3706. Estramustine

Nomenclature

CAS number: 2998-57-4
(17β)-Estra-1,3,5(10)-triene-3,17-diol 3-[bis(2-chloroethyl)carbamate]; estradiol 3-bis(2-chloroethyl)carbamate; estra-1,3,5(10)triene-3,17β-diol 3-[N,N-bis(2-chloroethyl)carbamate]; Ro-21-8837.
C23H31Cl2NO3; mol wt 440.40.
C 62.73%, H 7.09%, Cl 16.10%, N 3.18%, O 10.90%.

Description and references

Carbamate ester linking estradiol to nor-nitrogen mustard; depolymerizes microtubules by binding to microtubule associated proteins (MAPs). Prepn: BE 646319; Fex et al., US 3299104 (1963, 1967 to AB Leo); Niculescu-Duvaz et al., J. Med. Chem. 10, 172 (1967). Clinical results: Anderes, Praxis 60, 1375 (1971); Muntzing, Nilsson, Z. Krebsforsch. Klin. Onkol. 77, 166 (1972). Review of mechanism of action: K. D. Tew, M. E. Stearns, Pharmacol. Ther. 43, 299-319 (1989); of pharmacokinetics and pharmacodynamics: A. T. Bergenheim, R. Henriksson, Clin. Pharmacokinet. 34, 163-172 (1998).

Chemical structure

Properties

Crystals from benzene-petr ether, mp 104-105°. [α]D20 +50° (in dioxane). uv max (alcohol): 270.7, 276.5 nm.

Derivative

17-Phosphate.

Nomenclature

Estracyt (Pfizer).
C23H32Cl2NO6P; mol wt 520.38.
C 53.09%, H 6.20%, Cl 13.63%, N 2.69%, O 18.45%, P 5.95%.

Properties

mp 155° (dec). [α]D20 +30° (dioxane). Sol in aqueous and alkali solns.

Derivative

17-(Dihydrogenphosphate) disodium salt monohydrate.

Nomenclature

CAS number: 52205-73-9 (anhydrous)
Emcyt (Pfizer).
C23H30Cl2NNa2O6P.H2O; mol wt 582.36.
C 47.44%, H 5.54%, Cl 12.18%, N 2.41%, Na 7.90%, O 19.23%, P 5.32%.

Properties

Off-white powder; readily sol in water.

Therapeutic Category

Antineoplastic.

Keywords

Antineoplastic; Alkylating Agents; Nitrogen Mustards