BW373U86

Structural formula
General
Surname	BW373U86
other names	4 - [( R ) - [(2 S , 5 R ) -2,5-dimethyl-4-prop-2-enylpiperazin-1-yl] - (3-hydroxyphenyl) methyl] - N , N -diethylbenzamide ( IUPAC )
Molecular formula	C 27 H 37 N 3 O 2
Brief description	light brown powder
External identifiers / databases
PubChem	119029
Wikidata	Q4836836
properties
Molar mass	435.60 g mol −1
Physical state	firmly
Melting point	175-177 ° C
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

(+) - BW373U86 is an opioid analgesic drug that is used in research.

BWU373U86 is a selective agonist for the δ-opioid receptor , with about 15 times more affinity for the δ-opioid than the μ-opioid receptor. It has shown potent analgesic and antidepressant effects in animal studies . In studies on rats, BWU373U86 appears to protect cardiac muscle cells from apoptosis under ischemic conditions (lack of oxygen, myocardial infarction) . The mechanism for this is complex and possibly separate from the effects as a δ-agonist.

Individual evidence

↑ ^a ^b ^c ^d ^e data sheet BW373U86 hydrochloride from Sigma-Aldrich , accessed on August 26, 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 . tape 40 , no. 5 , February 1997, p. 695-704 , doi : 10.1021 / jm960319n .
↑ JB Thomas, XM Herault, RB Rothman, RN Atkinson, JP Burgess, SW Mascarella, CM Dersch, H. Xu, JL Flippen-Anderson, CF George, FI 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 . tape 44 , no. 6 , March 2001, p. 972-987 , PMID 11300879 .
↑ KJ Chang, GC Rigdon, JL Howard, RW McNutt: A novel, potent and selective nonpeptidic delta opioid receptor agonist BW373U86 . In: The Journal of Pharmacology and Experimental Therapeutics . tape 267 , no. 2 , November 1993, p. 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 . tape 303 , no. 2 , November 2002, p. 723-729 , doi : 10.1124 / jpet.102.036525 .
Jump up ↑ 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 . tape 26 , no. 6 , June 2002, p. 744-755 , doi : 10.1016 / S0893-133X (01) 00413-4 , PMID 12007745 .
↑ HH Patel, A. Hsu, J. Moore, GJ 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 . tape 33 , no. 8 , August 2001, p. 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 . tape 75 , no. 2 , May 2004, p. 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 . tape 102 , no. 4 , July 2007, p. 341-349 , doi : 10.1007 / s00395-007-0651-6 , PMID 17450314 .

[sigma-1] ↑ ^a ^b ^c ^d ^e data sheet BW373U86 hydrochloride from Sigma-Aldrich , accessed on August 26, 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 . tape 40 , no. 5 , February 1997, p. 695-704 , doi : 10.1021 / jm960319n .

[3] JB Thomas, XM Herault, RB Rothman, RN Atkinson, JP Burgess, SW Mascarella, CM Dersch, H. Xu, JL Flippen-Anderson, CF George, FI 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 . tape 44 , no. 6 , March 2001, p. 972-987 , PMID 11300879 .

[4] KJ Chang, GC Rigdon, JL Howard, RW McNutt: A novel, potent and selective nonpeptidic delta opioid receptor agonist BW373U86 . In: The Journal of Pharmacology and Experimental Therapeutics . tape 267 , no. 2 , November 1993, p. 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 . tape 303 , no. 2 , November 2002, p. 723-729 , doi : 10.1124 / jpet.102.036525 .

[6] Jump up ↑ 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 . tape 26 , no. 6 , June 2002, p. 744-755 , doi : 10.1016 / S0893-133X (01) 00413-4 , PMID 12007745 .

[7] HH Patel, A. Hsu, J. Moore, GJ 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 . tape 33 , no. 8 , August 2001, p. 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 . tape 75 , no. 2 , May 2004, p. 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 . tape 102 , no. 4 , July 2007, p. 341-349 , doi : 10.1007 / s00395-007-0651-6 , PMID 17450314 .