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[125I]CCK-8

[125I]CCK-8

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Also known as: 25126-32-3, Cck-8, Kinevac, Sq 19844, Cck c-terminal octapeptide, Cholecystokinin c-terminal octapeptide

Molecular Formula

C₄₉H₆₂N₁₀O₁₆S₃

Molecular Weight

1143.3 g/mol

InChI Key

IZTQOLKUZKXIRV-YRVFCXMDSA-N

FDA UNII

M03GIQ7Z6P

An octapeptide hormone present in the intestine and brain. When secreted from the gastric mucosa, it stimulates the release of bile from the gallbladder and digestive enzymes from the pancreas.

Sincalide is a Cholecystokinin Analog.

1 2D Structure

[125I]CCK-8

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(3S)-3-amino-4-[[(2S)-1-[[(2S)-1-[[2-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-4-methylsulfanyl-1-oxobutan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-4-methylsulfanyl-1-oxobutan-2-yl]amino]-1-oxo-3-(4-sulfooxyphenyl)propan-2-yl]amino]-4-oxobutanoic acid

2.1.2 InChI

InChI=1S/C49H62N10O16S3/c1-76-18-16-34(55-47(69)37(58-44(66)32(50)23-41(61)62)21-28-12-14-30(15-13-28)75-78(72,73)74)45(67)53-26-40(60)54-38(22-29-25-52-33-11-7-6-10-31(29)33)48(70)56-35(17-19-77-2)46(68)59-39(24-42(63)64)49(71)57-36(43(51)65)20-27-8-4-3-5-9-27/h3-15,25,32,34-39,52H,16-24,26,50H2,1-2H3,(H2,51,65)(H,53,67)(H,54,60)(H,55,69)(H,56,70)(H,57,71)(H,58,66)(H,59,68)(H,61,62)(H,63,64)(H,72,73,74)/t32-,34-,35-,36-,37-,38-,39-/m0/s1

2.1.3 InChI Key

IZTQOLKUZKXIRV-YRVFCXMDSA-N

2.1.4 Canonical SMILES

CSCCC(C(=O)NCC(=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)NC(=O)C(CC4=CC=C(C=C4)OS(=O)(=O)O)NC(=O)C(CC(=O)O)N

2.1.5 Isomeric SMILES

CSCC[C@@H](C(=O)NCC(=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)NC(=O)[C@H](CC4=CC=C(C=C4)OS(=O)(=O)O)NC(=O)[C@H](CC(=O)O)N

2.2 Other Identifiers

2.2.1 UNII

M03GIQ7Z6P

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Cck-8

2. Cck-op

3. Cholecystokinin Octapeptide

4. Cholecystokinin Pancreozymin C Terminal Octapeptide

5. Cholecystokinin Pancreozymin C-terminal Octapeptide

6. H-asp-tyr(so3h)-met-gly-trp-met-asp-phe-nh2

7. Kinevac

8. Op-cck

9. Sq 19,844

10. Sq 19844

11. Sq-19,844

12. Sq-19844

13. Sq19,844

14. Sq19844

15. Syncalide

2.3.2 Depositor-Supplied Synonyms

1. 25126-32-3

2. Cck-8

3. Kinevac

4. Sq 19844

5. Cck C-terminal Octapeptide

6. Cholecystokinin C-terminal Octapeptide

7. Sq-19844

8. Chembl1121

9. M03giq7z6p

10. Cholecystokinin Octapeptide

11. Caerulein, 1-de(5-oxo-l-proline)-2-de-l-glutamine-5-l-methionine-

12. H-asp-tyr(so3h)-met-gly-trp-met-asp-phe-nh2

13. Cholecystokinin 8

14. Dsstox_cid_28543

15. Dsstox_rid_82815

16. Dsstox_gsid_48617

17. L-aspartyl-l-tyrosyl-l-methionylglycyl-l-tryptophyl-l-methionyl-l-aspartylphenyl-l-alaninamide Hydrogen Sulfate (ester)

18. Sincalidum

19. Sincalida

20. Syncalide

21. (3s,6s,9s,15s,18s,21s)-9-((1h-indol-3-yl)methyl)-21-amino-3-(((s)-1-amino-1-oxo-3-phenylpropan-2-yl)carbamoyl)-6,15-bis(2-(methylthio)ethyl)-5,8,11,14,17,20-hexaoxo-18-(4-(sulfooxy)benzyl)-4,7,10,13,16,19-hexaazatricosanedioic Acid

22. Cas-25126-32-3

23. Human Cck-8

24. Cck-8 (sulphated)

25. Asp-tyr(so3h)-met-gly-trp-met-asp-phe-nh2

26. Sincalidum [inn-latin]

27. Sincalida [inn-spanish]

28. Unii-m03giq7z6p

29. Pancreozymin

30. Sincalide [usan:usp:inn:ban]

31. Ncgc00183278-01

32. Ncgc00183363-01

33. 3-10-caerulein, 5-l-methionine-

34. Einecs 246-639-0

35. Kinevac (tn)

36. Mfcd00079849

37. Sq19844

38. Sincalide [inn]

39. Sincalide [mi]

40. Sincalide (usan/inn)

41. Sincalide [usan]

42. Sincalide [vandf]

43. Cholecystokinin-pancreozymin

44. Sincalide [mart.]

45. Sincalide [who-dd]

46. Cholecystokinin Fragment 26-33 Amide (sulphated)

47. Gtpl864

48. Schembl122365

49. (tyr[so3h]27)cholecystokinin Fragment 26-33 Amide

50. Cck-8(so3)

51. Sincalide [orange Book]

52. Dtxsid7048617

53. Sincalide [usp Impurity]

54. Bdbm21147

55. Chebi:135946

56. (3s)-3-amino-4-[[(2s)-1-[[(2s)-1-[[2-[[(2s)-1-[[(2s)-1-[[(2s)-1-[[(2s)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-4-methylsulfanyl-1-oxobutan-2-yl]amino]-3-(1h-indol-3-yl)-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-4-methylsulfanyl-1-oxobutan-2-yl]amino]-1-oxo-3-(4-sulfooxyphenyl)propan-2-yl]amino]-4-oxobutanoic Acid

57. [125i]cck-8

58. 1-de(5-oxo-l-proline)-2-de-l-glutamine-5-l-methioninecaerulein

59. Hy-p0093

60. Sq19844cholecystokinin Octapeptide

61. Tox21_112955

62. Tox21_113481

63. Cholecystokinin Octapeptide, Sulfated

64. Coralynechloridehydrate,98+%

65. Akos016340423

66. Cs-5963

67. Db09142

68. Hs-2026

69. Ncgc00167273-01

70. L-alpha-aspartyl-o-sulfo-l-tyrosyl-l-methionylglycyl-l-tryptophyl-l-methionyl-l-alpha-aspartyl-l-phenylalaninamide

71. Cholecystokinin, Cck Octapeptide (26-33)

72. D05845

73. E78048

74. Asp26-tyr(so3h)-met-gly-trp-met-asp-phenh2

75. 126s323

76. Cholecystokinin C-terminal Octapeptide [mi]

77. Cholecystokinin Octapeptide (sulfated) Ammonium Salt

78. Q7521885

79. (3s)-3-[(2s)-2-[(2s)-2-{2-[(2s)-2-[(2s)-2-[(3s)-3-amino-3-formamidopropanoic Acid]-3-[4-(sulfooxy)phenyl]propanamido]-4-(methylsulfanyl)butanamido]acetamido}-3-(1h-indol-3-yl)propanamido]-4-(methylsulfanyl)butanamido]-3-{[(1s)-1-carbamoyl-2-phenylethyl]carbamoyl}propanoic Acid

80. (3s)-3-[[(2s)-2-[[(2s)-2-[[2-[[(2s)-2-[[(2s)-2-[[(2s)-2-amino-4-hydroxy-4-oxobutanoyl]amino]-3-(4-sulfooxyphenyl)propanoyl]amino]-4-methylsulfanylbutanoyl]amino]acetyl]amino]-3-(1h-indol-3-yl)propanoyl]amino]-4-methylsulfanylbutanoyl]amino]-4-[[(2s)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-4-oxobutanoic Acid

81. (3s,6s,9s,15s,18s,21s)-9-((1h-indol-3-yl)methyl)-21-amino-3-(((s)-1-amino-1-oxo-3-phenylpropan-2-yl)carbamoyl)-6,15-bis(2-(methylthio)ethyl)-5,8,11,14,17,20-hexaoxo-18-(4-(sulfooxy)benzyl)-4,7,10,13,16,19-hexaazatricosane-1,23-dioic Acid

82. (3s,6s,9s,15s,18s,21s)-9-((1h-indol-3-yl)methyl)-21-amino-3-((s)-1-amino-1-oxo-3-phenylpropan-2-ylcarbamoyl)-6,15-bis(2-(methylthio)ethyl)-5,8,11,14,17,20-hexaoxo-18-(4-(sulfooxy)benzyl)-4,7,10,13,16,19-hexaazatricosane-1,23-dioic Acid

83. L-.alpha.-aspartyl-o-sulfo-l-tyrosyl-l-methionylglycyl-l-tryptophyl-l-methionyl-l-.alpha.-aspartyl-l-phenylalaninamide

2.4 Create Date

2006-10-25

3 Chemical and Physical Properties

Molecular Formula	C₄₉H₆₂N₁₀O₁₆S₃
Molecular Weight	1143.3 g/mol
XLogP3	-2.6
Hydrogen Bond Donor Count	13
Hydrogen Bond Acceptor Count	19
Rotatable Bond Count	33
Exact Mass	1142.35073945 g/mol
Monoisotopic Mass	1142.35073945 g/mol
Topological Polar Surface Area	486 Å²
Heavy Atom Count	78
Formal Charge	0
Complexity	2180
Isotope Atom Count	0
Defined Atom Stereocenter Count	7
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

As the product Kinevac (FDA), sincalide is used for the following indications: 1) to stimulate gallbladder contraction, as may be assessed by various methods of diagnostic imaging, or to obtain by duodenal aspiration a sample of concentrated bile for analysis of cholesterol, bile salts, phospholipids, and crystals; (2) to stimulate pancreatic secretion (especially in conjunction with secretin) prior to obtaining a duodenal aspirate for analysis of enzyme activity, composition, and cytology; (3) to accelerate the transit of a barium meal through the small bowel, thereby decreasing the time and extent of radiation associated with fluoroscopy and x-ray examination of the intestinal tract.

FDA Label

5 Pharmacology and Biochemistry

5.1 FDA Pharmacological Classification

5.1.1 Active Moiety

SINCALIDE

5.1.2 FDA UNII

M03GIQ7Z6P

5.1.3 Pharmacological Classes

Cholecystokinin [CS]; Cholecystokinin Analog [EPC]

5.2 ATC Code

V - Various

V04 - Diagnostic agents

V04C - Other diagnostic agents

V04CC - Tests for bile duct patency

V04CC03 - Sincalide

5.3 Absorption, Distribution and Excretion

Absorption

The intravenous (bolus) administration of sincalide causes a prompt contraction of the gallbladder that becomes maximal in 5 to 15 minutes, as compared with the stimulus of a fatty meal which causes a progressive contraction that becomes maximal after approximately 40 minutes.

5.4 Mechanism of Action

When injected intravenously, sincalide produces a substantial reduction in gallbladder size by causing this organ to contract. The evacuation of bile that results is similar to that which occurs physiologically in response to endogenous cholecystokinin. Like cholecystokinin, sincalide stimulates pancreatic secretion; concurrent administration with secretin increases both the volume of pancreatic secretion and the output of bicarbonate and protein (enzymes) by the gland. This combined effect of secretin and sincalide permits the assessment of specific pancreatic function through measurement and analysis of the duodenal aspirate.