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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

Peptavlon
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 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)


REF. STANDARDS & IMPURITIES

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Peptavlon Manufacturers

A Peptavlon manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Peptavlon, including repackagers and relabelers. The FDA regulates Peptavlon manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Peptavlon API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

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Peptavlon Suppliers

A Peptavlon supplier is an individual or a company that provides Peptavlon active pharmaceutical ingredient (API) or Peptavlon finished formulations upon request. The Peptavlon suppliers may include Peptavlon API manufacturers, exporters, distributors and traders.

click here to find a list of Peptavlon suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Peptavlon GMP

Peptavlon Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Peptavlon GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Peptavlon GMP manufacturer or Peptavlon GMP API supplier for your needs.

Peptavlon CoA

A Peptavlon CoA (Certificate of Analysis) is a formal document that attests to Peptavlon's compliance with Peptavlon specifications and serves as a tool for batch-level quality control.

Peptavlon CoA mostly includes findings from lab analyses of a specific batch. For each Peptavlon CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Peptavlon may be tested according to a variety of international standards, such as European Pharmacopoeia (Peptavlon EP), Peptavlon JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Peptavlon USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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