BW373U86
 | |
| IUPAC ime | |
|---|---|
4-[(R)-[(2S,5R)-2,5-dimethyl-4-prop-2-enylpiperazin-1-yl]-(3-hydroxyphenyl)methyl]-N,N-diethylbenzamide | |
| Identifikatori | |
| CAS broj | 150428-54-9  |
| PubChem | CID 119029 |
| Sinonimi | (+)BW373U86 |
| Hemijski podaci | |
| Formula | C27H37N3O2 |
| Molarna masa | 435.602 g/mol |
| |
(+)BW373U86 je opioidni analgetik koji se koristi u naučnim istraživanjma.[1][2]
BW373U86 je selektivni agonist δ-opioidnog receptora, sa približno 15x većim afinitetom za δ-opioidni nego za μ-opioidni receptor.[3] On se pokazao kao potentan analgetik[4] i antidepresant u životinjskim studijama,[5] koji inicira oslobađanje neuronskog faktora rasta BDNF,[6][7] ali je njegova upotrebljivost ograničena usled stvaranja konvulzija na visokim dozama,[8][9] mada su ti efekti umanjeni kad se dozira zajedno sa μ-opioidnim agonistima.[10] Još jedna prednost kombinovanja je da BW373U86 poništava respiratornu depresiju proizvedenu μ-opioidnim agonistima, bez vršenja uticaja na umanjenje bola.[11]
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.[12][13][14]
Literatura
[уреди | уреди извор]- ^ 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.
- ^ 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 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.
- ^ Chang, KJ; Rigdon, GC; Howard, JL; McNutt, RW (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.
- ^ Broom, D. C.; Nitsche, JF; Pintar, JE; Rice, KC; Woods, JH; Traynor, JR (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.
- ^ Broom, D; 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. PMID 12007745. doi:10.1016/S0893-133X(01)00413-4.
- ^ Torregrossa, Mary M.; Folk, John E.; Rice, Kenner C.; Watson, Stanley J.; Woods, James H. (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.
- ^ Torregrossa, Mary M; Isgor, Ceylan; Folk, John E; Rice, Kenner C; Watson, Stanley J; Woods, James H (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.
- ^ Comer, SD; Hoenicke, EM; Sable, AI; McNutt, RW; Chang, KJ; De Costa, BR; Mosberg, HI; Woods, JH (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.
- ^ Broom, Daniel; Jutkiewicz, Emily; Folk, John; Traynor, John; Rice, Kenner; Woods, James (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.
- ^ O'Neill, SJ; Collins, MA; Pettit, HO; McNutt, RW; Chang, KJ (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.
- ^ Su, YF; McNutt, RW; Chang, KJ (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.
- ^ Patel, H; 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. PMID 11448134. doi:10.1006/jmcc.2001.1408.
- ^ Patel, H; Hsu, AK; Gross, GJ (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.
- ^ Gross, E. R.; Hsu, A. K.; Gross, G. J. (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
[уреди | уреди извор]
| Opijum i derivati makove stabljike |
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| Morfinani |
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| Benzomorfani | 5,9-DEHB • 8-Karboksamidociklazocin • Alazocin • Anazocin • Bremazocin • Cogazocin • Dezocin • Eptazocin • Etazocin • Etilketociklazocin • Fluorofen • Ketazocin • Metazocin • Pentazocin • Fenazocin • Kuadazocine • Tiazocin • Tonazocin • Volazocin • Zenazocin | ||||||||||||||||||||||||||||||||
| 4-Fenilpiperidini |
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| Opioidi otvorenog lanca |
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| Anilidopiperidini | 3-Alilfentanil • 3-Metilfentanil • 3-Metiltiofentanil • 4-fenilfentanil • Alfentanil • α-metilacetilfentanil • α-metilfentanil • α-metiltiofentanil • Benzilfentanil • β-hidroksifentanil • β-hidroksitiofentanil • β-metilfentanil • Brifentanil • Karfentanil • Fentanil • Lofentanil • Mirfentanil • Okfentanil • Ohmefentanil • Parafluorofentanil • fenaridin • Remifentanil • Sufentanil • Tenilfentanil • Tiofentanil • Trefentanil | ||||||||||||||||||||||||||||||||
| Oripavinski derivati | 6,14-Endoeteno tetrahidro oripavin • 7-PET • Acetorfin • Aletorfin • BU-48 • Buprenorfin • Butorfin • Ciprenorfin • Dihidroetorfin • Etorfin • 18,19-Dehidrobuprenorfin (HS-599) • N-ciklopropilmetil-noretorfin • Nepenton • Norbuprenorfin • N-fenetiletorfin • Tevinon • Tienorfin | ||||||||||||||||||||||||||||||||
| Fenazepani | |||||||||||||||||||||||||||||||||
| Pirinitramidi | |||||||||||||||||||||||||||||||||
| Benzimidazoli | Klonitazen • Etonitazen • Nitazen | ||||||||||||||||||||||||||||||||
| Indoli | 18-MC • 7-Acetoksimitraginin • 7-Hidroksimitraginin • Akuamidin • Akuamin • Eserolin • Hodgkinsin • Mitraginin • Pericin • ψ-Akuamigin | ||||||||||||||||||||||||||||||||
| Difenilmetilpiperazini | |||||||||||||||||||||||||||||||||
| Opioidni peptidi vidi još: Opioidni neuropeptidi | Adrenorfin • Amidorfin • Kasomorfin • DADLE • DALDA • DAMGO • Dermenkefalin • Dermorfin • Deltorfin • DPDPE • Dinorfin • Endomorfin • Endorfins • Enkefalin • Gliadorfin • Morficeptin • Nociceptin • Oktreotid • Opiorfin • Rubiskolin • TRIMU 5 | ||||||||||||||||||||||||||||||||
| Drugi | 3-(3-Metoksifenil)-3-etoksikarboniltropan • AD-1211 • AH-7921 • Azaprocin • BDPC • Bisnortilidin • BRL-52537 • Bromadolin • C-8813 • Ciramadol • Dokspikomin • Enadolin • Fakseladol • GR-89696 • Herkinorin • ICI-199,441 • ICI-204,448 • J-113,397 • JTC-801 • Ketamin • LPK-26 • Metofolin • MT-45 • N-Desmetilklozapin • NNC 63-0532 • Nortilidin • O-Desmetiltramadol • Fenadon • Fenciklidin • Prodilidin • Profadol • Ro64-6198 • Salvinorin A • SB-612,111 • SC-17599 • RWJ-394,674 • TAN-67 • Tapentadol • Tecodin • Tifluadom • Tilidin • Tramadol • Trimebutin • U-50,488 • U-69,593 • Viminol • W-18 • | ||||||||||||||||||||||||||||||||
| Opioidni antagonisti & Inverzni agonisti | 5'-Guanidinonaltrindol • β-Funaltreksamin • 6β-Naltreksol • Alvimopan • Binaltorfimin • Hlornaltreksamin • Hlocinamoks • Ciklazocin • Ciprodim • Diprenorfin (M5050) • Fedotozin • JDTic • Levalorfan • Metocinamoks • Metilnaltrekson • Nalfurafin • Nalmefen • Nalmekson • Naloksazon • Naloksonazin • Nalokson • Nalokson benzoilhidrazon • Nalorfin • Naltrekson • Naltriben • Naltrindol • Norbinaltorfimin • Oksilorfan • S-alil-3-hidroksi-17-tioniamorfinan (SAHTM) | ||||||||||||||||||||||||||||||||
 | Molimo Vas, obratite pažnju na važno upozorenje u vezi sa temama iz oblasti medicine (zdravlja). |
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