27-Hydroxycholesterol - Misplaced Pages

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27-Hydroxycholesterol
Names

IUPAC name Cholest-5-ene-3β,27-diol
Systematic IUPAC name (1R,3aS,3bS,7S,9aR,9bS,11aR)-1--9a,11a-dimethyl-2,3,3a,3b,4,6,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopentaphenanthren-7-ol
Identifiers
CAS Number	20380-11-4
3D model (JSmol)	Interactive image
ChemSpider	110495
IUPHAR/BPS	2752
PubChem CID	123976
UNII	6T2NA6P5SQ
CompTox Dashboard (EPA)	DTXSID40864941
InChI InChI=1S/C27H46O2/c1-18(17-28)6-5-7-19(2)23-10-11-24-22-9-8-20-16-21(29)12-14-26(20,3)25(22)13-15-27(23,24)4/h8,18-19,21-25,28-29H,5-7,9-17H2,1-4H3/t18-,19-,21+,22+,23-,24+,25+,26+,27-/m1/s1Key: FYHRJWMENCALJY-YSQMORBQSA-N
SMILES C(CCC(C)1CC21(CC32CC=C43(CC(C4)O)C)C)CO
Properties
Chemical formula	C₂₇H₄₆O₂
Molar mass	402.663 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

Chemical compound

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). It is a metabolite of cholesterol that is produced by the enzyme CYP27A1.

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. 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. 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.

References

^ 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.

Metabolites: 5α-Dihydrocortisol
3α,5α-Tetrahydrocortisol

Cholestanes: 24S-Hydroxycholesterol
Cholesterol

Others

Estrogen receptor modulators

ERTooltip Estrogen receptor

Agonists

Unknown/unsorted: ERB-26
ERA-45
ERB-79
ZK-283197

Xenoestrogens: Anise-related (e.g., anethole, anol, dianethole, dianol, photoanethole)
Chalconoids (e.g., isoliquiritigenin, phloretin, phlorizin (phloridzin), wedelolactone)
Coumestans (e.g., coumestrol, psoralidin)
Flavonoids (incl. 7,8-DHF, 8-prenylnaringenin, apigenin, baicalein, baicalin, biochanin A, calycosin, catechin, daidzein, daidzin, ECG, EGCG, epicatechin, equol, formononetin, glabrene, glabridin, genistein, genistin, glycitein, kaempferol, liquiritigenin, mirificin, myricetin, naringenin, penduletin, pinocembrin, prunetin, puerarin, quercetin, tectoridin, tectorigenin)
Lavender oil
Lignans (e.g., enterodiol, enterolactone, nyasol (cis-hinokiresinol))
Metalloestrogens (e.g., cadmium)
Pesticides (e.g., alternariol, dieldrin, endosulfan, fenarimol, HPTE, methiocarb, methoxychlor, triclocarban, triclosan)
Phytosteroids (e.g., digitoxin (digitalis), diosgenin, guggulsterone)
Phytosterols (e.g., β-sitosterol, campesterol, stigmasterol)
Resorcylic acid lactones (e.g., zearalanone, α-zearalenol, β-zearalenol, zearalenone, zeranol (α-zearalanol), taleranol (teranol, β-zearalanol))
Steroid-like (e.g., deoxymiroestrol, miroestrol)
Stilbenoids (e.g., resveratrol, rhaponticin)
Synthetic xenoestrogens (e.g., alkylphenols, bisphenols (e.g., BPA, BPF, BPS), DDT, parabens, PBBs, PHBA, phthalates, PCBs)
Others (e.g., agnuside, rotundifuran)

Mixed
(SERMsTooltip Selective estrogen receptor modulators)

Antagonists

Coregulator-binding modulators: ERX-11

Noncompetitive inhibitors: Trilostane

GPERTooltip G protein-coupled estrogen receptor

Agonists	2-Methoxyestradiol 7β-Hydroxyepiandrosterone Afimoxifene (4-hydroxytamoxifen) Aldosterone Atrazine Bisphenol A Daidzein DDT (p,p'-DDT, o',p'-DDE) Diarylpropionitrile Equol Estradiol Ethinylestradiol Fulvestrant (ICI-182780) G-1 Genistein GPER-L1 GPER-L2 Hydroxytyrosol Kepone Nicotinic acid Nicotinamide Nonylphenol Oleuropein PCBs (2,2',5'-PCB-4-OH) Propylpyrazoletriol Quercetin Raloxifene Resveratrol STX Tamoxifen Tectoridin
Antagonists	CCL18 Estriol G-15 G-36 MIBE
Unknown	Diethylstilbestrol Zearalenone

See also: Receptor/signaling modulators; Estrogens and antiestrogens; Androgen receptor modulators; Progesterone receptor modulators; List of estrogens

v t e FXRTooltip Farnesoid X receptor and LXRTooltip liver X receptor modulators
FXRTooltip Farnesoid X receptor	Agonists: Bile acids Cafestol Chenodeoxycholic acid Cilofexor Fexaramine GW-4064 Ivermectin Nidufexor Obeticholic acid Tropifexor Antagonists: Guggulsterone
LXRTooltip Liver X receptor	Agonists: 22R-Hydroxycholesterol 24S-Hydroxycholesterol 27-Hydroxycholesterol Abequolixron Cholestenoic acid DMHCA GW-3965 Hypocholamide T-0901317 Antagonists: Efavirenz Larsucosterol
See also Receptor/signaling modulators

FXRTooltip Farnesoid X receptor and LXRTooltip liver X receptor modulators

FXRTooltip Farnesoid X receptor

Antagonists: Guggulsterone

LXRTooltip Liver X receptor

Antagonists: Efavirenz
Larsucosterol

See also: Receptor/signaling modulators

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