arachidonoyl diethanolamine

Arachidonoyl diethanolamine (ADA) is a synthetic analog of the endocannabinoid anandamide (arachidonoyl ethanolamide) investigated for its potential antineoplastic properties. It was designed to improve the metabolic stability of anandamide by resisting degradation by fatty acid amide hydrolase (FAAH), an enzyme that typically hydrolyzes anandamide into arachidonic acid and ethanolamine. By adding steric bulk through an additional ethanolamine group, ADA resists FAAH-mediated breakdown. The therapeutic rationale for ADA involves its selective metabolism by cyclooxygenase-2 (COX-2)—which is frequently overexpressed in epithelial cancers—into cytotoxic J-series prostamides, such as 15d-PMJ2. However, preclinical studies in tumorigenic keratinocytes and other epithelial cancer cell lines have indicated that ADA possesses significantly lower cytotoxic potency compared to other anandamide derivatives like arvanil or R1-methanandamide.

Other names

N,N-bis(2-hydroxyethyl)arachidonamide