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Updated: Aug 16, 2026

Prostaglandin Extraction and Analysis in Caenorhabditis elegans
Published on: June 25, 2013
Enzymatic formation of prostamide F2alpha from anandamide involves a newly identified intermediate metabolite,
Wu Yang1, Jinsong Ni, David F Woodward
1Department of Pharmacokinetics and Drug Metabolism, Allergan, Inc., Irvine, CA 92623, USA. yang_wu@allergan.com
Abstract:
Prostaglandin F2alpha 1-ethanolamide (prostamide F2alpha) is a potent ocular hypotensive agent in animals and represents a new class of fatty acid amide compounds. Accumulated evidence indicated that anandamide, an endogenous bioactive ligand for cannabinoid receptors, may serve as a common substrate to produce all prostamides, including prostamide F2alpha. After incubation of anandamide with cyclooxygenase 2 (COX-2), the reaction mixture was profiled by HPLC and an intermediate metabolite was discovered and characterized as a cyclic endoperoxide ethanolamide using HPLC-tandem mass spectrometry. Formation of prostamide F2alpha was also demonstrated when the intermediate metabolite was isolated and incubated with prostaglandin F synthase (PGF synthase). These results suggest that the biosynthesis of prostamide F2alpha proceeds in two consecutive steps: oxidation of anandamide to form an endoperoxide intermediate by COX-2, and reduction of the endoperoxide intermediate to form prostamide F2alpha by PGF synthase. This endoperoxide ethanolamide intermediate has been proposed as prostamide H2.
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