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).
	verify (what is ?)
	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 Bentiromide is not available in the United States or Canada (it was withdrawn in the U.S. in October 1996.)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).

References

Bentiromide – Compound Summary, PubChem.
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.

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[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.

Bentiromide

Data

Synthesis

See also

References