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
	Soweit möglich und gebräuchlich, werden SI-Einheiten verwendet.; 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.^[2]^[3]

BWU373U86 ist ein selektiver Agonist für den δ-Opioidrezeptor, mit etwa 15-mal stärkerer Affinität für den δ-Opioidrezeptor als für den μ-Opioidrezeptor.^[4] In Tierstudien hat es potente analgetische und antidepressive Wirkung gezeigt.^[5]^[6] 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.^[7]^[8]^[9]

Einzelnachweise

↑ ^a ^b ^c ^d ^e 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-[(α R )-α-((2 S ,5 R )-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] 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-[(α R )-α-((2 S ,5 R )-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.

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BW373U86

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