CERULETIDE DIETHYLAMINE

US Previously Marketed

First approved in 1981

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 Search

SMILES

CCNCC.CSCC[C@H](NC(=O)[C@H](CC1=CNC2=C1C=CC=C2)NC(=O)CNC(=O)[C@@H](NC(=O)[C@H](CC3=CC=C(OS(O)(=O)=O)C=C3)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H]4CCC(=O)N4)[C@@H](C)O)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	C4H11N
Molecular Weight	73.1368
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C58H73N13O21S2
Molecular Weight	1352.405
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	10 / 10
E/Z Centers	3
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/mesh/68002108 | http://www.hmdb.ca/metabolites/HMDB0014547

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

Conditions

Condition	Modality	Targets	Highest Phase	Product
Chronic fecal stasis 2 Sources: https://www.tabletwise.com/us/tymtran-injectable	Diagnostic		Approved 8583	TYMTRAN Approved Use Unknown

Doses

Dose	Population	Adverse 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

AE	Significance	Dose	Population
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

Vendor/Aggregator	ID	URL
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

Title	Date	PubMed
Selective inhibition of NF-kappaB attenuates the severity of cerulein-induced acute pancreatitis.	2002-10	12375755
Expression of the chemokines MCP-1/JE and cytokine-induced neutrophil chemoattractant in early acute pancreatitis.	2002-10	12370537
Cerulein-induced acute pancreatitis in the rat is significantly ameliorated by treatment with MEK1/2 inhibitors U0126 and PD98059.	2002-10	12370536
Primary sensory neurons: a common final pathway for inflammation in experimental pancreatitis in rats.	2002-10	12223354
Effect of nitric oxide on gallbladder motility in patients with acalculous biliary pain: a cholescintigraphic study.	2002-09	12353840
Cathepsin B inhibition prevents trypsinogen activation and reduces pancreatitis severity.	2002-09	12181196
In vivo evidence for the role of GM-CSF as a mediator in acute pancreatitis-associated lung injury.	2002-09	12169573
Glutathione depletion with L-buthionine-(S,R)-sulfoximine demonstrates deleterious effects in acute pancreatitis of the rat.	2002-08	12184532
Pancreatic capillary blood flow in an improved model of necrotizing pancreatitis in the rat.	2002-08	12175989
Endothelin A but not endothelin B receptor blockade reduces capillary permeability in severe experimental pancreatitis.	2002-08	12142750
Mechanisms of Chinese herb emodin and somatostatin analogs on pancreatic regeneration in acute pancreatitis in rats.	2002-08	12142738
Different modes of NF-kappaB/Rel activation in pancreatic lobules.	2002-08	12121873
Natural history of long-term lung injury in mouse experimental pancreatitis.	2002-07	12130976
The effects of somatostatin on the microperfusion of the pancreas during acute necrotizing pancreatitis in rats.	2002-06-18	12064001
Effect of intravenous infusion of amino acids on pancreatic secretion.	2002-06-18	12063999
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	12121700
Absence of endogenous interleukin-6 enhances the inflammatory response during acute pancreatitis induced by cerulein in mice.	2002-06-07	12161103
The influence of cholecystokinin on gastric myoelectrical activity in duodenal ulcer following Helicobacter pylori eradication--an electrogastrographic study.	2002-06	12120894
Pancreatic stellate cell activation and MMP production in experimental pancreatic fibrosis.	2002-05-15	12020128
The effects of prostaglandin E1 on the microperfusion of the pancreas during acute necrotizing pancreatitis in rats.	2002-05-09	11995492
[The role of thiol oxidants in inhibition of pancreatic exocrine secretory function and glutathione].	2002-05	12133422
Selective tachykinin NK3-receptor agonists stimulate in vitro exocrine pancreatic secretion in the guinea pig.	2002-05	12084527
Inducible nitric oxide synthase-deficient mice exhibit resistance to the acute pancreatitis induced by cerulein.	2002-05	12022764
Intracerebroventricular administration of bacterial lipopolysaccharide prevents the development of acute experimental pancreatitis in the rat.	2002-04	11951059
Neutrophils and NADPH oxidase mediate intrapancreatic trypsin activation in murine experimental acute pancreatitis.	2002-04	11910350
Early changes of the expression of cathepsin B mRNA during cerulein supramaximal stimulation.	2002-04	11893943
Penetration of meropenem and cefepim into pancreatic tissue during the course of experimental acute pancreatitis.	2002-04	11893934
Modulation of cholestasis-induced antinociception by CCK receptor agonists and antagonists.	2002-04	11872326
Amelioration of cerulein-induced acute pancreatitis by 2,2'-dipyridyl in rats.	2002-03	11968852
Sensory nerves in central and peripheral control of pancreatic integrity by leptin and melatonin.	2002-03	11939719
Human interleukin 10 gene therapy decreases the severity and mortality of lethal pancreatitis in rats.	2002-03	11855927
Alcohols enhance caerulein-induced zymogen activation in pancreatic acinar cells.	2002-03	11842000
Persantine improves acute pancreatitis in vitro.	2002-02-07	11828675
Lung changes and cytokine levels in a model of experimental acute pancreatitis.	2002-02	12185654
Acute pancreatitis decreases pancreas phospholipid levels and increases susceptibility to lipid peroxidation in rat pancreas.	2002-02	11908908
Therapy of microcirculatory disorders in severe acute pancreatitis: what mediators should we block?	2002-02	11907656
Trypsin activity is not involved in premature, intrapancreatic trypsinogen activation.	2002-02	11804859
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	11805397
The gut origin of bacterial pancreatic infection during acute experimental pancreatitis in rats.	2002	12378112
The time course of gap-junctional protein connexin 32 expression in the pancreas after the induction of acute pancreatitis by caerulein in rats.	2002	12203079
Leptin modulates the inflammatory response in acute pancreatitis.	2002	12138320
Leptin protects the pancreas from damage induced by caerulein overstimulation by modulating cytokine production.	2002	12123099
Negative ion electrospray mass spectra of caerulein peptides: an aid to structural determination.	2002	11816042
Effect of sensory nerves and CGRP on the development of caerulein-induced pancreatitis and pancreatic recovery.	2001-12	11787767
Does chronic ethanol administration have influence on pancreatic regeneration in the course of caerulein induced acute pancreatitis in rats.	2001-12	11785777
Stress kinase inhibition modulates acute experimental pancreatitis.	2001-04	11819771
Effects of mast-cell stabilization in cerulein-induced acute pancreatitis in rats.	2001	12067220
The influence of nifedipine (calcium channel blocker) and Bay-K-8644 (calcium channel agonist) on the development of experimental acute pancreatitis.	2001	11977328
6-Hydroxydopamine infusions into the structures of mesolimbic dopaminergic system alter the memory enhancing effect of CK-8US and caerulein in rats.	2001	11820580
[Defecation properties after coloanal reconstruction in the pig model].	2001	11819177

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:59:01 GMT 2025` Edited by `admin` on `Mon Mar 31 17:59:01 GMT 2025`
Record UNII	4E1MIA8QQL
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CERULETIDE DIETHYLAMINE

Official Name

English

CERULETIDE DIETHYLAMINE SALT

Preferred 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

Classification Tree Code System Code

NCI_THESAURUS

C1937