Clinical data | |
---|---|
Other names | 11α-Methoxyethinylestradiol; 11α-Methoxy-17α-ethynylestradiol; 11α-Methoxy-19-nor-17α-pregna-1,3,5(10)-trien-20-yne-3,17-diol |
Routes of administration | By mouth [1] |
Drug class | Estrogen; Estrogen ether |
Identifiers | |
| |
CAS Number | |
PubChem CID | |
ChemSpider | |
CompTox Dashboard (EPA) | |
Chemical and physical data | |
Formula | C21H26O3 |
Molar mass | 326.436 g·mol−1 |
3D model (JSmol) | |
| |
|
RU-16117 is an estrogen medication which was investigated for the potential treatment of symptoms of estrogen deficiency such as hot flashes and osteoporosis in women but was never marketed. [1] It was developed for use by mouth. [1]
RU-16117 is an estrogen, or an agonist of the estrogen receptor (ER). [1] [2] In mouse uterine tissue, it shows about 5 to 13% of the affinity of estradiol for the ER and about 1% of the estrogenic activity of estradiol. [2] [3] [4] Conversely, it shows no affinity for the androgen, progesterone, glucocorticoid, and mineralocorticoid receptors, nor any activities associated with interactions with these receptors. [2] [5] [3] [4] While the association rate of RU-16117 to the ER is the same as that of moxestrol, it dissociates from the ER extremely rapidly at rates of about three times faster than estradiol and about 20 times faster than moxestrol. [1] [6] This is similar to the case of estriol, which RU-16117 is described as sharing similarities with. [1] [6] RU-16117 is described as a weak or partial estrogen or a mixed estrogen/antiestrogen. [1] [2] It has been described as having highly active antiestrogenic activity with very weak uterotrophic activity. [7] [2] However, higher doses and/or prolonged administration of RU-16117 have been reported to induce equivalent estrogenic responses relative to estradiol and moxestrol. [1] [6]
Compound | PR | AR | ER | GR | MR | SHBG | CBG | ||
---|---|---|---|---|---|---|---|---|---|
Estradiol | 2.6 | 7.9 | 100 | 0.6 | 0.13 | 8.7 | <0.1 | ||
Estriol | ? | ? | 15 | ? | ? | ? | ? | ||
Ethinylestradiol | 15–25 | 1–3 | 112 | 1–3 | <1 | ? | ? | ||
Moxestrol (11β-MeO-EE) | 0.8 | <0.1 | 12 | 3.2 | <0.1 | <0.2 | <0.1 | ||
RU-16117 (11α-MeO-EE) | 1–3 | <1 | 13 | <1 | <1 | ? | ? | ||
Values are percentages (%). Reference ligands (100%) were progesterone for the PR, testosterone for the AR, E2 for the ER, DEXA for the GR, aldosterone for the MR, DHT for SHBG, and cortisol for CBG. |
RU-16117, also known as 11α-methoxy-17α-ethynylestradiol (11α-MeO-EE) or as 11α-methoxy-17α-ethynylestra-1,3,5(10)-triene-3,17β-diol, is a synthetic estrane steroid and a derivative of estradiol. [1] It is specifically a derivative of ethinylestradiol (17α-ethynylestradiol) with a methoxy group at the C11α position. [1] The compound is the C11α isomer or C11 epimer of moxestrol (11β-methoxy-17α-ethynylestradiol). [1] [9]
Gestrinone, sold under the brand names Dimetrose and Nemestran among others, is a medication which is used in the treatment of endometriosis. It has also been used to treat other conditions such as uterine fibroids and heavy menstrual bleeding and has been investigated as a method of birth control. Gestrinone is used alone and is not formulated in combination with other medications. It is taken by mouth or in through the vagina.
Norgestrienone, sold under the brand names Ogyline, Planor, and Miniplanor, is a progestin medication which has been used in birth control pills, sometimes in combination with ethinylestradiol. It was developed by Roussel Uclaf and has been registered for use only in France. Under the brand name Planor, it has been marketed in France as 2 mg norgestrienone and 50 μg ethinylestradiol tablets. It is taken by mouth.
Trestolone, also known as 7α-methyl-19-nortestosterone (MENT), is an experimental androgen/anabolic steroid (AAS) and progestogen medication which has been under development for potential use as a form of hormonal birth control for men and in androgen replacement therapy for low testosterone levels in men but has never been marketed for medical use. It is given as an implant that is placed into fat. As trestolone acetate, an androgen ester and prodrug of trestolone, the medication can also be given by injection into muscle.
Metribolone is a synthetic and orally active anabolic–androgenic steroid (AAS) and a 17α-alkylated nandrolone (19-nortestosterone) derivative which was never marketed for medical use but has been widely used in scientific research as a hot ligand in androgen receptor (AR) ligand binding assays (LBAs) and as a photoaffinity label for the AR. More precisely, metribolone is the 17α-methylated derivative of trenbolone. It was investigated briefly for the treatment of advanced breast cancer in women in the late 1960s and early 1970s, but was found to produce signs of severe hepatotoxicity at very low dosages, and its development was subsequently discontinued.
Demegestone, sold under the brand name Lutionex, is a progestin medication which was previously used to treat luteal insufficiency but is now no longer marketed. It is taken by mouth.
Moxestrol, sold under the brand name Surestryl, is an estrogen medication which has been used in Europe for the treatment of menopausal symptoms and menstrual disorders. It is taken by mouth. In addition to its use as a medication, moxestrol has been used in scientific research as a radioligand of the estrogen receptor.
Methylestradiol, sold under the brand names Ginecosid, Ginecoside, Mediol, and Renodiol, is an estrogen medication which is used in the treatment of menopausal symptoms. It is formulated in combination with normethandrone, a progestin and androgen/anabolic steroid medication. Methylestradiol is taken by mouth.
Epiestriol (INN), or epioestriol (BAN), also known as 16β-epiestriol or simply 16-epiestriol as well as 16β-hydroxy-17β-estradiol, is a minor and weak endogenous estrogen, and the 16β-epimer of estriol. Epiestriol is used clinically in the treatment of acne. In addition to its estrogenic actions, epiestriol has been found to possess significant anti-inflammatory properties without glycogenic activity or immunosuppressive effects, an interesting finding that is in contrast to conventional anti-inflammatory steroids like hydrocortisone.
17α-Epiestriol, or simply 17-epiestriol, also known as 16α-hydroxy-17α-estradiol or estra-1,3,5(10)-triene-3,16α,17α-triol, is a minor and weak endogenous estrogen, and the 17α-epimer of estriol. It is formed from 16α-hydroxyestrone. In contrast to other endogenous estrogens like estradiol, 17α-epiestriol is a selective agonist of the ERβ. It is described as a relatively weak estrogen, which is in accordance with its relatively low affinity for the ERα. 17α-Epiestriol has been found to be approximately 400-fold more potent than estradiol in inhibiting tumor necrosis factor α (TNFα)-induced vascular cell adhesion molecule 1 (VCAM-1) expression in vitro.
Trimethyltrienolone (TMT), also known by its developmental code name R-2956 or RU-2956, is an antiandrogen medication which was never introduced for medical use but has been used in scientific research.
Dimethyltrienolone is a synthetic, orally active, and extremely potent anabolic–androgenic steroid (AAS) and 17α-alkylated 19-nortestosterone (nandrolone) derivative which was never marketed for medical use. It has among the highest known affinity of any AAS for the androgen receptors, and has been said to be perhaps the most potent AAS to have ever been developed.
2-Hydroxyestrone (2-OHE1), also known as estra-1,3,5(10)-trien-2,3-diol-17-one, is an endogenous, naturally occurring catechol estrogen and a major metabolite of estrone and estradiol. It is formed irreversibly from estrone in the liver and to a lesser extent in other tissues via 2-hydroxylation mediated by cytochrome P450 enzymes, mainly the CYP3A and CYP1A subfamilies. 2-OHE1 is the most abundant catechol estrogen in the body.
17α-Methyl-19-norprogesterone, also known as 17α-methyl-19-norpregn-4-ene-3,20-dione, is a progestin which was never marketed. It is a derivative of progesterone, and is the combined derivative of 17α-methylprogesterone and 19-norprogesterone. The drug is the parent compound of a subgroup of the 19-norprogesterone group of progestins, which includes demegestone, promegestone, and trimegestone.
5α-Dihydronormethandrone, also known as 17α-methyl-4,5α-dihydro-19-nortestosterone or as 17α-methyl-5α-estran-17β-ol-3-one, is an androgen/anabolic steroid and a likely metabolite of normethandrone formed by 5α-reductase. Analogously to nandrolone and its 5α-reduced metabolite 5α-dihydronandrolone, 5α-DHNMT shows reduced affinity for the androgen receptor relative to normethandrone. Its affinity for the androgen receptor is specifically about 33 to 60% of that of normethandrone.
RU-2309, also known as 18-methylmetribolone, δ9,11-17α,18-dimethyl-19-nortestosterone, or 17α,18-dimethylestr-4,9,11-trien-17β-ol-3-one, is a 17α-alkylated androgen/anabolic steroid (AAS) of the 19-nortestosterone group which was never marketed. It is the C18 methyl or C13β ethyl derivative of metribolone. The compound is closely related to tetrahydrogestrinone (THG), which has the same chemical structure as RU-2309 except for possessing an ethyl group at the C17α position instead of a methyl group. Hence, it could also be referred to as 17α-methyl-THG. RU-2309 shows high affinity for the androgen, progesterone, and glucocorticoid receptors.
Dimethyldienolone, or 7α,17α-dimethyldienolone, also known as δ9-7α,17α-dimethyl-19-nortestosterone or as 7α,17α-dimethylestr-4,9-dien-17β-ol-3-one, is a 17α-alkylated androgen/anabolic steroid of the 19-nortestosterone group which was never marketed. It is closely related to dimethyltrienolone, as well as to mibolerone and metribolone. Dimethyldienolone shows high affinity for the androgen and progesterone receptors.
7α-Methylestradiol (7α-Me-E2), also known as 7α-methylestra-1,3,5(10)-triene-3,17β-diol, is a synthetic estrogen and an active metabolite of the androgen/anabolic steroid trestolone. It is considered to be responsible for the estrogenic activity of trestolone. The compound shows about the same affinity for the estrogen receptor as estradiol.
Estriol (E3), sold under the brand name Ovestin among others, is an estrogen medication and naturally occurring steroid hormone which is used in menopausal hormone therapy. It is also used in veterinary medicine as Incurin to treat urinary incontinence due to estrogen deficiency in dogs. The medication is taken by mouth in the form of tablets, as a cream that is applied to the skin, as a cream or pessary that is applied in the vagina, and by injection into muscle.
5α-Dihydroethisterone is an active metabolite of the formerly clinically used but now-discontinued progestin ethisterone and the experimental and never-marketed hormonal antineoplastic agent ethynylandrostanediol (HE-3235). Its formation from its parent drugs is catalyzed by 5α-reductase in tissues that express the enzyme in high amounts like the liver, skin, hair follicles, and prostate gland. 5α-DHET has significant affinity for steroid hormone receptors and may contribute importantly to the activities of its parent drugs.
11β-Methoxyestradiol is a synthetic steroidal estrogen which was never marketed. It has about 86% of the relative binding affinity of estradiol for the estrogen receptor. 11β-MeOE2 is structurally related to moxestrol (11β-methoxy-17α-ethynylestradiol). 11β-MeOE2 and moxestrol are substantially more potent than their non-methoxylated analogues in mice.