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SC-4289

From Wikipedia, the free encyclopedia
SC-4289
Clinical data
Other names6-[1'-Ethyl-2',2'-dimethyl-3'-hydroxy]propyl-β-naphthol-2-benzyl ether[1]
Routes of
administration
By mouth
Drug classNonsteroidal estrogen
Identifiers
  • 2,2-Dimethyl-3-(6'-benzyloxy-2'-naphthyl)pentanol[2]
CAS Number
PubChem CID
Chemical and physical data
FormulaC24H28O2
Molar mass348.486 g·mol−1
3D model (JSmol)
  • CCC(C1=CC=C2C=C(OCC3=CC=CC=C3)C=CC2=C1)C(C)(C)CO
  • InChI=1S/C24H28O2/c1-4-23(24(2,3)17-25)21-11-10-20-15-22(13-12-19(20)14-21)26-16-18-8-6-5-7-9-18/h5-15,23,25H,4,16-17H2,1-3H3
  • Key:FRDCVULRLQYMDS-UHFFFAOYSA-N

SC-4289 is a synthetic nonsteroidal estrogen which, along with mytatrienediol (SC-6924; Manvene, Anvene), was developed in the late 1950s as a potential treatment for atherosclerosis in men but was never marketed.[2][3]

The chemical structure of SC-4289 is the same as for methallenestril but differs in that it is the benzyl ether and not the methyl ether.

SC-4289 makes an appearance in the allenestrol patent,[4] as well as a stand-alone compound in:[5]

References

[edit]
  1. Berichte über die gesamte Physiologie und experimentelle Pharmakologie. Springer-Verlag. 1958. p. 332,378.
  2. 1 2 Robinson, R. W., Cohen, W. D., & Higano, N. (1956, January). Serum lipid and estrogenic effects of two new „weak estrogens“ in male patients with coronary atherosclerosis. In Circulation (Vol. 14, No. 3, pp. 489-490). 227 EAST WASHINGTON SQ, PHILADELPHIA, PA 19106: LIPPINCOTT WILLIAMS & WILKINS. http://circ.ahajournals.org/content/circulationaha/14/3/local/back-matter.pdf
  3. 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". Am. J. Med. Sci. 235 (1): 50–9. doi:10.1097/00000441-195801000-00006. PMID 13487586. S2CID 762067.
  4. Raymond M Dodson & Paul B Sollman, U.S. patent 3,014,076 (1961 to GD Searle LLC).
  5. Raymond M Dodson & Paul B Sollman, U.S. patent 2,831,887 (1958 to GD Searle LLC).