BW373U86

BW373U86

Systematic (IUPAC) name
4-[(R)-[(2S,5R)-2,5-dimethyl-4-prop-2-enylpiperazin-1-yl]-(3-hydroxyphenyl)methyl]-N,N-diethylbenzamide
Identifiers
CAS Number	150428-54-9
PubChem	CID 10025998
ChemSpider	8201569
ChEMBL	CHEMBL25230
Synonyms	(+)BW373U86
Chemical data
Formula	C27H37N3O2
Molar mass	435.602 g/mol
SMILES O=C(N(CC)CC)c1ccc(cc1)[C@H](N2C[C@H](N(C\C=C)C[C@@H]2C)C)c3cccc(O)c3
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-SWYRRKHMSA-N
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(+)BW373U86 is an opioid analgesic drug used in scientific research.^[1][2]

BW373U86 is a selective agonist for the δ-opioid receptor, with approximately 15x 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

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 (1997). "Probes for narcotic receptor mediated phenomena. 23. Synthesis, opioid receptor binding, and bioassay of the highly selective δ agonist (+)-4-[(alpha R)-alpha-((2S,5R)-4-Allyl-2,5-dimethyl-1-piperazinyl)-3-methoxybenzyl]- N,N-diethylbenzamide (SNC 80) and related novel nonpeptide delta 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 (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 (1993). "A novel, potent and selective nonpeptidic δ 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 (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.
5. Broom DC, Jutkiewicz EM, Folk JE, Traynor JR, Rice KC, Woods JH (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 (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 (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 (2007). "GSK3β inhibition and KATP 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.