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 ;
3D model (JSmol)	Interactive image;
Abbreviations	Btpaba
ChEBI	CHEBI:31263 ;
ChEMBL	ChEMBL1200368 ;
ChemSpider	5329364 ;
DrugBank	DB00522 ;
ECHA InfoCard	100.048.484
EC Number	253-349-8;
PubChem CID	6957673;
UNII	239IF5W61J ;
CompTox Dashboard (EPA)	DTXSID2048377 ;
	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 (WHO)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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 Bentiromide is not available in the United States or Canada; it was withdrawn in the US in October 1996.^[2]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

References

^ Bentiromide – Compound Summary, PubChem.
^ ^a ^b Micromedex Detailed Consumer Information on bentiromide.
^ P. L. De Benneville, N. J. Greenberger, DE 2156835; eidem, U.S. Patent 3,801,562 (1972, 1974 both to Rohm & Haas).
^ 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.

[1] Bentiromide – Compound Summary, PubChem.

[Drugs.com-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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