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Mytatrienediol

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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
Identifiers
  • (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 mass316.43452 g/mol g·mol−1
3D model (JSmol)
  • CC12CCC3C(C1CC(C2O)(C)O)CCC4=C3C=CC(=C4)OC
  • 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

Mytatrienediol (developmental code name SC-6924; former tentative trade names Manvene, Anvene), also known as 16α-methyl-16β-epiestriol 3-methyl ether or 16β-hydroxy-16α-methylestradiol 3-methyl ether, is a semisynthetic, steroidal, weak estrogen and estrogen ether derived from estriol that was developed in the late 1950s but was never marketed.[1] It was investigated as a mildly estrogenic drug for men to treat atherosclerosis and improve serum lipid profiles and reduce the risk of myocardial infarction.[2][3][4][5][6][7] However, like other estrogens, mytatriendiol was found in clinical trials to produce estrogenic side effects such as breast pain and gynecomastia in men, and its side effects ultimately precluded its use.[8] The drug was also studied to treat bone pain in patients with multiple myeloma, metastatic bone disease, and osteoporosis, with effectiveness seen.[9]

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.
  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.
  4. ^ DAVIS FW, SCARBOROUGH WR, MASON RE, SINGEWALD 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. PMID 13487586.
  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.
  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.
  7. ^ Marmorston, Jessie (1960). "Estrogen Therapy in Men with Myocardial Infarction". JAMA. 174 (3): 241. doi:10.1001/jama.1960.03030030021004. ISSN 0098-7484.
  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.
  9. ^ Kabakow, Bernard (1960). "Effects of Mytatrienediol in Multiple Myeloma, Metastatic Bone Disease, and Osteoporosis". Archives of Internal Medicine. 105 (6): 905. doi:10.1001/archinte.1960.00270180083011. ISSN 0003-9926.


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