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Accession NumberDB00403  (APRD00861)
TypeSmall Molecule
DescriptionCaerulein 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 IDs Not Available
Product Ingredients
IngredientUNIICASInChI KeyDetails
Ceruletide diethylamine4E1MIA8QQL 71247-25-1FHDKSYKZXIFRKJ-CBCFNHQSSA-NDetails
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
Brand mixturesNot Available
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
[H][C@](NC(=O)[[email protected]](CC1=CC=C(OS(O)(=O)=O)C=C1)NC(=O)[[email protected]](CC(O)=O)NC(=O)[[email protected]](CCC(N)=O)NC(=O)[C@@H]1CCC(=O)N1)([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CC1=CNC2=CC=CC=C12)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC1=CC=CC=C1)C(N)=O
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.
Structured Indications Not Available
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.
TargetKindPharmacological actionActionsOrganismUniProt ID
Cholecystokinin receptor type AProteinyes
HumanP32238 details
Related Articles
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
Pharmacogenomic Effects/ADRs Not Available
Drug Interactions Not Available
Food InteractionsNot 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
Clinical Trials
Clinical Trials Not Available
  • 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
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 )
Mass Spec (NIST)Not Available
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
DescriptionThis compound belongs to the class of chemical entities known as polypeptides. These are peptides containing ten or more amino acid residues.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic Polymers
Sub ClassPolypeptides
Direct ParentPolypeptides
Alternative Parents
  • Polypeptide
  • Alpha peptide
  • Phenylalanine or derivatives
  • Glutamine or derivatives
  • Aspartic acid or derivatives
  • Methionine or derivatives
  • N-acyl-alpha amino acid or derivatives
  • Proline or derivatives
  • Alpha-amino acid amide
  • Triptan
  • Phenylsulfate
  • Arylsulfate
  • Amphetamine or derivatives
  • Alpha-amino acid or derivatives
  • 3-alkylindole
  • N-substituted-alpha-amino acid
  • Indole or derivatives
  • Indole
  • Phenoxy compound
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine-2-carboxamide
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Fatty amide
  • N-acyl-amine
  • Fatty acyl
  • Benzenoid
  • Pyrrolidone
  • 2-pyrrolidone
  • Substituted pyrrole
  • Sulfuric acid monoester
  • Sulfate-ester
  • Sulfuric acid ester
  • Pyrrole
  • Organic sulfuric acid or derivatives
  • Heteroaromatic compound
  • Pyrrolidine
  • Primary carboxylic acid amide
  • Carboxamide group
  • Lactam
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Dialkylthioether
  • Organoheterocyclic compound
  • Sulfenyl compound
  • Thioether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Azacycle
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors


Pharmacological action
General Function:
Peptide binding
Specific Function:
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 phosphatidylinos...
Gene Name:
Uniprot ID:
Molecular Weight:
47840.645 Da
  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:2087492 ]
  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:1620654 ]
  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:8182534 ]
  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:1356589 ]
  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:2587420 ]
  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:3440035 ]
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Drug created on June 13, 2005 07:24 / Updated on December 08, 2016 11:47