BW373U86

Strukturformel
Allgemeines
Name	BW373U86
Andere Namen	4-[(R)-[(2S,5R)-2,5-dimethyl-4-prop-2-enylpiperazin-1-yl]-(3-hydroxyphenyl)methyl]-N,N-diethylbenzamid (IUPAC)
Summenformel	C27H37N3O2
Kurzbeschreibung	hellbraunes Pulver
Externe Identifikatoren/Datenbanken
PubChem	119029
ChemSpider	8201569
Wikidata	Q4836836
Eigenschaften
Molare Masse	435,60 g·mol−1
Aggregatzustand	fest
Schmelzpunkt	175–177 °C
Sicherheitshinweise
GHS-Gefahrstoffkennzeichnung	keine GHS-Piktogramme
	keine GHS-Piktogramme
H- und P-Sätze	H: keine H-Sätze
	P: keine P-Sätze
	Wenn nicht anders vermerkt, gelten die angegebenen Daten bei Standardbedingungen (0 °C, 1000 hPa).

(+)-BW373U86 ist ein opioid-analgetisches Medikament, welches in der Forschung verwendet wird.

BWU373U86 ist ein selektiver Agonist für den δ-Opioidrezeptor, mit etwa 15-mal stärkerer Affinität für den δ-Opioidrezeptor als für den μ-Opioidrezeptor. In Tierstudien hat es potente analgetische und antidepressive Wirkung gezeigt. Bei Studien an Ratten scheint BWU373U86 Herzmuskelzellen bei den Bedingungen einer Ischämie (Sauerstoffmangel, Herzinfarkt) vor Apoptose zu schützen. Der Mechanismus hierfür ist komplex und möglicherweise getrennt von den Wirkungen als δ-Agonist.

Einzelnachweise

1 2 3 4 5 Datenblatt BW373U86 hydrochloride bei Sigma-Aldrich, abgerufen am 26. August 2016 (PDF).
↑ Silvia N. Calderon, Kenner C. Rice, Richard B. Rothman, Frank Porreca, Judith L. Flippen-Anderson, Heng Xu, Karen Becketts, Larren E. Smith, Edward J. Bilsky, Peg Davis, Robert Horvath: Probes for Narcotic Receptor Mediated Phenomena. 23. 1 Synthesis, Opioid Receptor Binding, and Bioassay of the Highly Selective δ Agonist (+)-4-[(αR)-α-((2S,5R)-4-Allyl-2,5-dimethyl-1-piperazinyl)-3-methoxybenzyl]-N,N-diethylbenzamide (SNC 80) and Related Novel Nonpeptide δ Opioid Receptor Ligands. In: Journal of Medicinal Chemistry. Band 40, Nr. 5, Februar 1997, S. 695–704, doi:10.1021/jm960319n.
↑ J. B. Thomas, X. M. Herault, R. B. Rothman, R. N. Atkinson, J. P. Burgess, S. W. Mascarella, C. M. Dersch, H. Xu, J. L. Flippen-Anderson, C. F. George, F. I. Carroll: Factors influencing agonist potency and selectivity for the opioid delta receptor are revealed in structure-activity relationship studies of the 4-[(N-substituted-4-piperidinyl)arylamino]-N,N-diethylbenzamides. In: Journal of Medicinal Chemistry. Band 44, Nr. 6, März 2001, S. 972–987, PMID 11300879.
↑ K. J. Chang, G. C. Rigdon, J. L. Howard, R. W. McNutt: A novel, potent and selective nonpeptidic delta opioid receptor agonist BW373U86. In: The Journal of Pharmacology and Experimental Therapeutics. Band 267, Nr. 2, November 1993, S. 852–857, PMID 8246159.
↑ Daniel C. Broom, Joshua F. Nitsche, John E. Pintar, Kenner C. Rice, James H. Woods, John R. Traynor: Comparison of Receptor Mechanisms and Efficacy Requirements for δ-Agonist-Induced Convulsive Activity and Antinociception in Mice. In: Journal of Pharmacology and Experimental Therapeutics. Band 303, Nr. 2, November 2002, S. 723–729, doi:10.1124/jpet.102.036525.
↑ Daniel C. Broom, Emily M. Jutkiewicz, John E. Folk, John R. Traynor, Kenner C. Rice, James H. Woods: Nonpeptidic delta-opioid receptor agonists reduce immobility in the forced swim assay in rats. In: Neuropsychopharmacology: Official Publication of the American College of Neuropsychopharmacology. Band 26, Nr. 6, Juni 2002, S. 744–755, doi:10.1016/S0893-133X(01)00413-4, PMID 12007745.
↑ H. H. Patel, A. Hsu, J. Moore, G. J. Gross: BW373U86, a delta opioid agonist, partially mediates delayed cardioprotection via a free radical mechanism that is independent of opioid receptor stimulation. In: Journal of Molecular and Cellular Cardiology. Band 33, Nr. 8, August 2001, S. 1455–1465, doi:10.1006/jmcc.2001.1408, PMID 11448134.
↑ Hemal H. Patel, Anna K. Hsu, Garrett J. Gross: COX-2 and iNOS in opioid-induced delayed cardioprotection in the intact rat. In: Life Sciences. Band 75, Nr. 2, Mai 2004, S. 129–140, doi:10.1016/j.lfs.2003.10.036, PMID 15120566.
↑ Eric R. Gross, Anna K. Hsu, Garrett J. Gross: GSK3beta inhibition and K(ATP) channel opening mediate acute opioid-induced cardioprotection at reperfusion. In: Basic Research in Cardiology. Band 102, Nr. 4, Juli 2007, S. 341–349, doi:10.1007/s00395-007-0651-6, PMID 17450314.

[sigma-1] 1 2 3 4 5 Datenblatt BW373U86 hydrochloride bei Sigma-Aldrich, abgerufen am 26. August 2016 (PDF).

[2] Silvia N. Calderon, Kenner C. Rice, Richard B. Rothman, Frank Porreca, Judith L. Flippen-Anderson, Heng Xu, Karen Becketts, Larren E. Smith, Edward J. Bilsky, Peg Davis, Robert Horvath: Probes for Narcotic Receptor Mediated Phenomena. 23. 1 Synthesis, Opioid Receptor Binding, and Bioassay of the Highly Selective δ Agonist (+)-4-[(αR)-α-((2S,5R)-4-Allyl-2,5-dimethyl-1-piperazinyl)-3-methoxybenzyl]-N,N-diethylbenzamide (SNC 80) and Related Novel Nonpeptide δ Opioid Receptor Ligands. In: Journal of Medicinal Chemistry. Band 40, Nr. 5, Februar 1997, S. 695–704, doi:10.1021/jm960319n.

[3] J. B. Thomas, X. M. Herault, R. B. Rothman, R. N. Atkinson, J. P. Burgess, S. W. Mascarella, C. M. Dersch, H. Xu, J. L. Flippen-Anderson, C. F. George, F. I. Carroll: Factors influencing agonist potency and selectivity for the opioid delta receptor are revealed in structure-activity relationship studies of the 4-[(N-substituted-4-piperidinyl)arylamino]-N,N-diethylbenzamides. In: Journal of Medicinal Chemistry. Band 44, Nr. 6, März 2001, S. 972–987, PMID 11300879.

[4] K. J. Chang, G. C. Rigdon, J. L. Howard, R. W. McNutt: A novel, potent and selective nonpeptidic delta opioid receptor agonist BW373U86. In: The Journal of Pharmacology and Experimental Therapeutics. Band 267, Nr. 2, November 1993, S. 852–857, PMID 8246159.

[5] Daniel C. Broom, Joshua F. Nitsche, John E. Pintar, Kenner C. Rice, James H. Woods, John R. Traynor: Comparison of Receptor Mechanisms and Efficacy Requirements for δ-Agonist-Induced Convulsive Activity and Antinociception in Mice. In: Journal of Pharmacology and Experimental Therapeutics. Band 303, Nr. 2, November 2002, S. 723–729, doi:10.1124/jpet.102.036525.

[6] Daniel C. Broom, Emily M. Jutkiewicz, John E. Folk, John R. Traynor, Kenner C. Rice, James H. Woods: Nonpeptidic delta-opioid receptor agonists reduce immobility in the forced swim assay in rats. In: Neuropsychopharmacology: Official Publication of the American College of Neuropsychopharmacology. Band 26, Nr. 6, Juni 2002, S. 744–755, doi:10.1016/S0893-133X(01)00413-4, PMID 12007745.

[7] H. H. Patel, A. Hsu, J. Moore, G. J. Gross: BW373U86, a delta opioid agonist, partially mediates delayed cardioprotection via a free radical mechanism that is independent of opioid receptor stimulation. In: Journal of Molecular and Cellular Cardiology. Band 33, Nr. 8, August 2001, S. 1455–1465, doi:10.1006/jmcc.2001.1408, PMID 11448134.

[8] Hemal H. Patel, Anna K. Hsu, Garrett J. Gross: COX-2 and iNOS in opioid-induced delayed cardioprotection in the intact rat. In: Life Sciences. Band 75, Nr. 2, Mai 2004, S. 129–140, doi:10.1016/j.lfs.2003.10.036, PMID 15120566.

[9] Eric R. Gross, Anna K. Hsu, Garrett J. Gross: GSK3beta inhibition and K(ATP) channel opening mediate acute opioid-induced cardioprotection at reperfusion. In: Basic Research in Cardiology. Band 102, Nr. 4, Juli 2007, S. 341–349, doi:10.1007/s00395-007-0651-6, PMID 17450314.