Piperine
Medicinal Chemistry
Molecular Weight
285.34
Molecular Formula
C17H19NO3
IUPAC Name
(1E,3E)-1-(1,3-benzodioxol-5-yl)-5-(piperidin-1-yl)penta-1,3-dien-5-one
Pharmacognosy
Biological Source
Piper nigrum (Black pepper), Piper longum
Active Constituents
Piperine
Pharmacology & Synthesis
Mechanism of Action
Inhibits P-glycoprotein and hepatic CYP3A4/CYP2C9, reducing drug efflux and metabolism.
Pharmacokinetics (ADME)
A: Highly absorbed.
D: Widely distributed.
M: Hepatic.
E: Renal and fecal.
Pharmacodynamics
Significantly enhances the bioavailability of co-administered drugs and supplements (e.g., curcumin).
Synthesis Pathway
Synthesized via condensation of piperidine and piperic acid.
Safety, Warnings & Interactions
Adverse Effects
GI irritation at high doses.
Contraindications
Contraindicated with narrow therapeutic index drugs metabolized by CYP3A4.
Drug Interactions
Phenytoin, Propranolol, Theophylline (increases their plasma levels).
Pharmaceutics & Compendia
Dosage Forms
Capsules, Extracts
Official Compendia
USP (Dietary)