Synonyms
BZ-TYR-4-ABZ-OH;n-benzoyl-l-tyrosyl-p-aminobenzoicacid
Molecular Formula
C23H20N2O5
Smiles
C1=CC=C(C=C1)C(=O)N[C@@H](CC2=CC=C(C=C2)O)C(=O)NC3=CC=C(C=C3)C(=O)O
Appearance
White to off-white solid
General Description
Bentiromide is a synthetic peptide-like compound that serves as a non-invasive diagnostic agent for assessing pancreatic exocrine function. Its chemical structure incorporates a benzoyl group linked through a peptide bond to p-aminobenzoic acid (PABA), allowing it to function as a chymotrypsin substrate.
Mechanism of Action
Bentiromide is hydrolyzed by pancreatic chymotrypsin in the small intestine, releasing p-aminobenzoic acid (PABA) from the benzoic acid moiety. The released PABA is absorbed from the intestine, conjugated in the liver, and excreted in the urine. In patients with pancreatic insufficiency, reduced chymotrypsin activity leads to diminished PABA recovery, providing a functional measure of pancreatic enzyme output.
Application
Bentiromide is used as a diagnostic aid in the clinical assessment of exocrine pancreatic function. The procedure involves oral administration of bentiromide followed by timed urine collection to measure para-aminobenzoic acid (PABA) recovery. Reduced PABA excretion indicates impaired pancreatic secretion and is suggestive of pancreatic exocrine insufficiency.
A multicenter Japanese study of 624 type 1 autoimmune pancreatitis patients examined risk factors for pancreatic stone formation, which occurred in 5% of patients. The bentiromide test value at diagnosis was significantly lower in stone-forming patients (48.6%) than in non-stone-forming patients (60.5%), indicating more severe exocrine dysfunction. Stone formation was also associated with higher hemoglobin A1c after corticosteroid treatment, pancreatic atrophy, hilar/intrahepatic bile duct stenosis, and pancreatic head swelling. Multivariate analysis confirmed pancreatic atrophy, hilar/intrahepatic bile duct stenosis, pancreatic head swelling, and longer follow-up as independent risk factors. Pancreatic head swelling likely causes juice stasis, leading to stone development and progressive pancreatic dysfunction over time.
Fig. 1 Clinical features with bentiromide test value at diagnosis. (Ito T.; et al. 2019)
References
- Ito T, et al. Risk factors for pancreatic stone formation in type 1 autoimmune pancreatitis: a long-term Japanese multicenter analysis of 624 patients. Pancreas, 2019, 48(1): 49-54.
Bentiromide, a drug for assessing pancreatic function, exists as six tautomers. DFT and PCM solvent models showed the most stable tautomer contains three carbonyl groups, with negligible amounts of others in water. NBO analysis explored frontier molecular orbitals. Interaction with a carbon nanotube and a γ-Fe₂O₃ nanoparticle was studied. Intermolecular hydrogen bonds critically influenced energy behavior during interaction with the γ-Fe₂O₃ nanoparticle.
References
- Tanhaei R, et al. Geometry, Tautomerism, and Noncovalent Interaction of Bentiromide with a Carbon-Nanotube and γ-Fe2O3 Nanoparticles: A Quantum Mechanical Study. Journal of Structural Chemistry, 2019, 60(6): 1008-1018.
What is the recommended storage condition for Bentiromide?
It should be stored at controlled room temperature in a well-sealed container, protected from moisture and direct light, to maintain its chemical integrity throughout the shelf life.
Is a Certificate of Analysis (COA) available for Bentiromide?
Yes, a fully verified COA is issued for every batch and can be shared electronically. Additional documentation such as MSDS or impurity profiles may be requested separately.
What is the minimum order quantity (MOQ) for Bentiromide?
Flexible MOQ options are available to support both early-stage research and large-scale manufacturing needs. Our team can tailor order quantities to match your specific requirements.
Is Bentiromide compatible with standard pharmaceutical formulation processes?
Pharmaceutical-grade material suitable for standard formulation processes is available. Technical data sheets and compatibility information can be provided upon request.