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Identification
NameBentiromide
Accession NumberDB00522  (APRD00818)
Typesmall molecule
Groupswithdrawn
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 Bentiromide is not available in the U.S. or Canada (It was withdrawn in the US in October 1996).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
Synonyms
SynonymLanguageCode
BentiromideNot AvailableINN, BAN, USAN, JAN
BentiromidoSpanishINN
BentiromidumLatinINN
BTPABANot AvailableNot Available
PFTNot AvailableNot Available
SaltsNot Available
Brand names
NameCompany
PFDSannova
Brand mixturesNot Available
Categories
CAS number37106-97-1
WeightAverage: 404.4153
Monoisotopic: 404.13722176
Chemical FormulaC23H20N2O5
InChI KeySPPTWHFVYKCNNK-FQEVSTJZSA-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)/t20-/m0/s1
IUPAC Name
4-[(2S)-3-(4-hydroxyphenyl)-2-(phenylformamido)propanamido]benzoic acid
SMILES
OC(=O)C1=CC=C(NC(=O)[C@H](CC2=CC=C(O)C=C2)NC(=O)C2=CC=CC=C2)C=C1
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassOrganic Acids and Derivatives
ClassCarboxylic Acids and Derivatives
SubclassAmino Acids, Peptides, and Analogues
Direct parentN-acyl-alpha Amino Acids and Derivatives
Alternative parentsAlpha Amino Acid Amides; Amphetamines and Derivatives; Phenylpropylamines; Aminobenzoic Acid Derivatives; Anilides; Benzoic Acids; Benzamides; Benzoyl Derivatives; Phenols and Derivatives; Secondary Carboxylic Acid Amides; Enolates; Enols; Polyamines; Carboxylic Acids
Substituentsaminobenzoate; amphetamine or derivative; acetanilide; phenylpropylamine; benzoic acid; benzamide; benzoic acid or derivative; benzoyl; phenol derivative; benzene; secondary carboxylic acid amide; carboxamide group; enol; polyamine; carboxylic acid; enolate; organonitrogen compound; amine
Classification descriptionThis compound belongs to the n-acyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at his terminal nitrogen atom.
Pharmacology
IndicationUsed as a screening test for exocrine pancreatic insufficiency and to monitor the adequacy of supplemental pancreatic therapy.
PharmacodynamicsBentiromide 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 actionBentiromide 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.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Primarily hepatic. Enzymatic activity capable of hydrolyzing bentiromide has also been found in normal small intestine.

Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicitySymptoms of overdose include shortness of breath and troubled breathing.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.5224
Blood Brain Barrier + 0.7085
Caco-2 permeable - 0.7954
P-glycoprotein substrate Non-substrate 0.5201
P-glycoprotein inhibitor I Non-inhibitor 0.9668
P-glycoprotein inhibitor II Non-inhibitor 0.9765
Renal organic cation transporter Non-inhibitor 0.9466
CYP450 2C9 substrate Non-substrate 0.7866
CYP450 2D6 substrate Non-substrate 0.8148
CYP450 3A4 substrate Non-substrate 0.6344
CYP450 1A2 substrate Non-inhibitor 0.8856
CYP450 2C9 substrate Non-inhibitor 0.7744
CYP450 2D6 substrate Non-inhibitor 0.9233
CYP450 2C19 substrate Non-inhibitor 0.8775
CYP450 3A4 substrate Non-inhibitor 0.9168
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9014
Ames test Non AMES toxic 0.9317
Carcinogenicity Non-carcinogens 0.8637
Biodegradation Not ready biodegradable 0.7682
Rat acute toxicity 1.8601 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9831
hERG inhibition (predictor II) Non-inhibitor 0.9543
Pharmacoeconomics
Manufacturers
  • Savage laboratories inc div altana inc
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point240-242DeBenneville, P.L.and Greenberger, N.J.; U.S. Patent 3,745,212; July 10,1973; assigned to Rohm & Haas Co.
logP3.3Not Available
Predicted Properties
PropertyValueSource
water solubility4.12e-03 g/lALOGPS
logP2.99ALOGPS
logP3.54ChemAxon
logS-5ALOGPS
pKa (strongest acidic)4.16ChemAxon
pKa (strongest basic)-1.3ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count5ChemAxon
hydrogen donor count4ChemAxon
polar surface area115.73ChemAxon
rotatable bond count7ChemAxon
refractivity112.75ChemAxon
polarizability42.16ChemAxon
number of rings3ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleYesChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

DeBenneville, P.L.and Greenberger, N.J.; U.S. Patent 3,745,212; July 10,1973; assigned to
Rohm & Haas Co.

General Reference
  1. Toskes PP: The bentiromide test for pancreatic exocrine insufficiency. Pharmacotherapy. 1984 Mar-Apr;4(2):74-80. Pubmed
External Links
ResourceLink
KEGG DrugD01346
ChEBI31263
ChEMBLCHEMBL1200368
PharmGKBPA164750572
WikipediaBentiromide
ATC CodesV04CK03
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Serine protease hepsin

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: ligand

Components

Name UniProt ID Details
Serine protease hepsin P05981 Details

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

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Drug created on June 13, 2005 07:24 / Updated on March 31, 2014 14:10