Bentiromide

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
CAS Number	37106-97-1
Abbreviations	Btpaba
ChEBI	CHEBI:31263
ChEMBL	ChEMBL1200368
ChemSpider	5329364
DrugBank	DB00522
EC Number	253-349-8
Jmol interactive 3D	Image
PubChem	6957673
UNII	239IF5W61J
InChI 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 Key: SPPTWHFVYKCNNK-FQEVSTJZSA-N 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
SMILES O=C(O)c1ccc(cc1)NC(=O)[C@@H](NC(=O)c2ccccc2)Cc3ccc(O)cc3
Properties
Chemical formula	C23H20N2O5
Molar mass	404.4153 g/mol
Pharmacology
ATC code	V04CK03
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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 Bentiromide is not available in the United States or Canada (it was withdrawn in the U.S. in October 1996.)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

• XLogP=3.201
• tautomers=12
• H_bond_donor=4
• H_bond_acceptor=5

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

• Chronic pancreatitis

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.