 | |
| Names | |
|---|---|
| IUPAC name Cholest-5-ene-3β,27-diol | |
| Systematic IUPAC name (1R,3aS,3bS,7S,9aR,9bS,11aR)-1-[(2R,6R)-7-Hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-2,3,3a,3b,4,6,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[a]phenanthren-7-ol | |
| Identifiers | |
3D model (JSmol) | |
| ChemSpider | |
| UNII | |
| |
| |
| Properties | |
| C27H46O2 | |
| Molar mass | 402.663 g·mol−1 |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
27-Hydroxycholesterol (27-HC) is anendogenousoxysterol with multiplebiological functions, including activity as aselective estrogen receptor modulator (SERM) (a mixed, tissue-specificagonist-antagonist of theestrogen receptor (ER)) and as anagonist of theliver X receptor (LXR).[1] It is ametabolite ofcholesterol that is produced by theenzymeCYP27A1.[1]
A link between high cholesterol and breast cancer has been identified, and it has been proposed that this is due to 27-HC production by CYP27A1.[2] Because of its estrogenic action, 27-HC stimulates the growth of ER-positivebreast cancer cells, and has been implicated in limiting the effectiveness ofaromatase inhibitors in the treatment of breast cancer.[1] As such, identified CYP27A1 inhibitors, including the marketed drugsanastrozole,fadrozole,bicalutamide,dexmedetomidine,ravuconazole, andposaconazole, have been proposed as potentialadjuvant therapies in ER-positive breast cancer.[1]
