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BW373U86

Clinical data
Other names	(+)BW373U86
Identifiers
IUPAC name 4--(3-hydroxyphenyl)methyl]-N,N-diethylbenzamide
CAS Number	150428-54-9
PubChem CID	119029
CompTox Dashboard (EPA)	DTXSID00933945
Chemical and physical data
Formula	C27H37N3O2
Molar mass	435.602 g/mol g·mol
(verify)

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

BW373U86 is a selective agonist for the δ-opioid receptor, with approximately 15x stronger affinity for the δ-opioid than the μ-opioid receptor. It has potent analgesic and antidepressant effects in animal studies, and triggers release of the neural growth factor BDNF, but its usefulness is limited by producing convulsions at high doses, although the convulsive effect is reduced when it is co-administered with μ-opioid agonists. Another advantage of the combination is that BW373U86 reverses the respiratory depression produced by μ-opioid agonists, without affecting pain relief.

Another useful effect of BW373U86 is that it protects heart muscle cells from death 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.

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 delta agonist (+)-4-- N,N-diethylbenzamide (SNC 80) and related novel nonpeptide delta opioid receptor ligands". J. Med. Chem. 40 (5): 695–704. doi:10.1021/jm960319n. PMID 9057856.{{cite journal}}: CS1 maint: multiple names: authors list (link)
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 delta 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): 972–87. doi:10.1021/jm000427g. PMID 11300879. {{cite journal}}: Cite has empty unknown parameter: |author-name-separator= (help); Unknown parameter |author-separator= ignored (help); Unknown parameter |month= ignored (help)
3. Chang, KJ; Rigdon, GC; Howard, JL; McNutt, RW (1993). "A novel, potent and selective nonpeptidic delta opioid receptor agonist BW373U86". The Journal of pharmacology and experimental therapeutics. 267 (2): 852–7. PMID 8246159. {{cite journal}}: Cite has empty unknown parameter: |author-name-separator= (help); Unknown parameter |author-separator= ignored (help); Unknown parameter |month= ignored (help)
4. Broom, D. C.; Nitsche, JF; Pintar, JE; Rice, KC; Woods, JH; Traynor, JR (2002). "Comparison of Receptor Mechanisms and Efficacy Requirements for delta -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. {{cite journal}}: Cite has empty unknown parameter: |author-name-separator= (help); Unknown parameter |author-separator= ignored (help); Unknown parameter |month= ignored (help)
5. Broom, D; 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. {{cite journal}}: Cite has empty unknown parameter: |author-name-separator= (help); Unknown parameter |author-separator= ignored (help); Unknown parameter |month= ignored (help)
6. Torregrossa, Mary M.; Folk, John E.; Rice, Kenner C.; Watson, Stanley J.; Woods, James H. (2005). "Chronic administration of the delta opioid receptor agonist (+)BW373U86 and antidepressants on behavior in the forced swim test and BDNF mRNA expression in rats". Psychopharmacology. 183 (1): 31–40. doi:10.1007/s00213-005-0113-5. PMC 1315298. PMID 16220339. {{cite journal}}: Cite has empty unknown parameter: |author-name-separator= (help); Unknown parameter |author-separator= ignored (help); Unknown parameter |month= ignored (help)
7. Torregrossa, Mary M; Isgor, Ceylan; Folk, John E; Rice, Kenner C; Watson, Stanley J; Woods, James H (2004). "The δ-Opioid Receptor Agonist (+)BW373U86 Regulates BDNF mRNA Expression in Rats". Neuropsychopharmacology. 29 (4): 649–659. doi:10.1038/sj.npp.1300345. PMID 14647482. {{cite journal}}: Cite has empty unknown parameter: |author-name-separator= (help); Unknown parameter |author-separator= ignored (help); Unknown parameter |month= ignored (help)
8. Comer, SD; Hoenicke, EM; Sable, AI; McNutt, RW; Chang, KJ; De Costa, BR; Mosberg, HI; Woods, JH (1993). "Convulsive effects of systemic administration of the delta opioid agonist BW373U86 in mice". The Journal of pharmacology and experimental therapeutics. 267 (2): 888–95. PMID 8246164. {{cite journal}}: Cite has empty unknown parameter: |author-name-separator= (help); Unknown parameter |author-separator= ignored (help); Unknown parameter |month= ignored (help)
9. Broom, Daniel; Jutkiewicz, Emily; Folk, John; Traynor, John; Rice, Kenner; Woods, James (2002). "Convulsant activity of a non-peptidic δ-opioid receptor agonist is not required for its antidepressant-like effects in Sprague-Dawley rats". Psychopharmacology. 164 (1): 42–48. doi:10.1007/s00213-002-1179-y. PMID 12373418. {{cite journal}}: Cite has empty unknown parameter: |author-name-separator= (help); Unknown parameter |author-separator= ignored (help); Unknown parameter |month= ignored (help)
10. O'Neill, SJ; Collins, MA; Pettit, HO; McNutt, RW; Chang, KJ (1997). "Antagonistic modulation between the delta opioid agonist BW373U86 and the mu opioid agonist fentanyl in mice". The Journal of pharmacology and experimental therapeutics. 282 (1): 271–7. PMID 9223564. {{cite journal}}: Cite has empty unknown parameter: |author-name-separator= (help); Unknown parameter |author-separator= ignored (help); Unknown parameter |month= ignored (help)
11. Su, YF; McNutt, RW; Chang, KJ (1998). "Delta-opioid ligands reverse alfentanil-induced respiratory depression but not antinociception". The Journal of pharmacology and experimental therapeutics. 287 (3): 815–23. PMID 9864259. {{cite journal}}: Cite has empty unknown parameter: |author-name-separator= (help); Unknown parameter |author-separator= ignored (help); Unknown parameter |month= ignored (help)
12. Patel, H; 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. {{cite journal}}: Cite has empty unknown parameter: |author-name-separator= (help); Unknown parameter |author-separator= ignored (help); Unknown parameter |month= ignored (help)
13. Patel, H; 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. {{cite journal}}: Cite has empty unknown parameter: |author-name-separator= (help); Unknown parameter |author-separator= ignored (help); Unknown parameter |month= ignored (help)
14. Gross, E. R.; Hsu, A. K.; Gross, G. J. (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. {{cite journal}}: Cite has empty unknown parameter: |author-name-separator= (help); Unknown parameter |author-separator= ignored (help); Unknown parameter |month= ignored (help)

• Synthetic opioids
• Respiratory agents
• Delta-opioid agonists
• Phenols
• Benzamides
• Piperazines
• Alkenes
• Mu-opioid agonists