650
500mg	USD 2950	2 Weeks
1g	USD 3850	2 Weeks
2g	USD 6450	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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

Synonym: SCH619734 SCH-619734; SCH 619734; Rolapitant HCl; Rolapitant hydrochloride, 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.

InChi Key: VEWAWEMXVUFANV-PVBCUUEWSA-N

InChi Code: InChI=1S/C25H26F6N2O2.ClH/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);1H/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.[H]Cl

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: To be determined

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).

HS Tariff Code: 2934.99.9001

More Info: 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. (last updated: 10/28/2016).

Product Data:

Product Data

Instruction:

View handling instruction

Biological target:	Rolapitant has a high affinity for the human NK1 receptor of 0.66 nM and high selectivity over the human NK2 and NK3 subtypes of >1000-fold, as well as preferential affinity for human, guinea pig, gerbil and monkey NK1 receptors over rat, mouse and rabbit.
In vitro activity:	Rolapitant was loaded into various lipid nanovesicles (LNVs), and the LNVs were evaluated for particle size, zeta potential, entrapment efficiency (EE%), storage stability and surface morphology. The selected ethosomal and transethosomal vesicles displayed a particle size less than 400 nm, a positive charge, and EE% exceeding 90% for rolapitant, with a sustained release pattern over 15 days. The developed rolapitant-LNVs were able to reach the metastatic organs of lung cancer. Reference: Eur J Pharm Sci. 2022 Apr 1;171:106119. https://pubmed.ncbi.nlm.nih.gov/34998905/
In vivo activity:	This study utilized a male Wistar rat model of regular alcohol intake and subsequent withdrawl episodes. Upon intraperitoneal administration, rolapitant rapidly penetrated into specific rat brain regions implicated in the control of anxiety and reward. Rolapitant did not affect basal voluntary alcohol intake, but significantly suppressed anxiety-like behaviour and alcohol consumption following withdrawal episodes. Reference: FEBS J. 2022 Aug;289(16):5021-5029. https://pubmed.ncbi.nlm.nih.gov/35175687/

Preparing Stock Solutions

The following data is based on the product molecular weight 536.94 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:	1. Kabil MF, Nasr M, Ibrahim IT, Hassan YA, El-Sherbiny IM. New repurposed rolapitant in nanovesicular systems for lung cancer treatment: Development, in-vitro assessment and in-vivo biodistribution study. Eur J Pharm Sci. 2022 Apr 1;171:106119. doi: 10.1016/j.ejps.2022.106119. Epub 2022 Jan 6. PMID: 34998905. 2. Kokhan VS, Anokhin PK, Abaimov DA, Shamakina IY, Soldatov VO, Deykin AV. Neurokinin-1 receptor antagonist rolapitant suppresses anxiety and alcohol intake produced by repeated withdrawal episodes. FEBS J. 2022 Aug;289(16):5021-5029. doi: 10.1111/febs.16400. Epub 2022 Feb 27. PMID: 35175687. 3. 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. PMID: 22497992.
In vitro protocol:	1. Kabil MF, Nasr M, Ibrahim IT, Hassan YA, El-Sherbiny IM. New repurposed rolapitant in nanovesicular systems for lung cancer treatment: Development, in-vitro assessment and in-vivo biodistribution study. Eur J Pharm Sci. 2022 Apr 1;171:106119. doi: 10.1016/j.ejps.2022.106119. Epub 2022 Jan 6. PMID: 34998905.
In vivo protocol:	1. Kokhan VS, Anokhin PK, Abaimov DA, Shamakina IY, Soldatov VO, Deykin AV. Neurokinin-1 receptor antagonist rolapitant suppresses anxiety and alcohol intake produced by repeated withdrawal episodes. FEBS J. 2022 Aug;289(16):5021-5029. doi: 10.1111/febs.16400. Epub 2022 Feb 27. PMID: 35175687. 2. 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. PMID: 22497992.

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1: LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012-. Available from http://www.ncbi.nlm.nih.gov/books/NBK548209/ PubMed PMID: 31643534.

2: Heo YA, Deeks ED. Rolapitant: A Review in Chemotherapy-Induced Nausea and Vomiting. Drugs. 2017 Oct;77(15):1687-1694. doi: 10.1007/s40265-017-0816-z. Review. PubMed PMID: 28929404.

3: Rapoport BL, Aapro M, Chasen MR, Jordan K, Navari RM, Schnadig I, Schwartzberg L. Recent developments in the clinical pharmacology of rolapitant: subanalyses in specific populations. Drug Des Devel Ther. 2017 Sep 5;11:2621-2629. doi: 10.2147/DDDT.S133943. eCollection 2017. Review. PubMed PMID: 28919712; PubMed Central PMCID: PMC5592904.

4: Rapoport BL. Rolapitant: An NK-1 Receptor Antagonist for the Prevention of Chemotherapy- Induced Nausea and Vomiting. Rev Recent Clin Trials. 2017;12(3):193-201. doi: 10.2174/1574887112666170406104854. Review. PubMed PMID: 28393710.

5: Rashad N, Abdel-Rahman O. Differential clinical pharmacology of rolapitant in delayed chemotherapy-induced nausea and vomiting (CINV). Drug Des Devel Ther. 2017 Mar 24;11:947-954. doi: 10.2147/DDDT.S108872. eCollection 2017. Review. PubMed PMID: 28392676; PubMed Central PMCID: PMC5373840.

6: Rapoport BL. Differential pharmacology and clinical utility of rolapitant in chemotherapy-induced nausea and vomiting. Cancer Manag Res. 2017 Feb 22;9:41-50. doi: 10.2147/CMAR.S97543. eCollection 2017. Review. PubMed PMID: 28260945; PubMed Central PMCID: PMC5327850.

7: 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. Epub 2016 Dec 15. Review. PubMed PMID: 27894202.

8: 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.

9: 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. Epub 2016 Feb 4. Review. PubMed PMID: 26842387.

10: 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.

11: 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. Epub 2016 Jan 25. Review. PubMed PMID: 26806790.

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

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. Epub 2015 Sep 26. Review. PubMed PMID: 26442475.

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