Z4349

Z4349 is an opioid analgesic drug developed in the 1990s by the pharmaceutical company Zambon. It is a derivative of an older drug viminol, which has been modified to improve potency and metabolic stability. In tests on mice it was found to be several hundred times the potency of morphine.[1][2]

Z4349
Identifiers
IUPAC name
  • (5S)-5-[(1S)-2-[bis[(2R)-butan-2-yl]amino]-1-hydroxyethyl]-1-(2-chlorobenzyl)pyrrolidin-2-one
PubChem CID
ChemSpider
Chemical and physical data
FormulaC21H33ClN2O2
Molar mass380.96 g·mol−1
3D model (JSmol)
SMILES
  • CC[C@@H](C)N(C[C@@H]([C@@H]1CCC(=O)N1CC2=CC=CC=C2Cl)O)[C@H](C)CC
InChI
  • InChI=1S/C21H33ClN2O2/c1-5-15(3)23(16(4)6-2)14-20(25)19-11-12-21(26)24(19)13-17-9-7-8-10-18(17)22/h7-10,15-16,19-20,25H,5-6,11-14H2,1-4H3/t15-,16-,19+,20+/m1/s1
  • Key:YNGZJSALRCLELM-YKCBXCCJSA-N

See also

References
  1. US 4960788, Carenzi A, Chiarino D, Bella DD, Grancini GC, Veneziani C, "Pyrrolidone-2 compounds and their use for central analgesic activity", issued 2 October 1990, assigned to Zambon Group S.P.A.
  2. Napoletano M, Delia BD, Fraire C, Grancini G, Masotto C, Ricciardi S, Zambon C (1995). "Stereoselective synthesis and evaluation of all stereoisomers of Z4349, a novel and selective μ-opioid analgesic". Bioorganic & Medicinal Chemistry Letters. 5 (6): 589–592. doi:10.1016/0960-894X(95)00077-7.


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