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PENTAGASTRIN

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Related articles

  • Mechanism of action of Pentagastrin
  • Pentagastrin is a gastrin-like molecule used as a diagnostic aid for the evaluation of gastric acid secretory function, gastri....
  • May 6,2022
PENTAGASTRIN Basic information
Description
Product Name:PENTAGASTRIN
Synonyms:T-BOC-BETA-ALA-TRP-MET-ASP-PHE-NH2;aspartyl]-l-phenylalaninamide;ay6608;boc-beta-ala-try-met-asp-phe(nh2);gastrodiagnost;ici50123;lanineamide;l-methionyl-l-alpha-aspartyl-
CAS:5534-95-2
MF:C37H49N7O9S
MW:767.9
EINECS:226-889-7
Product Categories:MARCAINE;Peptide
Mol File:5534-95-2.mol
PENTAGASTRIN Structure
PENTAGASTRIN Chemical Properties
Melting point 229-230° (dec)
alpha D22 -28.8 ±0.5° (DMF)
Boiling point 1196.6±65.0 °C(Predicted)
density 1.303±0.06 g/cm3(Predicted)
storage temp. -20°C
solubility Practically insoluble in water; soluble in 5M ammonia and in dimethylformamide; slightly soluble in ethanol (96%).
form powder
pka4.19±0.10(Predicted)
color White to off-white
SequenceN-t-Boc-β-Ala-Trp-Met-Asp-Phe-NH2
InChIKeyNEYNJQRKHLUJRU-DZUOILHNSA-N
SMILESC(C1=CNC2C=CC=CC1=2)[C@H](NC(=O)CCNC(=O)OC(C)(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@H](C(=O)N)CC1C=CC=CC=1 |&1:10,27,35,43,r|
Safety Information
Hazard Codes T
Risk Statements 61-36/38-20/21
Safety Statements 53-45-36/37/39-22
WGK Germany 1
RTECS AY2970000
Hazardous Substances Data5534-95-2(Hazardous Substances Data)
MSDS Information
ProviderLanguage
SigmaAldrich English
PENTAGASTRIN Usage And Synthesis
DescriptionPentagastrin is a synthetic polypeptide and cholecystokinin-2 (CCK2) receptor agonist. It binds selectively to CCK2 receptors in guinea pig brain over CCK1 receptors in rat pancreas (IC50s = 11 and 1,100 nM, respectively). Pentagastrin increases calcium influx and polyphosphoinositide turnover in rat GH3 pituitary cells (EC50s = 23 and 3.9 nM, respectively). It also increases histidine decarboxylase activity in mucous- and endocrine cell-enriched isolated rabbit fundic mucosal cells (EC50 = 2.9 nM). Pentagastrin induces contraction of isolated pig ileum smooth muscle cells in vitro (EC50 = 30 pM). It increases gastric acid and pepsin secretion in conscious cats in vivo (ED50s = 1.29 and 57.3 nmol/kg2 per hour, respectively). Formulations containing pentagastrin have previously been used as a diagnostic aid to evaluate gastric acid secretory function.
Chemical PropertiesA white or almost white powder.
OriginatorPeptavlon,I.C.I. ,UK,1967
Usesanesthetic (local)
UsesPentagastrin is a synthetic polypeptide that has effects like gastrin when given parenterally. It stimulates the secretion of gastric acid, pepsin, and intrinsic factor, and has been used as a diagnostic aid as the pentagastrin-stimulated calcitonin test.
Usesdiagnostic agent for gastric secretion disorders
DefinitionChEBI: Pentagastrin is an organic molecular entity.
Manufacturing ProcessA solution of 3.55 parts of L-tryptophanyl-L-methionyl-L-aspartyl-Lphenylalanine amide trifluoroacetate in 30 parts of dimethylformamide is cooled to 0°C, and 1.01 parts of triethylamine are added. The mixture is stirred while 1.84 parts of N-tert-butyloxycarbonyl-β-alanine 2,4,5trichlorophenyI ester are added at 0°C. The reaction mixture is kept at 0°C for 48 hours and then at 20°-23°C for 24 hours. The mixture is added to a mixture of 100 parts of ice-water, 0.37 part of concentrated hydrochloric acid (SG 1.18), 1.2 parts of acetic acid and 20 parts of ethyl acetate. The mixture is stirred for 15 minutes at 0°-10°C and is then filtered. The solid residue is washed with water and then with ethyl acetate, and is dried at 40°-50°C under reduced pressure. There is thus obtained N-tert-butyloxycarbonyl-βalanyl-L-tryptophanyl-L-methionyl-L-aspartyl-L-phenylalanine amide, MP 213°C with de composition.
Brand namePeptavlon (Wyeth).
Therapeutic FunctionGastrosecretory hormone
General DescriptionPentagastrin (Peptavlon), a physiologicalgastric acid secretagogue, is the synthetic pentapeptide derivative:N-t-butyloxycarbonyl-β-alanyl-L-tryptophyl-L-methionyl-L-aspartyl-L-phenylalanyl amide. It contains theCOOH-terminal tetrapeptide amide (H·Try·Met· Asp·Phe·NH2), which is considered to be the active center ofthe natural gastrins. Accordingly, pentagastrin appears tohave the physiological and pharmacological properties ofthe gastrins, including stimulation of gastric secretion,pepsin secretion, gastric motility, pancreatic secretion ofwater and bicarbonate, pancreatic enzyme secretion, biliaryflow and bicarbonate output, intrinsic factor secretion, andcontraction of the gallbladder.
Pentagastrin is indicated as a diagnostic agent to evaluategastric acid secretory function, and it is useful in testing foranacidity in patients with suspected pernicious anemia, atrophicgastritis or gastric carcinoma, hypersecretion in suspectedduodenal ulcer or postoperative stomal ulcers, andZollinger-Ellison tumor.
Biochem/physiol ActionsCCKB agonist that stimulates gastric acid secretion; anxiogenic.Pentagastrin is an agonist of the cholecystokinin-2 (CCK2) receptor. It helps to increase the excitability of neurons in the basolateral amygdala through the activation of a non-specific cation channel.
DescriptionPentagastrin Synthetic is a single, non-glycosylated polypeptide chain containing 5 amino acids, having a molecular mass of 768 Dalton and a Molecular formula of C37H49N7O9S .
References[1] ALISON J. SMITH  Stephen B F. CCk-B receptor-mediated stimulation of polyphosphoinositide turnover in gh3 pituitary cells in response to cholecystokinin and pentagastrin[J]. Life sciences, 1996, 58 11: Pages 883-895. DOI: 10.1016/0024-3205(96)00031-8
[2] F HOLLANDE  R M  J P Bali. Neurohormonal regulation of histamine synthesis in isolated rabbit fundic mucosal cells.[J]. American Journal of Physiology, 1994, 266 3 Pt 1: G395-402. DOI: 10.1152/ajpgi.1994.266.3.g395
[3] ALAIN BOTELLA. Cholecystokinin and gastrin induce cell contraction in pig ileum by interacting with different receptor subtypes[J]. Gastroenterology, 1992, 102 3: Pages 779-786. DOI: 10.1016/0016-5085(92)90158-u
[4] M. VAGNE . Effect of porcine gastrin releasing peptide on gastric secretion and motility and the release of hormonal peptides in conscious cats[J]. Peptides, 1987, 8 3: Pages 423-430. DOI: 10.1016/0196-9781(87)90004-0
PENTAGASTRIN Preparation Products And Raw materials
Raw materialsβ-Alanine-->Propionamide-->L-ASPARTIC ACID-->N-[(tert-Butoxy)carbonyl]-D-tryptophan
Tag:PENTAGASTRIN(5534-95-2) Related Product Information
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