Estromustine

Not to be confused with Estramustine phosphate or Estramustine.

Estromustine

Clinical data
Other names	EoM; Leo 271 f; Estrone 17β-3-N-bis(2-chloroethyl)carbamate; Estrone–cytostatic complex
Drug class	Chemotherapeutic agent; Estrogen; Estrogen ester
Pharmacokinetic data
Elimination half-life	14 hours[1]
Identifiers
IUPAC name [(8R,9S,13S,14S)-13-Methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-yl] N,N-bis(2-chloroethyl)carbamate
CAS Number	62899-40-5
PubChem CID	124946
ChemSpider	111241
CompTox Dashboard (EPA)	DTXSID40978673
Chemical and physical data
Formula	C23H29Cl2NO3
Molar mass	438.39 g·mol^−1
3D model (JSmol)	Interactive image
SMILES C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CCC4=C3C=CC(=C4)OC(=O)N(CCCl)CCCl
InChI InChI=1S/C23H29Cl2NO3/c1-23-9-8-18-17-5-3-16(29-22(28)26(12-10-24)13-11-25)14-15(17)2-4-19(18)20(23)6-7-21(23)27/h3,5,14,18-20H,2,4,6-13H2,1H3/t18-,19-,20+,23+/m1/s1 Key:AXWYROHIFVWHMR-UGTOYMOASA-N

Estromustine (developmental code name Leo 271 f), also known as estrone 17β-3-N-bis(2-chloroethyl)carbamate or estrone–cytostatic complex,^[2] is a major active metabolite of the cytostatic antineoplastic agent and estrogen estramustine phosphate, a medication used in the treatment of prostate cancer.^[1][3]

See also

• List of hormonal cytostatic antineoplastic agents
• List of estrogen esters § Estradiol esters

References

1. Chabner BA, Longo DL (7 December 2011). Cancer Chemotherapy and Biotherapy: Principles and Practice. Lippincott Williams & Wilkins. pp. 252–. ISBN 978-1-4511-4820-6.
2. Yamanaka H, Kitaura K, Imai K, Yuasa H, Nakai K, Matsumura Y, Uehara H, Shida K (1981). "In vivo studies of 3H-estramustine in castrated male rat". Acta Urologica Japonica. 27 (3): 243–50.
3. Medical Subject Headings: Supplementary chemical records. The Library. 1993. p. 684.