NAV

Ceruletide

Identification

Generic Name
Ceruletide
DrugBank Accession Number
DB00403
Background

Caerulein is a specific decapeptide similar in action and composition to the natural gastrointestinal peptide hormone cholecystokinin. It exerts stimulatory effects on the gastric, biliary, and pancreatic secretion, as well as on certain smooth muscles.

Type
Small Molecule
Groups
Approved
Structure
Similar Structures
Weight
Average: 1352.405
Monoisotopic: 1351.448537843
Chemical Formula
C58H73N13O21S2
Synonyms
  • Caerulein
  • Cerulein
  • Ceruletida
  • Ceruletide
  • Ceruletidum

Pharmacology

Indication

Caerulein is used in the treatment of paralytic ileus and as diagnostic aid in pancreatic malfunction.

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Pharmacodynamics

Caerulein is a specific decapeptide similar in action and composition to the natural gastrointestinal peptide hormone cholecystokinin that stimulates gastric, biliary, and pancreatic secretion. It also exerts stimulatory actions on certain smooth muscles.

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.

TargetActionsOrganism
ACholecystokinin receptor type A
inducer
Humans
Absorption

Absorbed following intravenous administration.

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Ceruletide diethylamine4E1MIA8QQL71247-25-1FHDKSYKZXIFRKJ-CBCFNHQSSA-N
International/Other Brands
Takus (Pfizer)

Categories

ATC Codes
V04CC04 — Ceruletide
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as polypeptides. These are peptides containing ten or more amino acid residues.
Kingdom
Organic compounds
Super Class
Organic Polymers
Class
Polypeptides
Sub Class
Not Available
Direct Parent
Polypeptides
Alternative Parents
Peptides / Phenylalanine and derivatives / Glutamine and derivatives / Aspartic acid and derivatives / Methionine and derivatives / Proline and derivatives / N-acyl-alpha amino acids and derivatives / Tryptamines and derivatives / Alpha amino acid amides / Phenylsulfates
show 23 more
Substituents
2-pyrrolidone / 3-alkylindole / Alcohol / Alpha peptide / Alpha-amino acid amide / Alpha-amino acid or derivatives / Amphetamine or derivatives / Aromatic heteropolycyclic compound / Arylsulfate / Aspartic acid or derivatives
show 50 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
oligopeptide (CHEBI:59219)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
888Y08971B
CAS number
17650-98-5
InChI Key
YRALAIOMGQZKOW-HYAOXDFASA-N
InChI
InChI=1S/C58H73N13O21S2/c1-29(72)49(71-57(87)40(23-31-12-14-33(15-13-31)92-94(89,90)91)68-56(86)43(26-48(78)79)69-52(82)37(16-18-44(59)73)65-51(81)36-17-19-45(74)63-36)58(88)62-28-46(75)64-41(24-32-27-61-35-11-7-6-10-34(32)35)54(84)66-38(20-21-93-2)53(83)70-42(25-47(76)77)55(85)67-39(50(60)80)22-30-8-4-3-5-9-30/h3-15,27,29,36-43,49,61,72H,16-26,28H2,1-2H3,(H2,59,73)(H2,60,80)(H,62,88)(H,63,74)(H,64,75)(H,65,81)(H,66,84)(H,67,85)(H,68,86)(H,69,82)(H,70,83)(H,71,87)(H,76,77)(H,78,79)(H,89,90,91)/t29-,36+,37+,38+,39+,40+,41+,42+,43+,49+/m1/s1
IUPAC Name
(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
SMILES
[H][C@](NC(=O)[C@H](CC1=CC=C(OS(O)(=O)=O)C=C1)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](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

References

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 References
Not Available
Human Metabolome Database
HMDB0014547
KEGG Drug
D03442
PubChem Compound
16129675
PubChem Substance
46505766
ChemSpider
10481982
ChEBI
59219
ChEMBL
CHEMBL1201355
Therapeutic Targets Database
DAP000961
PharmGKB
PA164774919
Wikipedia
Ceruletide

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
  • Pharmacia and upjohn co
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
logP-0.9Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0116 mg/mLALOGPS
logP-0.19ALOGPS
logP-5.2Chemaxon
logS-5.1ALOGPS
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
Polarizability130.33 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
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
CarcinogenicityNon-carcinogens0.6434
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

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Details1. Cholecystokinin receptor type A
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inducer
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 gas...
Gene Name
CCKAR
Uniprot ID
P32238
Uniprot Name
Cholecystokinin receptor type A
Molecular Weight
47840.645 Da
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at November 03, 2023 23:41