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Latest revision as of 16:01, 21 October 2024 edit undoJWBE (talk | contribs)Extended confirmed users10,126 edits removed Category:Phenols; added Category:3-Hydroxyphenyl compounds using HotCat |
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{{Short description|Opioid analgesic drug used in research}} |
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{{drugbox | verifiedrevid = 410878434 |
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{{Use dmy dates|date=April 2014}} |
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{{Drugbox |
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| IUPAC_name = 4--(3-hydroxyphenyl)methyl]-N,N-diethylbenzamide |
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| image = BW373U86.svg |
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| width = 220 |
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| verifiedrevid = 444653163 |
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| CAS_number = 150428-54-9 |
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| IUPAC_name = 4--(3-hydroxyphenyl)methyl]-N,N-diethylbenzamide |
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| synonyms = (+)BW373U86 |
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| image = BW373U86.svg |
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| ATC_prefix = |
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| PubChem = 119029 |
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<!--Clinical data--> |
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| tradename = |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| pregnancy_category = |
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> |
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| legal_CA = |
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<!--Pharmacokinetic data--> |
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| bioavailability = |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|CAS}} |
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| CAS_number = 150428-54-9 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = RR2QFN29K7 |
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| ATC_prefix = |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 25230 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = |
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| DrugBank = |
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| PubChem = 119029 |
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| C = 27 | H = 37 | N = 3 | O = 2 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| molecular_weight = 435.602 g/mol |
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| ChemSpiderID = 106357 |
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| bioavailability = |
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| smiles = CCN(CC)C(=O)C1=CC=C(C=C1)C(C2=CC(=CC=C2)O)N3CC(N(CC3C)CC=C)C |
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| protein_bound = |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| metabolism = |
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| StdInChI = 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 |
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| elimination_half-life = |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| excretion = |
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| StdInChIKey = LBLDMHBSVIVJPM-YZIHRLCOSA-N |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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<!--Chemical data--> |
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| pregnancy_category= |
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| C=27 | H=37 | N=3 | O=2 |
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> |
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| synonyms = (+)-BW373U86 |
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| legal_CA = |
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| legal_UK = |
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| legal_US = |
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}} |
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'''(+)BW373U86''' is an ] ] drug used in scientific research.<ref name="pmid9057856">{{cite journal | author = 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 | title = 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 | journal = J. Med. Chem. | volume = 40 | issue = 5 | pages = 695–704 | year = 1997 | pmid = 9057856 | doi = 10.1021/jm960319n | issn = }}</ref><ref>{{cite journal | pmid = 11300879 | author-separator =, | author-name-separator= | volume=44 | issue=6 | year=2001 | month=March | last1 = Thomas | first1 = JB | last2 = Herault | first2 = XM | last3 = Rothman | first3 = RB | last4 = Atkinson | first4 = RN | last5 = Burgess | first5 = JP | last6 = Mascarella | first6 = SW | last7 = Dersch | first7 = CM | last8 = Xu | first8 = H | last9 = Flippen-Anderson | first9 = JL | title = 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. | pages = 972–87 | journal = Journal of medicinal chemistry | doi=10.1021/jm000427g}}</ref> |
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'''(+)-BW373U86''' is an ] ] drug used in scientific research.<ref name="pmid9057856">{{cite journal | title=Probes for Narcotic Receptor Mediated Phenomena. 23.<sup>1</sup> Synthesis, Opioid Receptor Binding, and Bioassay of the Highly Selective δ Agonist (+)-4-- N,N-diethylbenzamide (SNC 80) and Related Novel Nonpeptide δ Opioid Receptor Ligands | journal=Journal of Medicinal Chemistry | vauthors=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 | date=February 1997 | volume=40 | issue=5 | pages=695–704 | doi=10.1021/jm960319n | pmid=9057856}}</ref><ref>{{cite journal | title=Factors Influencing Agonist Potency and Selectivity for the Opioid δ Receptor Are Revealed in Structure−Activity Relationship Studies of the 4--N,N-diethylbenzamides | journal=Journal of Medicinal Chemistry | vauthors=Thomas JB, Herault XM, Rothman RB, Atkinson RN, Burgess JP, Mascarella SW, Dersch CM, Xu H, Flippen-Anderson JL | date=March 2001 | volume=44 | issue=6 | pages=972–987 | doi=10.1021/jm000427g | pmid=11300879}}</ref> |
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BW373U86 is a ] for the ] ], with approximately 15× stronger affinity for the δ-opioid than the ].<ref>{{cite journal | url=http://jpet.aspetjournals.org/content/267/2/852.abstract | title=A novel, potent and selective nonpeptidic delta opioid receptor agonist BW373U86. | journal=The Journal of Pharmacology and Experimental Therapeutics | vauthors=Chang KJ, Rigdon GC, Howard JL, McNutt RW | date=November 1993 | volume=267 | issue=2 | pages=852–857 | pmid=8246159}}</ref> It has potent ] and ] effects in animal studies.<ref>{{cite journal | title=Comparison of Receptor Mechanisms and Efficacy Requirements for δ-Agonist-Induced Convulsive Activity and Antinociception in Mice | journal=Journal of Pharmacology and Experimental Therapeutics | vauthors=Broom DC, Nitsche JF, Pintar JE, Rice KC, Woods JH, Traynor JR | date=November 2002 | volume=303 | issue=2 | pages=723–729 | doi=10.1124/jpet.102.036525 | pmid=12388657| s2cid=25978130 }}</ref><ref>{{cite journal | title=Nonpeptidic δ-opioid Receptor Agonists Reduce Immobility in the Forced Swim Assay in Rats | journal=Neuropsychopharmacology | vauthors=Broom DC, Jutkiewicz EM, Folk JE, Traynor JR, Rice KC, Woods JH | date=June 2002 | volume=26 | issue=6 | pages=744–755 | doi=10.1016/S0893-133X(01)00413-4 | pmid=12007745| doi-access=free }}</ref> In studies on rats, BW373U86 appears to protect heart muscle cells from ] in conditions of ] (oxygen deprivation, such as in heart attack). The mechanism for this is complex and may be separate from its delta agonist effects.<ref>{{cite journal | title=BW373U86, a δ Opioid Agonist, Partially Mediates Delayed Cardioprotection via a Free Radical Mechanism that is Independent of Opioid Receptor Stimulation | journal=Journal of Molecular and Cellular Cardiology | vauthors=Patel HH, Hsu A, Moore J, Gross GJ | date=August 2001 | volume=33 | issue=8 | pages=1455–1465 | doi=10.1006/jmcc.2001.1408 | pmid=11448134}}</ref><ref>{{cite journal | title=COX-2 and iNOS in opioid-induced delayed cardioprotection in the intact rat | journal=Life Sciences | vauthors=Patel HH, Hsu AK, Gross GJ | date=May 2004 | volume=75 | issue=2 | pages=129–140 | doi=10.1016/j.lfs.2003.10.036 | pmid=15120566}}</ref><ref>{{cite journal | title=GSK<sub>3β</sub> inhibition and K<sub>ATP</sub> channel opening mediate acute opioid-induced cardioprotection at reperfusion | journal=Basic Research in Cardiology | vauthors=Gross ER, Hsu AK, Gross GJ | date=July 2007 | volume=102 | issue=4 | pages=341–349 | doi=10.1007/s00395-007-0651-6 | pmid=17450314| s2cid=28128170 }}</ref> |
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BW373U86 is a selective ] for the ] ], with approximately 15x stronger affinity for the δ-opioid than the μ-opioid receptor.<ref>{{cite journal | pmid = 8246159 | author-separator =, | author-name-separator= | volume=267 | issue=2 | year=1993 | month=November | last1 = Chang | first1 = KJ | last2 = Rigdon | first2 = GC | last3 = Howard | first3 = JL | last4 = McNutt | first4 = RW | title = A novel, potent and selective nonpeptidic delta opioid receptor agonist BW373U86 | pages = 852–7 | journal = The Journal of pharmacology and experimental therapeutics}}</ref> It has potent ]<ref>{{cite journal | pmid = 12388657 | author-separator =, | author-name-separator= | doi=10.1124/jpet.102.036525 | volume=303 | issue=2 | year=2002 | month=November | title = Comparison of Receptor Mechanisms and Efficacy Requirements for delta -Agonist-Induced Convulsive Activity and Antinociception in Mice | last1 = Broom | first1 = D. C. | journal = Journal of Pharmacology and Experimental Therapeutics | pages = 723–729 | last2 = Nitsche | first2 = JF | last3 = Pintar | first3 = JE | last4 = Rice | first4 = KC | last5 = Woods | first5 = JH | last6 = Traynor | first6 = JR}}</ref> and ] effects in animal studies,<ref>{{cite journal | pmid = 12007745 | author-separator =, | author-name-separator= | doi=10.1016/S0893-133X(01)00413-4 | volume=26 | issue=6 | year=2002 | month=June | title = Nonpeptidic δ-opioid Receptor Agonists Reduce Immobility in the Forced Swim Assay in Rats | last1 = Broom | first1 = D | journal = Neuropsychopharmacology | pages = 744–755 | last2 = Jutkiewicz | first2 = EM | last3 = Folk | first3 = JE | last4 = Traynor | first4 = JR | last5 = Rice | first5 = KC | last6 = Woods | first6 = JH}}</ref> and triggers release of the neural growth factor ],<ref>{{cite journal | pmid = 16220339 | author-separator =, | author-name-separator= | doi=10.1007/s00213-005-0113-5 | volume=183 | issue=1 | year=2005 | month=November | title = Chronic administration of the delta opioid receptor agonist (+)BW373U86 and antidepressants on behavior in the forced swim test and BDNF mRNA expression in rats | last1 = Torregrossa | first1 = Mary M. | last2 = Folk | first2 = John E. | last3 = Rice | first3 = Kenner C. | last4 = Watson | first4 = Stanley J. | last5 = Woods | first5 = James H. | journal = Psychopharmacology | pages = 31–40 | pmc = 1315298}}</ref><ref>{{cite journal | pmid = 14647482 | author-separator =, | author-name-separator= | doi=10.1038/sj.npp.1300345 | volume=29 | issue=4 | year=2004 | month=April | title = The δ-Opioid Receptor Agonist (+)BW373U86 Regulates BDNF mRNA Expression in Rats | last1 = Torregrossa | first1 = Mary M | last2 = Isgor | first2 = Ceylan | last3 = Folk | first3 = John E | last4 = Rice | first4 = Kenner C | last5 = Watson | first5 = Stanley J | last6 = Woods | first6 = James H | journal = Neuropsychopharmacology | pages = 649–659}}</ref> but its usefulness is limited by producing ]s at high doses,<ref>{{cite journal | pmid = 8246164 | author-separator =, | author-name-separator= | volume=267 | issue=2 | year=1993 | month=November | last1 = Comer | first1 = SD | last2 = Hoenicke | first2 = EM | last3 = Sable | first3 = AI | last4 = McNutt | first4 = RW | last5 = Chang | first5 = KJ | last6 = De Costa | first6 = BR | last7 = Mosberg | first7 = HI | last8 = Woods | first8 = JH | title = Convulsive effects of systemic administration of the delta opioid agonist BW373U86 in mice | pages = 888–95 | journal = The Journal of pharmacology and experimental therapeutics}}</ref><ref>{{cite journal | pmid = 12373418 | author-separator =, | author-name-separator= | doi=10.1007/s00213-002-1179-y | volume=164 | issue=1 | year=2002 | month=October | title = Convulsant activity of a non-peptidic δ-opioid receptor agonist is not required for its antidepressant-like effects in Sprague-Dawley rats | last1 = Broom | first1 = Daniel | last2 = Jutkiewicz | first2 = Emily | last3 = Folk | first3 = John | last4 = Traynor | first4 = John | last5 = Rice | first5 = Kenner | last6 = Woods | first6 = James | journal = Psychopharmacology | pages = 42–48}}</ref> although the convulsive effect is reduced when it is co-administered with μ-opioid agonists.<ref>{{cite journal | pmid = 9223564 | author-separator =, | author-name-separator= | volume=282 | issue=1 | year=1997 | month=July | last1 = O'Neill | first1 = SJ | last2 = Collins | first2 = MA | last3 = Pettit | first3 = HO | last4 = McNutt | first4 = RW | last5 = Chang | first5 = KJ | title = Antagonistic modulation between the delta opioid agonist BW373U86 and the mu opioid agonist fentanyl in mice | pages = 271–7 | journal = The Journal of pharmacology and experimental therapeutics}}</ref> Another advantage of the combination is that BW373U86 reverses the ] produced by μ-opioid agonists, without affecting pain relief.<ref>{{cite journal | pmid = 9864259 | author-separator =, | author-name-separator= | volume=287 | issue=3 | year=1998 | month=December | last1 = Su | first1 = YF | last2 = McNutt | first2 = RW | last3 = Chang | first3 = KJ | title = Delta-opioid ligands reverse alfentanil-induced respiratory depression but not antinociception | pages = 815–23 | journal = The Journal of pharmacology and experimental therapeutics}}</ref> |
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==See also== |
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Another useful effect of BW373U86 is that it protects heart muscle cells from death in conditions of ] (oxygen deprivation, such as in heart attack). The mechanism for this is complex and may be separate from its delta agonist effects.<ref>{{cite journal | pmid = 11448134 | author-separator =, | author-name-separator= | doi=10.1006/jmcc.2001.1408 | volume=33 | issue=8 | year=2001 | month=August | title = BW373U86, a δ Opioid Agonist, Partially Mediates Delayed Cardioprotection via a Free Radical Mechanism that is Independent of Opioid Receptor Stimulation | last1 = Patel | first1 = H | journal = Journal of Molecular and Cellular Cardiology | pages = 1455–1465 | last2 = Hsu | first2 = A | last3 = Moore | first3 = J | last4 = Gross | first4 = GJ}}</ref><ref>{{cite journal | pmid = 15120566 | author-separator =, | author-name-separator= | doi=10.1016/j.lfs.2003.10.036 | volume=75 | issue=2 | year=2004 | month=May | title = COX-2 and iNOS in opioid-induced delayed cardioprotection in the intact rat | last1 = Patel | first1 = H | journal = Life Sciences | pages = 129–140 | last2 = Hsu | first2 = AK | last3 = Gross | first3 = GJ}}</ref><ref>{{cite journal | pmid = 17450314 | author-separator =, | author-name-separator= | doi=10.1007/s00395-007-0651-6 | volume=102 | issue=4 | year=2007 | month=July | title = GSK3β inhibition and KATP channel opening mediate acute opioid-induced cardioprotection at reperfusion | last1 = Gross | first1 = E. R. | last2 = Hsu | first2 = A. K. | last3 = Gross | first3 = G. J. | journal = Basic Research in Cardiology | pages = 341–349}}</ref> |
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== References == |
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== References == |
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{{reflist}} |
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{{Reflist|2}} |
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{{Opioidergics}} |
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{{Other respiratory system products}} |
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{{DEFAULTSORT:Bw373u86}} |
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{{DEFAULTSORT:Bw373u86}} |
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