J-113,397

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J-113,397
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Systematic (IUPAC) name
1-[(3R,4R)-1-cyclooctylmethyl-3-hydroxymethyl-4-piperidyl]-3-ethyl-1, 3-dihydro-2H-benzimidazol-2-one
Identifiers
PubChem CID 5311194
IUPHAR/BPS 1691
Synonyms J-113,397
Chemical data
Formula C24H37N3O2
Molar mass 399.568 g/mol[[Script error: No such module "String".]]
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J-113,397 is an opioid analgesic drug which was the first compound found to be a highly selective antagonist for the nociceptin receptor, also known as the ORL-1 receptor.[1][2] It is several hundred times selective for the ORL-1 receptor over other opioid receptors,[3][4] and its effects in animals include preventing the development of tolerance to morphine[5], the prevention of hyperalgesia induced by intracerebroventricular administration of nociceptin (orphanin FQ),[6] as well as the stimulation of dopamine release in the striatum,[7] which increases the rewarding effects of cocaine,[8] but may have clinical application in the treatment of Parkinson's disease.[9][10][11]


See also

References

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  1. Kawamoto H, Ozaki S, Itoh Y, Miyaji M, Arai S, Nakashima H, Kato T, Ohta H, Iwasawa Y. 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. 1999 Dec 16;42(25):5061-3. PMID 10602690
  2. 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
  3. 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
  4. 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
  5. 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
  6. 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
  7. 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
  8. 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
  9. 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
  10. 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
  11. 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