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Chemical compound
Mytatrienediol
Other names 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
Routes of administration
By mouth
Drug class
Estrogen ;
Estrogen ether
(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 )
Formula C 20 H 28 O 3
Molar mass 316.441 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 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]
See also
References
^ Pincus G (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 .
^
a
b Marmorston J, Moore FJ, Kuzma OT, Magidson O, Weiner JM (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 .
^
a
b Marmorston J, Moore FJ, Hopkins CE, Kuzma OT, Weiner J (June 1962). "Clinical studies of long-term estrogen therapy in men with mvocardial infarction". Proceedings of the Society for Experimental Biology and Medicine . 110 (2): 400–408.
doi :
10.3181/00379727-110-27531 .
PMID
14470097 .
S2CID
24669631 .
^ Davis FW, Scarborough WR, Mason RE, Singewald ML, Baker BM (January 1958). "Experimental hormonal therapy of atherosclerosis: preliminary observations on the effects of two new compounds". The American Journal of the Medical Sciences . 235 (1): 50–59.
doi :
10.1097/00000441-195801000-00006 .
PMID
13487586 .
S2CID
762067 .
^ Cohen WD, Higano N, Robinson RW (June 1958).
"Serum lipid and estrogenic effect 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 .
PMID
13547367 .
^ Spencer H, Kabakow B, Samachson J, Laszlo D (December 1959). "Metabolic effects of mytatrienediol in man". The Journal of Clinical Endocrinology and Metabolism . 19 (12): 1581–1596.
doi :
10.1210/jcem-19-12-1581 .
PMID
13833251 .
^ Marmorston J, Magdison O, Kuzma O, Moore FJ (September 1960). "Estrogen therapy in men with myocardial infarction. Side-effects with increasing dosage and time". JAMA . 174 (3): 241–244.
doi :
10.1001/jama.1960.03030030021004 .
PMID
14421377 .
^ Bedford PD, Lodge B (December 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 .
PMID
13798190 .
S2CID
45355299 .
^ Kabakow B, Spencer H (June 1960). "Effects of mytatrienediol in multiple myeloma, metastatic bone disease, and osteoporosis". Archives of Internal Medicine . 105 (6): 905–913.
doi :
10.1001/archinte.1960.00270180083011 .
PMID
14408289 .
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