Bentiromide

"Chymex" redirects here. For the human body digestive fluid, see Chyme.
Bentiromide[1]
Names
IUPAC name
4-[2-benzamido-3- (4-hydroxyphenyl)- propanoyl] aminobenzoic acid
Other names
(S)-4-((2-(benzoylamino)-3-(4-hydroxyphenyl) -1-oxopropyl)amino)benzoic acid
(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)
Identifiers
37106-97-1 YesY
3D model (Jmol) Interactive image
Abbreviations Btpaba
ChEBI CHEBI:31263 YesY
ChEMBL ChEMBL1200368 N
ChemSpider 5329364 YesY
DrugBank DB00522 YesY
ECHA InfoCard 100.048.484
EC Number 253-349-8
PubChem 6957673
UNII 239IF5W61J YesY
Properties
C23H20N2O5
Molar mass 404.4153 g/mol
Pharmacology
V04CK03 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Bentiromide is a peptide used as a screening test for exocrine pancreatic insufficiency and to monitor the adequacy of supplemental pancreatic therapy. It is given by mouth as a noninvasive test. The amount of 4-aminobenzoic acid and its metabolites excreted in the urine is taken as a measure of the chymotrypsin-secreting activity of the pancreas. Headache and gastrointestinal disturbances have been reported in patients taking bentiromide. Bentiromide is not available in the United States or Canada (it was withdrawn in the U.S. in October 1996.)

Data

Synthesis

Synthetic chymotrypsin-labile peptide, used in diagnosis of exocrine pancreatic disease.

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

  1. ↑ Bentiromide – Compound Summary, PubChem.
  2. ↑ P. L. De Benneville, N. J. Greenberger, DE 2156835; eidem, U.S. Patent 3,801,562 (1972, 1974 both to Rohm & Haas).
  3. ↑ 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. doi:10.1021/jm00281a002. PMID 4654657.


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