CERULETIDE DIETHYLAMINE

US Previously Marketed

First approved in 1981

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 Search

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

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 1 Sources: https://www.tabletwise.com/us/tymtran-injectable	Diagnostic		Approved 4033	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 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

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 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

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
Melatonin reduces lipid peroxidation and tissue edema in cerulein-induced acute pancreatitis in rats.	1999 Nov	10573371
[Defecation properties after coloanal reconstruction in the pig model].	2001	11819177
Early microcirculatory derangement in mild and severe pancreatitis models in mice.	2001	11495159
Cholecystokinin octapeptide induces both proliferation and apoptosis in the rat pancreas.	2001 Apr 2	11179777
Arginine induced acute pancreatitis alters the actin cytoskeleton and increases heat shock protein expression in rat pancreatic acinar cells.	2001 Aug	11454802
Effect of sensory nerves and CGRP on the development of caerulein-induced pancreatitis and pancreatic recovery.	2001 Dec	11787767
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	11145574
Altered cytokine response in rat acute pancreatitis complicated with endotoxemia.	2001 Jan	11138968
Relationship between NF-kappaB and trypsinogen activation in rat pancreas after supramaximal caerulein stimulation.	2001 Jan 12	11162528
A novel screening for inhibitors of a pleiotropic drug resistant pump, Pdr5, in Saccharomyces cerevisiae.	2001 Jul	11515543
Cholecystokinin activation of 70-kDa S6 kinase in exocrine pancreas.	2001 Jul	11478495
Isolation, long-term culture, and characterization of rat pancreatic fibroblastoid/stellate cells.	2001 Jul	11451147
Acute pancreatitis signals activation of apoptosis-associated and survival genes in mice.	2001 Jul	11444106
ONO-1714, a new inducible nitric oxide synthase inhibitor, attenuates diaphragmatic dysfunction associated with cerulein-induced pancreatitis in rats.	2001 Jun	11395607
Cadmium inhibits stimulated amylase secretion from isolated pancreatic lobules of the guinea-pig.	2001 Mar	11401412
Functional expression of cholecystokinin-A receptor on ventromedial hypothalamic neurons in the immature rat brain.	2001 Mar 9	11207382
Sludge and stone formation in the gallbladder in bedridden elderly patients with cerebrovascular disease: influence of feeding method.	2001 May	11388396
Biliary lipid composition in cholesterol microlithiasis.	2001 May	11302972
Capsaicin vanilloid receptor-1 mediates substance P release in experimental pancreatitis.	2001 Nov	11668042
Persantine improves acute pancreatitis in vitro.	2001 Nov-Dec	11828675
Effects of dopexamine on acute necrotising pancreatitis in rats.	2001 Oct	11775728
Fecal elastase-1 determination: 'gold standard' of indirect pancreatic function tests?	2001 Oct	11589385
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	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
Neutrophils and NADPH oxidase mediate intrapancreatic trypsin activation in murine experimental acute pancreatitis.	2002 Apr	11910350
Glutathione depletion with L-buthionine-(S,R)-sulfoximine demonstrates deleterious effects in acute pancreatitis of the rat.	2002 Aug	12184532
Mechanisms of Chinese herb emodin and somatostatin analogs on pancreatic regeneration in acute pancreatitis in rats.	2002 Aug	12142738
Different modes of NF-kappaB/Rel activation in pancreatic lobules.	2002 Aug	12121873
Lung changes and cytokine levels in a model of experimental acute pancreatitis.	2002 Feb	12185654
Thermal stress-induced HSP70 mediates protection against intrapancreatic trypsinogen activation and acute pancreatitis in rats.	2002 Jan	11781290
Both thermal and non-thermal stress protect against caerulein induced pancreatitis and prevent trypsinogen activation in the pancreas.	2002 Jan	11772971
Glutathione might exert an important function in caerulein-stimulated amylase release in isolated rat pancreatic acini.	2002 Jan	11741183
Natural history of long-term lung injury in mouse experimental pancreatitis.	2002 Jul	12130976
Amelioration of cerulein-induced acute pancreatitis by 2,2'-dipyridyl in rats.	2002 Mar	11968852
[The role of thiol oxidants in inhibition of pancreatic exocrine secretory function and glutathione].	2002 May	12133422
Inducible nitric oxide synthase-deficient mice exhibit resistance to the acute pancreatitis induced by cerulein.	2002 May	12022764
The effects of somatostatin on the microperfusion of the pancreas during acute necrotizing pancreatitis in rats.	2002 May-Jun	12064001
Selective inhibition of NF-kappaB attenuates the severity of cerulein-induced acute pancreatitis.	2002 Oct	12375755
Expression of the chemokines MCP-1/JE and cytokine-induced neutrophil chemoattractant in early acute pancreatitis.	2002 Oct	12370537
Cerulein-induced acute pancreatitis in the rat is significantly ameliorated by treatment with MEK1/2 inhibitors U0126 and PD98059.	2002 Oct	12370536
Primary sensory neurons: a common final pathway for inflammation in experimental pancreatitis in rats.	2002 Oct	12223354
Effect of nitric oxide on gallbladder motility in patients with acalculous biliary pain: a cholescintigraphic study.	2002 Sep	12353840
Cathepsin B inhibition prevents trypsinogen activation and reduces pancreatitis severity.	2002 Sep	12181196

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

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Name

Type

Language

CERULETIDE DIETHYLAMINE

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

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1937