Ozanimod | RPC1063 | CAS#1306760-87-1 | Immunomodulator

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

MedKoo CAT#: 206177

CAS#: 1306760-87-1 (free base)

Description: Ozanimod, also known as RPC1063, is a selective sphingosine 1 phosphate receptor modulators and methods which may be useful in the treatment of S1P1-associated diseases.

Chemical Structure

Ozanimod

CAS# 1306760-87-1 (free base)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 206177
Name: Ozanimod
CAS#: 1306760-87-1 (free base)
Chemical Formula: C23H24N4O3
Exact Mass: 404.18
Molecular Weight: 404.460
Elemental Analysis: C, 68.30; H, 5.98; N, 13.85; O, 11.87

Price and Availability

Size	Price	Availability
10mg	USD 150	Ready to ship
25mg	USD 250	Ready to ship
50mg	USD 450	Ready to ship
100mg	USD 750	Ready to ship
200mg	USD 1250	Ready to ship
500mg	USD 2650	Ready to ship
1g	USD 3750	Ready to ship
2g	USD 6250	Ready to ship
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 #: 1306760-87-1 (free base) 1618636-37-5 (HCl)

Synonym: RPC1063; RPC-1063; RPC 1063; Ozanimod

IUPAC/Chemical Name: (S)-5-(3-(1-((2-hydroxyethyl)amino)-2,3-dihydro-1H-inden-4-yl)-1,2,4-oxadiazol-5-yl)-2-isopropoxybenzonitrile

InChi Key: XRVDGNKRPOAQTN-FQEVSTJZSA-N

InChi Code: InChI=1S/C23H24N4O3/c1-14(2)29-21-9-6-15(12-16(21)13-24)23-26-22(27-30-23)19-5-3-4-18-17(19)7-8-20(18)25-10-11-28/h3-6,9,12,14,20,25,28H,7-8,10-11H2,1-2H3/t20-/m0/s1

SMILES Code: N#CC1=CC(C2=NC(C3=CC=CC4=C3CC[C@@H]4NCCO)=NO2)=CC=C1OC(C)C

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, not in water

Shelf Life: >5 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

Certificate of Analysis:

View CoA: current batch, Lot#C9R04B19

QC Data:

View QC data: current batch, Lot#C9R04B19

Safety Data Sheet (SDS):

View Safety Data Sheet (SDS)

Instruction:

View handling instruction

Biological target:	Ozanimod (RPC-1063) is a potent and selective S1P1 and S1P5 receptor agonist with EC50s of 410 pM and 11 nM in [35S]-GTPγS binding, respectively
In vitro activity:	It was hypothesized that ozanimod, a selective S1PR type 1 ligand, will attenuate VSM synthetic phenotypic expression and autophagic flux in primary human brain VSM cells following acute hypoxia plus glucose deprivation (HGD; in vitro ischemic-like injury) exposure. Cells were treated with ozanimod and exposed to normoxia or HGD. Crystal violet staining, standard immunoblotting, and immunocytochemical labeling techniques assessed cellular morphology, vacuolization, phenotype, and autophagic state. It was observed that HGD temporally decreased VSM cell viability and concomitantly increased vacuolization, both of which ozanimod reversed. HGD induced a simultaneous elevation and reduction in levels of pro- and anti-autophagic proteins respectfully, and ozanimod attenuated this response. Protein levels of VSM phenotypic biomarkers, smoothelin and SM22, were decreased following HGD. Furthermore, it was observed that an HGD-induced epithelioid and synthetic morphological appearance accompanied by disorganized cytoskeletal filaments which was rescued by ozanimod. Thus, it is concluded that ozanimod, a selective S1PR1 ligand, protects against acute HGD-induced phenotypic switching and promotes cell survival, in part, by attenuating HGDinduced autophagic flux thus improving vascular patency in response to acute ischemia-like injury. Am J Physiol Cell Physiol. 2021 Mar 31. https://pubmed.ncbi.nlm.nih.gov/33788630/
In vivo activity:	The purpose of this study was to assess RPC1063 for its therapeutic utility in autoimmune diseases. The oral pharmacokinetic (PK) parameters and pharmacodynamic effects were established in rodents, and its activity in three models of autoimmune disease (experimental autoimmune encephalitis, 2,4,6‐trinitrobenzenesulfonic acid colitis and CD4+CD45RBhi T cell adoptive transfer colitis) was assessed. RPC1063 demonstrated potent agonist activity of S1P1 receptors. The EC50 values were subnanomolar for S1P1 receptors whether measuring inhibition of cAMP generation (160 ± 60 pM) or [35S]‐ GTPγS binding (410 ± 160 pM; Figure 2A and Table 1). RPC1063 also demonstrated agonist activity at the S1P5 receptor [11 ± 4.3 nM and 83% Emax (percentage of maximum stimulation)]. This represents a 27‐fold selectivity for S1P1 over S1P5 receptors. RPC1063 was specific for S1P1 and S1P5 receptors, induced S1P1 receptor internalization and induced a reversible reduction in circulating B and CCR7+ T lymphocytes in vivo. RPC1063 showed high oral bioavailability and volume of distribution, and a circulatory half‐life that supports once daily dosing. Oral RPC1063 reduced inflammation and disease parameters in all three autoimmune disease models. Br J Pharmacol. 2016 Jun; 173(11): 1778–1792. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4867749/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	20.0	49.40

Preparing Stock Solutions

The following data is based on the product molecular weight 404.46 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. Taylor Meadows KR, Steinberg MW, Clemons B, Stokes ME, Opiteck GJ, Peach R, Scott FL. Ozanimod (RPC1063), a selective S1PR1 and S1PR5 modulator, reduces chronic inflammation and alleviates kidney pathology in murine systemic lupus erythematosus. PLoS One. 2018 Apr 2;13(4):e0193236. doi: 10.1371/journal.pone.0193236. PMID: 29608575; PMCID: PMC5880347. 2. Wendt TS, Li YJ, Gonzales RJ. Ozanimod, an S1PR1 ligand, attenuates hypoxia plus glucose deprivation induced autophagic flux and phenotypic switching in human brain VSM cells. Am J Physiol Cell Physiol. 2021 Mar 31. doi: 10.1152/ajpcell.00044.2021. Epub ahead of print. PMID: 33788630. 3. 1. Scott FL, Clemons B, Brooks J, Brahmachary E, Powell R, Dedman H, Desale HG, Timony GA, Martinborough E, Rosen H, Roberts E, Boehm MF, Peach RJ. Ozanimod (RPC1063) is a potent sphingosine-1-phosphate receptor-1 (S1P1 ) and receptor-5 (S1P5) agonist with autoimmune disease-modifying activity. Br J Pharmacol. 2016 Jun;173(11):1778-92. doi: 10.1111/bph.13476. Epub 2016 Apr 28. PMID: 26990079; PMCID: PMC4867749. 4. Taylor Meadows KR, Steinberg MW, Clemons B, Stokes ME, Opiteck GJ, Peach R, Scott FL. Ozanimod (RPC1063), a selective S1PR1 and S1PR5 modulator, reduces chronic inflammation and alleviates kidney pathology in murine systemic lupus erythematosus. PLoS One. 2018 Apr 2;13(4):e0193236. doi: 10.1371/journal.pone.0193236. PMID: 29608575; PMCID: PMC5880347.
In vitro protocol:	1. Taylor Meadows KR, Steinberg MW, Clemons B, Stokes ME, Opiteck GJ, Peach R, Scott FL. Ozanimod (RPC1063), a selective S1PR1 and S1PR5 modulator, reduces chronic inflammation and alleviates kidney pathology in murine systemic lupus erythematosus. PLoS One. 2018 Apr 2;13(4):e0193236. doi: 10.1371/journal.pone.0193236. PMID: 29608575; PMCID: PMC5880347. 2. Wendt TS, Li YJ, Gonzales RJ. Ozanimod, an S1PR1 ligand, attenuates hypoxia plus glucose deprivation induced autophagic flux and phenotypic switching in human brain VSM cells. Am J Physiol Cell Physiol. 2021 Mar 31. doi: 10.1152/ajpcell.00044.2021. Epub ahead of print. PMID: 33788630.
In vivo protocol:	1. Scott FL, Clemons B, Brooks J, Brahmachary E, Powell R, Dedman H, Desale HG, Timony GA, Martinborough E, Rosen H, Roberts E, Boehm MF, Peach RJ. Ozanimod (RPC1063) is a potent sphingosine-1-phosphate receptor-1 (S1P1 ) and receptor-5 (S1P5) agonist with autoimmune disease-modifying activity. Br J Pharmacol. 2016 Jun;173(11):1778-92. doi: 10.1111/bph.13476. Epub 2016 Apr 28. PMID: 26990079; PMCID: PMC4867749. 2. Taylor Meadows KR, Steinberg MW, Clemons B, Stokes ME, Opiteck GJ, Peach R, Scott FL. Ozanimod (RPC1063), a selective S1PR1 and S1PR5 modulator, reduces chronic inflammation and alleviates kidney pathology in murine systemic lupus erythematosus. PLoS One. 2018 Apr 2;13(4):e0193236. doi: 10.1371/journal.pone.0193236. PMID: 29608575; PMCID: PMC5880347.

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1: Selkirk JV, Yan YG, Ching N, Paget K, Hargreaves R. In vitro assessment of the binding and functional reponses of ozanimod and its plasma metabolites across human sphingosine 1-phosphate receptors. Eur J Pharmacol. 2022 Dec 2:175442. doi: 10.1016/j.ejphar.2022.175442. Epub ahead of print. PMID: 36470447.

2: Corrigendum for Long-term safety and efficacy of ozanimod in relapsing multiple sclerosis: Up to 5 years of follow-up in the DAYBREAK open-label extension trial. Mult Scler. 2022 Nov 30:13524585221138507. doi: 10.1177/13524585221138507. Epub ahead of print. Erratum for: Mult Scler. 2022 Oct;28(12):1944-1962. PMID: 36448361.

3: Li X, Zhang H, Zheng W, Sun J, Wang L, He Z. Ozanimod-Dependent Activation of SIRT3/NF-κB/AIM2 Pathway Attenuates Secondary Injury After Intracerebral Hemorrhage. Mol Neurobiol. 2022 Nov 22. doi: 10.1007/s12035-022-03137-2. Epub ahead of print. PMID: 36417102.

4: Feagan BG, Schreiber S, Afzali A, Rieder F, Hyams J, Kollengode K, Pearlman J, Son V, Marta C, Wolf DC, D'Haens GG. Ozanimod as a novel oral small molecule therapy for the treatment of Crohn's disease: The YELLOWSTONE clinical trial program. Contemp Clin Trials. 2022 Nov;122:106958. doi: 10.1016/j.cct.2022.106958. Epub 2022 Oct 5. PMID: 36208720.

5: Becher N, Swaminath A, Sultan K. A Literature Review of Ozanimod Therapy in Inflammatory Bowel Disease: From Concept to Practical Application. Ther Clin Risk Manag. 2022 Sep 8;18:913-927. doi: 10.2147/TCRM.S336139. PMID: 36106049; PMCID: PMC9467694.

6: Paik J. Correction to: Ozanimod: A Review in Ulcerative Colitis. Drugs. 2022 Aug;82(12):1315. doi: 10.1007/s40265-022-01772-6. Erratum for: Drugs. 2022 Aug;82(12):1303-1313. PMID: 36050602; PMCID: PMC9499879.

7: Paik J. Ozanimod: A Review in Ulcerative Colitis. Drugs. 2022 Aug;82(12):1303-1313. doi: 10.1007/s40265-022-01762-8. Epub 2022 Aug 22. Erratum in: Drugs. 2022 Sep 1;: PMID: 35994200; PMCID: PMC9499884.

8: Cohen NA, Dalal SR, Choi D, Rubin DT. Ozanimod Maintenance Therapy After Cyclosporine Induction in Acute Severe Ulcerative Colitis. ACG Case Rep J. 2022 Jul 21;9(7):e00832. doi: 10.14309/crj.0000000000000832. PMID: 35919406; PMCID: PMC9302285.

9: Antonelli EK, Del Sordo R, Morelli O, Villanacci V, Bassotti G. Update on ozanimod for ulcerative colitis. Drugs Today (Barc). 2022 Jul;58(7):351-367. doi: 10.1358/dot.2022.58.7.3408818. PMID: 35851870.

10: Ziemssen T, Richter S, Mäurer M, Buttmann M, Kreusel B, Poehler AM, Lampl M, Linker RA. OzEAN Study to Collect Real-World Evidence of Persistent Use, Effectiveness, and Safety of Ozanimod Over 5 Years in Patients With Relapsing- Remitting Multiple Sclerosis in Germany. Front Neurol. 2022 Jun 27;13:913616. doi: 10.3389/fneur.2022.913616. PMID: 35832177; PMCID: PMC9271678.

11: Selkirk JV, Bortolato A, Yan YG, Ching N, Hargreaves R. Competitive Binding of Ozanimod and Other Sphingosine 1-Phosphate Receptor Modulators at Receptor Subtypes 1 and 5. Front Pharmacol. 2022 Jun 17;13:892097. doi: 10.3389/fphar.2022.892097. PMID: 35784713; PMCID: PMC9247443.

12: Wang F, Zhang X, Liu Y, Li Z, Wei R, Zhang Y, Zhang R, Khan S, Yong VW, Xue M. Neuroprotection by Ozanimod Following Intracerebral Hemorrhage in Mice. Front Mol Neurosci. 2022 Jun 15;15:927150. doi: 10.3389/fnmol.2022.927150. PMID: 35782389; PMCID: PMC9242004.

13: Cree BA, Selmaj KW, Steinman L, Comi G, Bar-Or A, Arnold DL, Hartung HP, Montalbán X, Havrdová EK, Sheffield JK, Minton N, Cheng CY, Silva D, Kappos L, Cohen JA. Long-term safety and efficacy of ozanimod in relapsing multiple sclerosis: Up to 5 years of follow-up in the DAYBREAK open-label extension trial. Mult Scler. 2022 Oct;28(12):1944-1962. doi: 10.1177/13524585221102584. Epub 2022 Jun 28. Erratum in: Mult Scler. 2022 Nov 30;:13524585221138507. PMID: 35765217; PMCID: PMC9493410.

14: Early Mucosal Healing at Week 10 With Ozanimod Predicts Clinical Outcomes at Week 52: Post Hoc Analysis of the Phase 3 True North Clinical Trial. Gastroenterol Hepatol (N Y). 2022 Apr;18(4 Suppl 1):11. PMID: 35610997; PMCID: PMC9122064.

15: Long-Term Use of Ozanimod in Patients With Moderately to Severely Active Ulcerative Colitis. Gastroenterol Hepatol (N Y). 2022 Apr;18(4 Suppl 1):6-7. PMID: 35610996; PMCID: PMC9122074.

16: Ozanimod Is an Efficacious Oral Therapy After 5-ASA Failure in Immunomodulator- and Biologic-Naive Patients With Ulcerative Colitis: Post Hoc Analysis From True North. Gastroenterol Hepatol (N Y). 2022 Apr;18(4 Suppl 1):4-5. PMID: 35610993; PMCID: PMC9122065.

17: Rapidity of Ozanimod-Induced Symptomatic Response and Remission in Patients With Moderately to Severely Active Ulcerative Colitis: Results From the Induction Period of True North. Gastroenterol Hepatol (N Y). 2022 Apr;18(4 Suppl 1):2-3. PMID: 35610988; PMCID: PMC9122069.

18: Long-Term Cardiac Safety of Ozanimod in a Phase 3 Clinical Program of Ulcerative Colitis and Relapsing Multiple Sclerosis. Gastroenterol Hepatol (N Y). 2022 Apr;18(4 Suppl 1):8-9. PMID: 35610987; PMCID: PMC9122073.

19: Rowan C, Ungaro R, Mehandru S, Colombel JF. An overview of ozanimod as a therapeutic option for adults with moderate-to-severe active ulcerative colitis. Expert Opin Pharmacother. 2022 Jun;23(8):893-904. doi: 10.1080/14656566.2022.2071605. Epub 2022 May 9. PMID: 35503955.

20: Aoun R, Hanauer S. A critical review of ozanimod for the treatment of adults with moderately to severely active ulcerative colitis. Expert Rev Gastroenterol Hepatol. 2022 May;16(5):411-423. doi: 10.1080/17474124.2022.2065258. PMID: 35400292.

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