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| {{chembox | {{chembox | ||
| | Verifiedfields = changed | | Verifiedfields = changed | ||
| | Watchedfields = changed | |||
| | verifiedrevid = |
| verifiedrevid = 459858799 | ||
| | ImageFile=Bentiromide.svg | | ImageFile=Bentiromide.svg | ||
| | ImageSize=150px | | ImageSize=150px | ||
| | |
| PIN=4-benzoic acid | ||
| | OtherNames=<small>(S)-4-((2-(benzoylamino)-3-(4-hydroxyphenyl) -1-oxopropyl)amino)benzoic acid<br />(S)-p-(α-benzamido-p-hydroxyhydrocinnamamido) benzoic acid |
| OtherNames=<small>(S)-4-((2-(benzoylamino)-3-(4-hydroxyphenyl) -1-oxopropyl)amino)benzoic acid<br />(S)-p-(α-benzamido-p-hydroxyhydrocinnamamido) benzoic acid<br />Benzoyltyrosyl-p-aminobenzoic acid (Btpaba)Chymex<br />N-benzoyl-L-tyrosyl-p-aminobenzoic acid<br />P-((N-benzoyl-L-tyrosin)amido)benzoic acid<br />Chymex (trade name)</small> | ||
| | Reference=<ref>, ].</ref> | | Reference=<ref>, ].</ref> | ||
| | |
|Section1={{Chembox Identifiers | ||
| | EINECS=253-349-8 | | EINECS=253-349-8 | ||
| | PubChem = 6957673 | | PubChem = 6957673 | ||
| ⚫ | | ATCCode_prefix= V04 | ||
| ⚫ | | ATCCode_suffix = CK03 | ||
| | ChEMBL_Ref = {{ebicite|changed|EBI}} | | ChEMBL_Ref = {{ebicite|changed|EBI}} | ||
| | ChEMBL = 1200368 | | ChEMBL = 1200368 | ||
| | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ||
| | ChemSpiderID=5329364 | | ChemSpiderID=5329364 | ||
| ⚫ | | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | ||
| ⚫ | | DrugBank= DB00522 | ||
| | Abbreviations=Btpaba | | Abbreviations=Btpaba | ||
| | UNII_Ref = {{fdacite|correct|FDA}} | | UNII_Ref = {{fdacite|correct|FDA}} | ||
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| | CASNo_Ref = {{cascite|correct|CAS}} | | CASNo_Ref = {{cascite|correct|CAS}} | ||
| | CASNo=37106-97-1 | | CASNo=37106-97-1 | ||
| | ChEBI_Ref = {{ebicite| |
| ChEBI_Ref = {{ebicite|correct|EBI}} | ||
| | ChEBI = 31263 | | ChEBI = 31263 | ||
| | SMILES = O=C(O)c1ccc(cc1)NC(=O)(NC(=O)c2ccccc2)Cc3ccc(O)cc3 | | SMILES = O=C(O)c1ccc(cc1)NC(=O)(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 | | 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 | ||
| }} | }} | ||
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|Section2={{Chembox Properties | ||
| | Formula=C<sub>23</sub>H<sub>20</sub>N<sub>2</sub>O<sub>5</sub> | | Formula=C<sub>23</sub>H<sub>20</sub>N<sub>2</sub>O<sub>5</sub> | ||
| | MolarMass=404.4153 | | MolarMass=404.4153 g/mol | ||
| | Density= | | Density= | ||
| | Solubility= | | Solubility= | ||
| | SolubleOther= | | SolubleOther= | ||
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| Dipole=}} | ||
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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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| ⚫ | | DrugBank= |
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| ⚫ | | ATCCode_prefix = V04 | ||
| | PregCat= | |||
| ⚫ | | ATCCode_suffix = CK03 | ||
| | AdminRoutes=}} | |||
| }} | |||
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|Section4={{Chembox Explosive | ||
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| ShockSens= | ||
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| | REFactor=}} | |||
| | Section7={{Chembox Hazards | | REFactor=}} | ||
| |Section7={{Chembox Hazards | |||
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| | AutoignitionPt = | |||
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| | ExploLimits = | |||
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| | FlashPt= | |||
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| | RTECS=}} | |||
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| }} | }} | ||
| ⚫ | |Section8={{Chembox Related | ||
| ⚫ | | OtherAnions= | ||
| ⚫ | | OtherCations= | ||
| | OtherFunction = | |||
| | OtherFunction_label = | |||
| | OtherCompounds =}} | |||
| }} | |||
| '''Bentiromide''' is a ] used as a screening test for ] ] 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.<ref name="Drugs.com">{{Drugs.com|cons|bentiromide}} on bentiromide.</ref> | |||
| == Side effects == | |||
| Headache and gastrointestinal disturbances have been reported in patients taking bentiromide.<ref name="Drugs.com" /> | |||
| == Mechanism of action == | |||
| Bentiromide is given by mouth as a noninvasive test. It is broken down by the pancreatic enzyme ], yielding ] (PABA). The amount of PABA and its ] excreted in the urine is taken as a measure of the chymotrypsin-secreting activity of the pancreas. | |||
| == Chemistry == | |||
| '''Bentiromide''' is a ] used as a screening test for ] ] insufficiency and to monitor the adequacy of supplemental pancreatic therapy. It is given by mouth as a noninvasive test. The amount of ] and its ] excreted in the urine is taken as a measure of the ]-secreting activity of the pancreas. Headache and gastrointestinal disturbances have been reported in patients taking bentiromide. Bentiromide is not available in the ] or ] (It was withdrawn in the US in October 1996.) | |||
| ⚫ | *]=3.201 | ||
| *H_bond_donor=4{{fact|date=February 2020}} | |||
| *H_bond_acceptor=5{{fact|date=February 2020}} | |||
| == |
=== Synthesis === | ||
| ] | |||
| ⚫ | *XLogP=3.201 | ||
| 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 ] (]) and dilute acid to give bentiromide ('''4'''). | |||
| *tautomers=12 | |||
| *H_bond_donor=4 | |||
| *H_bond_acceptor=5 | |||
| == See also == | == See also == | ||
| * ] | * ] | ||
| ==References== | == References == | ||
| {{reflist}} | {{reflist}} | ||
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| ] | ] | ||
| {{pharma-stub}} | |||
Latest revision as of 00:18, 10 December 2024
"Chymex" redirects here. For the human body digestive fluid, see Chyme. | |
| Names | |
|---|---|
| Preferred IUPAC name 4-benzoic 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 | |
| 3D model (JSmol) | |
| Abbreviations | Btpaba |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| DrugBank | |
| ECHA InfoCard | 100.048.484 
|
| EC Number |
|
| PubChem CID | |
| UNII | |
| CompTox Dashboard (EPA) | |
InChI
| |
SMILES
| |
| 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 , 100 kPa).
 N verify (what is ?)
Infobox references
| |
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.
Side effects
Headache and gastrointestinal disturbances have been reported in patients taking bentiromide.
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
- H_bond_acceptor=5
Synthesis
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).
See also
References
- Bentiromide – Compound Summary, PubChem.
- ^ Micromedex Detailed Consumer Information on bentiromide.
- 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): 1098–1100. doi:10.1021/jm00281a002. PMID 4654657.