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Thienorphine

Thienorphine
Clinical data
ATC code
  • None
Identifiers
  • (1R,2R,6S,15R)-3-(cyclopropylmethyl)-16-[(2R)-2-hydroxy-4-(thiophen-2-yl)butan-2-yl]-15-methoxy-13-oxa-3-azahexacyclo[13.2.2.12,8.01,6.06,14.07,12]icosa-7,9,11-trien-11-ol
PubChem CID
ChemSpider
Chemical and physical data
FormulaC31H39NO4S
Molar mass521.72 g·mol−1
3D model (JSmol)
  • C[C@@](CCc1cccs1)([C@H]2C[C@@]34CCC2([C@H]5[C@@]36CCN([C@@H]4Cc7c6c(c(cc7)O)O5)CC8CC8)OC)O
  • InChI=1S/C31H39NO4S/c1-28(34,10-9-21-4-3-15-37-21)23-17-29-11-12-31(23,35-2)27-30(29)13-14-32(18-19-5-6-19)24(29)16-20-7-8-22(33)26(36-27)25(20)30/h3-4,7-8,15,19,23-24,27,33-34H,5-6,9-14,16-18H2,1-2H3/t23-,24-,27-,28-,29-,30+,31-/m1/s1
  • Key:WTGSHWLSWVFVAH-JTTXIWGLSA-N

Thienorphine is a very potent, extremely long-acting, orally-active opioid analgesic with mixed agonist–antagonist properties which was developed by the Beijing Institute of Pharmacology and Toxicology as a potential treatment for opioid dependence.[1][2][3] It is a high-affinity, balanced ligand of the μ- (Ki = 0.22 nM), δ- (Ki = 0.69 nM), and κ-opioid receptors (Ki = 0.14 nM), behaving as a partial agonist of the μ- (Emax = 19%–28%) and κ-opioid receptors (Emax = 65–75%) and as an antagonist of the δ-opioid receptor.[4][5][6] It also possesses relatively low affinity for the nociceptin receptor (Ki = 36.5 nM), where it acts as an antagonist.[6]

See also

References

  1. ^ Liu H, Zhong BH, Liu CH, Wu B, Gong ZH (2005). "Synthesis, Crystal Structural and Pharmacological Study of N-Cyclopropylmehtyl-7α-[(R)-1-hydroxyl-1-methyl-3-(thien-2-yl)propyl]-6,14-endoethanotetrahydronooripavine" (PDF). Acta Chimica Slovenica. 52 (1): 80–85. ISSN 1318-0207.
  2. ^ Yu G, Liu YS, Yan LD, Wen Q, Gong ZH (July 2009). "[Structure-activity relationships analysis of thienorphine and its derivatives]". Yao Xue Xue Bao [Acta Pharmaceutica Sinica] (in Chinese). 44 (7): 726–730. PMID 19806910.
  3. ^ Yu G, Li SH, Cui MX, Yan LD, Yong Z, Zhou PL, et al. (March 2014). "Multiple mechanisms underlying the long duration of action of thienorphine, a novel partial opioid agonist for the treatment of addiction". CNS Neuroscience & Therapeutics. 20 (3): 282–288. doi:10.1111/cns.12210. PMC 6492997. PMID 24330593.
  4. ^ Yu G, Yue YJ, Cui MX, Gong ZH (July 2006). "Thienorphine is a potent long-acting partial opioid agonist: a comparative study with buprenorphine". The Journal of Pharmacology and Experimental Therapeutics. 318 (1): 282–287. doi:10.1124/jpet.105.099937. PMID 16569757. S2CID 24549788.
  5. ^ Li JX, Becker GL, Traynor JR, Gong ZH, France CP (April 2007). "Thienorphine: receptor binding and behavioral effects in rhesus monkeys". The Journal of Pharmacology and Experimental Therapeutics. 321 (1): 227–236. doi:10.1124/jpet.106.113290. PMID 17220427. S2CID 11477535.
  6. ^ a b Wen Q, Yu G, Li YL, Yan LD, Gong ZH (October 2011). "Pharmacological mechanisms underlying the antinociceptive and tolerance effects of the 6,14-bridged oripavine compound 030418". Acta Pharmacologica Sinica. 32 (10): 1215–1224. doi:10.1038/aps.2011.83. PMC 4010084. PMID 21863064.


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