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Rebeprazole sodium
- Iupac Name：sodium
2-[[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methylsulfinyl]
benzimidazol-1-ide
- CAS No.: 117976-90-6
- Molecular Weight：381.42447
- Modify Date.: 2022-11-09 08:08
- Introduction: Rebeprazole sodium was launched as Pariet in Japan, its first market, for the treatment of peptic ulcers including gastric and duodenal ulcers. From 4-chloro- 2,3-dimethylpyridine N-oxide, a six step synthesis allows access to the basic skeleton after successive condensations. Rabeprazole, a structural analog of Omeprazole, the first compound to have been marketed in this class up to now, is reported to be a more potent inhibitor of gastric H+/K+-adenosine triphosphate (ATPase) ; a common mechanism of action of this chemical class involves the conversion at low pH to a reactive sulphonamide that itself binds to cysteine residues located on the enzyme. Moreover, rabeprazole showed an antibacterial activity against Helicobacter Pylori, with a MIC90 of 1.56 μg/ml.Rebeprazole sodium has a faster onset of action compared with omeprazole, but a shorter duration of action, being extensively and rapidly metabolized in several animal species. In clinical studies in patients with gastric ulcers, 10 and 20 mg rabeprazole sodium once-daily significantly inhibited basal and stimulated acid output. Rabeprazole is awaiting registration in the US for treatment of gastrooesophageal reflux disease (GORD) and other pathologic hypersecretory conditions including Zollinger-Ellison syndrome.
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1. Names and Identifiers
- 1.1 Name
- Rebeprazole sodium
- 1.2 Synonyms
1H-Benzimidazole, 2-[[[4-(3-methoxypropoxy)-3-methyl-2-pyridinyl]methyl]sulfinyl]-, sodium salt (1:1) 2-([4-(3-Methoxypropoxy)-3-methylpyridin-2-yl]methylsulfinyl)-1H-benzo[d]imidazole,Pariprazole 2-[[[4-(3-METHOXYPROPOXY)-3-METHYL-2-PYRIDINYL]METHYL]SULFINYL]-1H-BENZIMIDAZOLE, SODIUM SALT Aciphex natrium-2-({[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methyl}sulfinyl)benzimidazol-1-id PARIET RABEPRAZOL SODIUM Rabeprazole (sodium) RABEPRAZOLE NA RABEPRAZOLE SODIUM Rabeprazole Sodium Salt RABEPRAZOLE, SODIUM SALT Rabonik Sodium 2-({[4-(3-methoxypropoxy)-3-methyl-2-pyridinyl]methyl}sulfinyl)benzimidazol-1-ide sodium 2-({[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methyl}sulfinyl)benzimidazol-1-ide sodium 2-[[4-(3-methoxypropoxy)-3-methyl-pyridin-2-yl]methylsulfinyl]benzoimidazole sodium 2-{[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methanesulfinyl}-1H-benzimidazol-1-ide SODIUM RABEPRAZOLE sodium,2-[[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methylsulfinyl]benzimidazol-1-ide Zechin
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- 1.3 CAS No.
- 117976-90-6
- 1.4 CID
- 14720269
- 1.5 EINECS(EC#)
- 211-134-6
- 1.6 Molecular Formula
- C18H20N3NaO3S (isomer)
- 1.7 Inchi
- InChI=1S/C18H20N3O3S.Na/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;/q-1;+1
- 1.8 InChIkey
- KRCQSTCYZUOBHN-UHFFFAOYSA-N
- 1.9 Canonical Smiles
- CC1=C(C=CN=C1CS(=O)C2=NC3=CC=CC=C3[N-]2)OCCCOC.[Na+]
- 1.10 Isomers Smiles
- CC1=C(C=CN=C1CS(=O)C2=NC3=CC=CC=C3[N-]2)OCCCOC.[Na+]
2. Properties
- 2.1 Density
- 0.45~0.55 g/ml
- 2.1 Melting point
- 140-141℃ dec.
- 2.1 Boiling point
- 603.9 °C at 760 mmHg
- 2.1 Flash Point
- 319.1 °C
- 2.1 Precise Quality
- 381.11200
- 2.1 PSA
- 93.41000
- 2.1 logP
- 3.48420
- 2.1 Solubility
- H2O: soluble10mg/mL (clear solution)
- 2.2 Appearance
- white or off white crystalline powder
- 2.3 Storage
- Hygroscopic, -20°C Freezer, Under Inert Atmosphere
- 2.4 Chemical Properties
- Rebeprazole sodium is White Crystalline Solid
- 2.5 Color/Form
- Powder
- 2.6 Water Solubility
- H2O: soluble10mg/mL (clear solution)
- 2.7 StorageTemp
- -20°C
3. Use and Manufacturing
- 3.1 General Description
- Rabeprazole sodium, 2[[[4-(3-methoxypropoxy)-3-methyl-2-pyridinyl]methyl]sulfinyl]-1H-benzimidazole sodium salt (Aciphex), is a white toslightly yellowish white solid. It is very soluble in water andmethanol, freely soluble in ethanol, chloroform, and ethyl acetate,and insoluble in ether and hexane. Rabeprazole is aweak base (pyridine N, pKa 4.53) and a weak acid (benzimidazoleN-H, pKa 0.62), faciliting sodium salt formation.Rabeprazole sodium is formulated as enteric-coated,delayed-release tablets to allow the drug to pass throughthe stomach relatively intact. After oral administration of20-mg peak plasma concentrations (Cmax) occur over arange of 2 to 5 hours (Tmax). Absolute bioavailability for a20-mg oral tablet of rabeprazole (vs. IV administration) isapproximately 52%. The plasma half-life ofrabeprazole ranges from 1 to 2 hours. The effects of foodon the absorption of rabeprazole have not been evaluated.Rabeprazole is 96% bound to human plasma proteins.Rabeprazole is extensively metabolized in the liver. Thethioether and sulfone are the primary metabolites measuredin human plasma resulting from CYP3A oxidation.Additionally, desmethyl rabeprazole is formed via the actionof CYP2C19. Approximately 90% of the drug is eliminatedin the urine, primarily as thioether carboxylic acidand its glucuronide and mercapturic acid metabolites. Theremainder of the dose is recovered in the feces. No unchangedrabeprazole is excreted in the urine or feces. Rebeprazole sodiumSupplier
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- 3.2 Usage
- It belongs to national second-class drug that can be used for the treatment of gastric ulcer. It can be used for the treatment of peptic ulcer, gastroesophageal reflux disease, zollinger-ellison syndrome and other diseases.
4. Safety and Handling
- 4.1 Exposure Standards and Regulations
- The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl rabeprazole sodium, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Rabeprazole Sodium/
- 4.2 Octanol/Water Partition Coefficient
- log Kow = 1.17 /Estimated/
- 4.3 DisposalMethods
- SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
- 4.4 RIDADR
- NONH for all modes of transport
- 4.4 WGK Germany
- 3
- 4.4 Specification
-
?1H-Benzimidazole,2-[[[4-(3-methoxypropoxy)-3-methyl-2-pyridinyl]methyl]sulfinyl]-, sodium salt(1:1) , its cas register number is 117976-90-6. It also can be called?Rebeprazole sodium ; amd?Sodium 2-[[4-(3-methoxypropoxy)-3-methyl-pyridin-2-yl]methylsulfinyl]benzoimidazole .
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Skin irritation, Category 2
2.2 GHS label elements, including precautionary statements
| Pictogram(s) |  |
| Signal word | Warning |
| Hazard statement(s) | H315 Causes skin irritation |
| Precautionary statement(s) | |
| Prevention | P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection. |
| Response | P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. |
| Storage | none |
| Disposal | none |
2.3 Other hazards which do not result in classification
none
6. Synthesis Route
117976-90-6Total: 4 Synthesis Route
8. Other Information
- 8.0 Target
- Value
- 8.1 Description
- Rebeprazole sodium was launched as Pariet in Japan, its first market, for the treatment of peptic ulcers including gastric and duodenal ulcers. From 4-chloro- 2,3-dimethylpyridine N-oxide, a six step synthesis allows access to the basic skeleton after successive condensations. Rabeprazole, a structural analog of Omeprazole, the first compound to have been marketed in this class up to now, is reported to be a more potent inhibitor of gastric H+/K+-adenosine triphosphate (ATPase) ; a common mechanism of action of this chemical class involves the conversion at low pH to a reactive sulphonamide that itself binds to cysteine residues located on the enzyme. Moreover, rabeprazole showed an antibacterial activity against Helicobacter Pylori, with a MIC90 of 1.56 μg/ml.
Rebeprazole sodium has a faster onset of action compared with omeprazole, but a shorter duration of action, being extensively and rapidly metabolized in several animal species. In clinical studies in patients with gastric ulcers, 10 and 20 mg rabeprazole sodium once-daily significantly inhibited basal and stimulated acid output. Rabeprazole is awaiting registration in the US for treatment of gastrooesophageal reflux disease (GORD) and other pathologic hypersecretory conditions including Zollinger-Ellison syndrome. - View all
- 8.2 Description
- Rabeprazole is a proton pump inhibitor that selectively and irreversibly inhibits the gastric H+/K+ ATPase (IC50 = 72 nM).1 It can be activated more rapidly and over a greater pH range than other proton pump inhibitors such as omeprazole (Item No. 14880), lansoprazole (Item No. 13627), and pantoprazole (Item No. 21345).2 Rabeprazole (30 mg/kg) inhibits gastric acid secretion in pylorus-ligated rats and a rat model of gastric fistula.3 It also inhibits the growth of several strains of H. pylori in vitro (MIC50s = 1.57-3.13 μg/mL).2 Formulations containing rabeprazole have been used in the treatment of ulcers, pathological hypersecretory conditions, and gastroesophageal reflux disease (GERD).
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- 8.3 Chemical Properties
- Rebeprazole sodium is White Crystalline Solid
- 8.4 Originator
- Eisai (Japan)
- 8.5 Uses
- Rebeprazole sodium is a partially reversible gastric proton pump inhibitor
- 8.6 General Description
- Rabeprazole sodium, 2[[[4-(3-methoxypropoxy)-3-methyl-2-pyridinyl]methyl]sulfinyl]-1H-benzimidazole sodium salt (Aciphex), is a white toslightly yellowish white solid. It is very soluble in water andmethanol, freely soluble in ethanol, chloroform, and ethyl acetate,and insoluble in ether and hexane. Rabeprazole is aweak base (pyridine N, pKa 4.53) and a weak acid (benzimidazoleN-H, pKa 0.62), faciliting sodium salt formation.
Rabeprazole sodium is formulated as enteric-coated,delayed-release tablets to allow the drug to pass throughthe stomach relatively intact. After oral administration of20-mg peak plasma concentrations (Cmax) occur over arange of 2 to 5 hours (Tmax). Absolute bioavailability for a20-mg oral tablet of rabeprazole (vs. IV administration) isapproximately 52%. The plasma half-life ofrabeprazole ranges from 1 to 2 hours. The effects of foodon the absorption of rabeprazole have not been evaluated.Rabeprazole is 96% bound to human plasma proteins.Rabeprazole is extensively metabolized in the liver. Thethioether and sulfone are the primary metabolites measuredin human plasma resulting from CYP3A oxidation.Additionally, desmethyl rabeprazole is formed via the actionof CYP2C19. Approximately 90% of the drug is eliminatedin the urine, primarily as thioether carboxylic acidand its glucuronide and mercapturic acid metabolites. Theremainder of the dose is recovered in the feces. No unchangedrabeprazole is excreted in the urine or feces. - View all
- 8.7 Biochem/physiol Actions
- Rabeprazole sodium is gastric proton pump inhibitor. It suppresses the production of acid in the stomach by inhibiting the gastric H+/K+ATPase (hydrogen-potassium adenosine triphosphatase) at the secretory surface of the gastric parietal cell. Rabeprazole sodium has been used clinically to treat acid-reflux disorders (GERD), peptic ulcer disease, H. pylori eradication, and prevent gastroinetestinal bleeds associated with NSAID use.
- 8.8 Merck
- 14,8089
- 8.9 Uses
- It belongs to national second-class drug that can be used for the treatment of gastric ulcer. It can be used for the treatment of peptic ulcer, gastroesophageal reflux disease, zollinger-ellison syndrome and other diseases.
- 8.10 Chemical Properties
- White Crystalline Solid
- 8.11 Uses
- anthelminthic, antiseptic, expectorant
- 8.12 Uses
- antibacterial and antifungal agent effective against gram-positive and gram-negative bacteria, yeast and fungi
- 8.13 Uses
- A partially reversible gastric proton pump inhibitor
- 8.14 Brand name
- Aciphex (Eisai Medical Research) .
9. Computational chemical data
- Molecular Weight: 381.42447g/mol
- Molecular Formula: C18H20N3NaO3S
- Compound Is Canonicalized: True
- XLogP3-AA: null
- Exact Mass: 381.11230696
- Monoisotopic Mass: 381.11230696
- Complexity: 446
- Rotatable Bond Count: 8
- Hydrogen Bond Donor Count: 0
- Hydrogen Bond Acceptor Count: 7
- Topological Polar Surface Area: 81.5
- Heavy Atom Count: 26
- Defined Atom Stereocenter Count: 0
- Undefined Atom Stereocenter Count: 1
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 2
- CACTVS Substructure Key Fingerprint: AAADceB7MCBAAAAAAAAAAAAAAAAAAWAAAAA8QAAAAAAAAFgB/AAAHgQAAAAADAzl3ga/1rYIFAqgAzRnZEDK2C1xMrAJ2CA+fJiMbuLkuZuWOCjvgBrI6CcQAAAOAAAAAAAAACAAAAAAAAAAQAAAAAAAAA==
10. Question & Answer
-
Rebeprazole sodium is a white to slightly yellow crystalline or crystalline powder. The contents of the enteric-coated capsule are off-white or pale yellow powder. What are the uses of Rebeprazole Sod..
-
Rebeprazole sodium is a typical representative of reversible proton pump inhibitors. It can regulate and reduce the secretion of gastric acid without causing excessive suppression. Therefore, it can a..
-
Rebeprazole sodium enteric capsules are a proton pump inhibitor that inhibits the activity of the proton pump in gastric mucosal cells, thereby suppressing the secretion of gastric acid. Its effect on..
-
Indications 1. Active duodenal ulcers; 2. Active benign gastric ulcers; 3. Symptomatic erosive or ulcerative gastroesophageal reflux disease (GERD); 4. Eradication of Helicobacter pylori in combinati..
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