References of (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
Title: Ceruletide
CAS Registry Number: 17650-98-5
CAS Name: Caerulein
Synonyms: 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.