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Bentiromide is a peptide used as a screening test for exocrine
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
pancreatic
The pancreas is an Organ (anatomy), organ of the digestive system and endocrine system of vertebrates. In humans, it is located in the abdominal cavity, abdomen behind the stomach and functions as a gland. The pancreas is a mixed or heterocrine ...
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 Bentiromide is not available in the United States or Canada; it was withdrawn in the US in October 1996. on bentiromide.
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 enzymechymotrypsin
Chymotrypsin (, chymotrypsins A and B, alpha-chymar ophth, avazyme, chymar, chymotest, enzeon, quimar, quimotrase, alpha-chymar, alpha-chymotrypsin A, alpha-chymotrypsin) is a digestive enzyme component of pancreatic juice acting in the duodenu ...
, 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=5Synthesis
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
Sodium methylsulfinylmethylide (also called NaDMSO or dimsyl sodium) is the sodium salt of the conjugate base of dimethyl sulfoxide. This unusual salt has some uses in organic chemistry as a base and nucleophile.
Since the first publication in 19 ...
( NaDMSO) and dilute acid to give bentiromide (4).
See also
*Chronic pancreatitis
Chronic pancreatitis is a long-standing inflammation of the pancreas that alters the organ's normal structure and functions. It can present as episodes of acute inflammation in a previously injured pancreas, or as chronic damage with persistent pa ...
References
{{Diagnostic agents Benzoic acids