Methylestradiol

Last updated
Methylestradiol
Methylestradiol.svg
Methylestradiol molecule ball.png
Clinical data
Trade names Ginecosid, Ginecoside, Mediol, Renodiol
Other namesNSC-52245; 17α-Methylestradiol; 17α-ME; 17α-Methylestra-1,3,5(10)-triene-3,17β-diol
Routes of
administration 		By mouth [1]
Drug class Estrogen
Identifiers
  • (8R,9S,13S,14S,17S)-13,17-dimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
ECHA InfoCard 100.005.572 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C19H26O2
Molar mass 286.415 g·mol−1
3D model (JSmol)
  • CC12CCC3C(C1CCC2(C)O)CCC4=C3C=CC(=C4)O
  • InChI=1S/C19H26O2/c1-18-9-7-15-14-6-4-13(20)11-12(14)3-5-16(15)17(18)8-10-19(18,2)21/h4,6,11,15-17,20-21H,3,5,7-10H2,1-2H3/t15-,16-,17+,18+,19+/m1/s1
  • Key:JXQJDYXWHSVOEF-GFEQUFNTSA-N

Methylestradiol, sold under the brand names Ginecosid, Ginecoside, Mediol, and Renodiol, is an estrogen medication which is used in the treatment of menopausal symptoms. [2] [3] [4] It is formulated in combination with normethandrone, a progestin and androgen/anabolic steroid medication. [3] [4] Methylestradiol is taken by mouth. [1]

Contents

Side effects of methylestradiol include nausea, breast tension, edema, and breakthrough bleeding among others. [5] It is an estrogen, or an agonist of the estrogen receptors, the biological target of estrogens like estradiol. [6]

Methylestradiol is or has been marketed in Brazil, Venezuela, and Indonesia. [3] In addition to its use as a medication, methylestradiol has been studied for use as a radiopharmaceutical for the estrogen receptor. [7]

Medical uses

Methylestradiol is used in combination with the progestin and androgen/anabolic steroid normethandrone (methylestrenolone) in the treatment of menopausal symptoms. [3] [4]

Available forms

Methylestradiol is marketed in combination with normethandrone in the form of oral tablets containing 0.3 mg methylestradiol and 5 mg normethandrone. [8] [9]

Side effects

Side effects of methylestradiol include nausea, breast tension, edema, and breakthrough bleeding. [5]

Pharmacology

Pharmacodynamics

Methylestradiol is an estrogen, or an agonist of the estrogen receptor. [6] It shows somewhat lower affinity for the estrogen receptor than estradiol or ethinylestradiol. [6]

Methylestradiol is an active metabolite of the androgens/anabolic steroids methyltestosterone (17α-methyltestosterone), metandienone (17α-methyl-δ1-testosterone), and normethandrone (17α-methyl-19-nortestosterone), and is responsible for their estrogenic side effects, such as gynecomastia and fluid retention. [10] [11] [12]

Relative affinities (%) of methylestradiol and related steroids
Compound PR Tooltip Progesterone receptor AR Tooltip Androgen receptor ER Tooltip Estrogen receptor GR Tooltip Glucocorticoid receptor MR Tooltip Mineralocorticoid receptor SHBG Tooltip Sex hormone-binding globulin CBG Tooltip Corticosteroid binding globulin
Estradiol 2.67.91000.60.138.7<0.1
Ethinylestradiol 15–251–31121–3<1 ? ?
Methylestradiol3–10, 15–251–3671–3<1 ? ?
Methyltestosterone 345, 100–125 ?1–5 ?5 ?
Normethandrone 100146<0.11.50.6 ? ?
Sources: Values are percentages (%). Reference ligands (100%) were progesterone for the PR Tooltip progesterone receptor, testosterone for the AR Tooltip androgen receptor, E2 for the ER Tooltip estrogen receptor, DEXA Tooltip dexamethasone for the GR Tooltip glucocorticoid receptor, aldosterone for the MR Tooltip mineralocorticoid receptor, DHT Tooltip dihydrotestosterone for SHBG Tooltip sex hormone-binding globulin, and cortisol for CBG Tooltip Corticosteroid-binding globulin. Sources: [13] [6] [14] [15]

Pharmacokinetics

Due to the presence of its C17α methyl group, methylestradiol cannot be deactivated by oxidation of the C17β hydroxyl group, resulting in improved metabolic stability and potency relative to estradiol. [10] This is analogous to the case of ethinylestradiol and its C17α ethynyl group. [10]

Chemistry

Methylestradiol, or 17α-methylestradiol (17α-ME), also known as 17α-methylestra-1,3,5(10)-triene-3,17β-diol, is a synthetic estrane steroid and a derivative of estradiol. [2] [3] It is specifically the derivative of estradiol with a methyl group at the C17α positions. [2] [3] Closely related steroids include ethinylestradiol (17α-ethynylestradiol) and ethylestradiol (17α-ethylestradiol). [2] The C3 cyclopentyl ether of methylestradiol has been studied and shows greater oral potency than methylestradiol in animals, similarly to quinestrol (ethinylestradiol 3-cyclopentyl ether) and quinestradol (estriol 3-cyclopentyl ether). [16]

History

Methylestradiol was first marketed, alone as Follikosid and in combination with methyltestosterone as Klimanosid, in 1955. [17] [18] [19] [20]

Society and culture

Generic names

Methylestradiol has not been assigned an INN Tooltip International Nonproprietary Name or other formal name designations. [2] [3] Its generic name in English and German is methylestradiol, in French is méthylestradiol, and in Spanish is metilestadiol. [3] It is also known as 17α-methylestradiol. [3]

Brand names

Methylestradiol is or has been marketed under the brand names Ginecosid, Ginecoside, Mediol, and Renodiol, all in combination with normethandrone. [3] [2]

Availability

Methylestradiol is or has been marketed in Brazil, Venezuela, and Indonesia. [3]

Related Research Articles

<span class="mw-page-title-main">Methyltestosterone</span> Chemical compound

Methyltestosterone, sold under the brand names Android, Metandren, and Testred among others, is an androgen and anabolic steroid (AAS) medication which is used in the treatment of low testosterone levels in men, delayed puberty in boys, at low doses as a component of menopausal hormone therapy for menopausal symptoms like hot flashes, osteoporosis, and low sexual desire in women, and to treat breast cancer in women. It is taken by mouth or held in the cheek or under the tongue.

<span class="mw-page-title-main">Quinestrol</span> Pharmaceutical drug

Quinestrol, also known as ethinylestradiol cyclopentyl ether (EECPE), sold under the brand name Estrovis among others, is an estrogen medication which has been used in menopausal hormone therapy, hormonal birth control, and to treat breast cancer and prostate cancer. It is taken once per week to once per month by mouth.

<span class="mw-page-title-main">Ethinylestradiol</span> Estrogen medication

Ethinylestradiol (EE) is an estrogen medication which is used widely in birth control pills in combination with progestins. In the past, EE was widely used for various indications such as the treatment of menopausal symptoms, gynecological disorders, and certain hormone-sensitive cancers. It is usually taken by mouth but is also used as a patch and vaginal ring.

<span class="mw-page-title-main">Gestrinone</span> Chemical compound

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.

<span class="mw-page-title-main">Norethisterone</span> Progestin medication

Norethisterone, also known as norethindrone and sold under many brand names, is a progestin medication used in birth control pills, menopausal hormone therapy, and for the treatment of gynecological disorders. The medication is available in both low-dose and high-dose formulations and both alone and in combination with an estrogen. It is used by mouth or, as norethisterone enanthate, by injection into muscle.

<span class="mw-page-title-main">Norgestrienone</span> Chemical compound

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.

<span class="mw-page-title-main">Trestolone</span> Chemical compound

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.

<span class="mw-page-title-main">Metribolone</span> Chemical compound

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.

<span class="mw-page-title-main">Normethandrone</span> Chemical compound

Normethandrone, also known as methylestrenolone or methylnortestosterone and sold under the brand name Metalutin among others, is a progestin and androgen/anabolic steroid (AAS) medication which is used in combination with an estrogen in the treatment of amenorrhea and menopausal symptoms in women. It is taken by mouth.

<span class="mw-page-title-main">Demegestone</span> Chemical compound

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.

<span class="mw-page-title-main">Trimegestone</span> Chemical compound

Trimegestone, sold under the brand names Ondeva and Totelle among others, is a progestin medication which is used in menopausal hormone therapy and in the prevention of postmenopausal osteoporosis. It was also under development for use in birth control pills to prevent pregnancy, but ultimately was not marketed for this purpose. The medication is available alone or in combination with an estrogen. It is taken by mouth.

<span class="mw-page-title-main">Moxestrol</span> Chemical compound

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.

<span class="mw-page-title-main">Quingestanol acetate</span> Chemical compound

Quingestanol acetate, sold under the brand names Demovis and Pilomin among others, is a progestin medication which was used in birth control pills but is no longer marketed. It is taken by mouth.

<span class="mw-page-title-main">17α-Epiestriol</span> Chemical compound

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.

<span class="mw-page-title-main">Trimethyltrienolone</span> Chemical compound

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.

<span class="mw-page-title-main">Dimethyltrienolone</span> Anabolic–androgenic steroid

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.

<span class="mw-page-title-main">RU-16117</span> Chemical compound

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. It was developed for use by mouth.

<span class="mw-page-title-main">RU-2309</span> Chemical compound

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.

<span class="mw-page-title-main">7α-Methylestradiol</span> Chemical compound

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 steroids trestolone/Methandienone. 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.

<span class="mw-page-title-main">Structure–activity relationships of anabolic steroids</span>

The structure–activity relationships (SAR) of anabolic steroids (AAS) have been extensively studied.

References

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  2. 1 2 3 4 5 6 Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 898–. ISBN   978-1-4757-2085-3.
  3. 1 2 3 4 5 6 7 8 9 10 11 "Methylestradiol". Drugs.com. Retrieved 2 January 2016.
  4. 1 2 3 IARC Working Group on the Evaluation of Carcinogenic Risks to Humans; World Health Organization; International Agency for Research on Cancer (2007). Combined Estrogen-progestogen Contraceptives and Combined Estrogen-progestogen Menopausal Therapy. World Health Organization. pp. 389–. ISBN   978-92-832-1291-1.
  5. 1 2 Wittlinger H (1980). "Clinical Effects of Estrogens". Functional Morphologic Changes in Female Sex Organs Induced by Exogenous Hormones. pp. 67–71. doi:10.1007/978-3-642-67568-3_10. ISBN   978-3-642-67570-6.
  6. 1 2 3 4 Ojasoo T, Raynaud JP (November 1978). "Unique steroid congeners for receptor studies". Cancer Research. 38 (11 Pt 2): 4186–4198. PMID   359134.
  7. ↑ Feenstra A, Vaalburg W, Nolten GM, Reiffers S, Talma AG, Wiegman T, et al. (June 1983). "Estrogen receptor binding radiopharmaceuticals: II. Tissue distribution of 17 alpha-methylestradiol in normal and tumor-bearing rats". Journal of Nuclear Medicine. 24 (6): 522–528. PMID   6406650.
  8. ↑ Unlisted Drugs. Pharmaceutical Section, Special Libraries Association. 1982. Batynid. C. Each dragee contains: normethandrone, 5 mg.; and methylestradiol, 0.3 mg. E. (Formerly) Gynaekosid. M. Boehringer Biochemia, Florence. A. Estrogenic; Rx of secondary amenorrhea. R. Notiz Med Farm 32;295, Nov-Dec 81.
  9. ↑ Akingba JB, Ayodeji EA (February 1966). "Amenorrhea as a leading symptom of choriocarcinoma". The Journal of Obstetrics and Gynaecology of the British Commonwealth. 73 (1): 153–155. doi:10.1111/j.1471-0528.1966.tb05137.x. PMID   5948541. S2CID   38008851.
  10. 1 2 3 Thieme D, Hemmersbach P (18 December 2009). Doping in Sports. Springer Science & Business Media. pp. 470–. ISBN   978-3-540-79088-4.
  11. ↑ Llewellyn W (2011). Anabolics. Molecular Nutrition Llc. pp. 533–. ISBN   978-0-9828280-1-4.
  12. ↑ Friedl KE (1990). "Reappraisal of the health risks associated with the use of high doses of oral and injectable androgenic steroids". NIDA Research Monograph. 102: 142–177. PMID   1964199.
  13. ↑ Raynaud JP, Ojasoo T, Bouton MM, Philibert D (1979). "Receptor Binding as a Tool in the Development of New Bioactive Steroids". Drug Design. pp. 169–214. doi:10.1016/B978-0-12-060308-4.50010-X. ISBN   9780120603084.
  14. ↑ Ojasoo T, Delettré J, Mornon JP, Turpin-VanDycke C, Raynaud JP (1987). "Towards the mapping of the progesterone and androgen receptors". Journal of Steroid Biochemistry. 27 (1–3): 255–269. doi:10.1016/0022-4731(87)90317-7. PMID   3695484.
  15. ↑ Raynaud JP, Bouton MM, Moguilewsky M, Ojasoo T, Philibert D, Beck G, et al. (January 1980). "Steroid hormone receptors and pharmacology". Journal of Steroid Biochemistry. 12: 143–157. doi:10.1016/0022-4731(80)90264-2. PMID   7421203.
  16. ↑ Falconi G, Rossi GL, Ercoli A (September 1970). James VH (ed.). Quinestrol and other cyclopentyl ethers of estrogenic steroids: different rates of storage in body fat. Third International Congress on Hormonal Steroids, Hamburg. International Congress Series No. 210. Amsterdam, Excerpta Medica. pp. 218–219. Archived from the original on 28 March 2018.
  17. ↑ "Neue Spezialitäten". Klinische Wochenschrift. 33 (31–32): 773–774. 1955. doi:10.1007/BF01473523. ISSN   0023-2173. S2CID   1678069.
  18. ↑ Kahr H (8 March 2013). Konservative Therapie der Frauenkrankheiten: Anzeigen, Grenzen und Methoden Einschliesslich der Rezeptur. Springer-Verlag. pp. 20–. ISBN   978-3-7091-5694-0.
  19. ↑ Arends G, Zörnig H, Hager H, Frerichs G, Kern W (14 December 2013). Hagers Handbuch der pharmazeutischen Praxis: Für Apotheker, Arzneimittelhersteller, Drogisten, Ärzte u. Medizinalbeamte. Springer-Verlag. pp. 1156–1157, 1164. ISBN   978-3-662-36329-4.
  20. ↑ Helwig B (1956). Moderne Arzneimittel: eine Spezialitätenkunde nach Indikationsgebieten für Ärzte und Apotheker. Wissenschaftliche Verlagsgesellschaft. p. 240.
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