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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 Bentiromide is not available in the United States or Canada (it was withdrawn in the U.S. in October 1996.)

Data

XLogP=3.201
tautomers=12
H_bond_donor=4
H_bond_acceptor=5

Synthesis

Synthetic chymotrypsin-labile peptide, used in diagnosis of exocrine pancreatic disease.

Bentiromide synthesis:^[2] Synthesis, in vitro and in vivo data:^[3]

It is synthesized by amide formation between ethyl p-aminobenzoate and N-benzoyl-tyrosine using N-methyl-morpholine and ethyl chlorocarbonate for activation. The resulting L-amide is selectively hydrolyzed by sequential use of dimsyl sodium (NaDMSO) and dilute acid to give bentiromide (4).

References

^ Bentiromide – Compound Summary, PubChem.
^ P. L. De Benneville, N. J. Greenberger, DE 2156835 ; eidem, U.S. Patent 3,801,562 (1972, 1974 both to Rohm & Haas).
^ Debenneville, Peter L.; Godfrey, William J.; Sims, Homer J.; Imondi, Anthony R. (1972). "New substrates for a pancreatic exocrine function test". Journal of Medicinal Chemistry. 15 (11): 1098. doi:10.1021/jm00281a002. PMID 4654657.

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UpToDate Contents

全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.

1. 膵外分泌機能検査 pancreatic exocrine function tests
2. 吸収不良の臨床的特徴および診断 clinical features and diagnosis of malabsorption
3. 成人における慢性膵炎の臨床症状および診断 clinical manifestations and diagnosis of chronic pancreatitis in adults
4. 患者情報：慢性膵炎（詳細） chronic pancreatitis beyond the basics

English Journal

Recovery from exocrine pancreatic insufficiency in a patient with fulminant type 1 diabetes.

Koyano HM, Matsumoto T.SourceDepartment of Internal Medicine, Tokyo Rinkai Hospital, Japan. ynishiza@juntendo.ac.jp
Internal medicine (Tokyo, Japan).Intern Med.2013;52(5):573-5. Epub 2013 Mar 1.
A 34-year-old man was admitted to our hospital with diabetic ketoacidosis due to fulminant type 1 diabetes. The patient's pancreatic exocrine and endocrine functions were as follows: the bentiromide (PABA) test value on day 14 was 33.9%, thus indicating exocrine dysfunction. One year and a half late
PMID 23448767

Pancreaticoduodenectomy versus Frey's procedure for chronic pancreatitis: preliminary data on outcome and pancreatic function.

Chiang KC, Yeh CN, Hsu JT, Chen HM, Chen HY, Hwang TL, Jan YY, Chen MF.SourceDepartment of General Surgery, Chang Gung Memorial Hospital, 5 Fu-Hsing Street, Kwei-Shan, Taoyuan, Taiwan.
Surgery today.Surg Today.2007;37(11):961-6. Epub 2007 Oct 25.
PURPOSE: Several surgical treatments have been proposed for treating chronic pancreatitis (CP), including standard pancreaticoduodenectomy (PD), pylorus-preserving PD, Beger's procedure, and Frey's procedure; however, few studies have compared pre- and postoperative pancreatic function in patients u
PMID 17952526

The outcome of a long-term follow-up of pancreatic function after recovery from acute pancreatitis.

Symersky T, van Hoorn B, Masclee AA.SourceDepartment of Gastroenterology-Hepatology, Leiden University Medical Center, Leiden, The Netherlands.
JOP : Journal of the pancreas.JOP.2006 Sep 10;7(5):447-53.
CONTEXT: It is generally assumed that pancreatic function recovers completely after mild but not after severe acute pancreatitis.OBJECTIVE: To evaluate both pancreatic function and quality of life in patients who had recovered from acute pancreatitis in a long-term follow-up study.PARTICIPANTS: Thir
PMID 16998241

Japanese Journal

The Assessment of Pancreatic Exocrine Function by Bentiromide Test in Patients with Chronic Portal Vein Thrombosis

EGESEL Turker,UNSAL Ibrahim,DIKMEN Gunnur,BAYRAKTAR Yusuf
Pancreas 25(4), 355-359, 2002-11-01
NAID 10013988429

Comparison of bentiromide test and rice flour breath by hydrogen test in the detection of exocrine pancreatic insufficiency

PATEL VP
Pancreas 1, 172-175, 1986
NAID 30018653778

Assessment of exocrine pancreatic function by oral administration of N-benzoyl-L-tyrosyl-p-aminobenzoic acid (bentiromide) : 5 years' clinical experience

LANG C
Br J Surg 68, 771-775, 1981
NAID 30026058564

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リンク元

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Bentiromide^[1]
Names
	IUPAC name 4-[2-benzamido-3- (4-hydroxyphenyl)- propanoyl] aminobenzoic acid
	Other names (S)-4-((2-(benzoylamino)-3-(4-hydroxyphenyl) -1-oxopropyl)amino)benzoic acid; (S)-p-(α-benzamido-p-hydroxyhydrocinnamamido) benzoic acid; Benzoyltyrosyl-p-aminobenzoic acid (Btpaba)Chymex; N-benzoyl-L-tyrosyl-p-aminobenzoic acid; P-((N-benzoyl-L-tyrosin)amido)benzoic acid; Chymex (trade name)
Identifiers
CAS Number	37106-97-1
3D model (Jmol)	Interactive image
Abbreviations	Btpaba
ChEBI	CHEBI:31263
ChEMBL	ChEMBL1200368
ChemSpider	5329364
DrugBank	DB00522
ECHA InfoCard	100.048.484
EC Number	253-349-8
PubChem	6957673
UNII	239IF5W61J
	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 Key: SPPTWHFVYKCNNK-FQEVSTJZSA-N ; 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)/t20-/m0/s1 Key: SPPTWHFVYKCNNK-FQEVSTJZBR ;
	SMILES O=C(O)c1ccc(cc1)NC(=O)[C@@H](NC(=O)c2ccccc2)Cc3ccc(O)cc3 ;
Properties
Chemical formula	C23H20N2O5
Molar mass	404.4153 g/mol
Pharmacology
ATC code	V04CK03 (WHO)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	Infobox references

　　[★]

英: bentiromide
商: 膵外分泌機能検査用PFD内服液
関: PFD試験

膵臓外分泌機能検査薬

[1] Bentiromide – Compound Summary, PubChem.

[2] P. L. De Benneville, N. J. Greenberger, DE 2156835 ; eidem, U.S. Patent 3,801,562 (1972, 1974 both to Rohm & Haas).

[3] Debenneville, Peter L.; Godfrey, William J.; Sims, Homer J.; Imondi, Anthony R. (1972). "New substrates for a pancreatic exocrine function test". Journal of Medicinal Chemistry. 15 (11): 1098. doi:10.1021/jm00281a002. PMID 4654657.

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bentiromide