Plomestane

Plomestane (INN, USAN; former developmental code name MDL-18962; also known as propargylestrenedione, PED) is a steroidal, irreversible aromatase inhibitor which was under development by Marion Merrell Dow/Hoechst Marion Russell (now Hoechst AG) as an antineoplastic agent for the treatment of breast cancer.[1][2][3][4][5] It was found to be effective in preclinical studies and was also found to produce few adverse effects in human clinical trials, significantly reducing estrogen levels with a single administration.[5] However, development of the drug for clinical use was halted due to "technical issues" and it was never marketed.[6]

Plomestane

Clinical data
Other names	MDL-18962; Propargylestrenedione; PED; 10-(2-Propyn-1-yl)estr-4-ene-3,17-dione; 10-Propargylestr-4-ene-3,17-dione
ATC code	None
Identifiers
IUPAC name 10H-(2-Propynyl)-estr-4-ene-3,17-dione
CAS Number	77016-85-4
PubChem CID	9904788
ChemSpider	8080442
UNII	FL3VS913TW
Chemical and physical data
Formula	C21H26O2
Molar mass	310.437 g·mol^−1
3D model (JSmol)	Interactive image
SMILES O=C4\C=C3/[C@@](CC#C)([C@H]2CC[C@@]1(C(=O)CC[C@H]1[C@@H]2CC3)C)CC4
InChI InChI=1S/C21H26O2/c1-3-10-21-12-8-15(22)13-14(21)4-5-16-17-6-7-19(23)20(17,2)11-9-18(16)21/h1,13,16-18H,4-12H2,2H3/t16-,17-,18-,20-,21-/m0/s1 Key:JKPDEYAOCSQBSZ-OEUJLIAZSA-N

In addition to its activity as an aromatase inhibitor, plomestane has weak androgenic properties.[5]

See also

• Minamestane

References

1. Macdonald F (1997). Dictionary of Pharmacological Agents. CRC Press. p. 1635. ISBN 978-0-412-46630-4. Retrieved 19 May 2012.
2. Morton IK, Hall JM (1999). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer. p. 227. ISBN 978-0-7514-0499-9. Retrieved 20 May 2012.
3. Lombardi P (June 1995). "The irreversible inhibition of aromatase (oestrogen synthetase) by steroidal compounds". Current Pharmaceutical Design. Bentham Science Publishers. 1: 23–50 (45). Retrieved 20 May 2012.
4. Kreider RB, Leutholtz BC, Katch FI, Katch VL (2009). Exercise and Sport Nutrition. Exercise & Sport Nutrition. p. 350. ISBN 978-0-9742965-6-2. Retrieved 20 May 2012.
5. Kelloff GJ, Lubet RA, Lieberman R, et al. (January 1998). "Aromatase inhibitors as potential cancer chemopreventives". Cancer Epidemiology, Biomarkers & Prevention. 7 (1): 65–78. PMID 9456245.
6. Avendaño C, Menéndez JC (4 June 2008). Medicinal Chemistry of Anticancer Drugs. Elsevier. p. 69. ISBN 978-0-444-52824-7. Retrieved 20 May 2012.