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Polymorphism of estramustine.

T Wadsten1, N O Lindberg

  • 1Pharmacia LEO Therapeutics AB, Pharmaceutical Department, Helsingborg, Sweden.

Journal of Pharmaceutical Sciences
|July 1, 1989
PubMed
Summary
This summary is machine-generated.

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Estramustine

Area of Science:

  • Solid-state chemistry
  • Pharmaceutical sciences
  • Crystallography

Background:

  • Estramustine's low water solubility (<1 mg/L) necessitates understanding its solid-state properties for oral bioavailability.
  • Polymorphism significantly influences drug performance and therapeutic efficacy.

Purpose of the Study:

  • To investigate the solid-state characteristics of estramustine polymorphs.
  • To identify and characterize different crystalline forms obtained from various solvents.
  • To determine the stable polymorphic form of estramustine.

Main Methods:

  • X-ray crystallography (single-crystal and powder)
  • Differential Scanning Calorimetry (DSC)
  • Infrared (IR) spectroscopy

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Main Results:

  • Four distinct estramustine forms (A, B, C, D) were identified.
  • Form A, an anhydrate, was found to be the most stable form, crystallizing from solvents with low dielectric constants.
  • Metastable solvates (Forms B and C) and a monohydrate (Form D) were observed, converting to Form A upon storage or heating.
  • The crystal structure of stable Form A was determined (orthorhombic, P212121).

Conclusions:

  • Estramustine exhibits significant polymorphism, with several solvates and a stable anhydrous form.
  • Understanding these polymorphic transitions is crucial for controlling estramustine's solid-state properties and ensuring consistent bioavailability.
  • Form A represents the therapeutically relevant stable crystalline form.