BW373U86

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

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
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC27H37N3O2
Molar mass435.612 g·mol−1
3D model (JSmol)
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 N
  • Key:LBLDMHBSVIVJPM-YZIHRLCOSA-N N
 NY (what is this?)  (verify)

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 (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). "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. S2CID 28128170.
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