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    Ceruletide

    ACTIVE PHARMA INGREDIENTS

    FINISHED DOSAGE FORMULATIONS

    REF. STANDARDS & IMPURITIES

    PharmaCompass
    Xls

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    2D Structure
    Also known as: Caerulein, 17650-98-5, Cerulein, Ceruletida, Ceruletidum, 5-oxo-l-prolyl-l-glutaminyl-l-alpha-aspartyl-o-sulfo-l-tyrosyl-l-threonylglycyl-l-tryptophyl-l-methionyl-l-alpha-aspartyl-l-phenylalaninamide
    Molecular Formula
    C58H73N13O21S2
    Molecular Weight
    1352.4  g/mol
    InChI Key
    YRALAIOMGQZKOW-HYAOXDFASA-N
    FDA UNII
    888Y08971B
    A specific decapeptide obtained from the skin of Hila caerulea, an Australian amphibian. Caerulein is similar in action and composition to CHOLECYSTOKININ. It stimulates gastric, biliary, and pancreatic secretion; and certain smooth muscle. It is used in paralytic ileus and as diagnostic aid in pancreatic malfunction.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (3S)-3-[[(2S)-5-amino-5-oxo-2-[[(2S)-5-oxopyrrolidine-2-carbonyl]amino]pentanoyl]amino]-4-[[(2S)-1-[[(2S,3R)-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]-3-hydroxy-1-oxobutan-2-yl]amino]-1-oxo-3-(4-sulfooxyphenyl)propan-2-yl]amino]-4-oxobutanoic acid
    2.1.2 InChI
    InChI=1S/C58H73N13O21S2/c1-29(72)49(71-57(87)40(23-31-12-14-33(15-13-31)92-94(89,90)91)68-56(86)43(26-48(78)79)69-52(82)37(16-18-44(59)73)65-51(81)36-17-19-45(74)63-36)58(88)62-28-46(75)64-41(24-32-27-61-35-11-7-6-10-34(32)35)54(84)66-38(20-21-93-2)53(83)70-42(25-47(76)77)55(85)67-39(50(60)80)22-30-8-4-3-5-9-30/h3-15,27,29,36-43,49,61,72H,16-26,28H2,1-2H3,(H2,59,73)(H2,60,80)(H,62,88)(H,63,74)(H,64,75)(H,65,81)(H,66,84)(H,67,85)(H,68,86)(H,69,82)(H,70,83)(H,71,87)(H,76,77)(H,78,79)(H,89,90,91)/t29-,36+,37+,38+,39+,40+,41+,42+,43+,49+/m1/s1
    2.1.3 InChI Key
    YRALAIOMGQZKOW-HYAOXDFASA-N
    2.1.4 Canonical SMILES
    CC(C(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)NC(=O)C(CCC(=O)N)NC(=O)C5CCC(=O)N5)O
    2.1.5 Isomeric SMILES
    C[C@H]([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)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@@H]5CCC(=O)N5)O
    2.2 Other Identifiers
    2.2.1 UNII
    888Y08971B
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Caerulein

    2. Cerulein

    3. Ceruletid

    4. Fi 6934

    5. Fi-6934

    6. Fi6934

    7. Takus

    2.3.2 Depositor-Supplied Synonyms

    1. Caerulein

    2. 17650-98-5

    3. Cerulein

    4. Ceruletida

    5. Ceruletidum

    6. 5-oxo-l-prolyl-l-glutaminyl-l-alpha-aspartyl-o-sulfo-l-tyrosyl-l-threonylglycyl-l-tryptophyl-l-methionyl-l-alpha-aspartyl-l-phenylalaninamide

    7. Fi-6934

    8. 5-oxo-l-prolyl-l-glutaminyl-l-aspartyl-l-tyrosyl-l-threonylglycyl-l-tryptophyl-l-methionyl-l-aspartylphenyl-l-alaninamide 4-(hydrogen Sulfate) (ester)

    9. Chebi:59219

    10. 888y08971b

    11. Ceruletidum [inn-latin]

    12. Ceruletida [inn-spanish]

    13. Ceruletide [usan:inn:ban]

    14. 5-oxo-l-prolyl-l-glutaminyl-l-a-aspartyl-o-sulfo-l-tyrosyl-l-threonylglycyl-l-tryptophyl-l-methionyl-l-a-aspartyl-l-phenylalaninamide

    15. Ccris 3063

    16. Ceruletide (usan/inn)

    17. Unii-888y08971b

    18. Caerulein, Sulfated

    19. Fi-6934caerulein

    20. Ceruletide [mi]

    21. Ceruletide [inn]

    22. Ceruletide [usan]

    23. Ceruletide [mart.]

    24. Ceruletide [who-dd]

    25. Schembl29520

    26. Gtpl7589

    27. Chembl1201355

    28. Dtxsid8040434

    29. Hy-a0190

    30. Pyr-qd-tyr(so3h)-tgwmdf-nh2

    31. Mfcd00076478

    32. Cs-5876

    33. Db00403

    34. As-56061

    35. C73362

    36. D03442

    37. Q5065299

    38. Pglu-gln-asp-tyr(so3h)-thr-gly-trp-met-asp-phe-nh2

    39. (3s)-3-{[(1s)-1-carbamoyl-2-phenylethyl]carbamoyl}-3-[(2s)-2-[(2s)-2-{2-[(2s,3r)-2-[(2s)-2-[(2s)-2-[(2s)-4-carbamoyl-2-{[(2s)-5-oxopyrrolidin-2-yl]formamido}butanamido]-3-carboxypropanamido]-3-[4-(sulfooxy)phenyl]propanamido]-3-hydroxybutanamido]acetamido}-3-(1h-indol-3-yl)propanamido]-4-(methylsulfanyl)butanamido]propanoic Acid

    40. 5-oxo-l-prolyl-l-glutaminyl-l-a-aspartyl-o-sulfo-l-tyrosyl-l-threonylglycyl-l-tryptophyl-l-methionyl-l-.alpha.-aspartyl-l-phenylalaninamide

    2.4 Create Date
    2007-07-03
    3 Chemical and Physical Properties
    Molecular Weight 1352.4 g/mol
    Molecular Formula C58H73N13O21S2
    XLogP3-3
    Hydrogen Bond Donor Count17
    Hydrogen Bond Acceptor Count22
    Rotatable Bond Count38
    Exact Mass1351.44853874 g/mol
    Monoisotopic Mass1351.44853874 g/mol
    Topological Polar Surface Area585 Ų
    Heavy Atom Count94
    Formal Charge0
    Complexity2840
    Isotope Atom Count0
    Defined Atom Stereocenter Count10
    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

    Caerulein is used in the treatment of paralytic ileus and as diagnostic aid in pancreatic malfunction.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Caerulein is a specific decapeptide similar in action and composition to the natural gastrointestinal peptide hormone cholecystokinin that stimulates gastric, biliary, and pancreatic secretion. It also exerts stimulatory actions on certain smooth muscles.

    5.2 ATC Code

    V - Various

    V04 - Diagnostic agents

    V04C - Other diagnostic agents

    V04CC - Tests for bile duct patency

    V04CC04 - Ceruletide

    5.3 Absorption, Distribution and Excretion

    Absorption

    Absorbed following intravenous administration.

    5.4 Mechanism of Action

    Caerulein acts according to its similarity to the natural gastrointestinal peptide hormone cholecystokinin. Cholecystokinin is a peptide hormone of the gastrointestinal system responsible for stimulating the digestion of fat and protein. Cholecystokinin is secreted by the duodenum, the first segment of the small intestine. There it binds to CCK receptors, activating them and causing downstream effects. Specifically, it results in the release of digestive enzymes and bile from the pancreas and gall bladder, respectively. It also acts as a hunger suppresant. Cholecystokinin is secreted by the duodenum when fat- or protein-rich chyme leaves the stomach and enters the duodenum. The hormone acts on the pancreas to stimulate the secretion of the enzymes lipase, amylase, trypsin, and chymotrypsin. Together these pancreatic enzymes catalyze the digestion of fat and protein. Cholecystokinin also stimulates both the contraction of the gall bladder, and the relaxtion of the Sphincter of Oddi (Glisson's Sphinctor), which delivers, (not secretes) bile into the small intestine. Bile salts serve to emulsify fats, thereby increasing the effectiveness with which enzymes can digest them.