SR-31747 HCl

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

MedKoo CAT#: 202700

CAS#: 132173-07-0

Description: SR-31747A is a synthetic peripheral sigma receptor ligand with immunomodulatory and potential antitumor activities. Although the exact mechanism by which SR31747A exerts its antitumor effects has not been fully established, SR31747A binds to and inhibits the sigma1 receptor (SR31747A-binding protein-1 or SR-BP1), human sterol isomerase (emopamil-binding protein) and the sigma2 receptor, which may result in a reduction in tumor cell proliferation and tumor cell apoptosis. In addition, this agent inhibits the production of pro-inflammatory cytokines while increasing anti-inflammatory cytokines.


Chemical Structure

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SR-31747 HCl
CAS# 132173-07-0

Theoretical Analysis

MedKoo Cat#: 202700
Name: SR-31747 HCl
CAS#: 132173-07-0
Chemical Formula: C23H34ClN
Exact Mass: 359.23798
Molecular Weight: 359.97576
Elemental Analysis: C, 69.68; H, 8.90; Cl, 17.89; N, 3.53.

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Related CAS #: 132173-06-9 (free base)  

Synonym: SR 31747; SR-31747; SR31747; SR3147A; SR-3147A; SR 3147A.

IUPAC/Chemical Name: (Z)-N-(3-(3-chloro-4-cyclohexylphenyl)allyl)-N-ethylcyclohexanamine hydrochloride

InChi Key: HKHPCMBPASXYGP-KVVVOXFISA-N

InChi Code: InChI=1S/C23H34ClN.ClH/c1-2-25(21-13-7-4-8-14-21)17-9-10-19-15-16-22(23(24)18-19)20-11-5-3-6-12-20;/h9-10,15-16,18,20-21H,2-8,11-14,17H2,1H3;1H/b10-9-;

SMILES Code: CCN(C/C=C\C1=CC=C(C2CCCCC2)C(Cl)=C1)C3CCCCC3.[H]Cl

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

Preparing Stock Solutions

The following data is based on the product molecular weight 359.97576 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: SR 31747. Peripheral sigma receptor antagonist. Drugs R D. 1999 Jan;1(1):108-9. PubMed PMID: 10566002.

2: Silve S, Leplatois P, Josse A, Dupuy PH, Lanau C, Kaghad M, Dhers C, Picard C, Rahier A, Taton M, Le Fur G, Caput D, Ferrara P, Loison G. The immunosuppressant SR 31747 blocks cell proliferation by inhibiting a steroid isomerase in Saccharomyces cerevisiae. Mol Cell Biol. 1996 Jun;16(6):2719-27. PubMed PMID: 8649379; PubMed Central PMCID: PMC231262.

3: Carayon P, Petitpretre G, Bourrie B, Le Fur G, Casellas P. In vivo effects of a new immunosuppressive sigma ligand, SR 31747, on mouse thymus. Immunopharmacol Immunotoxicol. 1996 May;18(2):179-91. PubMed PMID: 8771366.

4: Carayon P, Bouaboula M, Loubet JF, Bourrie B, Petitpretre G, Le Fur G, Casellas P. The sigma ligand SR 31747 prevents the development of acute graft-versus-host disease in mice by blocking IFN-gamma and GM-CSF mRNA expression. Int J Immunopharmacol. 1995 Sep;17(9):753-61. PubMed PMID: 8582787.

5: Derocq JM, Bourrié B, Ségui M, Le Fur G, Casellas P. In vivo inhibition of endotoxin-induced pro-inflammatory cytokines production by the sigma ligand SR 31747. J Pharmacol Exp Ther. 1995 Jan;272(1):224-30. PubMed PMID: 7815336.

6: Casellas P, Bourrié B, Canat X, Carayon P, Buisson I, Paul R, Brelière JC, Le Fur G. Immunopharmacological profile of SR 31747: in vitro and in vivo studies on humoral and cellular responses. J Neuroimmunol. 1994 Jul;52(2):193-203. PubMed PMID: 8034758.

7: Paul R, Lavastre S, Floutard D, Floutard R, Canat X, Casellas P, Le Fur G, Brelière JC. Allosteric modulation of peripheral sigma binding sites by a new selective ligand: SR 31747. J Neuroimmunol. 1994 Jul;52(2):183-92. PubMed PMID: 7794416.



Additional Information

SR 31747 is a novel immunosuppressant agent that arrests cell proliferation in the yeast Saccharomyces cerevisiae, SR 31747-treated cells accumulate the same aberrant sterols as those found in a mutant impaired in delta 8- delta 7-sterol isomerase. (from MCB).
 
SR31747 was shown to inhibit Δ8-Δ7 sterol isomerase in yeast. SR31747 is a high affinity ligand of recombinant mammalian sterol isomerase (Kd = 1 nM). For detail, please see: Pharmacology and Experimental Therapeutics