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Bentiromide

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Bentiromide is a peptide used as diagnostic for pancreatic function.

Category
Functional Peptides
Catalog number
BAT-008120
CAS number
37106-97-1
Molecular Formula
C23H20N2O5
Molecular Weight
404.42
Bentiromide
IUPAC Name
4-[[(2S)-2-benzamido-3-(4-hydroxyphenyl)propanoyl]amino]benzoic acid
Synonyms
Bz-Tyr-4-Abz-OH; 4-[[(2S)-2-benzamido-3-(4-hydroxyphenyl)propanoyl]amino]benzoic acid
Appearance
Yellow powder
Purity
≥ 99% (TLC)
Density
1.367g/cm3
Melting Point
240-242
Boiling Point
797.1ºC at 760mmHg
Storage
Store at 2-8°C
Solubility
Soluble in DMSO
Application
Diagnostic for pancreatic function
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
InChI Key
SPPTWHFVYKCNNK-FQEVSTJZSA-N
Canonical SMILES
C1=CC=C(C=C1)C(=O)NC(CC2=CC=C(C=C2)O)C(=O)NC3=CC=C(C=C3)C(=O)O
1."Mixed" triglyceride breath test: methodological problems and clinical applications.
Perri F;Andriulli A Rev Med Univ Navarra. 1998 Apr-Jun;42(2):99-103.
Laboratory assessment of pancreatic function is unpleasant for the patient and time-consuming for the investigator since it requires duodenal intubation and measurement of maximal pancreatic enzyme output by means of perfusion techniques. Non-invasive indirect tests such as bentiromide test, pancreolauryl test and faecal fat measurement have been introduced in clinical practice but their results depend on the collaboration of the patient in collecting urine or stool. Moreover, faecal fat reflects fat malabsorption but it is neither sensitive nor specific to evaluate exocrine pancreatic function. With the aim to determine whether steatorrhea is due to pancreatic insufficiency, several 14C- (or 13C) breath tests have been developed in which triolein, trioctanoin, tripalmitin, and cholesteryl-octanoate are used as marker substances. In 1989, G. Vantrappen and its group in Leuven developed a breath test in which a new substrate was used: the [1,3-distearyl, 2[carboxyl-13C]octanoyl glycerol] or 13C-"mixed"-triglyceride (MT). The "mixed triglyceride breath test" (MTBT) was shown to be an excellent test of exocrine pancreatic insufficiency when compared with the maximal lipase output after CCK-pancreozymin stimulation.
2.Short-term and long-term pancreatic exocrine and endocrine functions after pancreatectomy.
Sato N;Yamaguchi K;Yokohata K;Shimizu S;Morisaki T;Chijiiwa K;Tanaka M Dig Dis Sci. 1998 Dec;43(12):2616-21.
Exocrine and endocrine functions of the pancreas were assessed in 44 Japanese patients who underwent pancreatic head resection. Functions were analyzed comparing levels before surgery, at a short-term follow-up (<2 months), and at a long-term follow-up (12-31 months). The N-benzoyl-L-tyrosyl-p-aminobenzoic acid (BT-PABA) excretion test, fasting blood sugar (FBS) level, and oral glucose tolerance test (OGTT) were used to determine pancreatic function. The patients were divided into three groups according to the size of the main pancreatic duct: group 1, 15 patients with a normal sized duct (< or =3 mm); group 2, 20 with a moderately dilated duct (>3 mm, <10 mm); and group 3, 9 with a markedly dilated duct (> or =10 mm). The mean BT-PABA value (6-hr urinary PABA recovery rate) in group 1 showed no change during the postoperative period. In contrast, the BT-PABA values in groups 2 and 3 had dropped by the short-term follow-up and returned to the preoperative level by the long-term examination. FBS and 120-min OGTT levels were not different between the three groups preoperatively. Although these values showed no change in all the three groups at the short-term measurements, the FBS in group 3 and 120-min levels in all the three groups had increased at the long-term.
3.Clinical study of exocrine pancreatic function test by oral administration by N-benzoyl-L-tyrosyl-p-aminobenzoic acid.
Kimura T;Wakasugi H;Ibayashi H Digestion. 1981;21(3):133-9.
The clinical usefulness of a simple exocrine pancreatic function diagnostic test (PFT) was examined by the oral administration of 500 mg of N-benzoyl-L-tyrosyl-p-aminobenzoic acid. Recovery of p-aminobenzoic acid (PABA) in the urine was significantly lower in patients with calcifying chronic pancreatitis (58.6%) and noncalcifying chronic pancreatitis (68.6%) than in healthy normal subjects (81.0%; p less than 0.001 and p less than 0.05, respectively). Abnormally low values were demonstrated in 15 out of 19 (78.9%) chronic pancreatitis cases. In comparing the PFT with the pancreozymin secretin test, a good correlation (P less than 0.001) with maximum bicarbonate concentration was detected. In cases which were abnormal with respect to the PFT, the recovery rate of PABA was increased by the administration of antacids or digestive enzyme preparations (average increase of 24.1 or 29.8%, respectively). These results suggest that this test is also useful for the evaluation of therapeutic effects in patients with pancreatic diseases.
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