Bentiromide

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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 Bentiromide is not available in the United States or Canada; it was withdrawn in the US in October 1996.[1]

Side effects

Headache and gastrointestinal disturbances have been reported in patients taking bentiromide.[1]

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

Synthesis

File:Bentiromide synthesis.svg
Bentiromide synthesis:[2] Synthesis, in vitro and in vivo data:[3]

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

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  1. a b Template:Drugs.com on bentiromide.
  2. P. L. De Benneville, N. J. Greenberger, <templatestyles src="Citation/styles.css"/>Template:Citation/make link Script error: No such module "Check for unknown parameters".; eidem, U.S. patent 3801562 (1972, 1974 both to Rohm & Haas).
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