Ozanimod
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MedKoo CAT#: 206177

CAS#: 1306760-87-1

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

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Ozanimod
CAS# 1306760-87-1

Theoretical Analysis

MedKoo Cat#: 206177
Name: Ozanimod
CAS#: 1306760-87-1
Chemical Formula: C23H24N4O3
Exact Mass: 404.18484
Molecular Weight: 404.46
Elemental Analysis: C, 68.30; H, 5.98; N, 13.85; O, 11.87

Price and Availability

Size Price Availability Quantity
10.0mg USD 150.0 Ready to ship
25.0mg USD 250.0 Ready to ship
50.0mg USD 450.0 Ready to ship
100.0mg USD 750.0 Ready to ship
200.0mg USD 1250.0 Ready to ship
500.0mg USD 2650.0 Ready to ship
1.0g USD 3750.0 Ready to ship
2.0g USD 6250.0 Ready to ship
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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

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 49.4

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.

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. 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. Martinborough, Esther; Boehm, Marcus F.; Yeager, Adam Richard; Tamiya, Junko; Huang, Liming; Brahmachary, Enugurthi; Moorjani, Manisha; Timony, Gregg Alan; Brooks, Jennifer L.; Peach, Robert; et al. Selective sphingosine 1 phosphate receptor modulators and methods of chiral synthesis of aryl(indanyl)​oxadiazoles and their use in the treatment of S1P1-​associated diseases. PCT Int. Appl. (2011), WO 2011060392 A1 20110519.

Ozanimod

10.0mg / USD 150.0


Additional Information