Fluoxymesterone, sold under the brand names Halotestin and Ultandren 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, breast cancer in women, and anemia. It is taken by mouth.
Side effects of fluoxymesterone include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire. It can also cause liver damage and cardiovascular side effects like high blood pressure. The drug is a synthetic androgen and anabolic steroid and hence is an agonist of the androgen receptor (AR), the biological target of androgens like testosterone and dihydrotestosterone (DHT). It has strong androgenic effects and moderate anabolic effects, which make it useful for producing masculinization.
Fluoxymesterone was first described in 1956 and was introduced for medical use in 1957. In addition to its medical use, fluoxymesterone is used to improve physique and performance. The drug is a controlled substance in many countries and so non-medical use is generally illicit.
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InChI=1S/C21H26O2/c1-4-21(22)12-10-19-18-7-5-14-13-15(23-3)6-8-16(14)17(18)9-11-20(19,21)2/h1,6,8,13,17-19,22H,5,7,9-12H2,2-3H3/t17-,18-,19+,20+,21+/m1/s1 |
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xenoestrogen
A synthetic or semi-synthetic compound that has oestrogenic activity.
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prodrug
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
xenoestrogen
A synthetic or semi-synthetic compound that has oestrogenic activity.
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View more via ChEBI Ontology
17-ethynyl-3-methoxyestra-1(10),2,4-trien-17β-ol
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mestranol
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KEGG DRUG
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mestranolum
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ChemIDplus
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(+)-17α-Ethynyl-17β-hydroxy-3-methoxy-1,3,5(10)-estratriene
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NIST Chemistry WebBook
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(+)-17α-Ethynyl-17β-hydroxy-3-methoxy-1,3,5(10)-oestratriene
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NIST Chemistry WebBook
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17-ethynyl-3-methoxyoestra-1(10),2,4-trien-17β-ol
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ChEBI
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3-Methoxy-17α-ethynylestradiol
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NIST Chemistry WebBook
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3-Methoxy-19-norpregna-1,3,5(10)-trien-20-yn-17β-ol
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NIST Chemistry WebBook
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Ethynylestradiol 3-methyl ether
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NIST Chemistry WebBook
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Mestranol
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KEGG COMPOUND
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2625905
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Reaxys Registry Number
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Reaxys
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72-33-3
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CAS Registry Number
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KEGG COMPOUND
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72-33-3
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CAS Registry Number
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ChemIDplus
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Temes TA, Andersen H, Gilberg D, Bonerz M (2002) Determination of estrogens in sludge and sediments by liquid extraction and GC/MS/MS. Analytical chemistry 74, 3498-3504 [PubMed:12139060] [show Abstract] Two methods have been developed that enable the determination of estrogens down to 2 ng/g in digested and activated sludge from domestic sewage treatment plants (STPs) and down to 0.2 ng/g in freshwater sediments. The method for sludge analysis consists of solvent extraction; a gel permeation chromatography (GPC) cleanup step, a 1 g silica gel column; and finally, detection by GC-ion trap MS/MS of the silylated estrogens with MSTFA. For sediments, the solvent extraction was successively followed by silica gel cleanup, solid phase enrichment (SPE), and a HPLC cleanup before derivatization and GC/MS/MS detection. Mean recoveries of the estrogens mainly exceeded 70% in sludge and 90% in sediments. In activated and digested sewage sludge, estrone and 17beta-estradiol were detected up to 37 ng/g and 49 ng/g, respectively, and 17alpha-ethinylestradiol up to 17 ng/g. The occurrence of estrogens in digested sludge indicates that estrogens can be persistent during sludge digestion. In river sediments, estrone and 17beta-estradiol were detected up to 2 ng/g (estrone), and the contraceptive 17alpha-ethinylestradiol was found with a maximum of 0.9 ng/g. Mestranol, a prodrug for 17alpha-ethinylestradiol, was not detected either in sludge or in sediments. | Ahmad T, Akhtar S, Haider S (1991) A study on stability of mestranol. Pakistan journal of pharmaceutical sciences 4, 63-70 [PubMed:16414683] [show Abstract] Mestranol, a synthetic oestrogcn, is an oral contraceptive given alongwith progestogens. It is light, heat and air sensitive and on uv irradiation new polymeric species of glucosiduronate and sulphate conjugate are formed. The new species fractions of mestranol are separatable over sephadex in column chromatography and characterized by analytical techniques employed in this investigation. This investigation is aimed to study formation of these species quantitatively for stability induced formulations. |
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