S1RA
S1RA(E-52862) is a potent and selective sigma-1 receptor(1R, Ki=17 nM) antagonist, showed good selectivity against 2R (Ki > 1000 nM).
For research use only. We do not sell to patients.
Chemical Information
| Name | S1RA |
|---|---|
| Iupac Chemical Name | 4-(2-((5-Methyl-1-(naphthalen-2-yl)-1h-pyrazol-3-yl)oxy)ethyl)morpholine |
| Synonyms | E-52862; E 52862; E52862; S1RA; E-52862; E-52862; |
| Molecular Formula | C20H23N3O2 |
| Molecular Weight | 337.42 |
| Smile | CC1=CC(=NN1C1=CC2=CC=CC=C2C=C1)OCCN1CCOCC1 |
| InChiKey | DGPGXHRHNRYVDH-UHFFFAOYSA-N |
| InChi | InChI=1S/C20H23N3O2/c1-16-14-20(25-13-10-22-8-11-24-12-9-22)21-23(16)19-7-6-17-4-2-3-5-18(17)15-19/h2-7,14-15H,8-13H2,1H3 |
| CAS Number | 878141-96-9 |
| Related CAS |
Ordering Information
| Packaging | Price | Availability | Purity | Shipping Time |
|---|---|---|---|---|
| Bulk | Enquiry | Enquiry | Enquiry |
| Formulation | off-white solid |
|---|---|
| Purity | 98% |
| Storage | 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 |
| Handling | |
| Shipping Condition | Shipped under ambient temperature |
| HS Code |
| Targets | |
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| Mechanism | |
| Cell study | |
| Animal study | |
| Clinical study |
1: Paniagua N, Girón R, Goicoechea C, López-Miranda V, Vela JM, Merlos M, Martín Fontelles MI. Blockade of sigma 1 receptors alleviates sensory signs of diabetic neuropathy in rats. Eur J Pain. 2016 Jun 24. doi: 10.1002/ejp.897. [Epub ahead of print] PubMed PMID: 27341510.
2: Gris G, Portillo-Salido E, Aubel B, Darbaky Y, Deseure K, Vela JM, Merlos M, Zamanillo D. The selective sigma-1 receptor antagonist E-52862 attenuates neuropathic pain of different aetiology in rats. Sci Rep. 2016 Apr 18;6:24591. doi: 10.1038/srep24591. PubMed PMID: 27087602; PubMed Central PMCID: PMC4834548.
3: Romero L, Merlos M, Vela JM. Antinociception by Sigma-1 Receptor Antagonists: Central and Peripheral Effects. Adv Pharmacol. 2016;75:179-215. doi: 10.1016/bs.apha.2015.11.003. Epub 2016 Jan 27. PubMed PMID: 26920013.
4: Täubel J, Ferber G, Lorch U, Wang D, Sust M, Camm AJ. Single Doses up to 800 mg of E-52862 Do Not Prolong the QTc Interval--A Retrospective Validation by Pharmacokinetic-Pharmacodynamic Modelling of Electrocardiography Data Utilising the Effects of a Meal on QTc to Demonstrate ECG Assay Sensitivity. PLoS One. 2015 Aug 20;10(8):e0136369. doi: 10.1371/journal.pone.0136369. eCollection 2015. PubMed PMID: 26291080; PubMed Central PMCID: PMC4546378.
5: Vela JM, Merlos M, Almansa C. Investigational sigma-1 receptor antagonists for the treatment of pain. Expert Opin Investig Drugs. 2015;24(7):883-96. doi: 10.1517/13543784.2015.1048334. Epub 2015 Jun 3. Review. PubMed PMID: 26037209.
6: Ferber G, Wang D, Täubel J. Concentration-effect modeling based on change from baseline to assess the prolonging effect of drugs on QTc together with an estimate of the circadian time course. J Clin Pharmacol. 2014 Dec;54(12):1400-6. doi: 10.1002/jcph.347. Epub 2014 Jun 27. PubMed PMID: 24935561.
7: Gris G, Merlos M, Vela JM, Zamanillo D, Portillo-Salido E. S1RA, a selective sigma-1 receptor antagonist, inhibits inflammatory pain in the carrageenan and complete Freund's adjuvant models in mice. Behav Pharmacol. 2014 Jun;25(3):226-35. doi: 10.1097/FBP.0000000000000038. PubMed PMID: 24776490.
8: Vidal-Torres A, Fernández-Pastor B, Carceller A, Vela JM, Merlos M, Zamanillo D. Effects of the selective sigma-1 receptor antagonist S1RA on formalin-induced pain behavior and neurotransmitter release in the spinal cord in rats. J Neurochem. 2014 May;129(3):484-94. doi: 10.1111/jnc.12648. Epub 2014 Jan 29. PubMed PMID: 24384038.
9: Sánchez-Fernández C, Montilla-García Á, González-Cano R, Nieto FR, Romero L, Artacho-Cordón A, Montes R, Fernández-Pastor B, Merlos M, Baeyens JM, Entrena JM, Cobos EJ. Modulation of peripheral μ-opioid analgesia by σ1 receptors. J Pharmacol Exp Ther. 2014 Jan;348(1):32-45. doi: 10.1124/jpet.113.208272. Epub 2013 Oct 23. PubMed PMID: 24155346.
10: Vidal-Torres A, de la Puente B, Rocasalbas M, Touriño C, Bura SA, Fernández-Pastor B, Romero L, Codony X, Zamanillo D, Buschmann H, Merlos M, Baeyens JM, Maldonado R, Vela JM. Sigma-1 receptor antagonism as opioid adjuvant strategy: enhancement of opioid antinociception without increasing adverse effects. Eur J Pharmacol. 2013 Jul 5;711(1-3):63-72. doi: 10.1016/j.ejphar.2013.04.018. Epub 2013 Apr 28. PubMed PMID: 23632394.
11: Laurini E, Da Col V, Wünsch B, Pricl S. Analysis of the molecular interactions of the potent analgesic S1RA with the σ1 receptor. Bioorg Med Chem Lett. 2013 May 15;23(10):2868-71. doi: 10.1016/j.bmcl.2013.03.087. Epub 2013 Mar 30. PubMed PMID: 23582276.
12: Collina S, Gaggeri R, Marra A, Bassi A, Negrinotti S, Negri F, Rossi D. Sigma receptor modulators: a patent review. Expert Opin Ther Pat. 2013 May;23(5):597-613. doi: 10.1517/13543776.2013.769522. Epub 2013 Feb 7. Review. PubMed PMID: 23387851.
13: Nieto FR, Cendán CM, Sánchez-Fernández C, Cobos EJ, Entrena JM, Tejada MA, Zamanillo D, Vela JM, Baeyens JM. Role of sigma-1 receptors in paclitaxel-induced neuropathic pain in mice. J Pain. 2012 Nov;13(11):1107-21. doi: 10.1016/j.jpain.2012.08.006. Epub 2012 Oct 12. PubMed PMID: 23063344.
14: Wünsch B. The σ(1) receptor antagonist S1RA is a promising candidate for the treatment of neurogenic pain. J Med Chem. 2012 Oct 11;55(19):8209-10. doi: 10.1021/jm3011993. Epub 2012 Sep 5. PubMed PMID: 22951043.
15: Díaz JL, Cuberes R, Berrocal J, Contijoch M, Christmann U, Fernández A, Port A, Holenz J, Buschmann H, Laggner C, Serafini MT, Burgueño J, Zamanillo D, Merlos M, Vela JM, Almansa C. Synthesis and biological evaluation of the 1-arylpyrazole class of σ(1) receptor antagonists: identification of 4-{2-[5-methyl-1-(naphthalen-2-yl)-1H-pyrazol-3-yloxy]ethyl}morpholine (S1RA, E-52862). J Med Chem. 2012 Oct 11;55(19):8211-24. doi: 10.1021/jm3007323. Epub 2012 Jul 27. PubMed PMID: 22784008.
16: Abadias M, Escriche M, Vaqué A, Sust M, Encina G. Safety, tolerability and pharmacokinetics of single and multiple doses of a novel sigma-1 receptor antagonist in three randomized phase I studies. Br J Clin Pharmacol. 2013 Jan;75(1):103-17. doi: 10.1111/j.1365-2125.2012.04333.x. PubMed PMID: 22607269; PubMed Central PMCID: PMC3555050.
17: Romero L, Zamanillo D, Nadal X, Sánchez-Arroyos R, Rivera-Arconada I, Dordal A, Montero A, Muro A, Bura A, Segalés C, Laloya M, Hernández E, Portillo-Salido E, Escriche M, Codony X, Encina G, Burgueño J, Merlos M, Baeyens JM, Giraldo J, López-García JA, Maldonado R, Plata-Salamán CR, Vela JM. Pharmacological properties of S1RA, a new sigma-1 receptor antagonist that inhibits neuropathic pain and activity-induced spinal sensitization. Br J Pharmacol. 2012 Aug;166(8):2289-306. doi: 10.1111/j.1476-5381.2012.01942.x. PubMed PMID: 22404321; PubMed Central PMCID: PMC3448894.
Chemical Structure
