Efaroxan HCl | CAS# 89197-00-2 | α2-adrenergic receptor inhibitor

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

MedKoo CAT#: 540114

CAS#: 89197-00-2

Description: Efaroxan HCl is an inhibitor of α2-adrenergic receptors, imidazoline-1 receptors, and ATP-sensitive K channels. It improves glucose tolerance, alters opiod-mediated tolerance and antinociception signaling pathways, and decreases symptoms of Parkinson's Disease.

Chemical Structure

Efaroxan HCl

CAS# 89197-00-2

Instruction

Theoretical Analysis

MedKoo Cat#: 540114
Name: Efaroxan HCl
CAS#: 89197-00-2
Chemical Formula: C13H17ClN2O
Exact Mass: 252.10
Molecular Weight: 252.740
Elemental Analysis: C, 61.78; H, 6.78; Cl, 14.03; N, 11.08; O, 6.33

Price and Availability

Size	Price	Availability
10mg	USD 210	2 weeks
25mg	USD 350	2 weeks
50mg	USD 530	2 weeks
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.

Synonym: Efaroxan HCl; RX 821037A; RX821037A; RX-821037A; EU-0100521; EU0100521; EU 0100521;

IUPAC/Chemical Name: 2-(2-ethyl-2,3-dihydrobenzofuran-2-yl)-4,5-dihydro-1H-imidazole hydrochloride

InChi Key: DWOIUCRHVWIHAH-UHFFFAOYSA-N

InChi Code: InChI=1S/C13H16N2O.ClH/c1-2-13(12-14-7-8-15-12)9-10-5-3-4-6-11(10)16-13;/h3-6H,2,7-9H2,1H3,(H,14,15);1H

SMILES Code: CCC1(C2=NCCN2)OC3=C(C=CC=C3)C1.[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

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

More Info:

Instruction:

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Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 252.74 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:
In vitro protocol:
In vivo protocol:

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1: Rusu-Zota G, Burlui A, Rezus E, Paduraru L, Sorodoc V. Idazoxan and Efaroxan Potentiate the Endurance Performances and the Antioxidant Activity of Ephedrine in Rats. Medicina (Kaunas). 2021 Feb 25;57(3):194. doi: 10.3390/medicina57030194. PMID: 33668888; PMCID: PMC7996498.

2: Carlisle MA, Smyth DD, Glavin GB. Efaroxan acts peripherally to block the antisecretory and gastroprotective effects of moxonidine in rats. J Pharmacol Exp Ther. 1995 Aug;274(2):598-601. PMID: 7636718.

3: Couture K, Gouverneur V, Mioskowski C. A new approach to the synthesis of efaroxan. Bioorg Med Chem Lett. 1999 Oct 18;9(20):3023-6. doi: 10.1016/s0960-894x(99)00530-2. PMID: 10571168.

4: Rascol O, Sieradzan K, Peyro-Saint-Paul H, Thalamas C, Brefel-Courbon C, Senard JM, Ladure P, Montastruc JL, Lees A. Efaroxan, an alpha-2 antagonist, in the treatment of progressive supranuclear palsy. Mov Disord. 1998 Jul;13(4):673-6. doi: 10.1002/mds.870130411. PMID: 9686773.

5: de Vos H, de Backer JP, Vauquelin G. Efaroxan (RX 821037) is a potent and selective ?(2)-adrenoceptor antagonist in human frontal cortex membranes. Neurochem Int. 1991;18(1):137-40. doi: 10.1016/0197-0186(91)90047-h. PMID: 20504687.

6: Lehner Z, Stadlbauer K, Adorjan I, Rustenbeck I, Belz M, Fenzl A, de Cillia VA, Gruber D, Bauer L, Frobel K, Brunmair B, Luger A, Fürnsinn C. Mechanisms of antihyperglycaemic action of efaroxan in mice: time for reappraisal of α2A-adrenergic antagonism in the treatment of type 2 diabetes? Diabetologia. 2012 Nov;55(11):3071-82. doi: 10.1007/s00125-012-2679-x. Epub 2012 Aug 18. PMID: 22898767.

7: Chan SL, Dunne MJ, Stillings MR, Morgan NG. The alpha 2-adrenoceptor antagonist efaroxan modulates K+ATP channels in insulin-secreting cells. Eur J Pharmacol. 1991 Oct 29;204(1):41-8. doi: 10.1016/0014-2999(91)90833-c. PMID: 1687123.

8: Milne B, Jhamandas K, Sutak M, Grenier P, Cahill CM. Stereo-selective inhibition of spinal morphine tolerance and hyperalgesia by an ultra-low dose of the alpha-2-adrenoceptor antagonist efaroxan. Eur J Pharmacol. 2013 Feb 28;702(1-3):227-34. doi: 10.1016/j.ejphar.2013.01.022. Epub 2013 Jan 29. PMID: 23376415.

9: Berridge TL, Doxey JC, Roach AG. Comparison of the effects of efaroxan and glibenclamide on plasma glucose and insulin levels in rats. Eur J Pharmacol. 1992 Mar 24;213(2):213-8. doi: 10.1016/0014-2999(92)90684-v. PMID: 1355734.

10: Rusu G, Mititelu-Tartau L, Lupusoru CE, Lupusoru RV, Grigoraş I, Popa G, Nechifor M. Imidazoline receptor antagonists idazoxan and efaroxan enhance locomotor functions in rats. Rev Med Chir Soc Med Nat Iasi. 2015 Jan- Mar;119(1):193-200. PMID: 25970966.

11: Bleck C, Wienbergen A, Rustenbeck I. Essential role of the imidazoline moiety in the insulinotropic effect but not the KATP channel-blocking effect of imidazolines; a comparison of the effects of efaroxan and its imidazole analogue, KU14R. Diabetologia. 2005 Dec;48(12):2567-75. doi: 10.1007/s00125-005-0031-4. Epub 2005 Nov 11. PMID: 16283242.

12: Chan SL, Morgan NG. Stimulation of insulin secretion by efaroxan may involve interaction with potassium channels. Eur J Pharmacol. 1990 Jan 25;176(1):97-101. doi: 10.1016/0014-2999(90)90137-u. PMID: 2178947.

13: Berridge TL, Doxey JC, Roach AG, Smith CF. Selectivity profile of the alpha 2-adrenoceptor antagonist efaroxan in relation to plasma glucose and insulin levels in the rat. Eur J Pharmacol. 1992 Mar 24;213(2):205-12. doi: 10.1016/0014-2999(92)90683-u. PMID: 1355733.

14: Chan SL, Monks LK, Gao H, Deaville P, Morgan NG. Identification of the monomeric G-protein, Rhes, as an efaroxan-regulated protein in the pancreatic beta-cell. Br J Pharmacol. 2002 May;136(1):31-6. doi: 10.1038/sj.bjp.0704680. PMID: 11976265; PMCID: PMC1762110.

15: Mayer P, Brunel P, Imbert T. A new efficient synthesis of efaroxan. Bioorg Med Chem Lett. 1999 Oct 18;9(20):3021-2. doi: 10.1016/s0960-894x(99)00531-4. PMID: 10571167.

16: Mayer G, Taberner PV. Effects of the imidazoline ligands efaroxan and KU14R on blood glucose homeostasis in the mouse. Eur J Pharmacol. 2002 Nov 1;454(1):95-102. doi: 10.1016/s0014-2999(02)02473-1. PMID: 12409010.

17: Tellez S, Colpaert F, Marien M. The alpha 2-adrenoceptor antagonist, (+)-efaroxan, enhances acetylcholine release in the rat cortex in vivo. Eur J Pharmacol. 1995 Apr 13;277(1):113-6. doi: 10.1016/0014-2999(95)00110-7. PMID: 7635166.

18: Papaccio G, Graziano A, Valiante S, D'Aquino R, Travali S, Nicoletti F. Interleukin (IL)-1beta toxicity to islet beta cells: Efaroxan exerts a complete protection. J Cell Physiol. 2005 Apr;203(1):94-102. doi: 10.1002/jcp.20198. PMID: 15389634.

19: Chan SL, Mourtada M, Morgan NG. Characterization of a KATP channel- independent pathway involved in potentiation of insulin secretion by efaroxan. Diabetes. 2001 Feb;50(2):340-7. doi: 10.2337/diabetes.50.2.340. PMID: 11272145.

20: Taylor JP, Jackson DA, Morgan NG, Chan SL. Rhes expression in pancreatic beta-cells is regulated by efaroxan in a calcium-dependent process. Biochem Biophys Res Commun. 2006 Oct 20;349(2):809-15. doi: 10.1016/j.bbrc.2006.08.102. Epub 2006 Aug 24. PMID: 16945334.

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