Estramustine
Title: Estramustine
CAS Registry Number: 2998-57-4
CAS Name: (17b)-Estra-1,3,5(10)-triene-3,17-diol 3-[bis(2-chloroethyl)carbamate]
Additional Names: estradiol 3-bis(2-chloroethyl)carbamate; estra-1,3,5(10)triene-3,17b-diol 3-[N,N-bis(2-chloroethyl)carbamate]
Manufacturers' Codes: Ro-21-8837
Molecular Formula: C23H31Cl2NO3
Molecular Weight: 440.40
Percent Composition: C 62.73%, H 7.09%, Cl 16.10%, N 3.18%, O 10.90%
Literature 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).
Properties: Crystals from benzene-petr ether, mp 104-105°. [a]D20 +50° (in dioxane). uv max (alcohol): 270.7, 276.5 nm.
Melting point: mp 104-105°
Optical Rotation: [a]D20 +50° (in dioxane)
Absorption maximum: uv max (alcohol): 270.7, 276.5 nm
 
Derivative Type: 17-Phosphate
Trademarks: Estracyt (Pfizer)
Molecular Formula: C23H32Cl2NO6P
Molecular Weight: 520.38
Percent Composition: C 53.09%, H 6.20%, Cl 13.63%, N 2.69%, O 18.45%, P 5.95%
Properties: mp 155° (dec). [a]D20 +30° (dioxane). Sol in aqueous and alkali solns.
Melting point: mp 155° (dec)
Optical Rotation: [a]D20 +30° (dioxane)
 
Derivative Type: 17-(Dihydrogenphosphate) disodium salt monohydrate
CAS Registry Number: 52205-73-9 (anhydrous)
Trademarks: Emcyt (Pfizer)
Molecular Formula: C23H30Cl2NNa2O6P.H2O
Molecular Weight: 582.36
Percent Composition: 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.
 
Therap-Cat: Antineoplastic.
Keywords: Antineoplastic; Alkylating Agents; Nitrogen Mustards.

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