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Chemical compound
Clomestrone
Trade names Arterolo, Atheran, Colesterel, Iposclerone, Liprotene, Persclerol Other names SC-8246; 16α-Chloroestrone 3-methyl ether; 16α-Chloro-3-methoxyestra-1,3,5(10)-trien-17-one
Routes of administration
By mouth
Drug class
Estrogen ;
Estrogen ether
(8R ,9S ,13S ,14S ,16R )-16-chloro-3-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H -cyclopenta[a ]phenanthren-17-one
CAS Number
PubChem
CID
ChemSpider
UNII
CompTox Dashboard (
EPA )
ECHA InfoCard
100.021.669
Formula C 19 H 23 Cl O 2
Molar mass 318.84 g·mol−1 3D model (
JSmol )
CC12CCC3C(C1CC(C2=O)Cl)CCC4=C3C=CC(=C4)OC
InChI=1S/C19H23ClO2/c1-19-8-7-14-13-6-4-12(22-2)9-11(13)3-5-15(14)16(19)10-17(20)18(19)21/h4,6,9,14-17H,3,5,7-8,10H2,1-2H3/t14-,15-,16+,17-,19+/m1/s1
Key:UQIPVSBPFZSWGD-ILYVXUQDSA-N
Clomestrone (brand names Arterolo , Atheran , Colesterel , Iposclerone , Liprotene , Persclerol , others; former developmental code name SC-8246 ), also known as 16α-chloroestrone 3-methyl ether , is a
synthetic ,
steroidal , weak
estrogen derived from
estrone and used as an
anticholesterolemic agent in the treatment of
atherosclerosis .
[1]
[2] It is said to have beneficial effects on
serum
lipid profiles while producing minimal
feminization , though some estrogenic
side effects , including
breast tenderness , loss of
libido , and
fatigue or
avolition , were observed in most patients in clinical studies.
[3]
[4] The drug is a close
analogue of
mytatrienediol , and the two estrogens have similar drug profiles.
[5] Clomestrone was described in the literature in 1958 and introduced for medical use shortly thereafter.
[1]
See also
References
^
a
b J. Elks (14 November 2014).
The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies . Springer. pp. 297–298.
ISBN
978-1-4757-2085-3 .
^ Gregory Pincus (22 October 2013).
Hormones and Atherosclerosis: Proceedings of the Conference Held in Brighton, Utah, March 11-14, 1958 . Elsevier Science. pp. 253–374.
ISBN
978-1-4832-7064-7 .
^ RIVIN AU (1959). "SC 8246, a new estrogen analog: lipoprotein effects with minimal feminization". Metab. Clin. Exp . 8 : 704–8.
PMID
14437693 . SC-8246 (16-alpha chlorestrone 3-methyl ether) was administered for periods of six to twelve months to 20 male survivors of acute myocardial infarction ranging in age from 30 to 63 years. A significant decrease in serum cholesterol concentration occurred in only 6 of 13 patients with an initial cholesterol level above 250 mg. per 100 ml., and there was no change in the other 7. Of 7 initial cholesterol levels below 250 mg. per 100 ml., no level decreased, 3 increased, and 4 were unchanged. In 9 of 11 patients with an initial alpha:beta lipoprotein ratio of less than 20 per cent, a significant increase occurred, but no change in the other 2. Among 9 subjects with a ratio initially above 20 per cent, a further increase occurred in 8 while taking the drug. This estrogen appeared to have an advantage in terms of lessening side-effects. Mild breast tenderness or gynecomastia occurred in 15 of the 17 patients with a "favorable" lipoprotein change. When the dosage was reduced to 5 mg. daily or every other day, the lipoprotein effect in 8 of them could be sustained while the breast changes disappeared. Libido disappeared from 2 patients and was diminished in 1 other. Other side-effects were nausea in 1 patient, loss of ambition in 5, and itching or dryness of the skin in 4.
^ WINSOR T, FISHER EK, PAYNE JH (1959). "A method for the study of peripheral arteriosclerosis". J Am Geriatr Soc . 7 (2): 167–74.
doi :
10.1111/j.1532-5415.1959.tb01062.x .
PMID
13630690 .
S2CID
46048052 .
^
Cancer Chemotherapy Abstracts . Information Resources Press. January 1960. p. 143.
Estrogens
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Alfatradiol
Certain
androgens /
anabolic steroids (e.g.,
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testosterone esters ,
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Certain
progestins (e.g.,
norethisterone ,
noretynodrel ,
etynodiol diacetate ,
tibolone )
Clomestrone
Cloxestradiol acetate
Conjugated estriol
Conjugated estrogens
Epiestriol
Epimestrol
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Estradiol
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Metalloestrogens (e.g.,
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Phytosterols (e.g.,
β-sitosterol ,
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Resorcylic acid lactones (e.g.,
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zearalenone ,
zeranol (α-zearalanol) ,
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