BENTIROMIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H20N2O5
Molecular Weight	404.4153
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)C1=CC=C(NC(=O)[C@H](CC2=CC=C(O)C=C2)NC(=O)C3=CC=CC=C3)C=C1

InChI

InChIKey=SPPTWHFVYKCNNK-FQEVSTJZSA-N

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

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6371722
Curator's Comment: description was created based on several sources, including: http://www.medicatione.com/?c=drug&s=chymex&ingredient=bentiromide | http://edudrugs.com/C/Chymex/more.html | https://en.wikipedia.org/wiki/Bentiromide

Bentiromide (Chymex) is a diagnostic agent that was approved for the diagnosis of pancreatic exocrine insufficiency. 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 United States or Canada.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Chymotrypsin 1 Target ID: Chymotrypsin Sources: https://www.ncbi.nlm.nih.gov/pubmed/3258344 \| https://www.ncbi.nlm.nih.gov/pubmed/6371722	Substrate 661

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pancreatic exocrine insufficiency 1 Sources: http://edudrugs.com/C/Chymex/more.html	Diagnostic		Approved 8429	CHYMEX Approved Use Chymex is a peptide used as a screening test for exocrine pancreatic insufficiency and to monitor the adequacy of supplemental pancreatic therapy. Launch Date 1983

Doses

Dose	Population	Adverse events
5 g single, oral Highest studied dose Dose: 5 g Route: oral Route: single Dose: 5 g Sources: https://pubmed.ncbi.nlm.nih.gov/6603385	unhealthy, adult n = 47 Health Status: unhealthy Condition: ancreatic exocrine insufficiency Age Group: adult Population Size: 47 Sources: https://pubmed.ncbi.nlm.nih.gov/6603385	Other AEs: Nausea, Vomiting... Other AEs: Nausea Vomiting Diarrhea Sources: https://pubmed.ncbi.nlm.nih.gov/6603385

AEs

AE	Dose	Population
Diarrhea	5 g single, oral Highest studied dose Dose: 5 g Route: oral Route: single Dose: 5 g Sources: https://pubmed.ncbi.nlm.nih.gov/6603385	unhealthy, adult n = 47 Health Status: unhealthy Condition: ancreatic exocrine insufficiency Age Group: adult Population Size: 47 Sources: https://pubmed.ncbi.nlm.nih.gov/6603385
Nausea	5 g single, oral Highest studied dose Dose: 5 g Route: oral Route: single Dose: 5 g Sources: https://pubmed.ncbi.nlm.nih.gov/6603385	unhealthy, adult n = 47 Health Status: unhealthy Condition: ancreatic exocrine insufficiency Age Group: adult Population Size: 47 Sources: https://pubmed.ncbi.nlm.nih.gov/6603385
Vomiting	5 g single, oral Highest studied dose Dose: 5 g Route: oral Route: single Dose: 5 g Sources: https://pubmed.ncbi.nlm.nih.gov/6603385	unhealthy, adult n = 47 Health Status: unhealthy Condition: ancreatic exocrine insufficiency Age Group: adult Population Size: 47 Sources: https://pubmed.ncbi.nlm.nih.gov/6603385

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:31263	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:31263
MolPort	MolPort-006-127-559	https://www.molport.com/shop/molecule-link/MolPort-006-127-559
ZINC	ZINC000000608204	http://zinc15.docking.org/substances/ZINC000000608204

PubMed

Title	Date	PubMed
The bentiromide test for pancreatic exocrine insufficiency.	1984 Mar-Apr	6371722
Pancreatic polypeptide secretion in patients with chronic pancreatitis and after pancreatic surgery.	2001	12067221
Which is a less invasive pancreatic head resection: PD, PPPD, or DPPHR?	2001 Feb	11281176
The assessment of pancreatic exocrine function by bentiromide test in patients with chronic portal vein thrombosis.	2002 Nov	12409829
Human meprin beta: O-linked glycans in the intervening region of the type I membrane protein protect the C-terminal region from proteolytic cleavage and diminish its secretion.	2003 Feb 1	12387727
Review article: Pancreatic function testing.	2003 Mar 15	12641496
Pancreatoduodenectomy for chronic pancreatitis with an inflammatory mass of pancreatic head: preoperative and postoperative functional assessment.	2003 Nov-Dec	14696501
Pancreatic endocrine and exocrine function and salivary gland function in autoimmune pancreatitis before and after steroid therapy.	2003 Oct	14508128
Value of magnetic resonance cholangiopancreatography with secretin stimulation in the evaluation of pancreatic exocrine function after pancreaticogastrostomy.	2004	15754047
[The role of fecal elastase-1 in pancreatic diseases].	2006 Apr	16780673
The outcome of a long-term follow-up of pancreatic function after recovery from acute pancreatitis.	2006 Sep 10	16998241
Significance of pancreatic exocrine function in the perioperative management of pancreatoduodenectomy.	2006 Sep-Oct	17086890
Can measurement of chemokines become useful biological and functional markers of early-stage chronic pancreatitis?	2007 Jan	17238032
Metalloprotease meprin beta in rat kidney: glomerular localization and differential expression in glomerulonephritis.	2008 May 28	18509531
Influence of chronic ethanol consumption on extra-pancreatic secretory function in rat.	2009 Oct	22666702
Animal models of chronic pancreatitis.	2010	21197438
Let it flow: Morpholino knockdown in zebrafish embryos reveals a pro-angiogenic effect of the metalloprotease meprin alpha2.	2010 Jan 21	20098618
A case of lipomatous pseudohypertrophy of the pancreas diagnosed by typical imaging.	2010 Jul 5	20601816

Patents

Sample Use Guides

In Vivo Use Guide

500-mg dose. Immediately after dosing, 250 ml of water are given, then another 500 ml of water two to six hours after dosing. Urine is collected for six hours after dosing.

Route of Administration: Oral

In Vitro Use Guide

The concentration of bound tyrosine in the secretion is greater (P < 0-05) during perfusion with Bz-tyr-PABA at 2.35 mmol/l than in the N-free controls and is even greater (P < 0-001) with this compound at 18.8 mmol/I. Therefore some transport of bound tyrosine, as either benzoyl-tyrosine or intact Bz-Tyr-PABA, has occurred. However, the net transport of total tyrosine from the Bz-Tyr-PABA at 2.35 mmol/l is only 1.4% of that from tyrosyl-leucine at the same concentration.

Name

Type

Language

BENTIROMIDE

Official Name

English

BENZOIC ACID, 4-((2-(BENZOYLAMINO)-3-(4-HYDROXYPHENYL)-1-OXOPROPYL)AMINO)-, (S)-

Systematic Name

English

BTPABAPFT

Code

English

Bentiromide [WHO-DD]

Common Name

English

PFD

Brand Name

English

BTPABA, PFT

Code

English

BTPABA PFT

Code

English

CHYMEX

Brand Name

English

bentiromide [INN]

Common Name

English

E-2663

Code

English

BENTIROMIDE [MART.]

Common Name

English

BENTIROMIDE [ORANGE BOOK]

Common Name

English

BENTIROMIDE [JAN]

Common Name

English

(S)-P-(.ALPHA.-BENZAMIDO-P-HYDROXYHYDROCINNAMAMIDO)BENZOIC ACID

Systematic Name

English

BTPABA-PFT

Code

English

BENTIROMIDE [USAN]

Common Name

English

BENTIROMIDE [MI]

Common Name

English

BENTIROMIDE [VANDF]

Common Name

English

Classification Tree Code System Code

WHO-ATC

V04CK03