Antimalarial Activity of New Water-Soluble Dihydroartemisinin Derivatives

Abstract

Artemisinin a clinically useful antimalarial agent that was isolated from the plant Artemisia annua, is an unusual sesquiterpene lactone containing an epidioxide function. Dihydroartemisinin, obtained by sodium borohydride reduction, was reported to be more therapeutically active than the parent compound. Neither exhibit cross-resistance to chloroquine and both were proven efficacious against cerebral malaria in humans. Sodium artesunate, the salt of the succinic acid half-ester derivative of dihydroartemisinin, is water soluble and can be administered by intravenous injection. This makes the compound particularly useful in the treatment of cerebral malaria where rapid reversal of the parasitemia and restoration to consciousness of the patient is critical. The utility of sodium artesunate is, however, impaired by its poor stability in aqueous solution due to the ease of hydrolysis of the ester linkage. In order to overcome the stability problem, we have prepared a series of new water-soluble, stable derivatives in which the solubilizing group, carboxylate, is on a moiety that is joined to dihydroartemisinin by an ether rather than an ester linkage. Reprints.

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Document Details

Document Type
Technical Report
Publication Date
Nov 01, 1987
Accession Number
ADA196506

Entities

People

  • Ai J. Lin
  • Daniel L. Klayman
  • Wilbur K. Milhous

Organizations

  • Walter Reed Army Institute of Research

Tags

DTIC Thesaurus Topics

  • Acids
  • Alcohols
  • Antimalarials
  • Aqueous Solutions
  • Chemical Synthesis
  • Chemistry
  • Esters
  • Ethers
  • Hydrolysis
  • Malaria
  • Melting Point
  • Organic Chemistry
  • Peroxides
  • Succinic Acid
  • Water

Fields of Study

  • Medicine

Readers

  • Organic Chemistry
  • Parasitology and Pharmacology of Malaria.