Estrone

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Estrone
Systematic (IUPAC) name
3-hydroxy-13-methyl- 6,7,8,9,11,12,13,14,15,16- decahydrocyclopenta[a]phenanthren- 17- one
Identifiers
CAS number	53-16-7
ATC code	G03CA07 G03CC04
PubChem	5870
DrugBank	APRD00588
Chemical data
Formula	C18H22O2
Mol. weight	270.366 g/mol
Physical data
Melt. point	254.5 °C (490 °F)
Pharmacokinetic data
Bioavailability	?
Protein binding	>95%
Metabolism	?
Half life	19 hours
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status
Routes	?

Estrone (also oestrone) is an estrogenic hormone secreted by the ovary. Its molecular formula is C₁₈H₂₂O₂. Estrone has a melting point of 254.5 degrees Celsius. Estrone is one of the three estrogens, which also include estriol and estradiol. Estrone is the least prevalent of the three hormones, estradiol being prevalent almost always in a female body, estriol being prevalent primarily during pregnancy. Estrone is relevant to health and disease due to its conversion to estrone sulfate, a long-lived derivative of estrone. Estrone sulfate acts as a pool of estrone which can be converted as needed to the more active estradiol.

[edit] Synthesis

Estrone is synthesized from androstenedione, a derivative of progesterone. The conversion consists of the de-methylation of C-19 and the aromaticity of the 'A' ring. This reaction is similar to the conversion of testosterone to estradiol.

Sex hormones and related medications (primarily G03, also L02, H01C) edit
Progestogens: (receptor)	Desogestrel, Drospirenone, Dydrogesterone, Ethisterone, Etonogestrel, Ethynodiol diacetate, Gestodene, Gestonorone, Levonorgestrel, Lynestrenol, Medroxyprogesterone, Megestrol, Norelgestromin, Norethisterone, Norethynodrel, Norgestimate, Norgestrel, Norgestrienone, Tibolone Antiprogestogen: Mifepristone
Androgens: (receptor)	Androstanolone, Fluoxymesterone, Mesterolone, Methyltestosterone, Testosterone, (see also anabolic steroids) Antiandrogens: Bicalutamide, Cyproterone, Flutamide, Nilutamide, Spironolactone
Estrogens: (receptor)	Chlorotrianisene, Dienestrol, Diethylstilbestrol, Estradiol, Estriol, Estrone, Ethinylestradiol, Fosfestrol, Mestranol, Polyestradiol phosphate Selective estrogen receptor modulator: Bazedoxifene, Clomifene, Fulvestrant, Raloxifene, Tamoxifen, Toremifene Aromatase inhibitor: Aminogluthetimide, Anastrozole, Exemestane, Formestane, Letrozole, Vorozole
Gonadotropins: (FSHR/LHCGR)	ovulation stim.: Clomifene, Urofollitropin Antigonadotropins: Danazol, Gestrinone
GnRH: (receptor)	Gonadotropin-releasing hormone agonist: Buserelin, Goserelin, Leuprorelin, Nafarelin, Triptorelin Gonadotropin-releasing hormone antagonist: Histrelin, Abarelix