Bentiromide

"Chymex" redirects here. For the human body digestive fluid, see Chyme.

Bentiromide

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 Y
Abbreviations	Btpaba
ChEBI	CHEBI:31263 Y
ChEMBL	ChEMBL1200368 N
ChemSpider	5329364 Y
DrugBank	DB00522 Y
EC Number	253-349-8
Jmol 3D model	Interactive image
PubChem	6957673
UNII	239IF5W61J Y
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 Y Key: SPPTWHFVYKCNNK-FQEVSTJZSA-N Y 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
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
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 Bentiromide is not available in the United States or Canada (it was withdrawn in the U.S. in October 1996.)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: Synthesis, in vitro and in vivo data:

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