:Bentiromide
{{redirect|Chymex|the human body digestive fluid|Chyme}}
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 459858799
| ImageFile=Bentiromide.svg
| ImageSize=150px
| PIN=4-[(2S)-2-Benzamido-3-(4-hydroxyphenyl)propanamido]benzoic acid
| OtherNames=(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)
| Reference=[https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=2329&loc=ec_rcs Bentiromide – Compound Summary], PubChem.
|Section1={{Chembox Identifiers
| EINECS=253-349-8
| PubChem = 6957673
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1200368
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID=5329364
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank= DB00522
| Abbreviations=Btpaba
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 239IF5W61J
| InChIKey = SPPTWHFVYKCNNK-FQEVSTJZBR
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = SPPTWHFVYKCNNK-FQEVSTJZSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo=37106-97-1
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 31263
| SMILES = O=C(O)c1ccc(cc1)NC(=O)[C@@H](NC(=O)c2ccccc2)Cc3ccc(O)cc3
| 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
}}
|Section2={{Chembox Properties
| Formula=C23H20N2O5
| MolarMass=404.4153 g/mol
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|Section3={{Chembox Structure
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|Section5={{Chembox Thermochemistry
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|Section6={{Chembox Pharmacology
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| ATCCode_prefix = V04
| ATCCode_suffix = CK03
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|Section4={{Chembox Explosive
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|Section7={{Chembox Hazards
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|Section8={{Chembox Related
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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. Bentiromide is not available in the United States or Canada; it was withdrawn in the US in October 1996.{{Drugs.com|cons|bentiromide}} on bentiromide.
Side effects
Mechanism of action
Bentiromide is given by mouth as a noninvasive test. It is broken down by the pancreatic enzyme chymotrypsin, yielding p-aminobenzoic acid (PABA). The amount of PABA and its metabolites excreted in the urine is taken as a measure of the chymotrypsin-secreting activity of the pancreas.
Chemistry
- XLogP=3.201
- H_bond_donor=4{{fact|date=February 2020}}
- H_bond_acceptor=5{{fact|date=February 2020}}
= Synthesis =
File:Bentiromide synthesis.svg
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).