BW373U86

BW373U86
IUPAC命名法による物質名
	IUPAC名 4-[(R)-[(2S,5R)-2,5-dimethyl-4-prop-2-enylpiperazin-1-yl]-(3-hydroxyphenyl)methyl]-N,N-diethylbenzamide;
データベースID
CAS番号;	150428-54-9
PubChem	CID: 10025998
ChemSpider	8201569
ChEMBL	CHEMBL25230
別名	(+)BW373U86
化学的データ
化学式	C27H37N3O2
分子量	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 ;
	テンプレートを表示

(+)BW373U86は、オピオイド系の鎮痛剤であり、科学研究に用いられる^[1]^[2]。

BW373U86は、δ-オピオイド受容体の選択的アゴニストであり、δ-オピオイドに対するアフィニティが、μ-オピオイド受容体に対するものよりも約15倍も強い^[3]。動物実験では、強い鎮痛剤効果、抗うつ薬効果を持ち^[4]^[5]、ラットの実験では、BW373U86は虚血の状況下で心筋細胞をアポトーシスから保護するのが観察された。このメカニズムは複雑で、δ-アゴニスト効果とは別のものである可能性もある^[6]^[7]^[8]。

出典

^ 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.
^ 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 Medical Chemistry 44 (6): 972-987. doi:10.1021/jm000427g. PMID 11300879.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.

[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 (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 Medical 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.

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