4-[3-(4-hydroxyphenyl)-2-(phenylformamido)propanamido]benzoic acid

• ChemBase ID: 404
• Molecular Formular: C23H20N2O5
• Molecular Mass: 404.4153
• Monoisotopic Mass: 404.13722175
• SMILES: O=C(Nc1ccc(cc1)C(=O)O)C(NC(=O)c1ccccc1)Cc1ccc(O)cc1
• Canonical SMILES: O=C(C(NC(=O)c1ccccc1)Cc1ccc(cc1)O)Nc1ccc(cc1)C(=O)O
• 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)
• InChIKey: SPPTWHFVYKCNNK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[3-(4-hydroxyphenyl)-2-(phenylformamido)propanamido]benzoic acid
• IUPAC Traditional name: bentiromide
• Brand Name: Chymex
• Synonyms: Bentiromide [USAN:BAN:INN:JAN]; Bentiromido [INN-Spanish]; Bentiromidum [INN-Latin]; BTPABA; PFD; PFT; Bentiromide

Database IDs

• CAS Number: 37106-97-1
• PubChem SID: 160963867
• PubChem CID: 2329

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.157471
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 2.1798987
• LogD (pH = 7.4): 0.47363257
• Log P: 3.5389557
• Molar Refractivity: 112.745 cm^3
• Polarizability: 42.013195 Å^3
• Polar Surface Area: 115.73 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.99
• LOG S: -4.99
• Solubility (Water): 4.12e-03 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 3.3

DETAILS

DrugBank - DB00522

• Drug Groups: approved
• Description: 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 Bentiromide is not available in the U.S. or Canada (It was withdrawn in the US in October 1996).
• Indication: Used as a screening test for exocrine pancreatic insufficiency and to monitor the adequacy of supplemental pancreatic therapy.
• Pharmacology: 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 p-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 U.S. or Canada.
• Toxicity: Symptoms of overdose include shortness of breath and troubled breathing.
• Affected Organisms: Humans and other mammals
• Biotransformation: Primarily hepatic. Enzymatic activity capable of hydrolyzing bentiromide has also been found in normal small intestine.
• References: Toskes PP: The bentiromide test for pancreatic exocrine insufficiency. Pharmacotherapy. 1984 Mar-Apr;4(2):74-80. [Pubmed]
• External Links: Wikipedia

REFERENCES

• Toskes PP: The bentiromide test for pancreatic exocrine insufficiency. Pharmacotherapy. 1984 Mar-Apr;4(2):74-80. Pubmed