PF-4455242

PF-4455242 is a selective, short-acting (non-"inactivating") antagonist of the κ-opioid receptor.[1][2] Discovered by Pfizer in 2009, it was pursued in a phase I clinical trial for the treatment of bipolar disorder,[3] and was also investigated as a treatment for depression and substance abuse.[4] However, development was stopped in September 2010 due to toxicology findings in animals that had been exposed to the drug for three months.[3]

PF-4455242
Clinical data
Routes of
administration		Oral
ATC code
  • None
Identifiers
IUPAC name
  • 2-Methyl-N-{[2’-(1-pyrrolidinylsulfonyl)-4-biphenylyl]methyl}-1-propanamine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC21H28N2O2S
Molar mass372.53 g·mol−1
3D model (JSmol)
SMILES
  • CC(C)CNCC1=CC=C(C=C1)C2=CC=CC=C2S(=O)(=O)N3CCCC3
InChI
  • InChI=1S/C21H28N2O2S/c1-17(2)15-22-16-18-9-11-19(12-10-18)20-7-3-4-8-21(20)26(24,25)23-13-5-6-14-23/h3-4,7-12,17,22H,5-6,13-16H2,1-2H3
  • Key:OWVIKBRKPCTDEP-UHFFFAOYSA-N

See also

References
  1. Verhoest PR, Basak AS, Parikh V, et al. (August 2011). "Design and discovery of a selective small molecule κ opioid antagonist (2-methyl-N-((2'-(pyrrolidin-1-ylsulfonyl)biphenyl-4-yl)methyl)propan-1-amine, PF-4455242)". J. Med. Chem. 54 (16): 5868–77. doi:10.1021/jm2006035. PMID 21744827.
  2. Melief EJ, Miyatake M, Carroll FI, et al. (November 2011). "Duration of action of a broad range of selective κ-opioid receptor antagonists is positively correlated with c-Jun N-terminal kinase-1 activation". Mol. Pharmacol. 80 (5): 920–9. doi:10.1124/mol.111.074195. PMC 3198912. PMID 21832171.
  3. Zoran Rankovic; Richard Hargreaves; Matilda Bingham (2012). Drug Discovery for Psychiatric Disorders. Royal Society of Chemistry. pp. 314–317. ISBN 978-1-84973-365-6.
  4. Charlotte Allerton; David Fox (2013). Pain Therapeutics: Current and Future Treatment Paradigms. Royal Society of Chemistry. p. 50. ISBN 978-1-84973-645-9.


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