Estetrol

Estetrol
Names
	IUPAC name Estra-1,3,5(10)-triene-3,15α,16α,17β-tetrol
	Systematic IUPAC name (1R,2R,3R,3aS,3bR,9bS,11aS)-11a-Methyl-2,3,3a,3b,4,5,9b,10,11,11a-decahydro-1H-cyclopenta[a]phenanthrene-1,2,3,7-tetrol
	Other names Oestetrol; E4; 15α-Hydroxyestriol
Identifiers
CAS Number	15183-37-6 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:142773;
ChEMBL	ChEMBL1230314;
ChemSpider	25245;
DrugBank	DB12235;
ECHA InfoCard	100.276.707
EC Number	840-340-4;
KEGG	D11513;
PubChem CID	27125;
UNII	ENB39R14VF ;
CompTox Dashboard (EPA)	DTXSID50164888 ;
	InChI InChI=1S/C18H24O4/c1-18-7-6-12-11-5-3-10(19)8-9(11)2-4-13(12)14(18)15(20)16(21)17(18)22/h3,5,8,12-17,19-22H,2,4,6-7H2,1H3/t12-,13-,14-,15-,16-,17+,18+/m1/s1 Key: AJIPIJNNOJSSQC-NYLIRDPKSA-N;
	SMILES C[C@]12CC[C@H]3[C@H]([C@@H]1[C@H]([C@H]([C@@H]2O)O)O)CCC4=C3C=CC(=C4)O;
Properties
Chemical formula	C18H24O4
Molar mass	304.386 g/mol
Solubility in water	1.38 mg/mL
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Estetrol (E4), or oestetrol, is one of the four natural estrogenic steroid hormones found in humans, along with estrone (E1), estradiol (E2), and estriol (E3). Estetrol is a major estrogen in the body.^[1]^[2] In contrast to estrone and estradiol, estetrol is a native estrogen of fetal life. Estetrol is produced exclusively by the fetal liver^[1] and is found in detectable levels only during pregnancy, with relatively high levels in the fetus and lower levels in the maternal circulation.^[1]^[2]

In addition to its physiological role as a native hormone, estetrol can be used as a medication, see estetrol (medication). Estetrol, in combination with drospirenone, has recently been approved as a new estrogenic component of a combined oral contraceptive (COC) and estetrol alone is in clinical development for the treatment of menopausal symptoms as well as breast and prostate cancer.

^ ^a ^b ^c Holinka CF, Diczfalusy E, Coelingh Bennink HJ (May 2008). "Estetrol: a unique steroid in human pregnancy". The Journal of Steroid Biochemistry and Molecular Biology. 110 (1–2): 138–143. doi:10.1016/j.jsbmb.2008.03.027. PMID 18462934. S2CID 28007341.
^ ^a ^b Yen SS, Jaffe RB, eds. (1991). Reproductive Endocrinology: Physiology, Pathophysiology, and Clinical Management (3rd ed.). Copyright Elsevier/Saunders. pp. 936–981.

[pmid18462934-1] Holinka CF, Diczfalusy E, Coelingh Bennink HJ (May 2008). "Estetrol: a unique steroid in human pregnancy". The Journal of Steroid Biochemistry and Molecular Biology. 110 (1–2): 138–143. doi:10.1016/j.jsbmb.2008.03.027. PMID 18462934. S2CID 28007341.

[YenJaffe1991-2] Yen SS, Jaffe RB, eds. (1991). Reproductive Endocrinology: Physiology, Pathophysiology, and Clinical Management (3rd ed.). Copyright Elsevier/Saunders. pp. 936–981.

[1]

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