Mytatrienediol

{{Short description|Chemical compound}}

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| IUPAC_name = (8R,9S,13S,14S,16S,17R)-3-methoxy-13,16-dimethyl-7,8,9,11,12,14,15,17-octahydro-6H-cyclopenta[a]phenanthrene-16,17-diol

| image = Mytatrienediol.svg

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| routes_of_administration = By mouth

| class = Estrogen; Estrogen ether

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| CAS_number = 5108-94-1

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| PubChem = 5282364

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| ChemSpiderID = 4445527

| UNII = 1G3TKH1O14

| KEGG = C14242

| ChEBI = 34859

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| synonyms = SC-6924; Manvene; Anvene; 3-Methoxy-16α-methylestra-1,3,5(10)-triene-16β,17β-diol; 16α-Methylestriol 3-methyl ether; 16β-Hydroxy-16α-methylestradiol 3-methyl ether

| C=20 | H=28 | O=3

| SMILES = CC12CCC3C(C1CC(C2O)(C)O)CCC4=C3C=CC(=C4)OC

| StdInChI_Ref =

| StdInChI = 1S/C20H28O3/c1-19-9-8-15-14-7-5-13(23-3)10-12(14)4-6-16(15)17(19)11-20(2,22)18(19)21/h5,7,10,15-18,21-22H,4,6,8-9,11H2,1-3H3/t15-,16-,17+,18-,19+,20+/m1/s1

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| StdInChIKey = OOVXZFCPCSVSEM-NADOGSGZSA-N

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Mytatrienediol (developmental code name SC-6924; former tentative brand names Manvene, Anvene), also known as 16α-methyl-16β-epiestriol 3-methyl ether or 16β-hydroxy-16α-methylestradiol 3-methyl ether, is a synthetic steroidal estrogen medication and an estrogen ether which was derived from estriol and was developed for clinical use in the late 1950s but was never marketed.{{cite book| vauthors = Pincus G |title=Hormones and Atherosclerosis: Proceedings of the Conference Held in Brighton, Utah, March 11-14, 1958|url=https://books.google.com/books?id=NiXgBAAAQBAJ&pg=PA371|date=22 October 2013|publisher=Elsevier Science|isbn=978-1-4832-7064-7|pages=249, 254, 263, 371–374, 411–412, 443–447, 460–461}} It was investigated as a weak and mildly estrogenic medication for men to treat atherosclerosis, improve serum lipid profiles, and reduce the risk of myocardial infarction.{{cite journal| vauthors = Marmorston J, Moore FJ, Kuzma OT, Magidson O, Weiner JM |title=Effect of Estrogens on Interlipid Relations in Men with Myocardial Infarction.|journal=Experimental Biology and Medicine|volume=113|issue=2|year=1963|pages=357–361|issn=1535-3702|doi=10.3181/00379727-113-28365|s2cid=72677634}}{{cite journal | vauthors = Marmorston J, Moore FJ, Hopkins CE, Kuzma OT, Weiner J | title = Clinical studies of long-term estrogen therapy in men with mvocardial infarction | journal = Proceedings of the Society for Experimental Biology and Medicine | volume = 110 | issue = 2 | pages = 400–408 | date = June 1962 | pmid = 14470097 | doi = 10.3181/00379727-110-27531 | s2cid = 24669631 }}{{cite journal | vauthors = Davis FW, Scarborough WR, Mason RE, Singewald ML, Baker BM | title = Experimental hormonal therapy of atherosclerosis: preliminary observations on the effects of two new compounds | journal = The American Journal of the Medical Sciences | volume = 235 | issue = 1 | pages = 50–59 | date = January 1958 | pmid = 13487586 | doi = 10.1097/00000441-195801000-00006 | s2cid = 762067 }}{{cite journal | vauthors = Cohen WD, Higano N, Robinson RW | title = Serum lipid and estrogenic effect of manvene, a new estrogen analog; comparison with premarin in men with coronary heart disease | journal = Circulation | volume = 17 | issue = 6 | pages = 1035–1040 | date = June 1958 | pmid = 13547367 | doi = 10.1161/01.CIR.17.6.1035 | doi-access = free }}{{cite journal | vauthors = Spencer H, Kabakow B, Samachson J, Laszlo D | title = Metabolic effects of mytatrienediol in man | journal = The Journal of Clinical Endocrinology and Metabolism | volume = 19 | issue = 12 | pages = 1581–1596 | date = December 1959 | pmid = 13833251 | doi = 10.1210/jcem-19-12-1581 }}{{cite journal | vauthors = Marmorston J, Magdison O, Kuzma O, Moore FJ | title = Estrogen therapy in men with myocardial infarction. Side-effects with increasing dosage and time | journal = JAMA | volume = 174 | issue = 3 | pages = 241–244 | date = September 1960 | pmid = 14421377 | doi = 10.1001/jama.1960.03030030021004 }} However, while preclinical research supported the profile of mytatriendiol as a weak estrogen, the medication was found in clinical trials to produce estrogenic side effects including feminization, breast pain, and gynecomastia in men similarly and comparably to other estrogens such as ethinylestradiol and conjugated estrogens, and its side effects ultimately precluded its use.{{cite journal | vauthors = Bedford PD, Lodge B | title = Toxic effects of a new antilipaemic oestrogenic steroid (manvene) | journal = Journal of the American Geriatrics Society | volume = 7 | issue = 12 | pages = 911–915 | date = December 1959 | pmid = 13798190 | doi = 10.1111/j.1532-5415.1959.tb00364.x | s2cid = 45355299 }} The medication was also studied to treat bone pain in patients with multiple myeloma, metastatic bone disease, and osteoporosis, with effectiveness seen.{{cite journal | vauthors = Kabakow B, Spencer H | title = Effects of mytatrienediol in multiple myeloma, metastatic bone disease, and osteoporosis | journal = Archives of Internal Medicine | volume = 105 | issue = 6 | pages = 905–913 | date = June 1960 | pmid = 14408289 | doi = 10.1001/archinte.1960.00270180083011 }}