Bentiromide is a peptide used as a screening test for exocrine pancreatic insufficiency and to monitor the adequacy of supplemental pancreatic therapy. Bentiromide is not available in the United States or Canada; it was withdrawn in the US in October 1996.[2]
Side effects
Headache and gastrointestinal disturbances have been reported in patients taking bentiromide.[2]
Mechanism of action
Bentiromide is given by mouth as a noninvasive test. It is broken down by the pancreatic enzyme chymotrypsin, yielding p-aminobenzoic acid (PABA). The amount of PABA and its metabolites excreted in the urine is taken as a measure of the chymotrypsin-secreting activity of the pancreas.
Chemistry
- XLogP=3.201
- H_bond_donor=4[citation needed]
- H_bond_acceptor=5[citation needed]
Synthesis
It is synthesized by amide formation between ethyl p-aminobenzoate and N-benzoyl-tyrosine using N-methyl-morpholine and ethyl chlorocarbonate for activation. The resulting L-amide is selectively hydrolyzed by sequential use of dimsyl sodium (NaDMSO) and dilute acid to give bentiromide (4).
See also
References
- ^ Bentiromide – Compound Summary, PubChem.
- ^ a b Micromedex Detailed Consumer Information on bentiromide.
- ^ P. L. De Benneville, N. J. Greenberger, DE 2156835; eidem, U.S. patent 3,801,562 (1972, 1974 both to Rohm & Haas).
- ^ Debenneville, Peter L.; Godfrey, William J.; Sims, Homer J.; Imondi, Anthony R. (1972). "New substrates for a pancreatic exocrine function test". Journal of Medicinal Chemistry. 15 (11): 1098–1100. doi:10.1021/jm00281a002. PMID 4654657.
