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Peptavlon

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Chemistry

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Also known as: Peptavlon, 5534-95-2, Ici-50123, Ay-6608, Ici 50,123, Chembl1328

Molecular Formula

C₃₇H₄₉N₇O₉S

Molecular Weight

767.9 g/mol

InChI Key

NEYNJQRKHLUJRU-DZUOILHNSA-N

FDA UNII

EF0NX91490

A synthetic pentapeptide that has effects like gastrin when given parenterally. It stimulates the secretion of gastric acid, pepsin, and intrinsic factor, and has been used as a diagnostic aid.

1 2D Structure

Peptavlon

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(3S)-4-[[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-3-[[(2S)-2-[[(2S)-3-(1H-indol-3-yl)-2-[3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoylamino]propanoyl]amino]-4-methylsulfanylbutanoyl]amino]-4-oxobutanoic acid

2.1.2 InChI

InChI=1S/C37H49N7O9S/c1-37(2,3)53-36(52)39-16-14-30(45)41-28(19-23-21-40-25-13-9-8-12-24(23)25)34(50)42-26(15-17-54-4)33(49)44-29(20-31(46)47)35(51)43-27(32(38)48)18-22-10-6-5-7-11-22/h5-13,21,26-29,40H,14-20H2,1-4H3,(H2,38,48)(H,39,52)(H,41,45)(H,42,50)(H,43,51)(H,44,49)(H,46,47)/t26-,27-,28-,29-/m0/s1

2.1.3 InChI Key

NEYNJQRKHLUJRU-DZUOILHNSA-N

2.1.4 Canonical SMILES

CC(C)(C)OC(=O)NCCC(=O)NC(CC1=CNC2=CC=CC=C21)C(=O)NC(CCSC)C(=O)NC(CC(=O)O)C(=O)NC(CC3=CC=CC=C3)C(=O)N

2.1.5 Isomeric SMILES

CC(C)(C)OC(=O)NCCC(=O)N[C@@H](CC1=CNC2=CC=CC=C21)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](CC3=CC=CC=C3)C(=O)N

2.2 Other Identifiers

2.2.1 UNII

EF0NX91490

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Acignost

2. Gastrin Pentapeptide

3. Pentapeptide, Gastrin

4. Peptavlon

2.3.2 Depositor-Supplied Synonyms

1. Peptavlon

2. 5534-95-2

3. Ici-50123

4. Ay-6608

5. Ici 50,123

6. Chembl1328

7. Ef0nx91490

8. Nsc-367746

9. Dsstox_cid_28918

10. Dsstox_rid_83185

11. Dsstox_gsid_48992

12. Gastrodiagnost

13. Pentagastrina

14. Pentagastrine

15. Pentagastrinum

16. Petogasrin

17. Cas-5534-95-2

18. Ici 50123

19. Pentagastrine [inn-french]

20. Pentagastrinum [inn-latin]

21. Pentagastrina [inn-spanish]

22. Unii-ef0nx91490

23. Hsdb 3247

24. Peptavlon (tn)

25. Boc-beta-ala-try-met-asp-phe(nh2)

26. Einecs 226-889-7

27. Pentagastrin [usan:inn:ban:jan]

28. Mfcd00076515

29. Nsc 367746

30. Ay 6608

31. Brn 5472892

32. Pentagastrin [mi]

33. Pentagastrin [inn]

34. Pentagastrin [jan]

35. Pentagastrin [hsdb]

36. Pentagastrin [usan]

37. Pentagastrin [vandf]

38. Schembl26045

39. Pentagastrin [mart.]

40. L-phenylalaninamide, N-((1,1-dimethylethoxy)carbonyl)-beta-alanyl-l-tryptophyl-l-methionyl-l-alpha-aspartyl-

41. Mls006009992

42. Pentagastrin [who-dd]

43. Pentagastrin (jan/usan/inn)

44. Dtxsid3048992

45. Chebi:31974

46. Pentagastrin [orange Book]

47. (3s)-4-[[(2s)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-3-[[(2s)-2-[[(2s)-3-(1h-indol-3-yl)-2-[3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoylamino]propanoyl]amino]-4-methylsulfanylbutanoyl]amino]-4-oxobutanoic Acid

48. Hy-a0261

49. Zinc8214644

50. Boc-

51. A-ala-trp-met-asp-phe-nh2

52. Boc-beta-ala-trp-met-asp-phe-nh2

53. Tox21_113479

54. Bdbm50024321

55. Akos030213248

56. Tox21_113479_1

57. Cs-5667

58. Db00183

59. N-t-butyloxycarbonyl-beta-alanyl-l-tryptophyl-l-methion Yl-l-aspartyl-l-phenylalanine Amide

60. Ncgc00167300-01

61. Ncgc00183362-01

62. Ncgc00183362-02

63. Alaninamide, N-carboxy-beta-alanyl-l-tryptophyl-l-methionyl-l-aspartylphenyl-, N-tert-butyl Ester, L-

64. As-56396

65. N-(alpha-carbamoylphenethyl)-3-(2-(2-(3-(carboxyamino)propionamido)-3-indol-3-ylpropionamido)-4-(methylthio)butyramido)succinamic Acid N-tert-butyl Ester

66. N-(n-(n-(n-(n-tert-butoxycarbonyl-beta-alanyl)-l-tryptophanyl)-l-methionyl)-l-aspartyl)-l-phenylalaninamide

67. N-carboxy-beta-alanyl-l-tryptophyl-l-methionyl-l-aspartylphenyl-l-alaninamide N-tert-butyl Ester

68. Smr004701067

69. D01631

70. 534p952

71. Q423586

72. (10s,13s,16s)-10-((1h-indol-3-yl)methyl)-16-((s)-1-amino-1-oxo-3-phenylpropan-2-ylcarbamoyl)-2,2-dimethyl-13-(2-(methylthio)ethyl)-4,8,11,14-tetraoxo-3-oxa-5,9,12,15-tetraazaoctadecan-18-oic Acid

73. 3-{2-[2-(3-tert-butoxycarbonylamino-propionylamino)-3-(1h-indol-3-yl)-propionylamino]-4-methylsulfanyl-butyrylamino}-n-(1-carbamoyl-2-phenyl-ethyl)-succinamic Acid

74. Alaninamide, N-carboxy-beta-alanyl-l-tryptophyl-l-methionyl-l-aspartylphenyl-, N-tert-butylester, L-

75. L-phenylalaninamide, N-((1,1-dimethylethoxy)carbonyl)-.beta.-alanyl-l-tryptophyl-l-methionyl-l-.alpha.-aspartyl-

76. N-carboxy-.beta.-alanyl-l-tryptophyl-l-methionyl-l-aspartylphenyl-l-alaninamide N-tert-butyl Ester

2.4 Create Date

2006-10-25

3 Chemical and Physical Properties

Molecular Formula	C₃₇H₄₉N₇O₉S
Molecular Weight	767.9 g/mol
XLogP3	1.5
Hydrogen Bond Donor Count	8
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	22
Exact Mass	767.33124734 g/mol
Monoisotopic Mass	767.33124734 g/mol
Topological Polar Surface Area	276 Å²
Heavy Atom Count	54
Formal Charge	0
Complexity	1310
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
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 Therapeutic Uses

PENTAGASTRIN...USED WIDELY IN EUROPE SINCE 1966 TO MEASURE MAXIMAL ACID SECRETORY CAPACITY OF STOMACH. IT ELICITS REPRODUCIBLE SECRETORY RESPONSES COMPARABLE TO THOSE INDUCED BY HISTAMINE OR BETAZOLE...

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 601

.../IT/ OFFERS SEVERAL ADVANTAGES /TO HISTAMINE & BETAZOLE/. ...REQUIRES ONLY SINGLE SC OR IM INJECTION; IT IS RELATIVELY SHORT IN DURATION...

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 601

PENTAGASTRIN HAS DISTINCT EFFECT ON RATIOS OF NA+, K+, H+/AMINO ACID IN GASTRIC JUICE IN DIFFERENT STATES OF ACIDITY, VALUES OF ALL QUOTIENTS IN PT WITH HYPER, HYPO & ANACIDITY ARE SIGNIFICANTLY REDUCED.

DUNZENDORF R U; ARZNEIM FORSCH 26 (7) 1364-1365 (1976)

4.2 Drug Indication

Used as a diagnostic aid for evaluation of gastric acid secretory function

5 Pharmacology and Biochemistry

5.1 Pharmacology

Pentagastrin is indicated as a diagnostic aid for evaluation of gastric acid secretory function. It is effective in testing for anacidity (achlorhydria) in patients with suspected pernicious anemia, atrophic gastritis, or gastric carcinoma. It is also effective in determining the reduction in acid output after operations for peptic ulcer, such as vagotomy or gastric resection.

5.2 ATC Code

V - Various

V04 - Diagnostic agents

V04C - Other diagnostic agents

V04CG - Tests for gastric secretion

V04CG04 - Pentagastrin

5.3 Absorption, Distribution and Excretion

Absorption

Rapidly absorbed after parenteral administration.

ACTIVITY OF ORAL PENTAGASTRIN WAS DETERMINED BY ITS ACTION AS GASTRIC ACID STIMULANT IN 4 HEALTHY SUBJECTS, 2 PT WITH DUODENAL ULCERS, & 1 PT WITH ANNULAR PANCREAS IN ASSOC WITH DUODENAL ULCER.

MORRELL MT, KEYNES WM; ABSORPTION OF PENTAGASTRIN FROM GASTROINTESTINAL TRACT IN MAN; LANCET 2 (OCT 11) 712 (1975)

5.4 Metabolism/Metabolites

Primarily hepatic

5.5 Biological Half-Life

10 minutes or less

HALF-LIFE OF PENTAGASTRIN IN CIRCULATION APPEARS TO BE ABOUT 10 MIN...

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 601

5.6 Mechanism of Action

The exact mechanism by which pentagastrin stimulates gastric acid, pepsin, and intrinsic factor secretion is unknown; however, since pentagastrin is an analogue of natural gastrin, it is believed that it excites the oxyntic cells of the stomach to secrete to their maximum capacity. Pentagastrin stimulates pancreatic secretion, especially when administered in large intramuscular doses. Pentagastrin also increases gastrointestinal motility by a direct effect on the intestinal smooth muscle. However, it delays gastric emptying time probably by stimulation of terminal antral contractions, which enhance retropulsion.

MOST PROMINENT ACTION OF PENTAGASTRIN IS TO STIMULATE SECRETION OF GASTRIC ACID, PEPSIN, & INTRINSIC FACTOR OF CASTLE...STIMULATES PANCREATIC SECRETION, INHIBITS ABSORPTION OF WATER & ELECTROLYTES FROM ILEUM, CONTRACTS SMOOTH MUSCLE OF LOWER ESOPHAGEAL SPHINCTER & STOMACH (BUT DELAYS GASTRIC EMPTYING TIME)...

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 601

.../IT/ RELAXES SPHINCTER OF ODDI, INCR BLOOD FLOW IN GASTRIC MUCOSE, STIMULATES L-HISTIDINE DECARBOXYLASE ACTIVITY IN RAT GASTRIC MUCOSA, &, IN HIGH DOSES, STIMULATES VARIETY OF SMOOTH MUSCLES IN DIFFERENT SPECIES.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 601

IT ALSO MIMICS OR BLOCKS EFFECTS OF POLYPEPTIDES PANCREOZYMIN-CHOLECYSTOKININ, SECRETIN, CAERULIN, NATURALLY OCCURRING DECAPEPTIDE THAT, ALONG WITH PANCREOZYMIN-CHOLECYSTOKININ, SHARES COMMON C-TERMINAL HEPTAPEPTIDE RESIDUE WITH GASTRIN.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 601

PENTAGASTRIN ACTIVATES ADENYLATE CYCLASE IN GASTRIC MUCOSA...

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 601

PENTAGASTRIN INITIALLY PRODUCED MARKED ANTRAL ACTIVITY IN PHYSIOLOGICAL STRICTURE & SUBSEQUENT DELAY IN OVERALL RATE OF GASTRIC EMPTYING. FUNDAL MOTILITY WAS UNAFFECTED THOUGH REFLUX FROM ANTRUM OCCURRED.

HAMILTON SG ET AL; GUT 17 (4) 273-279 (1976)

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