Ceruletide

Title: Ceruletide
CAS Registry Number: 17650-98-5
CAS Name: Caerulein
Additional Names: cerulein
Manufacturers' Codes: FI-6934
Molecular Formula: C58H73N13O21S2
Molecular Weight: 1352.40
Percent Composition: C 51.51%, H 5.44%, N 13.46%, O 24.84%, S 4.74%
Literature References: Cholecystokinin analog; decapeptide discovered in the skins of Australian amphibians: V. Erspamer et al., Nature 212, 204 (1966). Isoln from Hyla caerulea and structure: A. Anastasi et al., Experientia 23, 699 (1967); eidem, Arch. Biochem. Biophys. 125, 57 (1968). Synthesis: L. Bernardi et al., Experientia 23, 700 (1967); eidem, ZA 6704716; eidem, US 3472832 (1968, 1969 to Soc. Farm. Italia). Shows hypotensive activity, stimulates smooth muscle and increases gastric, pancreatic, and biliary secretions: V. Erspamer et al., Experientia 23, 702 (1967). Series of articles on metabolism: Eur. J. Biochem. 91, 21-48 (1978). Pharmacodynamics: N. Iwatsuki, O. H. Petersen, J. Cell Biol. 79, 533 (1978); T. Fujita et al., Adv. Exp. Med. Biol. 106, 147 (1978). Diagnostic use: R. Fujita et al., Acta Gastroenterol. Belg. 40, 167 (1977); C. Monti et al., Radiology 129, 611 (1978). Toxicology: T. Chieli et al., Toxicol. Appl. Pharmacol. 23, 480 (1972). Reviews of pharmacology and clinical applications: G. Bertaccini, Pharmacol. Rev. 28, 127 (1976); and toxicology: M. E. Vincent et al., Pharmacotherapy 2, 223 (1982).
Properties: mp 224-226° (dec). [a]D20 -26° (c = 1 in DMF).
Melting point: mp 224-226° (dec)
Optical Rotation: [a]D20 -26° (c = 1 in DMF)
Derivative Type: Diethylamine salt
CAS Registry Number: 71247-25-1
Trademarks: Ceosunin (Kyowa); Takus (Montedison); Tymtran (Adria)
Properties: Off-white hygroscopic powder. Sol in DMF and DMSO. Insol in acetone, diethyl ether. LD50 i.v. in mice: 1012 mg/kg (Chieli).
Toxicity data: LD50 i.v. in mice: 1012 mg/kg (Chieli)
Therap-Cat: Stimulant (gastric secretory). Diagnostic aid (pancreatic function; cholecystokinetic agent in cholecystography).
Keywords: Diagnostic Aid; Gastric and Pancreatic Secretion Stimulant.
Ceruloplasmin Cervicarcin Cesium Bromide Cesium Carbonate Cesium Chloride

Ceruletide
Ceruletide.png
Systematic (IUPAC) name
(3S)-3-{[(1S)-1-carbamoyl-2-phenylethyl]carbamoyl}-3-[(2S)-2-[(2S)-2-{2-[(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
Clinical data
AHFS/Drugs.com International Drug Names
Legal status  ?
Identifiers
CAS number 17650-98-5 YesY
ATC code V04CC04
PubChem CID 16219178
DrugBank DB00403
ChemSpider 147304 N
UNII 888Y08971B N
KEGG D03442 N
ChEMBL CHEMBL1201355 N
Chemical data
Formula C58H73N13O21S2 
Mol. mass 1352.40 g/mol
 N (what is this?)  (verify)

Ceruletide (INN), also known as cerulein or caerulein, is a ten amino acid oligopeptide that stimulates smooth muscle and increases digestive secretions. Ceruletide 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. It is used to induce pancreatitis in experimental animal models.

The tree frog Litoria caerulae, formerly named Hyla caerulae.

Ceruletide was discovered and its structure elucidated in 1967 by Australian and Italian scientists from dried skins of the Australian green tree frog (Litoria caerulea, formerly Hyla caerulea). Its amino acid sequence is Pglu-Gln-Asp-Tyr[SO3H]-Thr-Gly-Trp-Met-Asp-Phe-NH2.[1][2]