27-Hydroxycholesterol
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 | |
CAS Number |
|
3D model (JSmol) |
|
ChemSpider |
|
IUPHAR/BPS |
|
PubChem CID |
|
UNII |
|
CompTox Dashboard (EPA) |
|
InChI
| |
| |
Properties | |
Chemical formula | 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
- ^ a b c d Mast N, Lin JB, Pikuleva IA (2015). "Marketed Drugs Can Inhibit Cytochrome P450 27A1, a Potential New Target for Breast Cancer Adjuvant Therapy". Mol. Pharmacol. 88 (3): 428–36. doi:10.1124/mol.115.099598. PMC 4551053. PMID 26082378.
- ^ Nelson ER, Wardell SE, Jasper JS, Park S, Suchindran S, Howe MK, Carver NJ, Pillai RV, Sullivan PM, Sondhi V, Umetani M, Geradts J, McDonnell DP (2013). "27-Hydroxycholesterol links hypercholesterolemia and breast cancer pathophysiology". Science. 342 (6162): 1094–8. Bibcode:2013Sci...342.1094N. doi:10.1126/science.1241908. PMC 3899689. PMID 24288332.
- v
- t
- e
- Cholesterol
- 22R-Hydroxycholesterol
- 20α,22R-Dihydroxycholesterol
- Pregnenolone
- 11β-Hydroxypregnenolone
- 17α-Hydroxypregnenolone
- 21-Hydroxypregnenolone
- 17α,21-Dihydroxypregnenolone
- 11β,17α,21-Trihydroxypregnenolone
- Cholestanes: 24S-Hydroxycholesterol
- Cholesterol
- Pregnanes: 3α-Dihydroprogesterone
- 3β-Dihydroprogesterone
- 5α-Dihydrocorticosterone
- 5α-Dihydroprogesterone
- 5β-Dihydroprogesterone
- Allopregnanolone
- Corticosterone
- DHC
- DHDOC
- 11-Deoxycorticosterone
- Epipregnanolone
- Isopregnanolone
- Pregnanolone
- Pregnenolone
- Pregnenolone sulfate
- Progesterone
- THB
- THDOC
This article about a steroid is a stub. You can help Wikipedia by expanding it. |
- v
- t
- e