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Identification
Name Bentiromide
Accession Number DB00522 (APRD00818)
Type small molecule
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 Bentiromide is not available in the U.S. or Canada (It was withdrawn in the US in October 1996).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • Bentiromide [USAN:BAN:INN:JAN]
  • Bentiromido [INN-Spanish]
  • Bentiromidum [INN-Latin]
  • BTPABA
  • PFD
  • PFT
Brand names
  • Chymex
Brand name mixtures Not Available
Categories
  • Diagnostic aids
  • Indicators and Reagents
CAS number 37106-97-1
Weight Average: 404.4153
Monoisotopic: 404.137221760
Chemical Formula C23H20N2O5
InChI Key InChIKey=SPPTWHFVYKCNNK-UHFFFAOYSA-N
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)
Plain Text
IUPAC Name
4-[3-(4-hydroxyphenyl)-2-(phenylformamido)propanamido]benzoic acid
SMILES
OC(=O)C1=CC=C(NC(=O)C(CC2=CC=C(O)C=C2)NC(=O)C2=CC=CC=C2)C=C1
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Acetanilides
  • Aminobenzoates
  • Phenethylamines
  • Polypeptides
  • Phenylpropylamines
  • Benzamides
  • Amphetamines
Substructures
  • Hydroxy Compounds
  • Benzyl Alcohols and Derivatives
  • Acetates
  • Benzoates
  • Phenols and Derivatives
  • Amino Ketones
  • Benzene and Derivatives
  • Acetanilides
  • Aminobenzoates
  • Carboxylic Acids and Derivatives
  • Phenethylamines
  • Polypeptides
  • Aromatic compounds
  • Carboxamides and Derivatives
  • Phenylpropylamines
  • Benzoyl Derivatives
  • Phenyl Esters
  • Benzamides
  • Anilines
  • Amphetamines
Pharmacology
Indication Used as a screening test for exocrine pancreatic insufficiency and to monitor the adequacy of supplemental pancreatic therapy.
Pharmacodynamics 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.
Mechanism of action Bentiromide is a peptide that is broken down in the pancreas by chymotrypsin. By determining the output of unchanged bentiromide in the urine following oral administration, it is possible to determine the sufficiency of pancreatic activity.
Absorption Not Available
Volume of distribution Not Available
Protein binding Not Available
Metabolism

Primarily hepatic. Enzymatic activity capable of hydrolyzing bentiromide has also been found in normal small intestine.
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity Symptoms of overdose include shortness of breath and troubled breathing.
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Savage laboratories inc div altana inc
Packagers Not Available
Dosage forms Not Available
Prices Not Available
Patents Not Available
Properties
State solid
Melting point 241 oC
Experimental Properties
Property Value Source
logP 3.3 PhysProp
Predicted Properties
Property Value Source
water solubility 4.12e-03 g/l ALOGPS
logP 2.99 ALOGPS
logP 3.54 ChemAxon Molconvert
logS -4.99 ALOGPS
pKa 9.50 ChemAxon Molconvert
hydrogen acceptor count 5 ChemAxon Molconvert
hydrogen donor count 4 ChemAxon Molconvert
polar surface area 115.73 ChemAxon Molconvert
rotatable bond count 7 ChemAxon Molconvert
refractivity 112.75 ChemAxon Molconvert
polarizability 41.72 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference
  1. Toskes PP: The bentiromide test for pancreatic exocrine insufficiency. Pharmacotherapy. 1984 Mar-Apr;4(2):74-80. Pubmed
External Links
Resource Link
KEGG Drug D01346 Link_out
PubChem Compound 2329 Link_out
PubChem Substance 46508175 Link_out
ChemSpider 2239 Link_out
ChEBI 31263 Link_out
ChEMBL 31263 Link_out
PharmGKB PA448566 Link_out
Drug Product Database 0 Link_out
Wikipedia http://en.wikipedia.org/wiki/Bentiromide Link_out
ATC Codes
  • V04CK03
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions
Drug Interaction
Food Interactions Not Available
Targets

1. Serine protease hepsin

Pharmacological action: yes
Actions: ligand

Plays an essential role in cell growth and maintenance of cell morphology

Organism class: human
UniProt ID: P05981 Link_out
Gene: HPN Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Chowdhury RS, Forsmark CE: Review article: Pancreatic function testing. Aliment Pharmacol Ther. 2003 Mar 15;17(6):733-50. Pubmed
  2. Bujanover Y, Harel A, Geter R, Blau H, Yahav J, Spirer Z: The development of the chymotryptic activity during postnatal life using the bentiromide test. Int J Pancreatol. 1988 Jan-Feb;3(1):53-8. Pubmed
  3. Toskes PP: The bentiromide test for pancreatic exocrine insufficiency. Pharmacotherapy. 1984 Mar-Apr;4(2):74-80. Pubmed
  4. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on August 03, 2011 15:43

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.