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

Details

Stereochemistry ABSOLUTE
Molecular Formula C58H73N13O21S2.C4H11N
Molecular Weight 1425.5462
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CERULETIDE DIETHYLAMINE

SMILES

C[C@]([H])([C@@]([H])(C(=NCC(=N[C@@]([H])(Cc1c[nH]c2ccccc12)C(=N[C@@]([H])(CCSC)C(=N[C@@]([H])(CC(=O)O)C(=N[C@@]([H])(Cc3ccccc3)C(=N)O)O)O)O)O)O)N=C([C@]([H])(Cc4ccc(cc4)OS(=O)(=O)O)N=C([C@]([H])(CC(=O)O)N=C([C@]([H])(CCC(=N)O)N=C([C@]5([H])CCC(=N5)O)O)O)O)O)O.CCNCC

InChI

InChIKey=FHDKSYKZXIFRKJ-CBCFNHQSSA-N
InChI=1S/C58H73N13O21S2.C4H11N/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;1-3-5-4-2/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);5H,3-4H2,1-2H3/t29-,36+,37+,38+,39+,40+,41+,42+,43+,49+;/m1./s1

HIDE SMILES / InChI

Molecular Formula C4H11N
Molecular Weight 73.137
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

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.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
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: Page: p.1483
unhealthy, 16
n = 16
Health Status: unhealthy
Condition: Schizophrenia
Age Group: 16
Population Size: 16
Sources: Page: p.1483
Disc. AE: Abdominal cramps...
AEs leading to
discontinuation/dose reduction:
Abdominal cramps (grade 1-2, 31.2%)
Sources: Page: p.1483
20 ug single, intramuscular
Highest studied dose
Dose: 20 ug
Route: intramuscular
Route: single
Dose: 20 ug
Sources: Page: p.517
healthy, 20-32
n = 16
Health Status: healthy
Condition: Pain
Age Group: 20-32
Sex: M
Population Size: 16
Sources: 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: 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: Page: p.226
unhealthy, 24-55
n = 6
Health Status: unhealthy
Condition: Chronic pancreatitis
Age Group: 24-55
Population Size: 6
Sources: 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: Page: p.1483
unhealthy
n = 16
Health Status: unhealthy
Condition: Schizophrenia
Population Size: 16
Sources: Page: p.1483
Disc. AE: Vomiting...
AEs leading to
discontinuation/dose reduction:
Vomiting (grade 1-2, 31.2%)
Sources: 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: Page: p.1483
unhealthy, 16
n = 16
Health Status: unhealthy
Condition: Schizophrenia
Age Group: 16
Population Size: 16
Sources: 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: Page: p.517
healthy, 20-32
n = 16
Health Status: healthy
Condition: Pain
Age Group: 20-32
Sex: M
Population Size: 16
Sources: 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: Page: p.517
healthy, 20-32
n = 16
Health Status: healthy
Condition: Pain
Age Group: 20-32
Sex: M
Population Size: 16
Sources: 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: Page: p.517
healthy, 20-32
n = 16
Health Status: healthy
Condition: Pain
Age Group: 20-32
Sex: M
Population Size: 16
Sources: 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: Page: p.517
healthy, 20-32
n = 16
Health Status: healthy
Condition: Pain
Age Group: 20-32
Sex: M
Population Size: 16
Sources: 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: Page: p.1483
unhealthy
n = 16
Health Status: unhealthy
Condition: Schizophrenia
Population Size: 16
Sources: Page: p.1483
PubMed

PubMed

TitleDatePubMed
Melatonin reduces lipid peroxidation and tissue edema in cerulein-induced acute pancreatitis in rats.
1999 Nov
[Defecation properties after coloanal reconstruction in the pig model].
2001
Early microcirculatory derangement in mild and severe pancreatitis models in mice.
2001
Cholecystokinin octapeptide induces both proliferation and apoptosis in the rat pancreas.
2001 Apr 2
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
Somatostatin inhibits Akt phosphorylation and cell cycle entry, but not p42/p44 mitogen-activated protein (MAP) kinase activation in normal and tumoral pancreatic acinar cells.
2001 Jan
Altered cytokine response in rat acute pancreatitis complicated with endotoxemia.
2001 Jan
Relationship between NF-kappaB and trypsinogen activation in rat pancreas after supramaximal caerulein stimulation.
2001 Jan 12
A novel screening for inhibitors of a pleiotropic drug resistant pump, Pdr5, in Saccharomyces cerevisiae.
2001 Jul
Cholecystokinin activation of 70-kDa S6 kinase in exocrine pancreas.
2001 Jul
Isolation, long-term culture, and characterization of rat pancreatic fibroblastoid/stellate cells.
2001 Jul
Acute pancreatitis signals activation of apoptosis-associated and survival genes in mice.
2001 Jul
ONO-1714, a new inducible nitric oxide synthase inhibitor, attenuates diaphragmatic dysfunction associated with cerulein-induced pancreatitis in rats.
2001 Jun
Cadmium inhibits stimulated amylase secretion from isolated pancreatic lobules of the guinea-pig.
2001 Mar
Functional expression of cholecystokinin-A receptor on ventromedial hypothalamic neurons in the immature rat brain.
2001 Mar 9
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
Capsaicin vanilloid receptor-1 mediates substance P release in experimental pancreatitis.
2001 Nov
Persantine improves acute pancreatitis in vitro.
2001 Nov-Dec
Effects of dopexamine on acute necrotising pancreatitis in rats.
2001 Oct
Fecal elastase-1 determination: 'gold standard' of indirect pancreatic function tests?
2001 Oct
A method using laser Doppler flowmetry to study intestinal and pancreatic perfusion during an acute intestinal ischaemic injury in rats with pancreatitis.
2001 Sep-Dec
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
Neutrophils and NADPH oxidase mediate intrapancreatic trypsin activation in murine experimental acute pancreatitis.
2002 Apr
Glutathione depletion with L-buthionine-(S,R)-sulfoximine demonstrates deleterious effects in acute pancreatitis of the rat.
2002 Aug
Mechanisms of Chinese herb emodin and somatostatin analogs on pancreatic regeneration in acute pancreatitis in rats.
2002 Aug
Different modes of NF-kappaB/Rel activation in pancreatic lobules.
2002 Aug
Lung changes and cytokine levels in a model of experimental acute pancreatitis.
2002 Feb
Thermal stress-induced HSP70 mediates protection against intrapancreatic trypsinogen activation and acute pancreatitis in rats.
2002 Jan
Both thermal and non-thermal stress protect against caerulein induced pancreatitis and prevent trypsinogen activation in the pancreas.
2002 Jan
Glutathione might exert an important function in caerulein-stimulated amylase release in isolated rat pancreatic acini.
2002 Jan
Natural history of long-term lung injury in mouse experimental pancreatitis.
2002 Jul
Amelioration of cerulein-induced acute pancreatitis by 2,2'-dipyridyl in rats.
2002 Mar
[The role of thiol oxidants in inhibition of pancreatic exocrine secretory function and glutathione].
2002 May
Inducible nitric oxide synthase-deficient mice exhibit resistance to the acute pancreatitis induced by cerulein.
2002 May
The effects of somatostatin on the microperfusion of the pancreas during acute necrotizing pancreatitis in rats.
2002 May-Jun
Selective inhibition of NF-kappaB attenuates the severity of cerulein-induced acute pancreatitis.
2002 Oct
Expression of the chemokines MCP-1/JE and cytokine-induced neutrophil chemoattractant in early acute pancreatitis.
2002 Oct
Cerulein-induced acute pancreatitis in the rat is significantly ameliorated by treatment with MEK1/2 inhibitors U0126 and PD98059.
2002 Oct
Primary sensory neurons: a common final pathway for inflammation in experimental pancreatitis in rats.
2002 Oct
Effect of nitric oxide on gallbladder motility in patients with acalculous biliary pain: a cholescintigraphic study.
2002 Sep
Cathepsin B inhibition prevents trypsinogen activation and reduces pancreatitis severity.
2002 Sep
Patents
Substance Class Chemical
Created
by admin
on Sat Jun 26 13:35:12 UTC 2021
Edited
by admin
on Sat Jun 26 13:35:12 UTC 2021
Record UNII
4E1MIA8QQL
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CERULETIDE DIETHYLAMINE
ORANGE BOOK   USAN   WHO-DD  
USAN  
Official Name English
TAKUS
Brand Name English
CAERULEIN COMPOUND WITH N-ETHYLETHANAMINE
Common Name English
CEOSUNIN
Brand Name English
CERULETIDE DIETHYLAMINE [USAN]
Common Name English
CERULETIDE DIETHYLAMINE SALT [MI]
Common Name English
5-OXO-L-PROLYL-L-GLUTAMINYL-L-ASPARTYL-L-TYROSYL-L-THREONYLGLYCYL-L-TRYPTOPHYL-L-METHIONYL-L-ASPARTYL-PHENYL-L-ALANINAMIDE 4-(HYDROGEN SULFATE) (ESTER) COMPOUND WITH DIETHYLAMINE
Common Name English
TYMTRAN
Brand Name English
CERULETIDE DIETHYLAMINE [WHO-DD]
Common Name English
5-OXO-L-PROLYL-L-GLUTAMINYL-L-ASPARTYL-L-TYROSYL-L-THREONYLGLYCYL-L-TRYPTOPHYL-L-METHIONYL-L-ASPARTYL-PHENYL-L-ALANINAMIDE 4-(HYDROGEN SULPHATE) (ESTER) COMPOUND WITH DIETHYLAMINE
Common Name English
CAERULEIN DIETHYLAMINE
Common Name English
5-OXO-L-PROLYL-L-GLUTAMINYL-L-.ALPHA.-ASPARTYL-O-SULFO-L-TYROSYL-L-THREONYLGLYCYL-L-TRYPTOPHYL-L-METHIONYL-L-.ALPHA.-ASPARTYL-L-PHENYLALANINAMIDE COMPOUND WITH N-ETHYLETHANAMINE
Common Name English
CAERULEIN COMPOUND WITH DIETHYLAMINE
Common Name English
CERULETIDE DIETHYLAMINE [ORANGE BOOK]
Common Name English
CERULETIDE DIETHYLAMINE [JAN]
Common Name English
CERULETIDE DIETHYLAMINE SALT
MI  
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1937
Created by admin on Sat Jun 26 13:35:12 UTC 2021 , Edited by admin on Sat Jun 26 13:35:12 UTC 2021
Code System Code Type Description
ECHA (EC/EINECS)
275-298-0
Created by admin on Sat Jun 26 13:35:12 UTC 2021 , Edited by admin on Sat Jun 26 13:35:12 UTC 2021
PRIMARY
MESH
C032637
Created by admin on Sat Jun 26 13:35:12 UTC 2021 , Edited by admin on Sat Jun 26 13:35:12 UTC 2021
PRIMARY
NCI_THESAURUS
C65310
Created by admin on Sat Jun 26 13:35:12 UTC 2021 , Edited by admin on Sat Jun 26 13:35:12 UTC 2021
PRIMARY
RXCUI
20024
Created by admin on Sat Jun 26 13:35:12 UTC 2021 , Edited by admin on Sat Jun 26 13:35:12 UTC 2021
PRIMARY RxNorm
CAS
71247-25-1
Created by admin on Sat Jun 26 13:35:12 UTC 2021 , Edited by admin on Sat Jun 26 13:35:12 UTC 2021
PRIMARY
FDA UNII
4E1MIA8QQL
Created by admin on Sat Jun 26 13:35:12 UTC 2021 , Edited by admin on Sat Jun 26 13:35:12 UTC 2021
PRIMARY
MERCK INDEX
M3274
Created by admin on Sat Jun 26 13:35:12 UTC 2021 , Edited by admin on Sat Jun 26 13:35:12 UTC 2021
PRIMARY Merck Index
DRUG BANK
DBSALT001364
Created by admin on Sat Jun 26 13:35:12 UTC 2021 , Edited by admin on Sat Jun 26 13:35:12 UTC 2021
PRIMARY
CAS
57363-15-2
Created by admin on Sat Jun 26 13:35:12 UTC 2021 , Edited by admin on Sat Jun 26 13:35:12 UTC 2021
ALTERNATIVE
ChEMBL
CHEMBL1201355
Created by admin on Sat Jun 26 13:35:12 UTC 2021 , Edited by admin on Sat Jun 26 13:35:12 UTC 2021
PRIMARY
EVMPD
SUB13298MIG
Created by admin on Sat Jun 26 13:35:12 UTC 2021 , Edited by admin on Sat Jun 26 13:35:12 UTC 2021
PRIMARY
PUBCHEM
16158172
Created by admin on Sat Jun 26 13:35:12 UTC 2021 , Edited by admin on Sat Jun 26 13:35:12 UTC 2021
PRIMARY
CAS
62152-49-2
Created by admin on Sat Jun 26 13:35:12 UTC 2021 , Edited by admin on Sat Jun 26 13:35:12 UTC 2021
ALTERNATIVE
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY