Clomestrone

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]

Trade namesArterolo, Atheran, Colesterel, Iposclerone, Liprotene, Persclerol

Other namesSC-8246; 16α-Chloroestrone 3-methyl ether; 16α-Chloro-3-methoxyestra-1,3,5(10)-trien-17-one

Routes of
administrationBy mouth

Drug classEstrogen; Estrogen ether

Quick facts Clinical data, Trade names ...

Clomestrone

Clinical data
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
Identifiers
IUPAC name (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	4091-75-2
PubChem CID	107501
ChemSpider	96732
UNII	P1L5F7667L
CompTox Dashboard (EPA)	DTXSID50878418
ECHA InfoCard	100.021.669
Chemical and physical data
Formula	C19H23ClO2
Molar mass	318.84 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC12CCC3C(C1CC(C2=O)Cl)CCC4=C3C=CC(=C4)OC
InChI 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

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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]