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SB-612,111

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SB-612,111 is an opioid receptor ligand which is a potent and selective antagonist for the nociceptin receptor (ORL-1), several times more potent than the older drug J-113,397.^[1] It does not have analgesic effects in its own right, but prevents the development of hyperalgesia,^[2] and also shows antidepressant effects in animal studies.^[3]

SB-612,111

Clinical data

Other names

SB-612,111

Identifiers

(5S,7S)-7-{[4-(2,6-dichlorophenyl)piperidin-1-yl]methyl}-1-methyl-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-ol

371980-98-2^N

10047612

1693

8223175^N

ChEMBL559569^N

CompTox Dashboard (EPA)

DTXSID301027159 DTXSID40610405, DTXSID301027159

Chemical and physical data

C₂₄H₂₉Cl₂NO

418.40 g·mol⁻¹

3D model (JSmol)

Interactive image

Interactive image

CC1=CC=CC2=C1CC[C@@H](C[C@@H]2O)CN3CCC(CC3)C4=C(C=CC=C4Cl)Cl

CC1=C2CC[C@@H](C[C@@H](C2=CC=C1)O)CN3CCC(CC3)C4=C(C=CC=C4Cl)Cl

InChI=1S/C24H29Cl2NO/c1-16-4-2-5-20-19(16)9-8-17(14-23(20)28)15-27-12-10-18(11-13-27)24-21(25)6-3-7-22(24)26/h2-7,17-18,23,28H,8-15H2,1H3/t17-,23-/m0/s1^N

Key:OHRDCQFCAWLDBP-SBUREZEXSA-N^N

^NY (what is this?) (verify)

See also

References

^ Spagnolo B, Carrà G, Fantin M, Fischetti C, Hebbes C, McDonald J, et al. (June 2007). "Pharmacological characterization of the nociceptin/orphanin FQ receptor antagonist SB-612111 [(-)-cis-1-methyl-7-4-(2,6-dichlorophenyl)piperidin-1-yl]methyl]-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-ol]: in vitro studies". The Journal of Pharmacology and Experimental Therapeutics. 321 (3): 961–7. doi:10.1124/jpet.106.116764. PMID 17329552. S2CID 17504101.

^ Zaratin PF, Petrone G, Sbacchi M, Garnier M, Fossati C, Petrillo P, et al. (February 2004). "Modification of nociception and morphine tolerance by the selective opiate receptor-like orphan receptor antagonist (-)-cis-1-methyl-7-4-(2,6-dichlorophenyl)piperidin-1-yl]methyl]-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-ol (SB-612111)". The Journal of Pharmacology and Experimental Therapeutics. 308 (2): 454–61. doi:10.1124/jpet.103.055848. PMID 14593080. S2CID 8036750.

^ Rizzi A, Gavioli EC, Marzola G, Spagnolo B, Zucchini S, Ciccocioppo R, et al. (June 2007). "Pharmacological characterization of the nociceptin/orphanin FQ receptor antagonist SB-612111 [(-)-cis-1-methyl-7-4-(2,6-dichlorophenyl)piperidin-1-yl]methyl]-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-ol]: in vivo studies". The Journal of Pharmacology and Experimental Therapeutics. 321 (3): 968–74. doi:10.1124/jpet.106.116780. PMID 17329551. S2CID 2557475.

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