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Chemistry

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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

Ceruletide
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

Ceruletide

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.


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