: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

| Density=

| Solubility=

| SolubleOther=

| Solvent=

| MeltingPt=

| BoilingPt=

| pKa=

| pKb=

| IsoelectricPt=

| SpecRotation=

| RefractIndex=

| Viscosity=

| Dipole=}}

|Section3={{Chembox Structure

| CrystalStruct=

| Coordination=

| MolShape=

| Dipole=}}

|Section5={{Chembox Thermochemistry

| DeltaHf=

| DeltaHc=

| Entropy=

| HeatCapacity=}}

|Section6={{Chembox Pharmacology

| Bioavail=

| Metabolism=

| HalfLife=

| Excretion=

| Pregnancy_category =

| AdminRoutes=

| ATCCode_prefix = V04

| ATCCode_suffix = CK03

}}

|Section4={{Chembox Explosive

| ShockSens=

| FrictionSens=

| DetonationV =

| REFactor=}}

|Section7={{Chembox Hazards

| MainHazards=

| NFPA-H=

| NFPA-F=

| NFPA-R=

| NFPA-S =

| FlashPt=

| AutoignitionPt =

| ExploLimits =

| PEL=

}}

|Section8={{Chembox Related

| OtherAnions=

| OtherCations=

| OtherFunction =

| OtherFunction_label =

| OtherCompounds =}}

}}

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

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{{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).

See also

References

{{reflist}}

{{Diagnostic agents}}

Category:Benzoic acids