基本情報
- CAS
5534-95-2- 標準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- 分子式
- C37H49N7O9S
- 平均分子量
- 767.9 g/mol
- 単同位体質量
- 767.33124734
概要
Pentagastrin is an organic molecular entity.
名称と識別子
- 優先名称
- 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
- 現地名
- ペンタガスリン
- 英語名
- PENTAGASTRIN
- 分子式
- C37H49N7O9S
- 分子量
- 767.9
名称と別名
名称をさらに表示
データベース識別子
- CAS
5534-95-2- PubChem CID
- 9853654
- DTXSID
DTXSID3048992- ChEMBL
CHEMBL1328- ChEBI
CHEBI:31974- UNII
- EF0NX91490
- EC Number
- 226-889-7
- Nikkaji
- J3.414B
物性
構造計算による物性
- XLogP
- 1.5
- 極性表面積
- 276 Ų
- 水素結合供与体数
- 8
- 水素結合受容体数
- 10
- 回転可能結合数
- 22
- 重原子数
- 54
- 形式電荷
- 0
- 複雑度
- 1,310
実験および物理化学的性質
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
物理化学的性質
- 融点
- 229 · 229-230° (dec)
- 比旋光度
- 22 · D22 -28.8 ±0.5° (DMF)
- 沸点
- 1196.6 · 1196.6±65.0 °C(Predicted)
- 比重(密度)
- 1.303 · 1.303±0.06 g/cm3(Predicted)
- 貯蔵温度
- -20 °C · -20°C
- 溶解性
- 5 M · 水にほとんど溶けず、5M アンモニアおよびジメチルホルムアミドに溶け、エタノールにわずかに溶ける (96%)。
- 酸解離定数(Pka)
- 4.19 · 4.19±0.10(Predicted)
- 外見
- 粉
- 色
- 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|
化学的性質
化学的特性A white or almost white powder.
安全と法規制
GHS分類
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.
危険有害性情報
毒性情報
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
安全データ
- wgk
- 1
- rtecs
- AY2970000
- risk_code
- 61-36/38-20/21
- hazard_code
- T
- safety_code
- 53-45-36/37/39-22
- ストレージクラス
- 11 - Combustible Solids
- 有毒物質データの
- 5534-95-2(Hazardous Substances Data)
化学と産業
薬理情報
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.
用途と製造
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).
応用分野
説明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.
使用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.
一般的な説明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.
上流・下流製品情報
上流原料
サプライヤー100 社
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