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 Bentiromide is not available in the U.S. or Canada (It was withdrawn in the US in October 1996).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
Bentiromide
Bentiromido
Bentiromidum
BTPABA
PFT
External IDs E 2663 / E-2663 / Ro 11-7891
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
PFDSannova
Brand mixturesNot Available
Categories
UNII239IF5W61J
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)[[email protected]](CC2=CC=C(O)C=C2)NC(=O)C2=CC=CC=C2)C=C1
Pharmacology
Indication

Used as a screening test for exocrine pancreatic insufficiency and to monitor the adequacy of supplemental pancreatic therapy.

Structured Indications Not Available
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.

TargetKindPharmacological actionActionsOrganismUniProt ID
Serine protease hepsinProteinyes
ligand
HumanP05981 details
Related Articles
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
Toxicity

Symptoms of overdose include shortness of breath and troubled breathing.

Affected organisms
  • Humans and other mammals
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot 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 References
  1. Toskes PP: The bentiromide test for pancreatic exocrine insufficiency. Pharmacotherapy. 1984 Mar-Apr;4(2):74-80. [PubMed:6371722 ]
External Links
ATC CodesV04CK03 — Bentiromide
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
1, 2RecruitingTreatmentAcne Vulgaris Superficial Mixed Comedonal and Inflammatory1
Pharmacoeconomics
Manufacturers
  • Savage laboratories inc div altana inc
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point (°C)240-242DeBenneville, 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 Solubility0.00412 mg/mLALOGPS
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 Area115.73 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity112.75 m3·mol-1ChemAxon
Polarizability42.16 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.5224
Blood Brain Barrier+0.7085
Caco-2 permeable-0.7954
P-glycoprotein substrateNon-substrate0.5201
P-glycoprotein inhibitor INon-inhibitor0.9668
P-glycoprotein inhibitor IINon-inhibitor0.9765
Renal organic cation transporterNon-inhibitor0.9466
CYP450 2C9 substrateNon-substrate0.7866
CYP450 2D6 substrateNon-substrate0.8148
CYP450 3A4 substrateNon-substrate0.6344
CYP450 1A2 substrateNon-inhibitor0.8856
CYP450 2C9 inhibitorNon-inhibitor0.7744
CYP450 2D6 inhibitorNon-inhibitor0.9233
CYP450 2C19 inhibitorNon-inhibitor0.8775
CYP450 3A4 inhibitorNon-inhibitor0.9168
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9014
Ames testNon AMES toxic0.9317
CarcinogenicityNon-carcinogens0.8637
BiodegradationNot ready biodegradable0.7682
Rat acute toxicity1.8601 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9831
hERG inhibition (predictor II)Non-inhibitor0.9543
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as tyrosine and derivatives. These are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentTyrosine and derivatives
Alternative ParentsPhenylalanine and derivatives / Acylaminobenzoic acid and derivatives / Hippuric acids and derivatives / N-acyl-alpha amino acids and derivatives / Alpha amino acid amides / Amphetamines and derivatives / Anilides / Benzoic acids / N-arylamides / Benzoyl derivatives
SubstituentsTyrosine or derivatives / Phenylalanine or derivatives / Hippuric acid or derivatives / N-acyl-alpha amino acid or derivatives / Acylaminobenzoic acid or derivatives / Alpha-amino acid amide / Amphetamine or derivatives / Benzoic acid or derivatives / Anilide / Benzoic acid
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptorsdipeptide (CHEBI:31263 )

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
ligand
General Function:
Serine-type peptidase activity
Specific Function:
Plays an essential role in cell growth and maintenance of cell morphology. May mediate the activating cleavage of HGF and MST1/HGFL. Plays a role in the proteolytic processing of ACE2.
Gene Name:
HPN
Uniprot ID:
P05981
Uniprot Name:
Serine protease hepsin
Molecular Weight:
45011.01 Da
References
  1. Chowdhury RS, Forsmark CE: Review article: Pancreatic function testing. Aliment Pharmacol Ther. 2003 Mar 15;17(6):733-50. [PubMed:12641496 ]
  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:3258344 ]
  3. Toskes PP: The bentiromide test for pancreatic exocrine insufficiency. Pharmacotherapy. 1984 Mar-Apr;4(2):74-80. [PubMed:6371722 ]
  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:10592235 ]
Drug created on June 13, 2005 07:24 / Updated on July 18, 2017 16:50