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Bentiromide

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ACTIVE PHARMA INGREDIENTS

2 API Suppliers, 2 USDMF

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INTERMEDIATES

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FINISHED DOSAGE FORMULATIONS

1 FDF Dossiers, 1 FDA Orange Book

1 FDF Dossiers
1 FDA Orange Book

Synopsis

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Chemistry

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Also known as: 37106-97-1, Btpaba, Chymex, Bz-tyr-4-abz-oh, Bentiromido, Bentiromidum

Molecular Formula

C₂₃H₂₀N₂O₅

Molecular Weight

404.4 g/mol

InChI Key

SPPTWHFVYKCNNK-FQEVSTJZSA-N

FDA UNII

239IF5W61J

Bentiromide is a dipeptide that is used in the bentiromide test, which is a screening test for evaluating pancreatic exocrine function and monitoring the adequacy of supplemental pancreatic therapy. It is typically administered orally. Cases of headache and gastrointestinal disturbances have been reported with the use of bentiromide. Bentiromide is currently not available in the U.S. or Canada.

1 2D Structure

Bentiromide

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-[[(2S)-2-benzamido-3-(4-hydroxyphenyl)propanoyl]amino]benzoic acid

2.1.2 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

2.1.3 InChI Key

SPPTWHFVYKCNNK-FQEVSTJZSA-N

2.1.4 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

2.1.5 Isomeric SMILES

C1=CC=C(C=C1)C(=O)N[C@@H](CC2=CC=C(C=C2)O)C(=O)NC3=CC=C(C=C3)C(=O)O

2.2 Other Identifiers

2.2.1 UNII

239IF5W61J

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Benzoyl-tyrosyl-paba

2. N-benzoyl-l-tyrosyl-p-aminobenzoic Acid

3. N-benzoyl-l-tyrosyl-paba

4. Paba-peptide

2.3.2 Depositor-Supplied Synonyms

1. 37106-97-1

2. Btpaba

3. Chymex

4. Bz-tyr-4-abz-oh

5. Bentiromido

6. Bentiromidum

7. Btpaba, Pft

8. Btpaba Pft

9. Bentiromidum [inn-latin]

10. Bentiromido [inn-spanish]

11. Btpabapft

12. Btpaba-pft

13. Benzoyltyrosyl-p-aminobenzoic Acid

14. E-2663

15. Pft

16. Chebi:31263

17. 239if5w61j

18. N-benzoyl-l-tyrosyl-p-aminobenzoic Acid

19. (s)-p-(alpha-benzamido-p-hydroxyhydrocinnamamido)benzoic Acid

20. 4-(n-benzoyl-l-tyrosyl)aminobenzoic Acid

21. 4-[[(2s)-2-benzamido-3-(4-hydroxyphenyl)propanoyl]amino]benzoic Acid

22. (s)-4-((2-(benzoylamino)-3-(4-hydroxyphenyl)-1-oxopropyl)amino)benzoic Acid

23. 4-[(2s)-3-(4-hydroxyphenyl)-2-(phenylformamido)propanamido]benzoic Acid

24. Benzoic Acid, 4-((2-(benzoylamino)-3-(4-hydroxyphenyl)-1-oxopropyl)amino)-, (s)-

25. P-((n-benzoyl-l-tyrosin)amido)benzoic Acid

26. Brn 2910938

27. Ro 11-7891

28. Unii-239if5w61j

29. 4-((2-(benzoylamino)-3-(4-hydroxyphenyl)-1-oxopropyl)amino)benzoic Acid

30. Bentiromide [usan:ban:inn:jan]

31. Bentiromide [usan:inn:ban:jan]

32. Einecs 253-349-8

33. Bt-paba

34. Bentiromide [mi]

35. Bentiromide [inn]

36. Bentiromide [jan]

37. Bentiromide [usan]

38. Bentiromide [vandf]

39. E 2663

40. Bentiromide [mart.]

41. Bentiromide [who-dd]

42. (s)-p-(.alpha.-benzamido-p-hydroxyhydrocinnamamido)benzoic Acid

43. Schembl151634

44. Chembl1200368

45. Dtxsid2048377

46. Bentiromide [orange Book]

47. Zinc608204

48. Hy-b1493

49. N-benzoyl-l-tyrosyl-p-aminobenzoate

50. Mfcd00055768

51. S4388

52. Ccg-268691

53. Db00522

54. 4-(n-benzoyl-l-tyrosyl)aminobenzoicacid

55. 4-(n-benzoyl-l-tyrosylamino)benzoic Acid

56. 4-[(n-benzoyl-l-tyrosyl)amino]benzoic Acid

57. Cs-0013190

58. Sw219774-1

59. Ab01566933_01

60. 106b971

61. Q793082

62. Sr-01000883958

63. Sr-01000883958-1

64. (s)-4-(2-benzamido-3-(4-hydroxyphenyl)propanamido)benzoic Acid

65. (4-[[(2s)-2-benzamido-3-(4-hydroxyphenyl)propanoyl]amino]benzoic Acid

2.4 Create Date

2006-07-28

3 Chemical and Physical Properties

Molecular Formula	C₂₃H₂₀N₂O₅
Molecular Weight	404.4 g/mol
XLogP3	3.3
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	7
Exact Mass	404.13722174 g/mol
Monoisotopic Mass	404.13722174 g/mol
Topological Polar Surface Area	116 Å²
Heavy Atom Count	30
Formal Charge	0
Complexity	588
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Indicated as a screening test for exocrine pancreatic insufficiency and to monitor the adequacy of supplemental pancreatic therapy.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Bentiromide is a peptide used as a screening test for exocrine pancreatic insufficiency and to monitor the adequacy of supplemental pancreatic therapy. The amount of p-aminobenzoic acid and its metabolites excreted in the urine is the quantitative measure of the chymotrypsin-secreting activity of the pancreas.

5.2 MeSH Pharmacological Classification

Indicators and Reagents

Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant and Hackh's Chemical Dictionary, 5th ed, p301, p499) (See all compounds classified as Indicators and Reagents.)

5.3 ATC Code

V - Various

V04 - Diagnostic agents

V04C - Other diagnostic agents

V04CK - Tests for pancreatic function

V04CK03 - Bentiromide

5.4 Metabolism/Metabolites

Primarily hepatic. Enzymatic activity capable of hydrolyzing bentiromide has also been found in normal small intestine.

5.5 Mechanism of Action

Bentiromide is a peptide that is broken down in the pancreas by chymotrypsin. By determining the output of unchanged bentiromide in the urine following oral administration, it is possible to determine the sufficiency of pancreatic activity.

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