BW373U86

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BW373U86
(IUPAC) ime
4-[(R)-[(2S,5R)-2,5-dimethyl-4-prop-2-enylpiperazin-1-yl]-(3-hydroxyphenyl)methyl]-N,N-diethylbenzamide
Klinički podaci
Identifikatori
CAS broj 150428-54-9
ATC kod  ?
PubChem[1][2] 119029
Hemijski podaci
Formula C27H37N3O2 
Mol. masa 435.602 g/mol
SMILES eMolekuli & PubHem
Sinonimi (+)BW373U86
Farmakoinformacioni podaci
Trudnoća  ?
Pravni status

(+)BW373U86 je opioidni analgetik koji se koristi u naučnim istraživanjma.[3][4]

BW373U86 je selektivni agonist δ-opioidnog receptora, sa aproksimativno 15x većim afinitetom za δ-opioidni nego za μ-opioidni receptor.[5] On se pokazao kao potentan analgetik[6] i antidepresant u životinjskim studijama,[7] koji inicira oslobađanje neuronskog faktora rasta BDNF,[8][9] ali je njegova upotrebljivost ograničena usled stvaranja konvulzija na visokim dozama,[10][11] mada su ti efekti umanjeni kad se dozira zajedno sa μ-opioidnim agonistima.[12] Još jedna prednost kombinovanja je da BW373U86 poništava respiratornu depresiju proizvedenu μ-opioidnim agonistima, bez vršenja uticaja na umanjenje bola.[13]

Jedno dodatno svojstvo BW373U86 je da zaštićuje ćelije mišića srca u ishemijskim uslovima (kiseonična deprivacija, kao što je to slučaj kod srčanog udara). Mehanizam za to je kompleksan i možda nije vezan sa delta agonistnim efektima.[14][15][16]

Literatura[uredi - уреди | uredi izvor]

  1. Li Q, Cheng T, Wang Y, Bryant SH (2010). "PubChem as a public resource for drug discovery.". Drug Discov Today 15 (23-24): 1052–7. PMID 20970519. doi:10.1016/j.drudis.2010.10.003.  edit
  2. Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). "Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities". Annual Reports in Computational Chemistry 4: 217–241. doi:10.1016/S1574-1400(08)00012-1. 
  3. 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-[(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". J. Med. Chem. 40 (5): 695–704. PMID 9057856. doi:10.1021/jm960319n. 
  4. 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 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. PMID 11300879. 
  5. 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): 852–7. PMID 8246159. 
  6. Broom, D. C.; Nitsche, JF; Pintar, JE; Rice, KC; Woods, JH; Traynor, JR (November 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. PMID 12388657. doi:10.1124/jpet.102.036525. 
  7. Broom, D; 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. PMID 12007745. doi:10.1016/S0893-133X(01)00413-4. 
  8. Torregrossa, Mary M.; Folk, John E.; Rice, Kenner C.; Watson, Stanley J.; Woods, James H. (November 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. PMC 1315298. PMID 16220339. doi:10.1007/s00213-005-0113-5. 
  9. Torregrossa, Mary M; Isgor, Ceylan; Folk, John E; Rice, Kenner C; Watson, Stanley J; Woods, James H (April 2004). "The δ-Opioid Receptor Agonist (+)BW373U86 Regulates BDNF mRNA Expression in Rats". Neuropsychopharmacology 29 (4): 649–659. PMID 14647482. doi:10.1038/sj.npp.1300345. 
  10. Comer, SD; Hoenicke, EM; Sable, AI; McNutt, RW; Chang, KJ; De Costa, BR; Mosberg, HI; Woods, JH (November 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. 
  11. Broom, Daniel; Jutkiewicz, Emily; Folk, John; Traynor, John; Rice, Kenner; Woods, James (October 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. PMID 12373418. doi:10.1007/s00213-002-1179-y. 
  12. O'Neill, SJ; Collins, MA; Pettit, HO; McNutt, RW; Chang, KJ (July 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. 
  13. Su, YF; McNutt, RW; Chang, KJ (December 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. 
  14. Patel, H; 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. PMID 11448134. doi:10.1006/jmcc.2001.1408. 
  15. Patel, H; 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. PMID 15120566. doi:10.1016/j.lfs.2003.10.036. 
  16. Gross, E. R.; Hsu, A. K.; Gross, G. J. (July 2007). "GSK3β inhibition and KATP channel opening mediate acute opioid-induced cardioprotection at reperfusion". Basic Research in Cardiology 102 (4): 341–349. PMID 17450314. doi:10.1007/s00395-007-0651-6. 

Spoljašnje veze[uredi - уреди | uredi izvor]


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