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
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
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.
Originator
Approval Year
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: 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%) Sources: Page: p.517Dizziness (grade 1, 12.5%) Headache (grade 1, 6.25%) Injection site pain (grade 1, 50%) |
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
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: 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
Title | Date | PubMed |
---|---|---|
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 |
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Cholecystokinin octapeptide induces both proliferation and apoptosis in the rat pancreas. | 2001 Apr 2 |
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Does chronic ethanol administration have influence on pancreatic regeneration in the course of caerulein induced acute pancreatitis in rats. | 2001 Dec |
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Pancreatitis-associated protein-I mRNA expression in mouse pancreas is upregulated by lipopolysaccharide independent of cerulein-pancreatitis. | 2001 Jan |
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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 |
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Susceptibility to cerulein-induced pancreatitis in inducible nitric oxide synthase-deficient mice. | 2001 Jul |
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Opsonin receptor expression on peritoneal exudative and circulatory neutrophils in murine acute pancreatitis. | 2001 Jul |
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Isolation, long-term culture, and characterization of rat pancreatic fibroblastoid/stellate cells. | 2001 Jul |
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Acute pancreatitis signals activation of apoptosis-associated and survival genes in mice. | 2001 Jul |
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Effects and mechanisms of somatostatin analogs on apoptosis of pancreatic acinar cells in acute pancreatitis in mice. | 2001 Jun |
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ONO-1714, a new inducible nitric oxide synthase inhibitor, attenuates diaphragmatic dysfunction associated with cerulein-induced pancreatitis in rats. | 2001 Jun |
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Localized pancreatic NF-kappaB activation and inflammatory response in taurocholate-induced pancreatitis. | 2001 Jun |
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Water immersion stress prevents caerulein-induced pancreatic acinar cell nf-kappa b activation by attenuating caerulein-induced intracellular Ca2+ changes. | 2001 Jun 1 |
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Involvement of cyclooxygenase-derived prostaglandin E2 and nitric oxide in the protection of rat pancreas afforded by low dose of lipopolysaccharide. | 2001 Mar |
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[The isolated perfused rat pancreas - an experimental model for investigation the early events in the pathogenesis of acute pancreatitis]. | 2001 Nov |
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Ethacrynic acid inhibits pancreatic exocrine secretion. | 2001 Nov |
|
Persantine improves acute pancreatitis in vitro. | 2001 Nov-Dec |
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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 |
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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 |
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Early changes of the expression of cathepsin B mRNA during cerulein supramaximal stimulation. | 2002 Apr |
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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 |
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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 |
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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 |
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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 |
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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 |
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:29:41 GMT 2023
by
admin
on
Fri Dec 15 15:29:41 GMT 2023
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Record UNII |
4E1MIA8QQL
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C1937
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Code System | Code | Type | Description | ||
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DTXSID001027524
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59223
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275-298-0
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C032637
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C65310
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100000076342
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20024
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71247-25-1
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4E1MIA8QQL
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m3274
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DBSALT001364
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57363-15-2
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CHEMBL1201355
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SUB13298MIG
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16158172
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62152-49-2
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ALTERNATIVE |
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PARENT -> SALT/SOLVATE | |||
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |