Bentiromide
Identification
- Generic Name
- Bentiromide
- DrugBank Accession Number
- DB00522
- Background
Bentiromide is a dipeptide that is used in the bentiromide test, which is a screening test for evaluating pancreatic exocrine function and monitoring the adequacy of supplemental pancreatic therapy. It is typically administered orally. Cases of headache and gastrointestinal disturbances have been reported with the use of bentiromide. Bentiromide is currently not available in the U.S. or Canada.
- Type
- Small Molecule
- Groups
- Investigational, Withdrawn
- Structure
- Weight
- Average: 404.4153
Monoisotopic: 404.13722176 - Chemical Formula
- C23H20N2O5
- Synonyms
- Bentiromide
- Bentiromido
- Bentiromidum
- BTPABA
- PFT
- External IDs
- E 2663
- E-2663
- Ro 11-7891
Pharmacology
- Indication
Indicated as a screening test for exocrine pancreatic insufficiency and to monitor the adequacy of supplemental pancreatic therapy.
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- Pharmacodynamics
Bentiromide is a peptide used as a screening test for exocrine pancreatic insufficiency and to monitor the adequacy of supplemental pancreatic therapy. The amount of p-aminobenzoic acid and its metabolites excreted in the urine is the quantitative measure of the chymotrypsin-secreting activity of the pancreas.
- 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.
Target Actions Organism ASerine protease hepsin ligandHumans - 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
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Symptoms of overdose include shortness of breath and troubled breathing.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- International/Other Brands
- PFD (Sannova)
Categories
- ATC Codes
- V04CK03 — Bentiromide
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds 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.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- Tyrosine and derivatives
- Alternative Parents
- Phenylalanine 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 show 9 more
- Substituents
- 1-hydroxy-2-unsubstituted benzenoid / Acylaminobenzoic acid or derivatives / Alpha-amino acid amide / Amphetamine or derivatives / Anilide / Aromatic homomonocyclic compound / Benzamide / Benzenoid / Benzoic acid / Benzoic acid or derivatives show 22 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- dipeptide (CHEBI:31263)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 239IF5W61J
- CAS number
- 37106-97-1
- InChI Key
- SPPTWHFVYKCNNK-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
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
- Toskes PP: The bentiromide test for pancreatic exocrine insufficiency. Pharmacotherapy. 1984 Mar-Apr;4(2):74-80. [Article]
- External Links
- Human Metabolome Database
- HMDB0014663
- KEGG Drug
- D01346
- PubChem Compound
- 6957673
- PubChem Substance
- 46508175
- ChemSpider
- 5329364
- BindingDB
- 50240073
- 18896
- ChEBI
- 31263
- ChEMBL
- CHEMBL1200368
- ZINC
- ZINC000000608204
- PharmGKB
- PA164750572
- Wikipedia
- Bentiromide
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Savage laboratories inc div altana inc
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 240-242 DeBenneville, P.L.and Greenberger, N.J.; U.S. Patent 3,745,212; July 10,1973; assigned to Rohm & Haas Co. logP 3.3 Not Available - Predicted Properties
Property Value Source Water Solubility 0.00412 mg/mL ALOGPS logP 2.99 ALOGPS logP 3.54 Chemaxon logS -5 ALOGPS pKa (Strongest Acidic) 4.16 Chemaxon pKa (Strongest Basic) -1.3 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 115.73 Å2 Chemaxon Rotatable Bond Count 7 Chemaxon Refractivity 112.74 m3·mol-1 Chemaxon Polarizability 42.12 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - 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 inhibitor Non-inhibitor 0.7744 CYP450 2D6 inhibitor Non-inhibitor 0.9233 CYP450 2C19 inhibitor Non-inhibitor 0.8775 CYP450 3A4 inhibitor 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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0a4l-0951000000-3408813d239b684fcca1 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-0795800000-9c5bf5ad4184cdf857e4 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0uxu-0865900000-a4c67f3204b43285247e Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0bta-0930100000-1b073620bb47b5862d03 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0f8m-2790000000-202090311aeeb786f68b Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0kor-2910000000-e264f6d22d0a9022c18d Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-01bc-5941000000-c0ea94056e3bcd17f3ef Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 208.8920146 predictedDarkChem Lite v0.1.0 [M-H]- 209.6462146 predictedDarkChem Lite v0.1.0 [M-H]- 193.92606 predictedDeepCCS 1.0 (2019) [M+H]+ 209.5849146 predictedDarkChem Lite v0.1.0 [M+H]+ 210.4293146 predictedDarkChem Lite v0.1.0 [M+H]+ 196.32161 predictedDeepCCS 1.0 (2019) [M+Na]+ 209.5085146 predictedDarkChem Lite v0.1.0 [M+Na]+ 209.9071146 predictedDarkChem Lite v0.1.0 [M+Na]+ 202.25203 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Humans
- 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
- Chowdhury RS, Forsmark CE: Review article: Pancreatic function testing. Aliment Pharmacol Ther. 2003 Mar 15;17(6):733-50. [Article]
- 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. [Article]
- Toskes PP: The bentiromide test for pancreatic exocrine insufficiency. Pharmacotherapy. 1984 Mar-Apr;4(2):74-80. [Article]
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at March 03, 2024 02:27