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Ceruletide

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Chemical compound
Pharmaceutical compound
Ceruletide
Clinical data
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
  • (3S)-3-{[(1S)-1-carbamoyl-2-phenylethyl]carbamoyl}-3-[(2S)-2-[(2S)-2-{2-[(3R)-2-[(2S)-2-[(2S)-2-[(2S)-4-carbamoyl-2-{[(2S)-5-oxopyrrolidin-2-yl]formamido}butanamido]-3-carboxypropanamido]-3-[4-(sulfooxy)phenyl]propanamido]-3-hydroxybutanamido]acetamido}-3-(1H-indol-3-yl)propanamido]-4-(methylsulfanyl)butanamido]propanoic acid
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Chemical and physical data
FormulaC58H73N13O21S2
Molar mass1352.41 g·mol−1
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Ceruletide (INN), also known ascerulein orcaerulein, is a ten amino acidoligopeptide that stimulatessmooth muscle and increases digestive secretions. Ceruletide is similar in action and composition tocholecystokinin. It stimulates gastric, biliary, and pancreatic secretion; and certain smooth muscle. It is used in paralytic ileus and as diagnostic aid in pancreatic malfunction. It is used to inducepancreatitis in experimental animal models.

The tree frogRanoidea caerulea, formerly namedHyla caerulae.

Ceruletide was discovered and its structure elucidated in 1967 by Australian and Italian scientists from dried skins of theAustralian green tree frog (Ranoidea caerulea, formerlyHyla caerulea). Its amino acid sequence is Pglu-Gln-Asp-Tyr[SO3H]-Thr-Gly-Trp-Met-Asp-Phe-NH2.[1][2]

Induction of pancreatitis

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Ceruletide upregulates pancreaticacinar cellintercellular adhesion molecule-1 (ICAM-1) proteins through intracellular upregulation ofNF-κB. Surface ICAM-1 in turn promotes neutrophil adhesion onto acinar cells enhancing pancreaticinflammation.[3] In addition to promoting the inflammatory cell reaction to acinar cells, ceruletide induces pancreatitis through dysregulation of digestive enzyme production and cytoplasmic vacuolization, leading to acinar cell death and pancreatic edema. Ceruletide also activatesNADPH oxidase, a source of reactive oxygen species contributing to inflammation, as well as theJanus kinase/signal transducer, another inflammation inducer.[4]

See also

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References

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  1. ^Anastasi A, Erspamer V, Endean R (September 1967). "Isolation and structure of caerulein, an active decapeptide from the skin of Hyla caerulea".Experientia.23 (9):699–700.doi:10.1007/BF02154119.PMID 6062875.
  2. ^De Caro G, Endean R, Erspamer V, Roseghini M (May 1968)."Occurrence of caerulein in extracts of the skin of Hyla caerulea and other Australian hylids".British Journal of Pharmacology and Chemotherapy.33 (1):48–58.doi:10.1111/j.1476-5381.1968.tb00473.x.PMC 1570274.PMID 5660165.
  3. ^Zaninovic V, Gukovskaya AS, Gukovsky I, Mouria M, Pandol SJ (October 2000)."Cerulein upregulates ICAM-1 in pancreatic acinar cells, which mediates neutrophil adhesion to these cells".American Journal of Physiology. Gastrointestinal and Liver Physiology.279 (4): G666-76.doi:10.1152/ajpgi.2000.279.4.G666.PMID 11005752.
  4. ^Kim H (September 2008)."Cerulein pancreatitis: oxidative stress, inflammation, and apoptosis".Gut and Liver.2 (2):74–80.doi:10.5009/gnl.2008.2.2.74.PMC 2871591.PMID 20485614.
Diagnostic agents (V04)
Digestive system
Diabetes
Fat absorption
Bile ductpatency
Liver functional capacity
Gastric secretion
Exocrinepancreatic function
Endocrine system
Pituitary function
Thyroid function
Fertility disturbances
Tuberculosis
Renal function
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