Salubrinal
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MedKoo CAT#: 326807

CAS#: 405060-95-9

Description: Salubrinal is a selective phosphatase inhibitor that prevents dephosphorylation of eukaryotic translation initiation factor 2 subunit α (eIF2α). Salubrinal reduces oxidative stress, neuroinflammation and impulsive-like behavior in a rodent model of traumatic brain injury. Salubrinal protects human lens epithelial cells against endoplasmic reticulum stress-associated apoptosis. Salubrinal improves cardiac function in rats with heart failure post myocardial infarction through reducing endoplasmic reticulum stress-associated apoptosis.


Chemical Structure

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Salubrinal
CAS# 405060-95-9

Theoretical Analysis

MedKoo Cat#: 326807
Name: Salubrinal
CAS#: 405060-95-9
Chemical Formula: C21H17Cl3N4OS
Exact Mass: 478.0189
Molecular Weight: 479.804
Elemental Analysis: C, 52.57; H, 3.57; Cl, 22.17; N, 11.68; O, 3.33; S, 6.68

Price and Availability

Size Price Availability Quantity
25.0mg USD 250.0 2 Weeks
50.0mg USD 450.0 2 Weeks
100.0mg USD 750.0 2 Weeks
200.0mg USD 1250.0 2 Weeks
500.0mg USD 2150.0 2 Weeks
1.0g USD 3250.0 2 Weeks
2.0g USD 5450.0 2 Weeks
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Synonym: Salubrinal

IUPAC/Chemical Name: (2E)-3-phenyl-N-[2,2,2-trichloro-1-[[(8-quinolinylamino)thioxomethyl]amino]ethyl]-2-propenamide

InChi Key: LCOIAYJMPKXARU-VAWYXSNFSA-N

InChi Code: InChI=1S/C21H17Cl3N4OS/c22-21(23,24)19(27-17(29)12-11-14-6-2-1-3-7-14)28-20(30)26-16-10-4-8-15-9-5-13-25-18(15)16/h1-13,19H,(H,27,29)(H2,26,28,30)/b12-11+

SMILES Code: O=C(NC(NC(NC1=C2N=CC=CC2=CC=C1)=S)C(Cl)(Cl)Cl)/C=C/C3=CC=CC=C3

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

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

Preparing Stock Solutions

The following data is based on the product molecular weight 479.804 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

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1: Li Y, Zheng GY, Liu Y. [Salubrinal protects human lens epithelial cells against endoplasmic reticulum stress-associated apoptosis]. Zhonghua Yan Ke Za Zhi. 2016 Jun 11;52(6):437-43. doi: 10.3760/cma.j.issn.0412-4081.2016.06.008. Chinese. PubMed PMID: 27373572.

2: Liu Y, Qi SY, Ru LS, Ding C, Wang HJ, Li AY, Xu BY, Zhang GH, Wang DM. [Salubrinal improves cardiac function in rats with heart failure post myocardial infarction through reducing endoplasmic reticulum stress-associated apoptosis]. Zhonghua Xin Xue Guan Bing Za Zhi. 2016 Jun 24;44(6):494-500. doi: 10.3760/cma.j.issn.0253-3758.2016.06.008. Chinese. PubMed PMID: 27346262.

3: Wen J, Jiang Y, Zhang C, Chen S, Li H. The Protective Effects of Salubrinal on the Cartilage and Subchondral Bone of the Temporomandibular Joint under Various Compressive Mechanical Stimulations. PLoS One. 2016 May 19;11(5):e0155514. doi: 10.1371/journal.pone.0155514. eCollection 2016. PubMed PMID: 27196267; PubMed Central PMCID: PMC4873203.

4: Logsdon AF, Lucke-Wold BP, Nguyen L, Matsumoto RR, Turner RC, Rosen CL, Huber JD. Salubrinal reduces oxidative stress, neuroinflammation and impulsive-like behavior in a rodent model of traumatic brain injury. Brain Res. 2016 Jul 15;1643:140-51. doi: 10.1016/j.brainres.2016.04.063. Epub 2016 Apr 27. PubMed PMID: 27131989.

5: Anuncibay-Soto B, Pérez-Rodríguez D, Santos-Galdiano M, Font E, Regueiro-Purriños M, Fernández-López A. Post-ischemic salubrinal treatment results in a neuroprotective role in global cerebral ischemia. J Neurochem. 2016 Jul;138(2):295-306. doi: 10.1111/jnc.13651. Epub 2016 May 16. PubMed PMID: 27123756.

6: Romero-Ramírez L, Nieto-Sampedro M, Barreda-Manso MA. All roads go to Salubrinal: endoplasmic reticulum stress, neuroprotection and glial scar formation. Neural Regen Res. 2015 Dec;10(12):1926-7. doi: 10.4103/1673-5374.169619. PubMed PMID: 26889171; PubMed Central PMCID: PMC4730807.

7: Jeon YJ, Kim JH, Shin JI, Jeong M, Cho J, Lee K. Salubrinal-Mediated Upregulation of eIF2α Phosphorylation Increases Doxorubicin Sensitivity in MCF-7/ADR Cells. Mol Cells. 2016 Feb;39(2):129-35. doi: 10.14348/molcells.2016.2243. Epub 2016 Jan 7. PubMed PMID: 26743901; PubMed Central PMCID: PMC4757800.

8: Gong N, Wu JH, Liang ZS, Jiang WH, Wang XW. Role of salubrinal in protecting cardiomyocytes from doxorubicin-induced apoptosis. Genet Mol Res. 2015 Oct 16;14(4):12377-85. doi: 10.4238/2015.October.16.4. PubMed PMID: 26505387.

9: Nakajima S, Chi Y, Gao K, Kono K, Yao J. eIF2α-Independent Inhibition of TNF-α-Triggered NF-κB Activation by Salubrinal. Biol Pharm Bull. 2015;38(9):1368-74. doi: 10.1248/bpb.b15-00312. PubMed PMID: 26328492.

10: Matsuoka M, Komoike Y. Experimental Evidence Shows Salubrinal, an eIF2α Dephosphorylation Inhibitor, Reduces Xenotoxicant-Induced Cellular Damage. Int J Mol Sci. 2015 Jul 17;16(7):16275-87. doi: 10.3390/ijms160716275. Review. PubMed PMID: 26193263; PubMed Central PMCID: PMC4519949.

11: Wang T, Zhang SJ, Cao SL, Guo WZ, Yan B, Fang HB. Protective effects of salubrinal on liver injury in rat models of brain death. Chin Med J (Engl). 2015 Jun 5;128(11):1523-8. doi: 10.4103/0366-6999.157684. PubMed PMID: 26021511; PubMed Central PMCID: PMC4733771.

12: Hamamura K, Nishimura A, Iino T, Takigawa S, Sudo A, Yokota H. Chondroprotective effects of Salubrinal in a mouse model of osteoarthritis. Bone Joint Res. 2015 May;4(5):84-92. doi: 10.1302/2046-3758.45.2000378. PubMed PMID: 25977571; PubMed Central PMCID: PMC4443296.

13: Barreda-Manso MA, Yanguas-Casás N, Nieto-Sampedro M, Romero-Ramírez L. Salubrinal inhibits the expression of proteoglycans and favors neurite outgrowth from cortical neurons in vitro. Exp Cell Res. 2015 Jul 1;335(1):82-90. doi: 10.1016/j.yexcr.2015.04.002. Epub 2015 Apr 13. PubMed PMID: 25882497.

14: Li RJ, He KL, Li X, Wang LL, Liu CL, He YY. Salubrinal protects cardiomyocytes against apoptosis in a rat myocardial infarction model via suppressing the dephosphorylation of eukaryotic translation initiation factor 2α. Mol Med Rep. 2015 Jul;12(1):1043-9. doi: 10.3892/mmr.2015.3508. Epub 2015 Mar 18. PubMed PMID: 25816071; PubMed Central PMCID: PMC4438964.

15: Hamamura K, Nishimura A, Chen A, Takigawa S, Sudo A, Yokota H. Salubrinal acts as a Dusp2 inhibitor and suppresses inflammation in anti-collagen antibody-induced arthritis. Cell Signal. 2015 Apr;27(4):828-35. doi: 10.1016/j.cellsig.2015.01.010. Epub 2015 Jan 22. PubMed PMID: 25619567; PubMed Central PMCID: PMC4339503.

16: Rubovitch V, Barak S, Rachmany L, Goldstein RB, Zilberstein Y, Pick CG. The neuroprotective effect of salubrinal in a mouse model of traumatic brain injury. Neuromolecular Med. 2015 Mar;17(1):58-70. doi: 10.1007/s12017-015-8340-3. Epub 2015 Jan 13. PubMed PMID: 25582550.

17: Hamamura K, Chen A, Tanjung N, Takigawa S, Sudo A, Yokota H. In vitro and in silico analysis of an inhibitory mechanism of osteoclastogenesis by salubrinal and guanabenz. Cell Signal. 2015 Feb;27(2):353-62. doi: 10.1016/j.cellsig.2014.11.020. Epub 2014 Nov 27. PubMed PMID: 25435425.

18: Li H, Xing B, Quan Y, Sun M. [The effect of selective phosphatase inhibitors Salubrinal on autophagy and apoptosis in the lung tissue of rats with acute paraquat poisoning]. Zhonghua Wei Zhong Bing Ji Jiu Yi Xue. 2014 Sep;26(9):671-5. doi: 10.3760/cma.j.issn.2095-4352.2014.09.013. Chinese. PubMed PMID: 25230871.

19: Wan Q, Xu W, Yan JL, Yokota H, Na S. Distinctive subcellular inhibition of cytokine-induced SRC by salubrinal and fluid flow. PLoS One. 2014 Aug 26;9(8):e105699. doi: 10.1371/journal.pone.0105699. eCollection 2014. PubMed PMID: 25157407; PubMed Central PMCID: PMC4144888.

20: Guo H, Jiang C, Sun X. Therapeutical effects and mechanism of salubrinal combined with ulinastatin on treating paraquat poisoning. Cell Biochem Biophys. 2014 Dec;70(3):1559-63. doi: 10.1007/s12013-014-0095-1. PubMed PMID: 25030410.