5534-95-2

Basic information

• 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 NO: 5534-95-2
• Molecular Formula: C₃₇H₄₉N₇O₉S
• Molecular Weight: 767.89
• EINECS: 226-889-7
• Product Categories: Peptide;MARCAINE
• Mol File: 5534-95-2.mol
• Article Data: 6

Chemical Properties

• Melting Point: 229-230° (dec)
• Boiling Point: 1196.6°Cat760mmHg
• Flash Point: 677.5°C
• Appearance: /powder
• Density: 1.303g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.604
• Storage Temp.: −20°C
• Solubility: Practically insoluble in water; soluble in 5M ammonia and in dimethylformamide; slightly soluble in ethanol (96%).
• PKA: 4.19±0.10(Predicted)
• CAS DataBase Reference: PENTAGASTRIN(CAS DataBase Reference)
• NIST Chemistry Reference: PENTAGASTRIN(5534-95-2)
• EPA Substance Registry System: PENTAGASTRIN(5534-95-2)

Safety Data

• Hazard Codes: T
• Statements: 61-36/38-20/21
• Safety Statements: 53-45-36/37/39-22
• WGK Germany: 1
• RTECS: AY2970000
• Hazardous Substances Data: 5534-95-2(Hazardous Substances Data)

Usage

Description

Pentagastrin 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 Properties

A white or almost white powder.

Originator

Peptavlon,I.C.I. ,UK,1967

Uses

Different sources of media describe the Uses of 5534-95-2 differently. You can refer to the following data:
1. Pentagastrin 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.
2. anesthetic (local)
3. diagnostic agent for gastric secretion disorders

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.

InChI:InChI=1/C37H49N7O9S/c1-37(2,3)53-36(52)39-16-14-30(45)41-28(19-23-21-40-25-13-9-8-12-24(23)25)34(50)42-26(15-17-54-4)33(49)44-29(20-31(46)47)35(51)43-27(32(38)48)18-22-10-6-5-7-11-22/h5-13,21,26-29,40H,14-20H2,1-4H3,(H2,38,48)(H,39,52)(H,41,45)(H,42,50)(H,43,51)(H,44,49)(H,46,47)/t26-,27-,28-,29-/m0/s1

Upstream product

• 88463-18-7 (S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropionamide 
• 51987-73-6 (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester 
• 60058-69-7 (tert-butyloxycarbonyl)-β-benzyl-L-aspartyl-L-phenylalanine amide 
• 5609-55-2 O-benzylaspartyl-phenylalanine amide 
• 5549-51-9 H-Met-Asp(OBzl)-Phe-NH₂ 
• 60369-28-0 H₂N-Trp-Met-Asp(Bzl)-Phe-NH₂ 
• 88463-49-4 C₄₄H₅₅N₇O₉S 
• 207744-21-6 Boc-βAla-Δ^ZTrp-Met-Asp-Phe-NH2 
• 53666-03-8 Boc-Trp-ONB 
• 54855-10-6 Boc-Trp-Met-OH 
• 5549-50-8 Boc-Trp-Met-Asp(OBu^t)-Phe-NH₂ 
• 5549-49-5 Z-Asp(OBu^t)-Phe-NH₂ 
• 5241-67-8 H-Asp(O-tBu)-Phe-NH₂ 
• 5241-58-7 L-Phenylalanine amide 

Downstream Products

• 207744-21-6 Boc-βAla-Δ^ZTrp-Met-Asp-Phe-NH2 

Relevant articles and documents

Microwave-assisted solution phase peptide synthesis in neat water

An environmentally benign protocol for solution phase peptide synthesis has been developed in neat water using TBTU/HOBt/DIEA as a coupling combination under microwave irradiation. Key features of this procedure are the replacement of commonly used toxic organic solvents like DMF and NMP, the use of lower amounts of reactants, compatibility with both N-α-Boc- and N-α-Fmoc-protected amino acids and all commonly used side-chain protective groups, short reaction time, and racemization-free synthesis in high yield and purity. The Royal Society of Chemistry 2013.

N-substituted cycloalkyl and polycycloalkyl α-substituted Trp-Phe- and phenethylamine derivatives

Novel unnatural dipeptoids of α-substituted Trp-Phe derivatives useful as agents in the treatment of obesity, hypersecretion of gastric acid in the gut, gastrin-dependent tumors, colorectal tumors, or as antipsychotics are disclosed. Further the compounds are antianxiety agents, antiulcer agents, antidepressant agents, and are agents useful for preventing the withdrawal response produced by chronic treatment or use followed by chronic treatment followed by withdrawal from nicotine, diazepam, alcohol, cocaine, caffeine, or opiods. Also disclosed are pharmaceutical compositions and methods of treatment using the dipeptoids as well as processes for preparing them and novel intermediates useful in their preparation. An additional feature of the invention is the use of the subject compounds to prepare pharmaceutical and diagnostic compositions.

An improved synthesis of pentagastrin (Acignost)

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