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Identification
Name Ceruletide
Accession Number DB00403 (APRD00861)
Type small molecule
Groups approved
Description

Caerulein is a specific decapeptide similar in action and composition to the natural gastrointestinal peptide hormone cholecystokinin. It stimulates gastric, biliary, and pancreatic secretion; and certain smooth muscle.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Brand names Not Available
Brand name mixtures Not Available
Categories
  • Diagnostic aids
CAS number 17650-98-5
Weight Average: 980.051
Monoisotopic: 979.374568267
Chemical Formula C45H57N9O14S
InChI Key InChIKey=GZCDGEPFXQGWOW-RMNOTBJOSA-N
InChI
InChI=1S/C45H57N9O14S/c1-3-4-13-33(42(61)53-36(22-38(57)58)44(63)52-34(40(47)59)20-26-10-6-5-7-11-26)51-43(62)35(21-28-23-48-32-14-9-8-12-30(28)32)50-37(56)24-49-45(64)39(25(2)55)54-41(60)31(46)19-27-15-17-29(18-16-27)68-69(65,66)67/h5-12,14-18,23,25,31,33-36,39,48,55H,3-4,13,19-22,24,46H2,1-2H3,(H2,47,59)(H,49,64)(H,50,56)(H,51,62)(H,52,63)(H,53,61)(H,54,60)(H,57,58)(H,65,66,67)/t25-,31+,33-,34+,35+,36+,39+/m1/s1
Plain Text
IUPAC Name
(3S)-3-[(2R)-2-[(2S)-2-{2-[(2S,3R)-2-[(2S)-2-amino-3-[4-(sulfooxy)phenyl]propanamido]-3-hydroxybutanamido]acetamido}-3-(1H-indol-3-yl)propanamido]hexanamido]-3-{[(1S)-1-carbamoyl-2-phenylethyl]carbamoyl}propanoic acid
SMILES
CCCC[C@@H](NC(=O)[C@H](CC1=CNC2=C1C=CC=C2)NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](N)CC1=CC=C(OS(O)(=O)=O)C=C1)[C@@H](C)O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC1=CC=CC=C1)C(N)=O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Polypeptides
  • Tryptamines and Derivatives
Substructures
  • Polypeptides
  • Hydroxy Compounds
  • Acetates
  • Indoles and Indole Derivatives
  • Phenols and Derivatives
  • Amino Ketones
  • Sulfuric Acids and Derivatives
  • Pyrroles
  • Sulfonyls
  • Aliphatic and Aryl Amines
  • Benzene and Derivatives
  • Sulfate Esters
  • Carboxylic Acids and Derivatives
  • Tryptamines and Derivatives
  • Carbamates and Derivatives
  • Phenethylamines
  • Heterocyclic compounds
  • Aromatic compounds
  • Carboxamides and Derivatives
  • Phenylpropylamines
  • Alcohols and Polyols
  • Keto-Acids
  • Phenyl Esters
  • Amphetamines
Pharmacology
Indication Caerulein stimulates gastric, biliary, and pancreatic secretion; and certain smooth muscle. As such, it is used in paralytic ileus and as diagnostic aid in pancreatic malfunction.
Pharmacodynamics Caerulein is a specific decapeptide similar in action and composition to the natural gastrointestinal peptide hormone cholecystokinin. It stimulates gastric, biliary, and pancreatic secretion; and certain smooth muscle.
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.
Absorption Absorbed following intravenous administration.
Volume of distribution Not Available
Protein binding Not Available
Metabolism
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Pharmacia and upjohn co
Packagers Not Available
Dosage forms Not Available
Prices Not Available
Patents Not Available
Properties
State solid
Melting point Not Available
Experimental Properties
Property Value Source
logP -0.9 PhysProp
Predicted Properties
Property Value Source
water solubility 5.67e-03 g/l ALOGPS
logP 0.35 ALOGPS
logP -3.60 ChemAxon Molconvert
logS -5.24 ALOGPS
pKa 3.76 ChemAxon Molconvert
hydrogen acceptor count 14 ChemAxon Molconvert
hydrogen donor count 12 ChemAxon Molconvert
polar surface area 380.63 ChemAxon Molconvert
rotatable bond count 27 ChemAxon Molconvert
refractivity 244.25 ChemAxon Molconvert
polarizability 98.24 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
PubChem Compound 168399 Link_out
PubChem Substance 46505766 Link_out
ChemSpider 147304 Link_out
ChEBI 59219 Link_out
ChEMBL 59219 Link_out
Therapeutic Targets Database DAP000961 Link_out
Drug Product Database 0 Link_out
ATC Codes
  • V04CC04
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions
Drug Interaction
Food Interactions Not Available
Targets

1. Cholecystokinin type A receptor

Pharmacological action: yes
Actions: inducer

Receptor for cholecystokinin. Mediates pancreatic growth and enzyme secretion, smooth muscle contraction of the gall bladder and stomach. Has a 1000-fold higher affinity for CCK rather than for gastrin. It modulates feeding and dopamine-induced behavior in the central and peripheral nervous system. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system

Organism class: human
UniProt ID: P32238 Link_out
Gene: CCKAR Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Ishikawa Y, Shimatsu A, Murakami Y, Imura H: Barrel rotation in rats induced by SMS 201-995: suppression by ceruletide. Pharmacol Biochem Behav. 1990 Nov;37(3):523-6. Pubmed
  2. Katsuura G, Ibii N, Matsushita A: Activation of CCK-A receptors induces elevation of plasma corticosterone in rats. Peptides. 1992 Jan-Feb;13(1):203-5. Pubmed
  3. Maurice T, Hiramatsu M, Kameyama T, Hasegawa T, Nabeshima T: Cholecystokinin-related peptides, after systemic or central administration, prevent carbon monoxide-induced amnesia in mice. J Pharmacol Exp Ther. 1994 May;269(2):665-73. Pubmed
  4. Shinohara S, Katsuura G, Eigyo M, Shintaku H, Ibii N, Matsushita A: Inhibitory effect of CCK-8 and ceruletide on glutamate-induced rises in intracellular free calcium concentrations in rat neuron cultures. Brain Res. 1992 Aug 21;588(2):223-8. Pubmed
  5. Ibii N, Ikeda M, Takahara Y, Eigyo M, Akiyoshi T, Matsushita A: Inhibitory effect of ceruletide on haloperidol-induced catalepsy in rats. Peptides. 1989 Jul-Aug;10(4):779-83. Pubmed
  6. Makovec F, Bani M, Cereda R, Chiste R, Pacini MA, Revel L, Rovati LA, Rovati LC, Setnikar I: Pharmacological properties of lorglumide as a member of a new class of cholecystokinin antagonists. Arzneimittelforschung. 1987 Nov;37(11):1265-8. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on April 19, 2011 15:03

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.