| Identification | Back Directory | [Name]
PENTAGASTRIN | [CAS]
5534-95-2 | [Synonyms]
GRP
ay6608
ici50123
petavlon
peptavlon
petogasrin
lanineamide
PENTAGASTRIN
gastrodiagnost
-tert-butylester
l-n-tert-butyleste
GASTRIN RELEASING PEPTIDE
aspartyl]-l-phenylalaninamide
l-methionyl-l-alpha-aspartyl-
BOC-β-Ala-Trp-Met-Asp-Phe-NH2
Boc-b-Ala-Trp-Met-Asp-Phe-NH2
Boc-(β-Ala13)-Gastrin (13-17)
BOC-BETA-ALA-TRP-MET-ASP-PHE-NH2
boc-beta-ala-try-met-asp-phe(nh2)
T-BOC-BETA-ALA-TRP-MET-ASP-PHE-NH2
n-t-boc-β-ala-trp-met-asp-phe amide
N-T-boc-B-ala-trp-met-asp-phe amide
N-Boc-βAla-L-Trp-L-Met-L-Asp-L-Phe-NH2
N-T-BOC-BETA-ALA-TRP-MET-ASP-PHE AMIDE
PENTAGASTRIN (ICI 50123) SYNTHETIC >99%
N-(1,1-Dimethylethoxy)carbonyl-βAla-L-Trp-L-Met-L-Asp-L-Phe-NH2
ylpropionamido]-4-(methylthio)butyramido]succinamicacidn-tert-butylester
n-carboxy-beta-alanyl-l-tryptophyl-l-methionyl-l-aspartylphenyl-alaninamid
n-((1,1-dimethylethoxy)carbonyl)-beta-alanyl-l-tryptophyl-l-phenylalaninamid
n-(alpha-carbamoylphenethyl)-3-[2-[2-[3-(carboxyamino)propionamido]-3-indol-3-
n-[n-[n-[n-(n-tert-butoxycarbonyl-beta-alanyl)-l-tryptophanyl]-l-methionyl]-l-
n-carboxy-beta-alanyl-l-tryptophyl-l-methionyl-l-aspartylphenyl-l-alaninamiden
n-t-butyloxycarbonyl-beta-alanyl-l-tryptophyl-l-methionyl-l-aspartyl-l-phenyla
AY 6608, ICI 50123, NSC 367746, Boc-(b-Ala13)-Gastrin (13-17), Boc-b-Ala-CCK-4 | [EINECS(EC#)]
226-889-7 | [Molecular Formula]
C37H49N7O9S | [MDL Number]
MFCD00076515 | [MOL File]
5534-95-2.mol | [Molecular Weight]
767.89 |
| Chemical Properties | Back Directory | [Appearance]
A white or almost white powder. | [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
| [pka]
4.19±0.10(Predicted) | [color ]
White to off-white | [Sequence]
N-t-Boc-β-Ala-Trp-Met-Asp-Phe-NH2 | [InChIKey]
NEYNJQRKHLUJRU-DZUOILHNSA-N |
| Hazard Information | Back Directory | [Uses]
anesthetic (local) | [Uses]
diagnostic agent for gastric secretion disorders | [Description]
Pentagastrin is a synthetic polypeptide and cholecystokinin-2 (CCK2) receptor agonist.1 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).2 Pentagastrin induces contraction of isolated pig ileum smooth muscle cells in vitro (EC50 = 30 pM).3 It increases gastric acid and pepsin secretion in conscious cats in vivo (ED50s = 1.29 and 57.3 nmol/kg2 per hour, respectively).4 Formulations containing pentagastrin have previously been used as a diagnostic aid to evaluate gastric acid secretory function. | [Chemical Properties]
A white or almost white powder. | [Originator]
Peptavlon,I.C.I. ,UK,1967 | [Definition]
ChEBI: Pentagastrin is an organic molecular entity. | [Manufacturing Process]
A 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 name]
Peptavlon (Wyeth). | [Therapeutic Function]
Gastrosecretory hormone | [General Description]
Pentagastrin (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 Actions]
CCKB 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. |
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