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Also known as caerulein, cerulein, ceruletide diethylamine, Tymtran®, Ceruletide, Caerulein, Ceruletidum, Cerulein

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.

Chemical data

Formula: C58H73N13O21S2
Molecular weight: 1352.4 g/mol
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
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
InChIKey: YRALAIOMGQZKOW-HYAOXDFASA-N
XLogP: -3
Polar surface area: 585 Å²
H-bond donors: 17
H-bond acceptors: 22
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Protein
First approval: 1982
Admin. routes: parenteral

via ChEMBL · EBI

Research

3,220 papers

Ceruletide for schizophrenia: a review.Psychopharmacology bulletin · 1986
Caerulein (ceruletide). A review.Acta gastro-enterologica Belgica · 1976
Pharmacology, clinical uses, and adverse effects of ceruletide, a cholecystokinetic agent.Pharmacotherapy · 1982
Ceruletide acts in the abdomen, not in the brain, to produce satiety.Peptides · 1984
Ceruletide inhibits phencyclidine-induced dopamine and serotonin release in rat prefrontal cortex.Pharmacology, biochemistry, and behavior · 1998

via PubMed

Wikidata facts

Mass: 1351.448538
Has use: medication

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found in taxon: Giant leaf frog
chemical formula: C₅₈H₇₃N₁₃O₂₁S₂
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
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
World Health Organisation international non-proprietary name: ceruletide

Sources (2)

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via Wikidata sitelinks · CC0