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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
    Sincalide
    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

    Sincalide

    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 Weight 1143.3 g/mol
    Molecular Formula C49H62N10O16S3
    XLogP3-2.6
    Hydrogen Bond Donor Count13
    Hydrogen Bond Acceptor Count19
    Rotatable Bond Count33
    Exact Mass1142.35073945 g/mol
    Monoisotopic Mass1142.35073945 g/mol
    Topological Polar Surface Area486 Ų
    Heavy Atom Count78
    Formal Charge0
    Complexity2180
    Isotope Atom Count0
    Defined Atom Stereocenter Count7
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    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.

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    DOSAGE - POWDER;INTRAVENOUS - 0.005MG/VIAL

    USFDA APPLICATION NUMBER - 17697

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    DOSAGE - POWDER;INTRAVENOUS - 0.005MG/VIAL

    USFDA APPLICATION NUMBER - 210850

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