PF-00446687

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	862281-92-3 ;
PubChem CID	11328898;
ChemSpider	24669573;
UNII	63P236Z73I;
Chemical and physical data
Formula	C28H36F2N2O2
Molar mass	470.605 g·mol−1
3D model (JSmol)	Interactive image;
	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;

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.

Research

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]

References

^ US 7649002, Calabrese A, Fradet D, Hepworth D, Lansdell M, "Pharmaceutically active compounds.", published 11 August 2005, assigned to Pfizer Inc
^ 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.

External links

Prosolution Plus Clinical Study

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[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.

[1]

[2]

PF-00446687

Contents

Research

See also

References

External links

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	862281-92-3^Y
PubChem CID	11328898
ChemSpider	24669573
UNII	63P236Z73I
Chemical and physical data
Formula	C₂₈H₃₆F₂N₂O₂
Molar mass	470.605 g·mol⁻¹
3D model (JSmol)	Interactive image
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