BW373U86

BW373U86
Clinical data
Other names	(+)-BW373U86
Identifiers
	IUPAC name 4-[(R)-[(2S,5R)-2,5-dimethyl-4-prop-2-enylpiperazin-1-yl]-(3-hydroxyphenyl)methyl]-N,N-diethylbenzamide;
CAS Number	150428-54-9 ;
PubChem CID	119029;
ChemSpider	106357 ;
UNII	RR2QFN29K7;
ChEMBL	ChEMBL25230 ;
CompTox Dashboard (EPA)	DTXSID00933945 ;
Chemical and physical data
Formula	C27H37N3O2
Molar mass	435.612 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCN(CC)C(=O)C1=CC=C(C=C1)C(C2=CC(=CC=C2)O)N3CC(N(CC3C)CC=C)C;
	InChI InChI=1S/C27H37N3O2/c1-6-16-29-18-21(5)30(19-20(29)4)26(24-10-9-11-25(31)17-24)22-12-14-23(15-13-22)27(32)28(7-2)8-3/h6,9-15,17,20-21,26,31H,1,7-8,16,18-19H2,2-5H3/t20-,21+,26-/m1/s1 ; Key:LBLDMHBSVIVJPM-YZIHRLCOSA-N ;
	(what is this?) (verify)

(+)-BW373U86 is an opioid analgesic drug used in scientific research.^[1]^[2]

BW373U86 is a selective agonist for the δ-opioid receptor, with approximately 15× stronger affinity for the δ-opioid than the μ-opioid receptor.^[3] It has potent analgesic and antidepressant effects in animal studies.^[4]^[5] In studies on rats, BW373U86 appears to protect heart muscle cells from apoptosis in conditions of ischemia (oxygen deprivation, such as in heart attack). The mechanism for this is complex and may be separate from its delta agonist effects.^[6]^[7]^[8]

References

^ Calderon SN, Rice KC, Rothman RB, Porreca F, Flippen-Anderson JL, Kayakiri H, Xu H, Becketts K, Smith LE, Bilsky EJ, Davis P, Horvath R (February 1997). "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". Journal of Medicinal Chemistry. 40 (5): 695–704. doi:10.1021/jm960319n. PMID 9057856.
^ Thomas JB, Herault XM, Rothman RB, Atkinson RN, Burgess JP, Mascarella SW, Dersch CM, Xu H, Flippen-Anderson JL (March 2001). "Factors Influencing Agonist Potency and Selectivity for the Opioid δ Receptor Are Revealed in Structure−Activity Relationship Studies of the 4-[(N-Substituted-4-piperidinyl)arylamino]-N,N-diethylbenzamides". Journal of Medicinal Chemistry. 44 (6): 972–987. doi:10.1021/jm000427g. PMID 11300879.
^ Chang KJ, Rigdon GC, Howard JL, McNutt RW (November 1993). "A novel, potent and selective nonpeptidic delta opioid receptor agonist BW373U86". The Journal of Pharmacology and Experimental Therapeutics. 267 (2): 852–857. PMID 8246159.
^ Broom DC, Nitsche JF, Pintar JE, Rice KC, Woods JH, Traynor JR (November 2002). "Comparison of Receptor Mechanisms and Efficacy Requirements for δ-Agonist-Induced Convulsive Activity and Antinociception in Mice". Journal of Pharmacology and Experimental Therapeutics. 303 (2): 723–729. doi:10.1124/jpet.102.036525. PMID 12388657. S2CID 25978130.
^ Broom DC, Jutkiewicz EM, Folk JE, Traynor JR, Rice KC, Woods JH (June 2002). "Nonpeptidic δ-opioid Receptor Agonists Reduce Immobility in the Forced Swim Assay in Rats". Neuropsychopharmacology. 26 (6): 744–755. doi:10.1016/S0893-133X(01)00413-4. PMID 12007745.
^ Patel HH, Hsu A, Moore J, Gross GJ (August 2001). "BW373U86, a δ Opioid Agonist, Partially Mediates Delayed Cardioprotection via a Free Radical Mechanism that is Independent of Opioid Receptor Stimulation". Journal of Molecular and Cellular Cardiology. 33 (8): 1455–1465. doi:10.1006/jmcc.2001.1408. PMID 11448134.
^ Patel HH, Hsu AK, Gross GJ (May 2004). "COX-2 and iNOS in opioid-induced delayed cardioprotection in the intact rat". Life Sciences. 75 (2): 129–140. doi:10.1016/j.lfs.2003.10.036. PMID 15120566.
^ Gross ER, Hsu AK, Gross GJ (July 2007). "GSK_3β inhibition and K_ATP channel opening mediate acute opioid-induced cardioprotection at reperfusion". Basic Research in Cardiology. 102 (4): 341–349. doi:10.1007/s00395-007-0651-6. PMID 17450314. S2CID 28128170.

[pmid9057856-1] Calderon SN, Rice KC, Rothman RB, Porreca F, Flippen-Anderson JL, Kayakiri H, Xu H, Becketts K, Smith LE, Bilsky EJ, Davis P, Horvath R (February 1997). "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". Journal of Medicinal Chemistry. 40 (5): 695–704. doi:10.1021/jm960319n. PMID 9057856.

[2] Thomas JB, Herault XM, Rothman RB, Atkinson RN, Burgess JP, Mascarella SW, Dersch CM, Xu H, Flippen-Anderson JL (March 2001). "Factors Influencing Agonist Potency and Selectivity for the Opioid δ Receptor Are Revealed in Structure−Activity Relationship Studies of the 4-[(N-Substituted-4-piperidinyl)arylamino]-N,N-diethylbenzamides". Journal of Medicinal Chemistry. 44 (6): 972–987. doi:10.1021/jm000427g. PMID 11300879.

[3] Chang KJ, Rigdon GC, Howard JL, McNutt RW (November 1993). "A novel, potent and selective nonpeptidic delta opioid receptor agonist BW373U86". The Journal of Pharmacology and Experimental Therapeutics. 267 (2): 852–857. PMID 8246159.

[4] Broom DC, Nitsche JF, Pintar JE, Rice KC, Woods JH, Traynor JR (November 2002). "Comparison of Receptor Mechanisms and Efficacy Requirements for δ-Agonist-Induced Convulsive Activity and Antinociception in Mice". Journal of Pharmacology and Experimental Therapeutics. 303 (2): 723–729. doi:10.1124/jpet.102.036525. PMID 12388657. S2CID 25978130.

[5] Broom DC, Jutkiewicz EM, Folk JE, Traynor JR, Rice KC, Woods JH (June 2002). "Nonpeptidic δ-opioid Receptor Agonists Reduce Immobility in the Forced Swim Assay in Rats". Neuropsychopharmacology. 26 (6): 744–755. doi:10.1016/S0893-133X(01)00413-4. PMID 12007745.

[6] Patel HH, Hsu A, Moore J, Gross GJ (August 2001). "BW373U86, a δ Opioid Agonist, Partially Mediates Delayed Cardioprotection via a Free Radical Mechanism that is Independent of Opioid Receptor Stimulation". Journal of Molecular and Cellular Cardiology. 33 (8): 1455–1465. doi:10.1006/jmcc.2001.1408. PMID 11448134.

[7] Patel HH, Hsu AK, Gross GJ (May 2004). "COX-2 and iNOS in opioid-induced delayed cardioprotection in the intact rat". Life Sciences. 75 (2): 129–140. doi:10.1016/j.lfs.2003.10.036. PMID 15120566.

[8] Gross ER, Hsu AK, Gross GJ (July 2007). "GSK_3β inhibition and K_ATP channel opening mediate acute opioid-induced cardioprotection at reperfusion". Basic Research in Cardiology. 102 (4): 341–349. doi:10.1007/s00395-007-0651-6. PMID 17450314. S2CID 28128170.

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See also

References