Pentagastrin
Grundinformationen
- CAS
5534-95-2- Standard-SMILES
CSCC[C@H](NC(=O)[C@H](Cc1c[nH]c2ccccc12)NC(=O)CCNC(=O)OC(C)(C)C)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](Cc1ccccc1)C(N)=O- InChIKey
NEYNJQRKHLUJRU-DZUOILHNSA-N- Summenformel
- C37H49N7O9S
- Durchschnittliche Molmasse
- 767,9 g/mol
- Monoisotopische Masse
- 767,33124734
Überblick
Pentagastrin is an organic molecular entity.
Namen und Bezeichner
- Bevorzugter Name
- Pentagastrin
- IUPAC
- (3S)-4-[[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-3-[[(2S)-2-[[(2S)-3-(1H-indol-3-yl)-2-[3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoylamino]propanoyl]amino]-4-methylsulfanylbutanoyl]amino]-4-oxobutanoic acid
- Lokaler Name
- Pentagastrin
- Englischer Name
- PENTAGASTRIN
- Summenformel
- C37H49N7O9S
- Molmasse
- 767.9
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
5534-95-2- PubChem CID
- 9853654
- DTXSID
DTXSID3048992- ChEMBL
CHEMBL1328- ChEBI
CHEBI:31974- UNII
- EF0NX91490
- EC Number
- 226-889-7
- Nikkaji
- J3.414B
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 1,5
- Polarare Oberfläche (TPSA)
- 276 Ų
- H-Brücken-Donoren
- 8
- H-Brücken-Akzeptoren
- 10
- Frei drehbare Bindungen
- 22
- Schwere Atome
- 54
- Formalladung
- 0
- Komplexität
- 1.310
Experimentelle und physikochemische Eigenschaften
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Physikochemische Eigenschaften
- Schmelzpunkt
- 229 · 229-230° (dec)
- Siedepunkt
- 1196.6 · 1196.6±65.0 °C(Predicted)
- Dichte
- 1.303 · 1.303±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C
- Löslichkeit
- 5 M · Practically insoluble in water; soluble in 5M ammonia and in dimethylformamide; slightly soluble in ethanol (96%).
- pka
- 4.19 · 4.19±0.10(Predicted)
- Aggregatzustand
- powder
- Farbe
- White to off-white
- InChIKey
- NEYNJQRKHLUJRU-DZUOILHNSA-N
- SMILES
- C(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|
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Warning
H302+H312+H332 (100%): Harmful if swallowed, in contact with skin or if inhaled [Warning Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]
P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Gefahrenhinweise
Toxikologische Informationen
Human Toxicity Excerpts
...SIDE EFFECTS ARE MINOR & TRANSIENT. THESE MAY INCL NAUSEA, DIZZINESS, FAINTNESS, FLUSHING, & SENSATION OF WARMTH.
NOT MORE THAN 40 UG OF PENTAGASTRIN HAD BEEN INFUSED WHEN 56-YR-OLD MALE PT FAINTED & BECAME COLD & WHITE WITH NO RADIAL PULSE PALPABLE FOR 3 MIN. ONCE PULSE RETURNED PT HAD SEVERE BRADYCARDIA OF 35/MIN.
PT WITH DIFFUSE ESOPHAGEAL SPASM DEVELOPED POWERFUL, SPONTANEOUS, IRREGULAR CONTRACTIONS FOLLOWING ADMIN OF PENTAGASTRIN.
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Pentagastrin
vNo-DILI-concern
0
No match
DOI:10.1016/j.drudis.2016.02.015
Sicherheitsdaten
- wgk
- 1
- RTECS-Nr.
- AY2970000
- risk_code
- 61-36/38-20/21
- hazard_code
- T
- safety_code
- 53-45-36/37/39-22
- Speicherklasse
- 11 - Combustible Solids
- Giftige Stoffe Daten
- 5534-95-2(Hazardous Substances Data)
Chemie und Industrie
Pharmakologische Informationen
ATC Code
V - Various
QV - Various
Pharmacodynamics
Pentagastrin is indicated as a diagnostic aid for evaluation of gastric acid secretory function. It is effective in testing for anacidity (achlorhydria) in patients with suspected pernicious anemia, atrophic gastritis, or gastric carcinoma. It is also effective in determining the reduction in acid output after operations for peptic ulcer, such as vagotomy or gastric resection.
Mechanism of Action
The exact mechanism by which pentagastrin stimulates gastric acid, pepsin, and intrinsic factor secretion is unknown; however, since pentagastrin is an analogue of natural gastrin, it is believed that it excites the oxyntic cells of the stomach to secrete to their maximum capacity. Pentagastrin stimulates pancreatic secretion, especially when administered in large intramuscular doses. Pentagastrin also increases gastrointestinal motility by a direct effect on the intestinal smooth muscle. However, it delays gastric emptying time probably by stimulation of terminal antral contractions, which enhance retropulsion.
MOST PROMINENT ACTION OF PENTAGASTRIN IS TO STIMULATE SECRETION OF GASTRIC ACID, PEPSIN, & INTRINSIC FACTOR OF CASTLE...STIMULATES PANCREATIC SECRETION, INHIBITS ABSORPTION OF WATER & ELECTROLYTES FROM ILEUM, CONTRACTS SMOOTH MUSCLE OF LOWER ESOPHAGEAL SPHINCTER & STOMACH (BUT DELAYS GASTRIC EMPTYING TIME)...
.../IT/ RELAXES SPHINCTER OF ODDI, INCR BLOOD FLOW IN GASTRIC MUCOSE, STIMULATES L-HISTIDINE DECARBOXYLASE ACTIVITY IN RAT GASTRIC MUCOSA, &, IN HIGH DOSES, STIMULATES VARIETY OF SMOOTH MUSCLES IN DIFFERENT SPECIES.
IT ALSO MIMICS OR BLOCKS EFFECTS OF POLYPEPTIDES PANCREOZYMIN-CHOLECYSTOKININ, SECRETIN, CAERULIN, NATURALLY OCCURRING DECAPEPTIDE THAT, ALONG WITH PANCREOZYMIN-CHOLECYSTOKININ, SHARES COMMON C-TERMINAL HEPTAPEPTIDE RESIDUE WITH GASTRIN.
PENTAGASTRIN ACTIVATES ADENYLATE CYCLASE IN GASTRIC MUCOSA...
PENTAGASTRIN INITIALLY PRODUCED MARKED ANTRAL ACTIVITY IN PHYSIOLOGICAL STRICTURE & SUBSEQUENT DELAY IN OVERALL RATE OF GASTRIC EMPTYING. FUNDAL MOTILITY WAS UNAFFECTED THOUGH REFLUX FROM ANTRUM OCCURRED.
Biological Half-Life
10 minutes or less
HALF-LIFE OF PENTAGASTRIN IN CIRCULATION APPEARS TO BE ABOUT 10 MIN...
Absorption, Distribution and Excretion
Rapidly absorbed after parenteral administration.
ACTIVITY OF ORAL PENTAGASTRIN WAS DETERMINED BY ITS ACTION AS GASTRIC ACID STIMULANT IN 4 HEALTHY SUBJECTS, 2 PT WITH DUODENAL ULCERS, & 1 PT WITH ANNULAR PANCREAS IN ASSOC WITH DUODENAL ULCER.
Verwendung und Herstellung
Methods of Manufacturing
HARDY ET AL, BELGIAN PATENT 665,591 & BRITISH PATENT 1,042,487 (1965 TO ICI), CA 64, 19774G (1966); DAVEY ET AL, J CHEM SOC (C) 1966, 555; SAKAKIBARA ET AL, BULL CHEM SOC JAPAN 41, 438 (1968). STRUCTURE-FUNCTION RELATIONSHIP STUDIES: MORLEY ET AL, NATURE 207, 1356 (1965).
Formulations/Preparations
FORMULATION & PHARMACOLOGICAL STUDIES: WAI ET AL, J PHARM PHARMACOL 22, 923 (1970). REVIEWS: MAKHLOUF, FED PROC 27, 1322 (1968); SANDERS, SCHIMMEL, AM J MED 49, 380 (1970).
PEPTAVLON- IN 2 ML AMPULS. EACH ML CONTAINS 0.25 MG (250 MCG) PENTAGASTRIN. ALSO CONTAINS 0.88% SODIUM CHLORIDE, & WATER FOR INJECTION USP. PH IS ADJUSTED WITH AMMONIUM HYDROXIDE. CARTONS OF 10 (NDC 0046-3290-10).
Anwendungen
BeschreibungPentagastrin 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.
VerwendenPentagastrin 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.
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