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Details

Stereochemistry ABSOLUTE
Molecular Formula C58H73N13O21S2
Molecular Weight 1352.405
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 1352.405
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 10 / 10
E/Z Centers 3
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
138
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Approved
8429
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
Page: p.1483
unhealthy, 16
n = 16
Health Status: unhealthy
Condition: Schizophrenia
Age Group: 16
Population Size: 16
Sources:
https://pubmed.ncbi.nlm.nih.gov/3907376
Page: p.1483
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
Page: p.1483
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
Page: p.517
healthy, 20-32
n = 16
Health Status: healthy
Condition: Pain
Age Group: 20-32
Sex: M
Population Size: 16
Sources:
https://pubmed.ncbi.nlm.nih.gov/6714795
Page: p.517
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
Page: p.517
100 ng/kg/h single, intravenous
Studied dose
Dose: 100 ng/kg/h
Route: intravenous
Route: single
Dose: 100 ng/kg/h
Co-administed with::
secretin iv(1 CU/kg/h)
Sources:
https://pubmed.ncbi.nlm.nih.gov/3065099
Page: p.226
unhealthy, 24-55
n = 6
Health Status: unhealthy
Condition: Chronic pancreatitis
Age Group: 24-55
Population Size: 6
Sources:
https://pubmed.ncbi.nlm.nih.gov/3065099
Page: p.226
Sources:
https://pubmed.ncbi.nlm.nih.gov/3065099
Page: p.226
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
Page: p.1483
unhealthy
n = 16
Health Status: unhealthy
Condition: Schizophrenia
Population Size: 16
Sources:
https://pubmed.ncbi.nlm.nih.gov/3907376
Page: p.1483
Disc. AE: Vomiting...
AEs leading to
discontinuation/dose reduction:
Vomiting (grade 1-2, 31.2%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/3907376
Page: p.1483
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
Page: p.1483
unhealthy, 16
n = 16
Health Status: unhealthy
Condition: Schizophrenia
Age Group: 16
Population Size: 16
Sources:
https://pubmed.ncbi.nlm.nih.gov/3907376
Page: p.1483
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
Page: p.517
healthy, 20-32
n = 16
Health Status: healthy
Condition: Pain
Age Group: 20-32
Sex: M
Population Size: 16
Sources:
https://pubmed.ncbi.nlm.nih.gov/6714795
Page: p.517
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
Page: p.517
healthy, 20-32
n = 16
Health Status: healthy
Condition: Pain
Age Group: 20-32
Sex: M
Population Size: 16
Sources:
https://pubmed.ncbi.nlm.nih.gov/6714795
Page: p.517
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
Page: p.517
healthy, 20-32
n = 16
Health Status: healthy
Condition: Pain
Age Group: 20-32
Sex: M
Population Size: 16
Sources:
https://pubmed.ncbi.nlm.nih.gov/6714795
Page: p.517
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
Page: p.517
healthy, 20-32
n = 16
Health Status: healthy
Condition: Pain
Age Group: 20-32
Sex: M
Population Size: 16
Sources:
https://pubmed.ncbi.nlm.nih.gov/6714795
Page: p.517
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
Page: p.1483
unhealthy
n = 16
Health Status: unhealthy
Condition: Schizophrenia
Population Size: 16
Sources:
https://pubmed.ncbi.nlm.nih.gov/3907376
Page: p.1483
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
Early microcirculatory derangement in mild and severe pancreatitis models in mice.
2001
Arginine induced acute pancreatitis alters the actin cytoskeleton and increases heat shock protein expression in rat pancreatic acinar cells.
2001 Aug
Effect of sensory nerves and CGRP on the development of caerulein-induced pancreatitis and pancreatic recovery.
2001 Dec
Pancreatitis-associated protein-I mRNA expression in mouse pancreas is upregulated by lipopolysaccharide independent of cerulein-pancreatitis.
2001 Jan
Cholecystokinin activation of 70-kDa S6 kinase in exocrine pancreas.
2001 Jul
Linkage of oxidative and nonoxidative ethanol metabolism in the pancreas and toxicity of nonoxidative ethanol metabolites for pancreatic acinar cells.
2001 Jun
Serine protease inhibitor causes F-actin redistribution and inhibition of calcium-mediated secretion in pancreatic acini.
2001 Jun
Sludge and stone formation in the gallbladder in bedridden elderly patients with cerebrovascular disease: influence of feeding method.
2001 May
Biliary lipid composition in cholesterol microlithiasis.
2001 May
[The isolated perfused rat pancreas - an experimental model for investigation the early events in the pathogenesis of acute pancreatitis].
2001 Nov
Persantine improves acute pancreatitis in vitro.
2001 Nov-Dec
Hepatocyte growth factor attenuates pancreatic damage in caerulein-induced pancreatitis in rats.
2001 Oct 26
The gut origin of bacterial pancreatic infection during acute experimental pancreatitis in rats.
2002
Early changes of the expression of cathepsin B mRNA during cerulein supramaximal stimulation.
2002 Apr
Endothelin A but not endothelin B receptor blockade reduces capillary permeability in severe experimental pancreatitis.
2002 Aug
Therapy of microcirculatory disorders in severe acute pancreatitis: what mediators should we block?
2002 Feb
Activation of adenosine A2a receptor pathway reduces leukocyte infiltration but enhances edema formation in rat caerulein pancreatitis.
2002 Jan
Glutathione might exert an important function in caerulein-stimulated amylase release in isolated rat pancreatic acini.
2002 Jan
Sensory nerves in central and peripheral control of pancreatic integrity by leptin and melatonin.
2002 Mar
Human interleukin 10 gene therapy decreases the severity and mortality of lethal pancreatitis in rats.
2002 Mar
Inducible nitric oxide synthase-deficient mice exhibit resistance to the acute pancreatitis induced by cerulein.
2002 May
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 Fri Dec 15 15:29:40 GMT 2023
Edited
by admin
on Fri Dec 15 15:29:40 GMT 2023
Record UNII
888Y08971B
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CERULETIDE
INN   MART.   MI   USAN   WHO-DD  
USAN   INN  
Official Name English
CERULEIN
Common Name English
CERULETIDE [USAN]
Common Name English
5-OXO-L-PROLYL-L-GLUTAMINYL-L-A-ASPARTYL-O-SULFO-L-TYROSYL-L-THREONYLGLYCYL-L-TRYPTOPHYL-L-METHIONYL-L-.ALPHA.-ASPARTYL-L-PHENYLALANINAMIDE
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 Fri Dec 15 15:29:40 GMT 2023 , Edited by admin on Fri Dec 15 15:29:40 GMT 2023
WHO-ATC V04CC04
Created by admin on Fri Dec 15 15:29:40 GMT 2023 , Edited by admin on Fri Dec 15 15:29:40 GMT 2023
NCI_THESAURUS C1937
Created by admin on Fri Dec 15 15:29:40 GMT 2023 , Edited by admin on Fri Dec 15 15:29:40 GMT 2023
Code System Code Type Description
DRUG CENTRAL
579
Created by admin on Fri Dec 15 15:29:40 GMT 2023 , Edited by admin on Fri Dec 15 15:29:40 GMT 2023
PRIMARY
MESH
D002108
Created by admin on Fri Dec 15 15:29:40 GMT 2023 , Edited by admin on Fri Dec 15 15:29:40 GMT 2023
PRIMARY
SMS_ID
100000082047
Created by admin on Fri Dec 15 15:29:40 GMT 2023 , Edited by admin on Fri Dec 15 15:29:40 GMT 2023
PRIMARY
NCI_THESAURUS
C65309
Created by admin on Fri Dec 15 15:29:40 GMT 2023 , Edited by admin on Fri Dec 15 15:29:40 GMT 2023
PRIMARY
CHEBI
59219
Created by admin on Fri Dec 15 15:29:40 GMT 2023 , Edited by admin on Fri Dec 15 15:29:40 GMT 2023
PRIMARY
EPA CompTox
DTXSID8040434
Created by admin on Fri Dec 15 15:29:40 GMT 2023 , Edited by admin on Fri Dec 15 15:29:40 GMT 2023
PRIMARY
ChEMBL
CHEMBL1201355
Created by admin on Fri Dec 15 15:29:40 GMT 2023 , Edited by admin on Fri Dec 15 15:29:40 GMT 2023
PRIMARY
WIKIPEDIA
CERULETIDE
Created by admin on Fri Dec 15 15:29:40 GMT 2023 , Edited by admin on Fri Dec 15 15:29:40 GMT 2023
PRIMARY
MERCK INDEX
m3274
Created by admin on Fri Dec 15 15:29:40 GMT 2023 , Edited by admin on Fri Dec 15 15:29:40 GMT 2023
PRIMARY Merck Index
CAS
17650-98-5
Created by admin on Fri Dec 15 15:29:40 GMT 2023 , Edited by admin on Fri Dec 15 15:29:40 GMT 2023
PRIMARY
PUBCHEM
16129675
Created by admin on Fri Dec 15 15:29:40 GMT 2023 , Edited by admin on Fri Dec 15 15:29:40 GMT 2023
PRIMARY
IUPHAR
7589
Created by admin on Fri Dec 15 15:29:40 GMT 2023 , Edited by admin on Fri Dec 15 15:29:40 GMT 2023
PRIMARY
EVMPD
SUB07442MIG
Created by admin on Fri Dec 15 15:29:40 GMT 2023 , Edited by admin on Fri Dec 15 15:29:40 GMT 2023
PRIMARY
INN
3351
Created by admin on Fri Dec 15 15:29:40 GMT 2023 , Edited by admin on Fri Dec 15 15:29:40 GMT 2023
PRIMARY
FDA UNII
888Y08971B
Created by admin on Fri Dec 15 15:29:40 GMT 2023 , Edited by admin on Fri Dec 15 15:29:40 GMT 2023
PRIMARY
DRUG BANK
DB00403
Created by admin on Fri Dec 15 15:29:40 GMT 2023 , Edited by admin on Fri Dec 15 15:29:40 GMT 2023
PRIMARY
Related Record Type Details
Structure of CERULETIDE DIETHYLAMINE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of CERULETIDE
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