パリエット
WordNet
- a large order of dicotyledonous plants of subclass Dilleniidae (同)order Parietales, Hypericales, order Hypericales
- small genus of stingless herbs (同)genus Parietaria
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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/04/02 03:10:48」(JST)
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Rabeprazole
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|
| Systematic (IUPAC) name |
|
(RS)-2-([4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methylsulfinyl)-1H-benzo[d]imidazole
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| Clinical data |
| AHFS/Drugs.com |
monograph |
| MedlinePlus |
a699060 |
| License data |
- US FDA: Finix&SearchType=BasicSearch AcipHex Finix
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Pregnancy
category |
- US: B (No risk in non-human studies)
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Routes of
administration |
Oral |
| Legal status |
| Legal status |
- UK: POM (Prescription only)
- US: ℞-only
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| Pharmacokinetic data |
| Bioavailability |
52% |
| Metabolism |
mostly non-enzymatic,
partly hepatic (CYP2C19) |
| Biological half-life |
1 - 1.5 hours |
| Excretion |
90% renal |
| Identifiers |
| CAS Number |
117976-89-3 Y |
| ATC code |
A02BC04 (WHO) |
| PubChem |
CID 5029 |
| IUPHAR/BPS |
7290 |
| DrugBank |
DB01129 Y |
| ChemSpider |
4853 Y |
| UNII |
32828355LL Y |
| ChEBI |
CHEBI:8768 Y |
| ChEMBL |
CHEMBL1219 Y |
| PDB ligand ID |
RZX (PDBe, RCSB PDB) |
| Chemical data |
| Formula |
C18H21N3O3S |
| Molar mass |
359.444 g/mol |
| Chirality |
Racemic mixture |
SMILES
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O=S(c2nc1ccccc1n2)Cc3nccc(OCCCOC)c3C
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InChI
-
InChI=1S/C18H21N3O3S/c1-13-16(19-9-8-17(13)24-11-5-10-23-2)12-25(22)18-20-14-6-3-4-7-15(14)21-18/h3-4,6-9H,5,10-12H2,1-2H3,(H,20,21) Y
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Key:YREYEVIYCVEVJK-UHFFFAOYSA-N Y
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| (verify) |
Rabeprazole is an antiulcer drug in the class of proton pump inhibitors. It was developed by Eisai Co. and is available worldwide under many brand names.
Contents
- 1 Indications and usage
- 2 Contraindications
- 3 Restriction of usage
- 4 Side effects
- 5 Drug interactions
- 6 Overdosage
- 7 Synthesis
- 8 References
- 9 External links
Indications and usage
Short-term treatment in healing and symptomatic relief of duodenal ulcers and erosive or gastroesophageal reflux disease (GERD); maintaining healing and reducing relapse rates of heartburn symptoms in patients with GERD; treatment of daytime and nighttime heartburn and other symptoms associated with GERD; long-term treatment of pathological hypersecretory conditions, including Zollinger-Ellison syndrome and in combination with amoxicillin and clarithromycin to eradicate Helicobacter pylori.
- Gastric ulcer (GU)
- Peptic ulcer disease (PUD)
- Maintenance of healing of erosive or ulcerative GERD
- Healing of erosive and ulcerative GERD
- Healing of duodenal ulcers.
- Treatment of symptomatic GERD
- Treatment of pathological hypersecretory conditions (Zollinger-Ellison syndrome)
- Helicobacter pylori eradication to reduce risk of duodenal ulcer recurrence
Contraindications
- hypersensitivity to rabeprazole, substituted benzimidazoles or any of components of its pharmaceutical forms.
- lactation: Thomson Lactation Ratings: Infant risk cannot be ruled out.
Restriction of usage
Bottle of rabeprazole 20 mg tablets.
- acute liver failure
- pediatric use in patients under 18 years of age (there are insufficient data about safety and efficiency of rabeprazole in this group of patients)
Side effects
Rabeprazole adverse reactions/side effects include[citation needed]:
- In clinical trials the most common side effect assessed as possibly or probably related to AcipHex was headache in 2.4% of patients vs 1.6% taking placebo.
- abdominal pains
- anxiety
- arthralgia
- asthenia
- constipation
- diarrhea
- dry mouth
- erythema
- granulocytopenia
- headache
- increased or decreased appetite
- insomnia
- leukocytopenia
- meteorism
- muscle or bone pain
- myalgia
- nausea
- skin eruption
- thrombocytopenia
- vertigo
- vomiting
Drug interactions
Rabeprazole decreases the concentration of ketoconazole in the plasma (in 33%), increases the concentration of digoxin (in 22%), and does not interact with liquid antacids. Rabeprazole is compatible with any medicine metabolized by the CYP450 (theophylline, warfarin, diazepam, phenytoin).
Overdosage
Studies in mice and rats indicated the symptoms of acute toxicity due to overdose included: hypoactivity, labored respiration, convulsion, diarrhea, tremor, and coma. A study in dogs indicated that a dose of 2000 mg/kg was not lethal.
Synthesis
Rabeprazole synthesis:
[1] patents:
[2]
Nitration of 2,3-dimethylpyridine N-oxide affords the nitro derivative. The newly introduced nitro group is then displaced by the alkoxide from 3-methoxypropanol to affords the corresponding ether (3). Treatment with Ac2O results in the Polonovski reaction. Saponification followed by treatment with SOCl2 then chlorinates the primary alcohol (5). Condensation with benzimidazole-2-thiol (6) followed by oxidation of the resulting thioether to the sulfoxide then affords rabeprazole (8).
References
- ^ Tagami, K.; Chiku, S.; Sohda, S. (1993). "Synthesis of 14C-labelled sodium pariprazole (E3810)". Journal of Labelled Compounds and Radiopharmaceuticals 33 (9): 849. doi:10.1002/jlcr.2580330908.
- ^ S. Souda et al., EP 268956 ; eidem, U.S. Patent 5,045,552 (1988, 1991 both to Eisai).
- Morii M, Takata H, Fujisaki H, Takeguchi N., The potency of substituted benzimidazoles such as E3810, omeprazole, Ro 18-5364 to inhibit gastric H+, K(+)-ATPase is correlatedwith the rate of acid-activation of the inhibitor, Biochem. Pharmacol. 1990 Feb 15;39(4):661-7.
- Prakash A, Faulds D., Rabeprazole, Drugs. 1998 Feb;55(2):261-7; discussion 268.
External links
- AcipHex official product site
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Drugs for peptic ulcer and GERD/GORD (A02B)
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| H2 antagonists ("-tidine") |
- Cimetidine
- Famotidine
- Lafutidine
- Lavoltidine (loxtidine)
- Niperotidine
- Nizatidine
- Ranitidine
- Roxatidine
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| Prostaglandins (E)/analogues ("-prost-") |
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| Proton-pump inhibitors ("-prazole") |
- Dexlansoprazole
- Esomeprazole
- Ilaprazole
- Lansoprazole
- Omeprazole
- Pantoprazole
- Picoprazole
- Rabeprazole
- Tenatoprazole
- Timoprazole
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| Potassium-competitive acid blockers ("-prazan") |
- Linaprazan
- Revaprazan
- Soraprazan
- Vonoprazan
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| Other |
- Acetoxolone
- Alginic acid
- Arbaclofen placarbil
- Carbenoxolone
- Cetraxate
- Gefarnate
- Lesogaberan
- Pirenzepine
- Proglumide
- Rebamipide
- Sucralfate
- Sulglicotide
- Telenzepine
- Teprenone
- Troxipide
- Zolimidine
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| Combinations |
- Bismuth subcitrate/metronidazole/tetracycline
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- See also: Helicobacter pylori eradication protocols
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English Journal
- Spectrophotometric methods manipulating ratio spectra for simultaneous determination of binary mixtures with sever overlapping spectra: A comparative study.
- Moustafa H1, Fayez Y2.
- Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.Spectrochim Acta A Mol Biomol Spectrosc.2014 Dec 10;133:759-66. doi: 10.1016/j.saa.2014.06.059. Epub 2014 Jun 17.
- Three simple, specific and accurate spectrophotometric methods manipulating ratio spectra were developed and validated for simultaneous determination of Rabeprazole sodium (RB) and Domperidone (DP) in their binary mixture without prior separation. Method A, is constant center spectrophotometric meth
- PMID 24998682
- Development of alginate-reinforced chitosan nanoparticles utilizing W/O nanoemulsification/internal crosslinking technique for transdermal delivery of rabeprazole.
- Ahmed TA1, El-Say KM2.
- Life sciences.Life Sci.2014 Aug 6;110(1):35-43. doi: 10.1016/j.lfs.2014.06.019. Epub 2014 Jul 2.
- AIMS: First; to develop rabeprazole (RP)-alginate core coated chitosan nanoparticles (NP) utilizing water in oil (W/O) nanoemulsion technique. Second; formulation of transdermal patches loaded RP-NP that avoid drug peroral acid sensitivity and first pass effect.MAIN METHODS: The influence of six fac
- PMID 24997393
- Treatment of esophageal (noncardiac) chest pain: an expert review.
- Coss-Adame E1, Erdogan A1, Rao SS2.
- Clinical gastroenterology and hepatology : the official clinical practice journal of the American Gastroenterological Association.Clin Gastroenterol Hepatol.2014 Aug;12(8):1224-45. doi: 10.1016/j.cgh.2013.08.036. Epub 2013 Aug 28.
- BACKGROUND & AIMS: Chest pain is a common and frightening symptom. Once cardiac disease has been excluded, an esophageal source is most likely. Pathophysiologically, gastroesophageal reflux disease, esophageal dysmotility, esophageal hypersensitivity, and anxiety disorders have been implicated.
- PMID 23994670
Related Links
- 10 mg: Each enteric-coated delayed release tablet contains 10 mg of rabeprazole sodium, equivalent to 9,42 mg rabeprazole (racemate). 20 mg: Each enteric-coated delayed release tablet contains 20 mg of rabeprazole sodium, equivalent to ...
- 13 Apr 2007 ... Pariet (rabeprazole sodium): Pariet is used for the treatment of Stomach ulcers, ulcers in the duodenum (the area of the small intestine that lies just after the stomach) and to aid with the symptoms of gastroesophageal reflux ...
Related Pictures
★リンクテーブル★
[★]
- 英
- rabeprazole
- 化
- ラベプラゾールナトリウム sodium rabeprazole
- 商
- パリエット Pariet
- 関
- 消化性潰瘍用剤
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特徴
- 胃酸分泌を速やかに抑制かつ酸分泌回復性に優れガストリン濃度への影響少ない。リバウンドが少ない。
- ガストリン濃度を上げず酸分泌↓→リバウンドが少ない。