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Showing drug card for Bentiromide (DB00522)

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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-02-19 16:03:33
Primary Accession Number DB00522
Secondary Accession Number
  • APRD00818
Name Bentiromide
Drug Type
  • Approved
  • Small Molecule
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 Bentiromide is not available in the U.S. or Canada (It was withdrawn in the US in October 1996).
Synonyms
  1. BTPABA
  2. Bentiromide [USAN:BAN:INN:JAN]
  3. Bentiromido [INN-Spanish]
  4. Bentiromidum [INN-Latin]
  5. PFD
  6. PFT
Brand Names
  1. Chymex
Brand Mixtures Not Available
Chemical IUPAC Name 4-[[2-(benzoylamino)-3-(4-hydroxyphenyl)propanoyl]amino]benzoic acid
Chemical Formula C23H20N2O5
Chemical Structure Structure
CAS Registry Number 37106-97-1
InChI Identifier InChI=1/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)/f/h24-25,29H
InChI Key SPPTWHFVYKCNNK-LMDSNWCACU
KEGG Drug D01346 Link Image
KEGG Compound Not Available
PubChem Compound 2329 Link Image
PubChem Substance 7848409 Link Image
ChEBI ID Not Available
PharmGKB ID PA448566 Link Image
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] Not Available
RxList Link Not Available
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Bentiromide Link Image
FDA Label Not Available
Material Safety Data Sheet (MSDS) Not Available
Synthesis Reference Not Available
Average Molecular Weight 404.4153
Monoisotopic Molecular Weight 404.1372
State Solid
Melting Point 241 oC
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 4.12e-03 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity 3.3 Source: PhysProp
Predicted LogP 2.99 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -4.99 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES OC(=O)C1=CC=C(NC(=O)[C@@H](CC2=CC=C(O)C=C2)NC(=O)C2=CC=CC=C2)C=C1
Canonical SMILES OC(=O)C1=CC=C(NC(=O)C(CC2=CC=C(O)C=C2)NC(=O)C2=CC=CC=C2)C=C1
Drug Category
  • Diagnostic aids
  • Indicators and Reagents
ATC Codes
AHFS Codes Not Available
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.
Mechanism of Action Bentiromide is a peptide that is broken down in the pancreas by lipase, protease, and amylase. 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
Toxicity Symptoms of overdose include shortness of breath and troubled breathing.
Protein Binding Not Available
Biotransformation Primarily hepatic. Enzymatic activity capable of hydrolyzing bentiromide has also been found in normal small intestine.
Half Life Not Available
Dosage Forms Not Available
Patient Information Show Link Image
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions Not Available
Food Interactions Not Available
Pathways Not Available
General References
  1. Drugs.com Link Image
  2. Wikipedia Link Image
Organisms Affected
  • Humans and other mammals
Phase 1 Metabolizing Enzymes
  1. Alpha-amylase
Targets
  1. Pancreatic triacylglycerol lipase
Phase 1 Metabolizing Enzyme 1 [top]
Enzyme 1 Name Alpha-amylase
Enzyme 1 Gene Name AMY2A
Enzyme 1 SwissProt ID P04746 Link Image
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 Protein Sequence >sp|P04746|AMYP_HUMAN Pancreatic alpha-amylase precursor 
MKFFLLLFTIGFCWAQYSPNTQQGRTSIVHLFEWRWVDIALECERYLAPKGFGGVQVSPP
NENVAIYNPFRPWWERYQPVSYKLCTRSGNEDEFRNMVTRCNNVGVRIYVDAVINHMCGN
AVSAGTSSTCGSYFNPGSRDFPAVPYSGWDFNDGKCKTGSGDIENYNDATQVRDCRLTGL
LDLALEKDYVRSKIAEYMNHLIDIGVAGFRLDASKHMWPGDIKAILDKLHNLNSNWFPAG
SKPFIYQEVIDLGGEPIKSSDYFGNGRVTEFKYGAKLGTVIRKWNGEKMSYLKNWGEGWG
FVPSDRALVFVDNHDNQRGHGAGGASILTFWDARLYKMAVGFMLAHPYGFTRVMSSYRWP
RQFQNGNDVNDWVGPPNNNGVIKEVTINPDTTCGNDWVCEHRWRQIRNMVIFRNVVDGQP
FTNWYDNGSNQVAFGRGNRGFIVFNNDDWSFSLTLQTGLPAGTYCDVISGDKINGNCTGI
KIYVSDDGKAHFSISNSAEDPFIAIHAESKL
Drug Target 1 [top]
Target 1 ID 754
Target 1 Name Pancreatic triacylglycerol lipase
Target 1 Synonyms
  1. EC 3.1.1.3
  2. PL
  3. Pancreatic lipase
  4. Pancreatic triacylglycerol lipase precursor
Target 1 Gene Name PNLIP
Target 1 Protein Sequence >Pancreatic triacylglycerol lipase precursor 
MLPLWTLSLLLGAVAGKEVCYERLGCFSDDSPWSGITERPLHILPWSPKDVNTRFLLYTN
ENPNNFQEVAADSSSISGSNFKTNRKTRFIIHGFIDKGEENWLANVCKNLFKVESVNCIC
VDWKGGSRTGYTQASQNIRIVGAEVAYFVEFLQSAFGYSPSNVHVIGHSLGAHAAGEAGR
RTNGTIGRITGLDPAEPCFQGTPELVRLDPSDAKFVDVIHTDGAPIVPNLGFGMSQVVGH
LDFFPNGGVEMPGCKKNILSQIVDIDGIWEGTRDFAACNHLRSYKYYTDSIVNPDGFAGF
PCASYNVFTANKCFPCPSGGCPQMGHYADRYPGKTNDVGQKFYLDTGDASNFARWRYKVS
VTLSGKKVTGHILVSLFGNKGNSKQYEIFKGTLKPDSTHSNEFDSDVDVGDLQMVKFIWY
NNVINPTLPRVGASKIIVETNVGKQFNFCSPETVREEVLLTLTPC
Target 1 Number of Residues 472
Target 1 Molecular Weight 51157
Target 1 Theoretical pI 6.72
Target 1 GO Classification
Function
hydrolase activity
hydrolase activity, acting on ester bonds
carboxylic ester hydrolase activity
lipase activity
triacylglycerol lipase activity
catalytic activity
Process
physiological process
metabolism
primary metabolism
lipid metabolism
Component
Not Available
Target 1 General Function Involved in triacylglycerol lipase activity
Target 1 Specific Function Not Available
Target 1 Pathways
Name SMPDB Link KEGG Link
Glycerolipid metabolism SMP00039 Link Image map00561 Link Image
Target 1 Reactions
  • triacylglycerol + H2O = diacylglycerol + a carboxylate
Target 1 Pfam Domain Function
Target 1 Signals
  • 1-16
Target 1 Transmembrane Regions
  • None
Target 1 Essentiality Non-Essential
Target 1 GenBank ID Protein 339597 Link Image
Target 1 UniProtKB/Swiss-Prot ID P16233 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name LIPP_HUMAN Link Image
Target 1 PDB ID 1N8S Link Image
Target 1 PDB File Show
Target 1 3D Structure
Target 1 Cellular Location
  • Secreted protein
Target 1 Gene Sequence >1398 bp 
ATGCTGCCACTTTGGACTCTTTCACTGCTGCTGGGAGCAGTAGCAGGAAAAGAAGTTTGC
TACGAAAGACTCGGCTGCTTCAGTGATGACTCCCCATGGTCAGGAATTACGGAAAGACCC
CTCCATATATTGCCTTGGTCTCCAAAAGATGTCAACACCCGCTTCCTCCTATATACTAAT
GAGAACCCAAACAACTTTCAAGAAGTTGCCGCAGATTCATCAAGCATCAGTGGCTCCAAT
TTCAAAACAAATAGAAAAACTCGCTTTATTATTCATGGATTCATAGACAAGGGAGAAGAA
AACTGGCTGGCCAATGTGTGCAAGAATCTGTTCAAGGTGGAAAGTGTGAACTGTATCTGT
GTGGACTGGAAAGGTGGCTCCCGAACTGGATACACACAAGCCTCGCAGAACATCAGGATC
GTGGGAGCAGAAGTGGCATATTTTGTTGAATTTCTTCAGTCGGCGTTCGGTTACTCACCT
TCCAACGTGCATGTCATTGGCCACAGCCTGGGTGCCCACGCTGCTGGGGAGGCTGGAAGG
AGAACCAATGGGACCATTGGACGCATCACAGGGTTGGACCCAGCAGAACCTTGCTTTCAG
GGCACACCTGAATTAGTCCGATTGGACCCCAGCGATGCCAAATTTGTGGATGTAATTCAC
ACGGATGGTGCCCCCATAGTCCCCAATTTGGGGTTTGGAATGAGCCAAGTCGTGGGCCAC
CTAGATTTCTTTCCAAATGGAGGAGTGGAAATGCCTGGATGTAAAAAGAACATTCTCTCT
CAGATTGTGGACATAGACGGAATCTGGGAAGGGACTCGAGACTTTGCGGCCTGTAATCAC
TTAAGAAGCTACAAATATTACACTGATAGCATCGTCAACCCTGATGGCTTTGCTGGATTC
CCCTGTGCCTCTTACAACGTCTTCACTGCAAACAAGTGTTTCCCTTGTCCAAGTGGAGGC
TGCCCACAGATGGGTCACTATGCTGATAGATATCCTGGGAAAACAAATGATGTGGGCCAG
AAATTTTATCTAGACACTGGTGATGCCAGTAATTTTGCACGTTGGAGGTATAAGGTATCT
GTCACACTGTCTGGAAAAAAGGTTACAGGACACATACTAGTTTCTTTGTTCGGAAATAAA
GGAAACTCTAAGCAGTATGAAATTTTCAAGGGCACTCTCAAACCAGATAGTACTCATTCC
AATGAATTTGACTCAGATGTGGATGTTGGGGACTTGCAGATGGTTAAATTTATTTGGTAT
AACAATGTGATCAACCCAACTTTACCTAGAGTGGGAGCATCCAAGATTATAGTGGAGACA
AATGTTGGAAAACAGTTCAACTTCTGTAGTCCAGAAACCGTCAGGGAGGAAGTTCTGCTC
ACCCTCACACCGTGTTAG
Target 1 GenBank Gene ID
Target 1 GeneCard ID PNLIP Link Image
Target 1 GenAtlas ID PNLIP Link Image
Target 1 HGNC ID HGNC:9155 Link Image
Target 1 Chromosome Location 10
Target 1 Locus 10q26.1
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Giller T, Buchwald P, Blum-Kaelin D, Hunziker W: Two novel human pancreatic lipase related proteins, hPLRP1 and hPLRP2. Differences in colipase dependence and in lipase activity. J Biol Chem. 1992 Aug 15;267(23):16509-16. [PubMed Link Image]
  2. van Tilbeurgh H, Sarda L, Verger R, Cambillau C: Structure of the pancreatic lipase-procolipase complex. Nature. 1992 Sep 10;359(6391):159-62. [PubMed Link Image]
  3. Winkler FK, D'Arcy A, Hunziker W: Structure of human pancreatic lipase. Nature. 1990 Feb 22;343(6260):771-4. [PubMed Link Image]
  4. Lowe ME, Rosenblum JL, Strauss AW: Cloning and characterization of human pancreatic lipase cDNA. J Biol Chem. 1989 Nov 25;264(33):20042-8. [PubMed Link Image]
  5. Carriere F, Thirstrup K, Boel E, Verger R, Thim L: Structure-function relationships in naturally occurring mutants of pancreatic lipase. Protein Eng. 1994 Apr;7(4):563-9. [PubMed Link Image]
  6. Sims HF, Jennens ML, Lowe ME: The human pancreatic lipase-encoding gene: structure and conservation of an Alu sequence in the lipase gene family. Gene. 1993 Sep 15;131(2):281-5. [PubMed Link Image]
  7. van Tilbeurgh H, Egloff MP, Martinez C, Rugani N, Verger R, Cambillau C: Interfacial activation of the lipase-procolipase complex by mixed micelles revealed by X-ray crystallography. Nature. 1993 Apr 29;362(6423):814-20. [PubMed Link Image]
Target 1 Drug References
  1. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed Link Image]
  2. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed Link Image]

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.