Chemistry:27-Hydroxycholesterol
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| IUPAC name
Cholest-5-ene-3β,27-diol
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| 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)
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PubChem CID
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| Properties | |
| C27H46O2 | |
| Molar mass | 402.663 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
27-Hydroxycholesterol (27-HC) is an endogenous oxysterol with multiple biological functions, including activity as a selective estrogen receptor modulator (SERM) (a mixed, tissue-specific agonist-antagonist of the estrogen receptor (ER)) and as an agonist of the liver X receptor (LXR).[1] It is a metabolite of cholesterol that is produced by the enzyme CYP27A1.[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-positive breast cancer cells, and has been implicated in limiting the effectiveness of aromatase inhibitors in the treatment of breast cancer.[1] As such, identified CYP27A1 inhibitors, including the marketed drugs anastrozole, fadrozole, bicalutamide, dexmedetomidine, ravuconazole, and posaconazole, have been proposed as potential adjuvant therapies in ER-positive breast cancer.[1]
See also
References
- ↑ 1.0 1.1 1.2 1.3 "Marketed Drugs Can Inhibit Cytochrome P450 27A1, a Potential New Target for Breast Cancer Adjuvant Therapy". Mol. Pharmacol. 88 (3): 428–36. 2015. doi:10.1124/mol.115.099598. PMID 26082378.
- ↑ "27-Hydroxycholesterol links hypercholesterolemia and breast cancer pathophysiology". Science 342 (6162): 1094–8. 2013. doi:10.1126/science.1241908. PMID 24288332. Bibcode: 2013Sci...342.1094N.
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