MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 206785 | Name: Rolapitant free base
Featured New

Description:

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

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

Theoretical Analysis

MedKoo Cat#: 206785

Name: Rolapitant free base

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

Chemical Formula: C25H26F6N2O2

Exact Mass: 500.1898

Molecular Weight: 500.49

Elemental Analysis: C, 60.00; H, 5.24; F, 22.78; N, 5.60; O, 6.39

Price and Availability

Size Price Availability Quantity
25mg USD 150.00 2 Weeks
100mg USD 750.00 2 Weeks
500mg USD 1,250.00 2 Weeks
1g USD 2,250.00 2 Weeks
2g USD 4,250.00 2 Weeks
5g USD 6,950.00 2 Weeks
Show More
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
858102-79-1 (HCl) 552292-08-7 (free base) 914462-92-3 (HCl hydrate)
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
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
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 500.49 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.

Recalculate based on batch purity %
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.
1: Salama EA, Elgammal Y, Utturkar SM, Lanman NA, Hazbun TR, Seleem MN. Overcoming amphotericin B resistance in Candida auris using the antiemetic drug rolapitant. Antimicrob Agents Chemother. 2024 Oct 10:e0055624. doi: 10.1128/aac.00556-24. Epub ahead of print. PMID: 39387581. 2: Kim JY, Dalton JC, Cort N, Herndon JE 2nd, Affronti ML, Peters KB, Jones CA, Johnson MO. Comparing Knowledge and Perceptions of Palliative Care Among Neuro- Oncology Patients, Caregivers, and Providers to a Representative U.S. Sample. Am J Hosp Palliat Care. 2024 Sep 5:10499091241280610. doi: 10.1177/10499091241280610. Epub ahead of print. PMID: 39236147. 3: Du T, Gu Q, Zhang Y, Gan Y, Liang R, Yang W, Lu Y, Xu C, Wu J, Ma R, Cao H, Jiang J, Wang J, Feng J. Rolapitant treats lung cancer by targeting deubiquitinase OTUD3. Cell Commun Signal. 2024 Mar 27;22(1):195. doi: 10.1186/s12964-024-01519-8. PMID: 38539203; PMCID: PMC10967203. 4: LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012–. Rolapitant. 2024 Mar 1. PMID: 31643534. 5: Soltani A, Hashemy SI. Homology modeling, virtual screening, molecular docking, and ADME approaches to identify a potent agent targeting NK2R protein. Biotechnol Appl Biochem. 2024 Feb;71(1):213-222. doi: 10.1002/bab.2533. Epub 2023 Oct 30. PMID: 37904319. 6: Deb S, Hopefl R. Simulation of drug-drug interactions between breast cancer chemotherapeutic agents and antiemetic drugs. Daru. 2023 Dec;31(2):95-105. doi: 10.1007/s40199-023-00463-1. Epub 2023 May 24. PMID: 37223851; PMCID: PMC10624783. 7: Solanki S, Yadav Y, Dutta S, Kaul NV, Belodu R, Kumar HR. Morphological and Skeletal Abnormalities Induced by Rolapitant: An Antiemetic Agent. Cureus. 2022 Aug 17;14(8):e28097. doi: 10.7759/cureus.28097. PMID: 36127969; PMCID: PMC9479433. 8: Detroja TS, Samson AO. Virtual Screening for FDA-Approved Drugs That Selectively Inhibit Arginase Type 1 and 2. Molecules. 2022 Aug 12;27(16):5134. doi: 10.3390/molecules27165134. PMID: 36014374; PMCID: PMC9416497. 9: Kabil MF, Mahmoud MY, Bakr AF, Zaafar D, El-Sherbiny IM. Switching indication of PEGylated lipid nanocapsules-loaded with rolapitant and deferasirox against breast cancer: Enhanced in-vitro and in-vivo cytotoxicity. Life Sci. 2022 Sep 15;305:120731. doi: 10.1016/j.lfs.2022.120731. Epub 2022 Jun 24. PMID: 35753435. 10: 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. 11: 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. 12: Piechotta V, Adams A, Haque M, Scheckel B, Kreuzberger N, Monsef I, Jordan K, Kuhr K, Skoetz N. Antiemetics for adults for prevention of nausea and vomiting caused by moderately or highly emetogenic chemotherapy: a network meta- analysis. Cochrane Database Syst Rev. 2021 Nov 16;11(11):CD012775. doi: 10.1002/14651858.CD012775.pub2. PMID: 34784425; PMCID: PMC8594936. 13: Tran K, Loshak H. Palonosetron for Patients Undergoing High or Moderate Emetogenic Chemotherapy [Internet]. Ottawa (ON): Canadian Agency for Drugs and Technologies in Health; 2021 Jul. PMID: 36191121. 14: Hosseini M, Chen W, Xiao D, Wang C. Computational molecular docking and virtual screening revealed promising SARS-CoV-2 drugs. Precis Clin Med. 2021 Jan 18;4(1):1-16. doi: 10.1093/pcmedi/pbab001. PMID: 33842834; PMCID: PMC7928605. 15: Kokhan VS, Mariasina S, Pikalov VA, Abaimov DA, Somasundaram SG, Kirkland CE, Aliev G. Neurokinin-1 Receptor Antagonist Reverses Functional CNS Alteration Caused by Combined γ-rays and Carbon Nuclei Irradiation. CNS Neurol Disord Drug Targets. 2022;21(3):278-289. doi: 10.2174/1871527320666210122092330. PMID: 33480350. 16: Tan HS, Dewinter G, Habib AS. The next generation of antiemetics for the management of postoperative nausea and vomiting. Best Pract Res Clin Anaesthesiol. 2020 Dec;34(4):759-769. doi: 10.1016/j.bpa.2020.11.004. Epub 2020 Nov 14. PMID: 33288125. 17: Gupta A, Zhou HX. Profiling SARS-CoV-2 Main Protease (MPRO) Binding to Repurposed Drugs Using Molecular Dynamics Simulations in Classical and Neural Network-Trained Force Fields. ACS Comb Sci. 2020 Dec 14;22(12):826-832. doi: 10.1021/acscombsci.0c00140. Epub 2020 Oct 29. PMID: 33119257; PMCID: PMC7605330. 18: Weibel S, Rücker G, Eberhart LH, Pace NL, Hartl HM, Jordan OL, Mayer D, Riemer M, Schaefer MS, Raj D, Backhaus I, Helf A, Schlesinger T, Kienbaum P, Kranke P. Drugs for preventing postoperative nausea and vomiting in adults after general anaesthesia: a network meta-analysis. Cochrane Database Syst Rev. 2020 Oct 19;10(10):CD012859. doi: 10.1002/14651858.CD012859.pub2. PMID: 33075160; PMCID: PMC8094506. 19: Navari RM. The safety of rolapitant for the treatment of nausea and vomiting associated with chemotherapy. Expert Opin Drug Saf. 2019 Dec;18(12):1127-1132. doi: 10.1080/14740338.2019.1682547. Epub 2019 Oct 22. PMID: 31622113. 20: Wang X, Wang J, Zhang ZY, Kansra V. Population Pharmacokinetics of Rolapitant in Patients With Chemotherapy-Induced Nausea and Vomiting. Clin Pharmacol Drug Dev. 2019 Oct;8(7):850-860. doi: 10.1002/cpdd.733. Epub 2019 Aug 16. PMID: 31418538.