U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C58H73N13O21S2
Molecular Weight 1352.4092
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CERULETIDE

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]2CCC(=O)N2)([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CC3=CNC4=CC=CC=C34)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC5=CC=CC=C5)C(N)=O

InChI

InChIKey=YRALAIOMGQZKOW-HYAOXDFASA-N
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

HIDE SMILES / InChI
Molecular Formula C58H73N13O21S2
Molecular Weight 1352.4092
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 10 / 10
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

CERULETIDE, also known as caerulein, is a specific decapeptide obtained from the skin of Hila caerulea, an Australian amphibian. It is similar in action and composition to the natural gastrointestinal peptide hormone cholecystokinin. It stimulates gastric, biliary, and pancreatic secretion; and certain smooth muscle. In the research setting, CERULETIDE can be used to induce pancreatitis in experimental animal models.

Originator

Approval Year

1981
142
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Approved
8583
TYMTRAN

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse events​
0.6 ug/kg 2 times / day multiple, intravenous
Studied dose
Dose: 0.6 ug/kg, 2 times / day
Route: intravenous
Route: multiple
Dose: 0.6 ug/kg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/3907376
unhealthy, 16
Health Status: unhealthy
Age Group: 16
Sources:
https://pubmed.ncbi.nlm.nih.gov/3907376
Disc. AE: Abdominal cramps...
AEs leading to
discontinuation/dose reduction:
Abdominal cramps (grade 1-2, 31.2%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/3907376
20 ug single, intramuscular
Highest studied dose
Dose: 20 ug
Route: intramuscular
Route: single
Dose: 20 ug
Sources:
https://pubmed.ncbi.nlm.nih.gov/6714795
healthy, 20-32
Health Status: healthy
Age Group: 20-32
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/6714795
Other AEs: Sickness, Dizziness...
Other AEs:
Sickness (grade 1, 12.5%)
Dizziness (grade 1, 12.5%)
Headache (grade 1, 6.25%)
Injection site pain (grade 1, 50%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/6714795
100 ng/kg/h single, intravenous
Studied dose
Dose: 100 ng/kg/h
Route: intravenous
Route: single
Dose: 100 ng/kg/h
Sources:
https://pubmed.ncbi.nlm.nih.gov/3065099
unhealthy, 24-55
Health Status: unhealthy
Age Group: 24-55
Sources:
https://pubmed.ncbi.nlm.nih.gov/3065099
Sources:
https://pubmed.ncbi.nlm.nih.gov/3065099
0.6 ug/kg 2 times / day multiple, intravenous
Studied dose
Dose: 0.6 ug/kg, 2 times / day
Route: intravenous
Route: multiple
Dose: 0.6 ug/kg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/3907376
unhealthy
Health Status: unhealthy
Sources:
https://pubmed.ncbi.nlm.nih.gov/3907376
Disc. AE: Vomiting...
AEs leading to
discontinuation/dose reduction:
Vomiting (grade 1-2, 31.2%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/3907376
AEs

AEs

AESignificanceDosePopulation
Abdominal cramps grade 1-2, 31.2%
Disc. AE
0.6 ug/kg 2 times / day multiple, intravenous
Studied dose
Dose: 0.6 ug/kg, 2 times / day
Route: intravenous
Route: multiple
Dose: 0.6 ug/kg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/3907376
unhealthy, 16
Health Status: unhealthy
Age Group: 16
Sources:
https://pubmed.ncbi.nlm.nih.gov/3907376
Dizziness grade 1, 12.5%
20 ug single, intramuscular
Highest studied dose
Dose: 20 ug
Route: intramuscular
Route: single
Dose: 20 ug
Sources:
https://pubmed.ncbi.nlm.nih.gov/6714795
healthy, 20-32
Health Status: healthy
Age Group: 20-32
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/6714795
Sickness grade 1, 12.5%
20 ug single, intramuscular
Highest studied dose
Dose: 20 ug
Route: intramuscular
Route: single
Dose: 20 ug
Sources:
https://pubmed.ncbi.nlm.nih.gov/6714795
healthy, 20-32
Health Status: healthy
Age Group: 20-32
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/6714795
Injection site pain grade 1, 50%
20 ug single, intramuscular
Highest studied dose
Dose: 20 ug
Route: intramuscular
Route: single
Dose: 20 ug
Sources:
https://pubmed.ncbi.nlm.nih.gov/6714795
healthy, 20-32
Health Status: healthy
Age Group: 20-32
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/6714795
Headache grade 1, 6.25%
20 ug single, intramuscular
Highest studied dose
Dose: 20 ug
Route: intramuscular
Route: single
Dose: 20 ug
Sources:
https://pubmed.ncbi.nlm.nih.gov/6714795
healthy, 20-32
Health Status: healthy
Age Group: 20-32
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/6714795
Vomiting grade 1-2, 31.2%
Disc. AE
0.6 ug/kg 2 times / day multiple, intravenous
Studied dose
Dose: 0.6 ug/kg, 2 times / day
Route: intravenous
Route: multiple
Dose: 0.6 ug/kg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/3907376
unhealthy
Health Status: unhealthy
Sources:
https://pubmed.ncbi.nlm.nih.gov/3907376
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:59219
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:59219
ChemicalBook
CB2384634
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB2384634
MolPort
MolPort-042-652-784
https://www.molport.com/shop/molecule-link/MolPort-042-652-784
PubMed

PubMed

TitleDatePubMed
Selective inhibition of NF-kappaB attenuates the severity of cerulein-induced acute pancreatitis.
2002-10
Expression of the chemokines MCP-1/JE and cytokine-induced neutrophil chemoattractant in early acute pancreatitis.
2002-10
Cerulein-induced acute pancreatitis in the rat is significantly ameliorated by treatment with MEK1/2 inhibitors U0126 and PD98059.
2002-10
Primary sensory neurons: a common final pathway for inflammation in experimental pancreatitis in rats.
2002-10
Effect of nitric oxide on gallbladder motility in patients with acalculous biliary pain: a cholescintigraphic study.
2002-09
Cathepsin B inhibition prevents trypsinogen activation and reduces pancreatitis severity.
2002-09
In vivo evidence for the role of GM-CSF as a mediator in acute pancreatitis-associated lung injury.
2002-09
Glutathione depletion with L-buthionine-(S,R)-sulfoximine demonstrates deleterious effects in acute pancreatitis of the rat.
2002-08
Pancreatic capillary blood flow in an improved model of necrotizing pancreatitis in the rat.
2002-08
Endothelin A but not endothelin B receptor blockade reduces capillary permeability in severe experimental pancreatitis.
2002-08
Mechanisms of Chinese herb emodin and somatostatin analogs on pancreatic regeneration in acute pancreatitis in rats.
2002-08
Different modes of NF-kappaB/Rel activation in pancreatic lobules.
2002-08
Natural history of long-term lung injury in mouse experimental pancreatitis.
2002-07
The effects of somatostatin on the microperfusion of the pancreas during acute necrotizing pancreatitis in rats.
2002-06-18
Effect of intravenous infusion of amino acids on pancreatic secretion.
2002-06-18
Coordinate regulation of secretory stress proteins (PSP/reg, PAP I, PAP II, and PAP III) in the rat exocrine pancreas during experimental acute pancreatitis.
2002-06-15
Absence of endogenous interleukin-6 enhances the inflammatory response during acute pancreatitis induced by cerulein in mice.
2002-06-07
The influence of cholecystokinin on gastric myoelectrical activity in duodenal ulcer following Helicobacter pylori eradication--an electrogastrographic study.
2002-06
Pancreatic stellate cell activation and MMP production in experimental pancreatic fibrosis.
2002-05-15
The effects of prostaglandin E1 on the microperfusion of the pancreas during acute necrotizing pancreatitis in rats.
2002-05-09
[The role of thiol oxidants in inhibition of pancreatic exocrine secretory function and glutathione].
2002-05
Selective tachykinin NK3-receptor agonists stimulate in vitro exocrine pancreatic secretion in the guinea pig.
2002-05
Inducible nitric oxide synthase-deficient mice exhibit resistance to the acute pancreatitis induced by cerulein.
2002-05
Intracerebroventricular administration of bacterial lipopolysaccharide prevents the development of acute experimental pancreatitis in the rat.
2002-04
Neutrophils and NADPH oxidase mediate intrapancreatic trypsin activation in murine experimental acute pancreatitis.
2002-04
Early changes of the expression of cathepsin B mRNA during cerulein supramaximal stimulation.
2002-04
Penetration of meropenem and cefepim into pancreatic tissue during the course of experimental acute pancreatitis.
2002-04
Modulation of cholestasis-induced antinociception by CCK receptor agonists and antagonists.
2002-04
Amelioration of cerulein-induced acute pancreatitis by 2,2'-dipyridyl in rats.
2002-03
Sensory nerves in central and peripheral control of pancreatic integrity by leptin and melatonin.
2002-03
Human interleukin 10 gene therapy decreases the severity and mortality of lethal pancreatitis in rats.
2002-03
Alcohols enhance caerulein-induced zymogen activation in pancreatic acinar cells.
2002-03
Persantine improves acute pancreatitis in vitro.
2002-02-07
Lung changes and cytokine levels in a model of experimental acute pancreatitis.
2002-02
Acute pancreatitis decreases pancreas phospholipid levels and increases susceptibility to lipid peroxidation in rat pancreas.
2002-02
Therapy of microcirculatory disorders in severe acute pancreatitis: what mediators should we block?
2002-02
Trypsin activity is not involved in premature, intrapancreatic trypsinogen activation.
2002-02
A method using laser Doppler flowmetry to study intestinal and pancreatic perfusion during an acute intestinal ischaemic injury in rats with pancreatitis.
2002-01-24
The gut origin of bacterial pancreatic infection during acute experimental pancreatitis in rats.
2002
The time course of gap-junctional protein connexin 32 expression in the pancreas after the induction of acute pancreatitis by caerulein in rats.
2002
Leptin modulates the inflammatory response in acute pancreatitis.
2002
Leptin protects the pancreas from damage induced by caerulein overstimulation by modulating cytokine production.
2002
Negative ion electrospray mass spectra of caerulein peptides: an aid to structural determination.
2002
Effect of sensory nerves and CGRP on the development of caerulein-induced pancreatitis and pancreatic recovery.
2001-12
Does chronic ethanol administration have influence on pancreatic regeneration in the course of caerulein induced acute pancreatitis in rats.
2001-12
Stress kinase inhibition modulates acute experimental pancreatitis.
2001-04
Effects of mast-cell stabilization in cerulein-induced acute pancreatitis in rats.
2001
The influence of nifedipine (calcium channel blocker) and Bay-K-8644 (calcium channel agonist) on the development of experimental acute pancreatitis.
2001
6-Hydroxydopamine infusions into the structures of mesolimbic dopaminergic system alter the memory enhancing effect of CK-8US and caerulein in rats.
2001
[Defecation properties after coloanal reconstruction in the pig model].
2001
Patents

Patents

JP2002522463A
2
JPH01275533A
2
JPH0687887A
6
JPS5463072A
2
JPS55100348A
2
JPS57167922A
2
JPS58208257A
2
JPS5967254A
2
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:58:59 GMT 2025
Edited
by admin
on Mon Mar 31 17:58:59 GMT 2025
Record UNII
888Y08971B
Record Status FAILED
Record Version
  • Download
Name Type Language
5-OXO-L-PROLYL-L-GLUTAMINYL-L-A-ASPARTYL-O-SULFO-L-TYROSYL-L-THREONYLGLYCYL-L-TRYPTOPHYL-L-METHIONYL-L-.ALPHA.-ASPARTYL-L-PHENYLALANINAMIDE
Preferred Name English
CERULETIDE
INN   MART.   MI   USAN   WHO-DD  
USAN   INN  
Official Name English
CERULEIN
Common Name English
CERULETIDE [USAN]
Common Name English
Ceruletide [WHO-DD]
Common Name English
CERULETIDE [MART.]
Common Name English
CAERULEIN
Common Name English
PGLU-GLN-ASP-TYR(SO3H)-THR-GLY-TRP-MET-ASP-PHE-NH2
Common Name English
ceruletide [INN]
Common Name English
5-OXO-L-PROLYL-L-GLUTAMINYL-L-ASPARTYL-L-TYROSYL-L-THREONYLGLYCYL-L-TRYPTOPHYL-L-METHIONYL-L-ASPARTYLPHENYL-L-ALANINAMIDE 4-(HYDROGEN SULFATE) (ESTER)
Common Name English
CERULETIDE [MI]
Common Name English
Classification Tree Code System Code
WHO-VATC QV04CC04
Created by admin on Mon Mar 31 17:58:59 GMT 2025 , Edited by admin on Mon Mar 31 17:58:59 GMT 2025
WHO-ATC V04CC04
Created by admin on Mon Mar 31 17:58:59 GMT 2025 , Edited by admin on Mon Mar 31 17:58:59 GMT 2025
NCI_THESAURUS C1937
Created by admin on Mon Mar 31 17:58:59 GMT 2025 , Edited by admin on Mon Mar 31 17:58:59 GMT 2025
Code System Code Type Description
DRUG CENTRAL
579
Created by admin on Mon Mar 31 17:58:59 GMT 2025 , Edited by admin on Mon Mar 31 17:58:59 GMT 2025
PRIMARY
MESH
D002108
Created by admin on Mon Mar 31 17:58:59 GMT 2025 , Edited by admin on Mon Mar 31 17:58:59 GMT 2025
PRIMARY
SMS_ID
100000082047
Created by admin on Mon Mar 31 17:58:59 GMT 2025 , Edited by admin on Mon Mar 31 17:58:59 GMT 2025
PRIMARY
NCI_THESAURUS
C65309
Created by admin on Mon Mar 31 17:58:59 GMT 2025 , Edited by admin on Mon Mar 31 17:58:59 GMT 2025
PRIMARY
CHEBI
59219
Created by admin on Mon Mar 31 17:58:59 GMT 2025 , Edited by admin on Mon Mar 31 17:58:59 GMT 2025
PRIMARY
EPA CompTox
DTXSID8040434
Created by admin on Mon Mar 31 17:58:59 GMT 2025 , Edited by admin on Mon Mar 31 17:58:59 GMT 2025
PRIMARY
ChEMBL
CHEMBL1201355
Created by admin on Mon Mar 31 17:58:59 GMT 2025 , Edited by admin on Mon Mar 31 17:58:59 GMT 2025
PRIMARY
WIKIPEDIA
CERULETIDE
Created by admin on Mon Mar 31 17:58:59 GMT 2025 , Edited by admin on Mon Mar 31 17:58:59 GMT 2025
PRIMARY
MERCK INDEX
m3274
Created by admin on Mon Mar 31 17:58:59 GMT 2025 , Edited by admin on Mon Mar 31 17:58:59 GMT 2025
PRIMARY Merck Index
CAS
17650-98-5
Created by admin on Mon Mar 31 17:58:59 GMT 2025 , Edited by admin on Mon Mar 31 17:58:59 GMT 2025
PRIMARY
PUBCHEM
16129675
Created by admin on Mon Mar 31 17:58:59 GMT 2025 , Edited by admin on Mon Mar 31 17:58:59 GMT 2025
PRIMARY
IUPHAR
7589
Created by admin on Mon Mar 31 17:58:59 GMT 2025 , Edited by admin on Mon Mar 31 17:58:59 GMT 2025
PRIMARY
EVMPD
SUB07442MIG
Created by admin on Mon Mar 31 17:58:59 GMT 2025 , Edited by admin on Mon Mar 31 17:58:59 GMT 2025
PRIMARY
INN
3351
Created by admin on Mon Mar 31 17:58:59 GMT 2025 , Edited by admin on Mon Mar 31 17:58:59 GMT 2025
PRIMARY
FDA UNII
888Y08971B
Created by admin on Mon Mar 31 17:58:59 GMT 2025 , Edited by admin on Mon Mar 31 17:58:59 GMT 2025
PRIMARY
DRUG BANK
DB00403
Created by admin on Mon Mar 31 17:58:59 GMT 2025 , Edited by admin on Mon Mar 31 17:58:59 GMT 2025
PRIMARY
Related Record Type Details
Structure of CERULETIDE DIETHYLAMINE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of CERULETIDE
ACTIVE MOIETY
NIH
NCATS
PRIVACY NOTICE
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966