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Bentiromide

Bentiromide

(S)-p-(α-benzamido-p-hydroxyhydrocinnamamido) benzoic acid Benzoyltyrosyl-p-aminobenzoic acid (Btpaba)Chymex N-benzoyl-L-tyrosyl-p-aminobenzoic acid P-((N-benzoyl-L-tyrosin)amido)benzoic acid Chymex (trade name) | NFPA-H= | NFPA-F= | NFPA-R= | NFPA-S =

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 Bentiromide is not available in the United States or Canada; it was withdrawn in the US in October 1996.

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

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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).

References

References

  1. [https://pubchem.ncbi.nlm.nih.gov/compound/2329 Bentiromide – Compound Summary], [[PubChem]].
  2. {{Drugs.com. cons. bentiromide on bentiromide.
  3. P. L. De Benneville, N. J. Greenberger, {{cite patent. 3801562 (1972, 1974 both to Rohm & Haas).
  4. (1972). "New substrates for a pancreatic exocrine function test". Journal of Medicinal Chemistry.
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