Senecionine
Medicinal Chemistry
Molecular Weight
335.4
Molecular Formula
C18H25NO5
IUPAC Name
(1R,2R,4Z,8E,10S,14R)-2-hydroxy-2,10-dimethyl-5,16-dioxo-4,14-dioxa-17-azatricyclo[12.3.0.017,6]heptadeca-8-en-11-ylideneacetic acid
Pharmacognosy
Biological Source
Senecio species (Groundsel)
Active Constituents
Senecionine
Pharmacology & Synthesis
Mechanism of Action
Metabolized in liver to reactive pyrroles that cross-link DNA and proteins.
Pharmacokinetics (ADME)
A: Well absorbed.
D: Concentrates in the liver.
M: Hepatic CYP450 to toxic pyrrole derivatives.
E: Renal.
Pharmacodynamics
Causes severe hepatovenous occlusive disease (VOD), highly hepatotoxic and carcinogenic.
Synthesis Pathway
Derived from ornithine via putrescine.
Safety, Warnings & Interactions
Adverse Effects
Hepatic veno-occlusive disease, cirrhosis, liver failure.
Contraindications
Highly toxic; not used clinically.
Drug Interactions
CYP450 inducers significantly increase toxicity.
Pharmaceutics & Compendia
Dosage Forms
Toxic contaminant in herbs