Bentiromide[1]
Names
Preferred IUPAC name
4-[(2S)-2-Benzamido-3-(4-hydroxyphenyl)propanamido]benzoic 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
3D model (JSmol)
Abbreviations Btpaba
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.048.484
EC Number
  • 253-349-8
UNII
  • 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 checkY
    Key: SPPTWHFVYKCNNK-FQEVSTJZSA-N checkY
  • InChI=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/s1
    Key: SPPTWHFVYKCNNK-FQEVSTJZBR
  • O=C(O)c1ccc(cc1)NC(=O)[C@@H](NC(=O)c2ccccc2)Cc3ccc(O)cc3
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 checkY☒N ?)
Infobox references

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 Bentiromide is not available in the United States or Canada; it was withdrawn in the US in October 1996.[2]

Side effects

Headache and gastrointestinal disturbances have been reported in patients taking bentiromide.[2]

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:[3] Synthesis, in vitro and in vivo data:[4]

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. 1 2 Micromedex Detailed Consumer Information on bentiromide.
  3. ↑ P. L. De Benneville, N. J. Greenberger, DE 2156835; eidem, U.S. Patent 3,801,562 (1972, 1974 both to Rohm & Haas).
  4. ↑ 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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