bentiromide bentiromide 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 bentiromide is not available in the united states or canada; it was withdrawn in the us in october 1996. "chymex" redirects here. for the human body digestive fluid, see chyme. bentiromide names preferred iupac name 4-benzoic acid other names (s)-4-((2-(benzoylamino)-3-(4-hydroxyphenyl) -1-oxopropyl)amino)benzoic acid(s)-p-(α-benzamido-p-hydroxyhydrocinnamamido) benzoic acidbenzoyltyrosyl-p-aminobenzoic acid (btpaba)chymexn-benzoyl-l-tyrosyl-p-aminobenzoic acidp-((n-benzoyl-l-tyrosin)amido)benzoic acidchymex (trade name) identifiers cas number 37106-97-1 y 3d model (jsmol) interactive image abbreviations btpaba chebi chebi:31263 y chembl chembl1200368 n chemspider 5329364 y drugbank db00522 y echa infocard 100.048.484 ec number 253-349-8 pubchem cid 6957673 unii 239if5w61j y comptox dashboard (epa) dtxsid2048377 inchi inchi=1s/c23h20n2o5/c26-19-12-6-15(7-13-19)14-20(25-21(27)16-4-2-1-3-5-16)22(28)24-18-10-8-17(9-11-18)23(29)30/h1-13,20,26h,14h2,(h,24,28)(h,25,27)(h,29,30)/t20-/m0/s1 ykey: spptwhfvykcnnk-fqevstjzsa-n yinchi=1/c23h20n2o5/c26-19-12-6-15(7-13-19)14-20(25-21(27)16-4-2-1-3-5-16)22(28)24-18-10-8-17(9-11-18)23(29)30/h1-13,20,26h,14h2,(h,24,28)(h,25,27)(h,29,30)/t20-/m0/s1key: spptwhfvykcnnk-fqevstjzbr smiles o=c(o)c1ccc(cc1)nc(=o)(nc(=o)c2ccccc2)cc3ccc(o)cc3 properties chemical formula c23h20n2o5 molar mass 404.4153 g/mol pharmacology atc code v04ck03 (who) except where otherwise noted, data are given for materials in their standard state (at 25 °c , 100 kpa). n verify (what is yn ?) infobox references side effects headache and gastrointestinal disturbances have been reported in patients taking bentiromide. 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 h_bond_acceptor=5 synthesis bentiromide synthesis: synthesis, in vitro and in vivo data: 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).