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 1425.542
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CERULETIDE DIETHYLAMINE

SMILES

CCNCC.[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=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 C58H73N13O21S2
Molecular Weight 1352.405
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 10 / 10
E/Z Centers 3
Optical Activity UNSPECIFIED

Molecular Formula C4H11N
Molecular Weight 73.1368
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
The influence of nifedipine (calcium channel blocker) and Bay-K-8644 (calcium channel agonist) on the development of experimental acute pancreatitis.
2001
[Defecation properties after coloanal reconstruction in the pig model].
2001
Cholecystokinin octapeptide induces both proliferation and apoptosis in the rat pancreas.
2001 Apr 2
Does chronic ethanol administration have influence on pancreatic regeneration in the course of caerulein induced acute pancreatitis in rats.
2001 Dec
Pancreatitis-associated protein-I mRNA expression in mouse pancreas is upregulated by lipopolysaccharide independent of cerulein-pancreatitis.
2001 Jan
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
Susceptibility to cerulein-induced pancreatitis in inducible nitric oxide synthase-deficient mice.
2001 Jul
Opsonin receptor expression on peritoneal exudative and circulatory neutrophils in murine acute pancreatitis.
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
Effects and mechanisms of somatostatin analogs on apoptosis of pancreatic acinar cells in acute pancreatitis in mice.
2001 Jun
ONO-1714, a new inducible nitric oxide synthase inhibitor, attenuates diaphragmatic dysfunction associated with cerulein-induced pancreatitis in rats.
2001 Jun
Localized pancreatic NF-kappaB activation and inflammatory response in taurocholate-induced pancreatitis.
2001 Jun
Water immersion stress prevents caerulein-induced pancreatic acinar cell nf-kappa b activation by attenuating caerulein-induced intracellular Ca2+ changes.
2001 Jun 1
Involvement of cyclooxygenase-derived prostaglandin E2 and nitric oxide in the protection of rat pancreas afforded by low dose of lipopolysaccharide.
2001 Mar
[The isolated perfused rat pancreas - an experimental model for investigation the early events in the pathogenesis of acute pancreatitis].
2001 Nov
Ethacrynic acid inhibits pancreatic exocrine secretion.
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 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
Intracerebroventricular administration of bacterial lipopolysaccharide prevents the development of acute experimental pancreatitis in the rat.
2002 Apr
Neutrophils and NADPH oxidase mediate intrapancreatic trypsin activation in murine experimental acute pancreatitis.
2002 Apr
Early changes of the expression of cathepsin B mRNA during cerulein supramaximal stimulation.
2002 Apr
Penetration of meropenem and cefepim into pancreatic tissue during the course of experimental acute pancreatitis.
2002 Apr
Endothelin A but not endothelin B receptor blockade reduces capillary permeability in severe experimental pancreatitis.
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
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
Natural history of long-term lung injury in mouse experimental pancreatitis.
2002 Jul
The influence of cholecystokinin on gastric myoelectrical activity in duodenal ulcer following Helicobacter pylori eradication--an electrogastrographic study.
2002 Jun
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 Jun 15
Amelioration of cerulein-induced acute pancreatitis by 2,2'-dipyridyl in rats.
2002 Mar
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
Alcohols enhance caerulein-induced zymogen activation in pancreatic acinar cells.
2002 Mar
[The role of thiol oxidants in inhibition of pancreatic exocrine secretory function and glutathione].
2002 May
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
Effect of nitric oxide on gallbladder motility in patients with acalculous biliary pain: a cholescintigraphic study.
2002 Sep
In vivo evidence for the role of GM-CSF as a mediator in acute pancreatitis-associated lung injury.
2002 Sep
Patents
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:29:41 GMT 2023
Edited
by admin
on Fri Dec 15 15:29:41 GMT 2023
Record UNII
4E1MIA8QQL
Record Status Validated (UNII)
Record Version
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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
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
Ceruletide diethylamine [WHO-DD]
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 Fri Dec 15 15:29:41 GMT 2023 , Edited by admin on Fri Dec 15 15:29:41 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID001027524
Created by admin on Fri Dec 15 15:29:41 GMT 2023 , Edited by admin on Fri Dec 15 15:29:41 GMT 2023
PRIMARY
CHEBI
59223
Created by admin on Fri Dec 15 15:29:41 GMT 2023 , Edited by admin on Fri Dec 15 15:29:41 GMT 2023
PRIMARY
ECHA (EC/EINECS)
275-298-0
Created by admin on Fri Dec 15 15:29:41 GMT 2023 , Edited by admin on Fri Dec 15 15:29:41 GMT 2023
PRIMARY
MESH
C032637
Created by admin on Fri Dec 15 15:29:41 GMT 2023 , Edited by admin on Fri Dec 15 15:29:41 GMT 2023
PRIMARY
NCI_THESAURUS
C65310
Created by admin on Fri Dec 15 15:29:41 GMT 2023 , Edited by admin on Fri Dec 15 15:29:41 GMT 2023
PRIMARY
SMS_ID
100000076342
Created by admin on Fri Dec 15 15:29:41 GMT 2023 , Edited by admin on Fri Dec 15 15:29:41 GMT 2023
PRIMARY
RXCUI
20024
Created by admin on Fri Dec 15 15:29:41 GMT 2023 , Edited by admin on Fri Dec 15 15:29:41 GMT 2023
PRIMARY RxNorm
CAS
71247-25-1
Created by admin on Fri Dec 15 15:29:41 GMT 2023 , Edited by admin on Fri Dec 15 15:29:41 GMT 2023
PRIMARY
FDA UNII
4E1MIA8QQL
Created by admin on Fri Dec 15 15:29:41 GMT 2023 , Edited by admin on Fri Dec 15 15:29:41 GMT 2023
PRIMARY
MERCK INDEX
m3274
Created by admin on Fri Dec 15 15:29:41 GMT 2023 , Edited by admin on Fri Dec 15 15:29:41 GMT 2023
PRIMARY Merck Index
DRUG BANK
DBSALT001364
Created by admin on Fri Dec 15 15:29:41 GMT 2023 , Edited by admin on Fri Dec 15 15:29:41 GMT 2023
PRIMARY
CAS
57363-15-2
Created by admin on Fri Dec 15 15:29:41 GMT 2023 , Edited by admin on Fri Dec 15 15:29:41 GMT 2023
ALTERNATIVE
ChEMBL
CHEMBL1201355
Created by admin on Fri Dec 15 15:29:41 GMT 2023 , Edited by admin on Fri Dec 15 15:29:41 GMT 2023
PRIMARY
EVMPD
SUB13298MIG
Created by admin on Fri Dec 15 15:29:41 GMT 2023 , Edited by admin on Fri Dec 15 15:29:41 GMT 2023
PRIMARY
PUBCHEM
16158172
Created by admin on Fri Dec 15 15:29:41 GMT 2023 , Edited by admin on Fri Dec 15 15:29:41 GMT 2023
PRIMARY
CAS
62152-49-2
Created by admin on Fri Dec 15 15:29:41 GMT 2023 , Edited by admin on Fri Dec 15 15:29:41 GMT 2023
ALTERNATIVE
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY