PF-00446687

PF-00446687 is a drug developed by Pfizer for the treatment of erectile dysfunction, which is a non-peptide agonist selective for the melanocortin receptor subtype MC4. It was found to be active in preliminary human trials, with the 200mg dose being of similar effectiveness to 100mg sildenafil, though lower doses were ineffective.

PF-00446687
Identifiers
IUPAC name
  • (3R,4R,5S)-1-([(3S,4R)-1-tert-butyl-4-(2,4-difluorophenyl)pyrrolidin-3-yl]carbonyl)-3,5-dimethyl-4-phenylpiperidin-4-ol
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC28H36F2N2O2
Molar mass470.593 g·mol−1
3D model (JSmol)
SMILES
  • C[C@@H]1CN(C[C@@H]([C@]1(c2ccccc2)O)C)C(=O)[C@@H]3CN(C[C@H]3c4ccc(cc4F)F)C(C)(C)C
InChI
  • InChI=1S/C28H36F2N2O2/c1-18-14-31(15-19(2)28(18,34)20-9-7-6-8-10-20)26(33)24-17-32(27(3,4)5)16-23(24)22-12-11-21(29)13-25(22)30/h6-13,18-19,23-24,34H,14-17H2,1-5H3/t18-,19+,23-,24+,28-/m0/s1
  • Key:WHPJOAUPIZDJNX-AGGGUQDCSA-N

While it is unclear whether PF-00446687 itself will be potent and effective enough to be developed for medical use, it has demonstrated that selectively targeting the MC4 subtype can produce similar aphrodisiac effects to older non-selective peptide-based melanocortin receptor agonists like melanotan II and bremelanotide, without the side effects caused by action at the other melanocortin receptor subtypes.[1][2]

See also

References
  1. US 7649002, Calabrese A, Fradet D, Hepworth D, Lansdell M, "Pharmaceutically active compounds.", published 11 August 2005, assigned to Pfizer Inc
  2. Lansdell MI, Hepworth D, Calabrese A, Brown AD, Blagg J, Burring DJ, et al. (April 2010). "Discovery of a selective small-molecule melanocortin-4 receptor agonist with efficacy in a pilot study of sexual dysfunction in humans". Journal of Medicinal Chemistry. 53 (8): 3183–97. doi:10.1021/jm9017866. PMID 20329799.
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