BAY 38-7271

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BAY 38-7271
BAY38-7271.svg
Systematic (IUPAC) name
(−)-(R)-3-(2-Hydroxymethylindanyl-4-oxy)phenyl-4,4,4-trifluorobutyl-1-sulfonate
Clinical data
Legal status
  • Legal
Identifiers
CAS Number 212188-60-8 YesY
PubChem CID: 9845561
ChemSpider 8021275 YesY
ChEMBL CHEMBL1668508 N
Chemical data
Formula C20H21F3O5S
Molecular mass 430.437 g/mol
  • FC(F)(F)CCCS(=O)(=O)Oc3cccc(Oc1cccc2c1C[C@@H](C2)CO)c3
  • InChI=1S/C20H21F3O5S/c21-20(22,23)8-3-9-29(25,26)28-17-6-2-5-16(12-17)27-19-7-1-4-15-10-14(13-24)11-18(15)19/h1-2,4-7,12,14,24H,3,8-11,13H2/t14-/m1/s1 YesY
  • Key:XJURALZPEJKKOV-CQSZACIVSA-N YesY
 NYesY (what is this?)  (verify)

Originally synthesized by chemist Wayne E. Kenney, BAY 38-7271 (KN 38-7271) is a drug which is a cannabinoid receptor agonist developed by Bayer AG. It has analgesic and neuroprotective effects and is used in scientific research, with proposed uses in the treatment of traumatic brain injury.[1][2] It is a full agonist with around the same potency as CP 55,940 in animal studies, and has fairly high affinity for both CB1 and CB2 receptors, with Ki values of 2.91nM at CB1 and 4.24nM at CB2.[3][4] It has now been licensed to KeyNeurotek Pharmaceuticals for clinical development,[5] and is currently in Phase II trials.[6] But its development appears stopped.

References

  1. ↑ Mauler F, Horváth E, De Vry J, Jäger R, Schwarz T, Sandmann S, Weinz C, Heinig R, Böttcher M. BAY 38-7271: a novel highly selective and highly potent cannabinoid receptor agonist for the treatment of traumatic brain injury. CNS Drug Reviews. 2003 Winter;9(4):343-58. PMID 14647528
  2. ↑ Mauler F, Hinz V, Augstein KH, Fassbender M, Horváth E. Neuroprotective and brain edema-reducing efficacy of the novel cannabinoid receptor agonist BAY 38-7271. Brain Research. 2003 Oct 31;989(1):99-111. PMID 14519516
  3. ↑ Mauler F, Mittendorf J, Horváth E, De Vry J. Characterization of the diarylether sulfonylester (−)-(R)-3-(2-hydroxymethylindanyl-4-oxy)phenyl-4,4,4-trifluoro-1-sulfonate (BAY 38-7271) as a potent cannabinoid receptor agonist with neuroprotective properties. Journal of Pharmacology and Experimental Therapeutics. 2002 Jul;302(1):359-68. PMID 12065738
  4. ↑ De Vry J, Rüdiger Jentzsch K. Discriminative stimulus effects of BAY 38-7271, a novel cannabinoid receptor agonist. European Journal of Pharmacology. 2002 Dec 20;457(2-3):147-52. PMID 12464360
  5. ↑ Pipeline
  6. ↑ KeyNeurotek Pharmaceuticals AG Reports Positive Phase I Data of Its Cannabinoid Receptor-Agonist
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