Mytatrienediol

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.[1] 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.[2][3][4][5][6][7] 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.[8][3][2] The medication was also studied to treat bone pain in patients with multiple myeloma, metastatic bone disease, and osteoporosis, with effectiveness seen.[9]

Mytatrienediol
Clinical data
Other namesSC-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
Routes of
administration		By mouth
Drug classEstrogen; Estrogen ether
Identifiers
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
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC20H28O3
Molar mass316.441 g·mol−1
3D model (JSmol)
SMILES
  • CC12CCC3C(C1CC(C2O)(C)O)CCC4=C3C=CC(=C4)OC
InChI
  • InChI=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
  • Key:OOVXZFCPCSVSEM-NADOGSGZSA-N

See also

References
  1. Gregory Pincus (22 October 2013). Hormones and Atherosclerosis: Proceedings of the Conference Held in Brighton, Utah, March 11-14, 1958. Elsevier Science. pp. 249, 254, 263, 371–374, 411–412, 443–447, 460–461. ISBN 978-1-4832-7064-7.
  2. Marmorston, J.; Moore, F. J.; Kuzma, O. T.; Magidson, O.; Weiner, J. M. (1963). "Effect of Estrogens on Interlipid Relations in Men with Myocardial Infarction". Experimental Biology and Medicine. 113 (2): 357–361. doi:10.3181/00379727-113-28365. ISSN 1535-3702. S2CID 72677634.
  3. Marmorston, J.; Moore, F. J.; Hopkins, C. E.; Kuzma, O. T.; Weiner, J. (1962). "Clinical Studies of Long-Term Estrogen Therapy in Men with Myocardial Infarction". Experimental Biology and Medicine. 110 (2): 400–408. doi:10.3181/00379727-110-27531. ISSN 1535-3702. PMID 14470097. S2CID 24669631.
  4. Davis FW, Scarborough WR, Mason RE, Singlewald ML, Baker BM (1958). "Experimental hormonal therapy of atherosclerosis: preliminary observations on the effects of two new compounds". The American Journal of the Medical Sciences. 235 (1): 50–9. doi:10.1097/00000441-195801000-00006. PMID 13487586. S2CID 762067.
  5. Cohen, W. D.; Higano, N.; Robinson, R. W. (1958). "Serum Lipid and Estrogenic Effects of Manvene, a New Estrogen Analog: Comparison with Premarin in Men with Coronary Heart Disease". Circulation. 17 (6): 1035–1040. doi:10.1161/01.CIR.17.6.1035. ISSN 0009-7322. PMID 13547367.
  6. Spencer, Herta; Kabakow, Bernard; Samachson, Joseph; Laszlo, Daniel (1959). "Metabolic Effects of Mytatrienediol in Man". The Journal of Clinical Endocrinology & Metabolism. 19 (12): 1581–1596. doi:10.1210/jcem-19-12-1581. ISSN 0021-972X. PMID 13833251.
  7. Marmorston, Jessie (1960). "Estrogen Therapy in Men with Myocardial Infarction". JAMA. 174 (3): 241–4. doi:10.1001/jama.1960.03030030021004. ISSN 0098-7484. PMID 14421377.
  8. Bedford, P. D.; Lodge, Brian (1959). "Toxic effects of a new antilipaemic oestrogenic steroid (Manvene)". Journal of the American Geriatrics Society. 7 (12): 911–915. doi:10.1111/j.1532-5415.1959.tb00364.x. ISSN 0002-8614. PMID 13798190. S2CID 45355299.
  9. Kabakow, Bernard (1960). "Effects of Mytatrienediol in Multiple Myeloma, Metastatic Bone Disease, and Osteoporosis". Archives of Internal Medicine. 105 (6): 905–13. doi:10.1001/archinte.1960.00270180083011. ISSN 0003-9926. PMID 14408289.


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