J-113,397

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J-113,397
(IUPAC) ime
1-[(3R,4R)-1-ciklooktilmetil-3-hidrokismetil-4-piperidil]-3-etil-1, 3-dihidro-2H-benzimidazol-2-on
Klinički podaci
Identifikatori
ATC kod ?
PubChem[1][2] 5311194
ChEMBL[3] CHEMBL357076
Hemijski podaci
Formula C24H37N3O2 
Mol. masa 399,568 g/mol
SMILES eMolekuli & PubHem
Sinonimi J-113,397
Farmakoinformacioni podaci
Trudnoća ?
Pravni status

J-113,397 je opioidni analgetik koji je bio prvi visoko selektivni antagonist nociceptinskog receptora (ORL-1).[4][5] On je nekoliko stotina puta selektivniji za ORL-1 receptor nego za druge opioidne receptore.[6][7] Njegovi efekti u studijama na životinjama su sprečavanje razvoja tolerancije za morfin[8], prevencija hiperalgezije indukovane intracerebroventrikularnom administracijom nociceptina (orfanina FQ),[9] kao i stimulacija oslobađanja dopamina u strijatumu,[10] što povišava efekte nagrađivanja kokaina,[11] ali može da ima kliničku primenu u lečenju Parkinsonove bolesti.[12][13][14]

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Reference[uredi | uredi kod]

  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. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519.  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. ↑ Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594.  edit
  4. ↑ H. Kawamoto, S. Ozaki, Y. Itoh, M. Miyaji, S. Arai, H. Nakashima, T. Kato, H. Ohta & Y. Iwasawa (December 1999). „Discovery of the first potent and selective small molecule opioid receptor-like (ORL1) antagonist: 1-[(3R,4R)-1-cyclooctylmethyl-3- hydroxymethyl-4-piperidyl]-3-ethyl-1, 3-dihydro-2H-benzimidazol-2-one (J-113397)”. Journal of medicinal chemistry 42 (25): 5061–5063. PMID 10602690. 
  5. ↑ De Risi C, Piero Pollini G, Trapella C, Peretto I, Ronzoni S, Giardina GA. A new synthetic approach to 1-[(3R,4R)-1-cyclooctylmethyl-3-hydroxymethyl-4-piperidyl]-3-ethyl-1,3-dihydro-benzimidazol-2-one(J-113397), the first non-peptide ORL-1 receptor antagonist. Bioorganic and Medicinal Chemistry. 2001 Jul;9(7):1871-7. PMID 11425589
  6. ↑ Ozaki S, Kawamoto H, Itoh Y, Miyaji M, Iwasawa Y, Ohta H. A potent and highly selective nonpeptidyl nociceptin/orphanin FQ receptor (ORL1) antagonist: J-113397. European Journal of Pharmacology. 2000 Jan 17;387(3):R17-8. PMID 10650183
  7. ↑ Smith ED, Ariane Vinson N, Zhong D, Berrang BD, Catanzaro JL, Thomas JB, Navarro HA, Gilmour BP, Deschamps J, Carroll FI. A new synthesis of the ORL-1 antagonist 1-[(3R,4R)-1-cyclooctylmethyl-3-hydroxymethyl-4-piperidinyl]-3-ethyl-1,3-dihydro-2H-benzimidazol-2-one (J-113397) and activity in a calcium mobilization assay. Bioorganic and Medicinal Chemistry. 2008 Jan 15;16(2):822-9. PMID 17976996
  8. ↑ Chung S, Pohl S, Zeng J, Civelli O, Reinscheid RK. Endogenous orphanin FQ/nociceptin is involved in the development of morphine tolerance. Journal of Pharmacology and Experimental Therapeutics. 2006 Jul;318(1):262-7. PMID 16595734
  9. ↑ Ozaki S, Kawamoto H, Itoh Y, Miyaji M, Azuma T, Ichikawa D, Nambu H, Iguchi T, Iwasawa Y, Ohta H. In vitro and in vivo pharmacological characterization of J-113397, a potent and selective non-peptidyl ORL1 receptor antagonist. European Journal of Pharmacology. 2000 Aug 18;402(1-2):45-53. PMID 10940356
  10. ↑ Marti M, Mela F, Veronesi C, Guerrini R, Salvadori S, Federici M, Mercuri NB, Rizzi A, Franchi G, Beani L, Bianchi C, Morari M. Blockade of nociceptin/orphanin FQ receptor signaling in rat substantia nigra pars reticulata stimulates nigrostriatal dopaminergic transmission and motor behavior. Journal of Neuroscience. 2004 Jul 28;24(30):6659-66. PMID 15282268
  11. ↑ Marquez P, Nguyen AT, Hamid A, Lutfy K. The endogenous OFQ/N/ORL-1 receptor system regulates the rewarding effects of acute cocaine. Neuropharmacology. 2008 Mar;54(3):564-8. PMID 18082848
  12. ↑ Marti M, Trapella C, Viaro R, Morari M. The nociceptin/orphanin FQ receptor antagonist J-113397 and L-DOPA additively attenuate experimental parkinsonism through overinhibition of the nigrothalamic pathway. Journal of Neuroscience. 2007 Feb 7;27(6):1297-307. PMID 17287504
  13. ↑ Viaro R, Sanchez-Pernaute R, Marti M, Trapella C, Isacson O, Morari M. Nociceptin/orphanin FQ receptor blockade attenuates MPTP-induced parkinsonism. Neurobiology of Disease. 2008 Jun;30(3):430-8. PMID 18413287
  14. ↑ Visanji NP, de Bie RM, Johnston TH, McCreary AC, Brotchie JM, Fox SH. The nociceptin/orphanin FQ (NOP) receptor antagonist J-113397 enhances the effects of levodopa in the MPTP-lesioned nonhuman primate model of Parkinson's disease. Movement Disorders. 2008 Oct 15;23(13):1922-5. PMID 18759357

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