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Accession NumberDB00403  (APRD00861)
TypeSmall Molecule

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.

External Identifiers Not Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
Brand mixturesNot Available
Ceruletide diethylamine
ThumbNot applicableDBSALT001364
CAS number17650-98-5
WeightAverage: 1352.405
Monoisotopic: 1351.448537843
Chemical FormulaC58H73N13O21S2
(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
DescriptionThis compound belongs to the class of organic compounds known as polypeptides. These are peptides containing ten or more amino acid residues.
KingdomOrganic compounds
Super ClassOrganic Polymers
Sub ClassNot Available
Direct ParentPolypeptides
Alternative Parents
  • Polypeptide
  • Alpha peptide
  • N-acyl-alpha amino acid or derivatives
  • Triptan
  • Alpha-amino acid amide
  • Phenylsulfate
  • Phenylpropylamine
  • Amphetamine or derivatives
  • N-substituted-alpha-amino acid
  • Indole or derivatives
  • Indole
  • Pyrrolidine-2-carboxamide
  • Pyrrolidine carboxylic acid or derivatives
  • Sulfuric acid monoester
  • Amino fatty acid
  • Fatty acyl
  • Benzenoid
  • Sulfuric acid ester
  • Sulfate-ester
  • Substituted pyrrole
  • 2-pyrrolidone
  • Pyrrolidone
  • N-acyl-amine
  • Fatty amide
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Pyrrolidine
  • Pyrrole
  • Organic sulfuric acid or derivatives
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Primary carboxylic acid amide
  • Lactam
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Dialkylthioether
  • Sulfenyl compound
  • Thioether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
IndicationCaerulein 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.
PharmacodynamicsCaerulein 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 actionCaerulein 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.
AbsorptionAbsorbed following intravenous administration.
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Predicted ADMET features
Human Intestinal Absorption+0.8428
Blood Brain Barrier-0.7051
Caco-2 permeable-0.7114
P-glycoprotein substrateSubstrate0.7616
P-glycoprotein inhibitor INon-inhibitor0.8646
P-glycoprotein inhibitor IINon-inhibitor0.9946
Renal organic cation transporterNon-inhibitor0.8644
CYP450 2C9 substrateNon-substrate0.8617
CYP450 2D6 substrateNon-substrate0.7832
CYP450 3A4 substrateSubstrate0.5706
CYP450 1A2 substrateNon-inhibitor0.7836
CYP450 2C9 inhibitorNon-inhibitor0.7725
CYP450 2D6 inhibitorNon-inhibitor0.8592
CYP450 2C19 inhibitorNon-inhibitor0.7546
CYP450 3A4 inhibitorNon-inhibitor0.9364
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8493
Ames testNon AMES toxic0.6179
BiodegradationNot ready biodegradable0.9879
Rat acute toxicity2.6037 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8006
hERG inhibition (predictor II)Inhibitor0.5939
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
  • Pharmacia and upjohn co
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Experimental Properties
logP-0.9Not Available
Predicted Properties
Water Solubility0.0116 mg/mLALOGPS
pKa (Strongest Acidic)-2ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count20ChemAxon
Hydrogen Donor Count17ChemAxon
Polar Surface Area551.4 Å2ChemAxon
Rotatable Bond Count38ChemAxon
Refractivity325.74 m3·mol-1ChemAxon
Polarizability129.96 Å3ChemAxon
Number of Rings5ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Mass Spec (NIST)Not Available
SpectraNot Available
Synthesis Reference

Bernardi, L., Bosisio, G., De Castiglione, R. and Goffredo, O. ;U.S. Patent 3,472,832; Oct. 14,
1969; assigned to Societa Farmaceutici ltalia (Italy).

General ReferencesNot Available
External Links
ATC CodesV04CC04
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Drug InteractionsNot Available
Food InteractionsNot Available


1. Cholecystokinin receptor type A

Kind: Protein

Organism: Human

Pharmacological action: yes

Actions: inducer


Name UniProt ID Details
Cholecystokinin receptor type A P32238 Details


  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

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Drug created on June 13, 2005 07:24 / Updated on November 27, 2015 14:06