| Revision as of 16:49, 13 August 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{drugbox}} (no changed fields - updated 'ChemSpiderID_Ref', 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEBI_Ref') per [[Misplaced Pages:WikiProject Chemicals/Chembox validation|Chem/Dru← Previous edit | Latest revision as of 16:01, 21 October 2024 edit undoJWBE (talk | contribs)Extended confirmed users10,129 edits removed Category:Phenols; added Category:3-Hydroxyphenyl compounds using HotCat | ||
| (38 intermediate revisions by 24 users not shown) | |||
| Line 1: | Line 1: | ||
| {{Short description|Opioid analgesic drug used in research}} | |||
| ⚫ | |||
| {{Use dmy dates|date=April 2014}} | |||
| | | |||
| {{Drugbox | |||
| ⚫ | | IUPAC_name |
||
| | Verifiedfields = changed | |||
| ⚫ | | image |
||
| | Watchedfields = changed | |||
| | width = 220 | |||
| ⚫ | | verifiedrevid = 444653163 | ||
| ⚫ | | CAS_number |
||
| ⚫ | | IUPAC_name = 4--(3-hydroxyphenyl)methyl]-N,N-diethylbenzamide | ||
| ⚫ | | synonyms |
||
| ⚫ | | image = BW373U86.svg | ||
| ⚫ | | ATC_prefix |
||
| | |
| width = | ||
| ⚫ | | PubChem |
||
| <!--Clinical data--> | |||
| | tradename = | |||
| ⚫ | | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | ||
| ⚫ | | pregnancy_US = <!-- A / B / C / D / X --> | ||
| ⚫ | | pregnancy_category = | ||
| ⚫ | | legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> | ||
| ⚫ | | legal_CA = | ||
| ⚫ | | legal_UK = | ||
| ⚫ | | legal_US = | ||
| ⚫ | | legal_status = | ||
| ⚫ | | routes_of_administration = | ||
| <!--Pharmacokinetic data--> | |||
| ⚫ | | bioavailability = | ||
| ⚫ | | protein_bound = | ||
| ⚫ | | metabolism = | ||
| ⚫ | | elimination_half-life = | ||
| ⚫ | | excretion = | ||
| <!--Identifiers--> | |||
| | CAS_number_Ref = {{cascite|correct|CAS}} | |||
| ⚫ | | CAS_number = 150428-54-9 | ||
| | UNII_Ref = {{fdacite|correct|FDA}} | |||
| | UNII = RR2QFN29K7 | |||
| ⚫ | | ATC_prefix = | ||
| | ATC_suffix = | |||
| | ChEMBL_Ref = {{ebicite|changed|EBI}} | |||
| | ChEMBL = 25230 | |||
| | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | ||
| | DrugBank |
| DrugBank = | ||
| ⚫ | | PubChem = 119029 | ||
| ⚫ | | C |
||
| | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | |||
| | molecular_weight = 435.602 g/mol | |||
| | ChemSpiderID = 106357 | |||
| ⚫ | | bioavailability |
||
| | smiles = CCN(CC)C(=O)C1=CC=C(C=C1)C(C2=CC(=CC=C2)O)N3CC(N(CC3C)CC=C)C | |||
| ⚫ | | protein_bound |
||
| | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | |||
| ⚫ | | metabolism |
||
| | 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 | |||
| ⚫ | | elimination_half-life = | ||
| | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | |||
| ⚫ | | excretion |
||
| | StdInChIKey = LBLDMHBSVIVJPM-YZIHRLCOSA-N | |||
| ⚫ | | pregnancy_AU |
||
| ⚫ | | pregnancy_US |
||
| <!--Chemical data--> | |||
| ⚫ | | pregnancy_category= | ||
| ⚫ | | C=27 | H=37 | N=3 | O=2 | ||
| ⚫ | | legal_AU |
||
| ⚫ | | synonyms = (+)-BW373U86 | ||
| ⚫ | | legal_CA |
||
| ⚫ | | legal_UK |
||
| ⚫ | | legal_US |
||
| ⚫ | | legal_status |
||
| ⚫ | | routes_of_administration = |
||
| }} | }} | ||
| '''(+)BW373U86''' is an ] ] drug used in scientific research.<ref name="pmid9057856">{{cite journal |
'''(+)-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> | ||
| 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> | |||
| 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> | |||
| ==See also== | |||
| 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> | |||
| * ] | |||
| * ] | |||
| * ] | |||
| == References == | == References == | ||
| {{ |
{{Reflist|2}} | ||
| {{Opioidergics}} | |||
| {{Other respiratory system products}} | |||
| {{DEFAULTSORT:Bw373u86}} | {{DEFAULTSORT:Bw373u86}} | ||
| ] | ] | ||
| ] | ] | ||
| ] | ] | ||
| ] | ] | ||
| ] | ] | ||
| ] | ] | ||
| ] | ] | ||
| ] | ] | ||
| ] | |||
Latest revision as of 16:01, 21 October 2024
Opioid analgesic drug used in researchPharmaceutical compound
 | |
| Clinical data | |
|---|---|
| Other names | (+)-BW373U86 |
| Identifiers | |
IUPAC name
| |
| CAS Number | |
| PubChem CID | |
| ChemSpider | |
| UNII | |
| ChEMBL | |
| CompTox Dashboard (EPA) | |
| Chemical and physical data | |
| Formula | C27H37N3O2 |
| Molar mass | 435.612 g·mol |
| 3D model (JSmol) | |
SMILES
| |
InChI
| |
| (what is this?) (verify) | |
(+)-BW373U86 is an opioid analgesic drug used in scientific research.
BW373U86 is a selective agonist for the δ-opioid receptor, with approximately 15× stronger affinity for the δ-opioid than the μ-opioid receptor. It has potent analgesic and antidepressant effects in animal studies. 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.
See also
References
- 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. 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 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 (March 2001). "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 of Medicinal Chemistry. 44 (6): 972–987. doi:10.1021/jm000427g. PMID 11300879.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.