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    Peptavlon

    ACTIVE PHARMA INGREDIENTS

    FINISHED DOSAGE FORMULATIONS

    REF. STANDARDS & IMPURITIES

    PharmaCompass
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    2D Structure
    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

    2D Structure

    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 Weight 767.9 g/mol
    Molecular Formula C37H49N7O9S
    XLogP31.5
    Hydrogen Bond Donor Count8
    Hydrogen Bond Acceptor Count10
    Rotatable Bond Count22
    Exact Mass767.33124734 g/mol
    Monoisotopic Mass767.33124734 g/mol
    Topological Polar Surface Area276 Ų
    Heavy Atom Count54
    Formal Charge0
    Complexity1310
    Isotope Atom Count0
    Defined Atom Stereocenter Count4
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    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)