Bromadoline

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Bromadoline
(1:1 mixture of trans isomers)
Bromadoline.png
Systematic (IUPAC) name
trans-4-bromo-N-(2-(dimethylamino)cyclohexyl)benzamide
Clinical data
Legal status ?
Identifiers
CAS number 67579-24-2 YesY
ATC code None
PubChem CID 54753
ChemSpider 49457 YesY
UNII R8DWN01P1M YesY
ChEMBL CHEMBL2110893
Synonyms Bromadoline
Chemical data
Formula C15H21BrN2O 
Mol. mass 325.244 g/mol
 YesY (what is this?)  (verify)

Bromadoline (U-47931E)[1] is an opioid analgesic selective for the mu-opioid receptor[2] developed by the Upjohn company in the 1970s.[3] The drug has a potency lying between that of codeine and morphine being slightly stronger than pentazocine.[4] It is presumed that the (1R,2R) isomer is the active opioid, overlaying as it does with many other mu agonists.[5] Bromadoline is related to AH-7921 and U-47700.[6]

Synthesis[edit]

Preparation of Bromadoline: U.S. Patent 4,098,904 Szmuszkovicz (1978) The Upjohn Company

See also[edit]

References[edit]

  1. ^ Unlisted Drugs, volumes 34-35, page 392
  2. ^ Hayes, A. G.; Skingle, M.; Tyers, M. B. (1987). "Evaluation of the receptor selectivities of opioid drugs by investigating the block of their effect on urine output by beta-funaltrexamine". The Journal of Pharmacology and Experimental Therapeutics 240 (3): 984–988. PMID 3559988.  edit
  3. ^ U.S. Patent 4,098,904
  4. ^ 'Differential sensitivity of models of antinociception in the rat, mouse and guinea-pig to IL- and K-opioid receptor agonists' A.G. Hayes, M.J. Sheehan & M.B. Tyers - Br. J. Pharmac. (1987), 91, 823-832
  5. ^ J Mol Model 'Insights into subtype selectivity of opioid agonists by ligand-based and structure-based methods' Jianxin Cheng & Guixia Liu & Jing Zhang & Zhejun Xu & Yun Tang
  6. ^ 'Factors Affecting Binding of trans-N-[2-(Methylamino)cyclohexyl]benzamides at the Primary Morphine receptor' B. Vernon Cheney, Jacob Smuszkovicz, Robert A. Lahtr & Dominic A. Zichi - J Med Chem. 1985 Dec;28(12):1853-64.