estrone (medication) estrone (medication) estrone (e1), sold under the brand names estragyn, kestrin, and theelin among many others, is an estrogen medication and naturally occurring steroid hormone which has been used in menopausal hormone therapy and for other indications. it has been provided as an aqueous suspension or oil solution given by injection into muscle and as a vaginal cream applied inside of the vagina. it can also be taken by mouth as estradiol/estrone/estriol (brand name hormonin) and in the form of prodrugs like estropipate (estrone sulfate; brand name ogen) and conjugated estrogens (mostly estrone sulfate; brand name premarin). this article is about estrone as a medication. for its role as a hormone, see estrone. estrone (medication)clinical datatrade namesestragyn, kestrin, theelin, many othersother namesoestrone; e1; follicular hormone; folliculin; folliculine; follikulin; theelin; ketohydroxyestrin; oxohydroxyestrin; 3-hydroxyestra-1,3,5(10)-trien-17-oneroutes ofadministrationintramuscular injection, vaginal, by mouth (as e2/e1/e3 or as estrone sulfate)drug classestrogenatc codeg03ca07 (who) g03cc04 (who)legal statuslegal status us: ℞-only pharmacokinetic databioavailabilityoral: very lowprotein binding96.0–98.0%:• albumin: ~80%• shbg: ~16%• free: 2.0–4.0%metabolismliver (via hydroxylation, sulfation, glucuronidation)metabolites• estradiol• estrone sulfate• estrone glucuronide• otherselimination half-lifeiv: 20–30 minutesexcretionurineidentifiers iupac name (8r,9s,13s,14s)-3-hydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6h-cyclopentaphenanthren-17-one cas number53-16-7 ypubchem cid5870iuphar/bps2818drugbankdb00655 ychemspider5660 yunii2di9ha706akeggd00067 ychebichebi:17263 ychemblchembl1405 ychemical and physical dataformulac18h22o2molar mass270.372 g·mol−13d model (jsmol)interactive imagemelting point254.5 °c (490.1 °f) smiles o=c43(cc2c1ccc(o)cc1cc23cc4)c inchi inchi=1s/c18h22o2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-16,19h,2,4,6-9h2,1h3/t14-,15-,16+,18+/m1/s1 nkey:dnxheguupjumqt-cbzijgrnsa-n n (verify) side effects of estrogens like estrone include breast tenderness, breast enlargement, headache, nausea, fluid retention, and edema, among others. estrone is a naturally occurring and bioidentical estrogen, or an agonist of the estrogen receptor, the biological target of estrogens like endogenous estradiol. it is a relatively weak estrogen, with much lower activity than estradiol. however, estrone is converted in the body into estradiol, which provides most or all of its estrogenic potency. as such, estrone is a prodrug of estradiol. estrone was first discovered in 1929, and was introduced for medical use shortly thereafter. although it has been used clinically in the past, estrone has largely been discontinued and is mostly no longer marketed. medical uses estrone has been marketed in intramuscular and vaginal formulations and was used as an estrogen in the treatment of symptoms of low estrogen levels such as hot flashes and vaginal atrophy in postmenopausal or ovariectomized women. estrone has also been used as an antigonadotropin and form of high-dose estrogen to treat prostate cancer in men as well as a form of high-dose estrogen to treat breast cancer in women. it has since largely been discontinued and is mostly no longer available, having been superseded by other estrogens with better potency and pharmacokinetics (namely oral bioavailability and duration). regardless of route of administration, if estrone is taken by a woman with an intact uterus, it should be combined with a progestogen such as progesterone to offset the risk of endometrial hyperplasia and cancer. estrone has been used by intramuscular injection at a dosage of 0.1 to 2 mg per week, or 0.1 to 0.5 mg given 2 or 3 times per week, for the treatment of menopausal symptoms such as hot flashes and vaginal atrophy, and at a dosage of 0.1 to 1.0 mg weekly in single or divided doses for the treatment of female hypogonadism, surgical castration, and primary ovarian failure. the range of single doses of estrone by intramuscular injection that are typically used clinically in women is 0.1 to 5 mg. high doses of intramuscular estrone have been used for prostate cancer in men and for breast cancer in women. available forms