Rabeprazole

Iupac Name：2-[[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methylsulfinyl]-1H-
benzimidazole

Molecular Weight：359.44264

Modify Date.: 2022-11-07 20:18

Introduction: Rabeprazole is an antiulcer drug in the class of proton pump inhibitors.Target: Proton PumpRabeprazole belongs to a class of antisecretory compounds (substituted benzimidazole proton-pump inhibitors) that do not exhibit anticholinergic or histamine H2-receptor antagonist properties, but suppress gastric acid secretion by inhibiting the gastric H+/K+ATPase (hydrogen-potassium adenosine triphosphatase) at the secretory surface of the gastric parietal cell. Because this enzyme is regarded a View more+

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1. Names and Identifiers

1.1 Name: Rabeprazole
1.2 Synonyms: (±)-Rabeprazole 1H-1,3-benzimidazol-2-yl [4-(3-methoxypropoxy)-3-methyl-2-pyridinyl]methyl sulfoxide-sodium salt 1H-Benzimidazole, 2-[[[4-(3-methoxypropoxy)-3-methyl-2-pyridinyl]methyl]sulfinyl]- 2-(CHOLROMETHYL)-4-(3-METHOXYPROPOXY)-3-METHYLPYRIDINE 2-[[(3-METHYL-4-(3-METHOXYPROPOXY)-2-PYRIDINYL)METHYL]SULPHINYL]-1H-BENZIMIDAZOLE 2-[[[3-Methyl-4-(3-methoxypropoxy)-2-pyridinyl]methyl]sulfinyl]-1H-benzimidazole 2-[[[3-Methyl-4-(3-methoxypropoxy)-2-pyridyl]methyl]sulfinyl]-1H-benzimidazole 2-[[[4-(3-Methoxypropoxy)-3-methyl-2-pyridinyl]methyl]sulfinyl]-1H-benzimidazole 2-[[[4-(3-Methoxypropoxy)-3-methyl-2-pyridyl]methyl]sulfinyl]-1H-benzimidazole 2-[[[4-(3-Methoxypropoxy)-3-methyl-2-pyridyl]methyl]sulfinyl]benzimidazole 2-[[[4-(3-Methoxypropoxy)-3-methylpyridin-2-yl]methyl]sulfinyl]-1H-benzimidazole 2-[[4-(3-methoxypropoxy)-3-methyl-pyridin-2-yl]methylsulfinyl]-1h-benzoimidazole 2-[4-(3-Methoxy-propoxy)-3-methyl-pyridin-2-ylmethanesulfinyl]-1H-benzoimidazole Dexrabeprazol Habeprazole LY 307640 ly-307640 Newprazole Pariets Rabeloc Rabemax Rabiral

1.3 CAS No.: 117976-89-3

1.4 CID: 5029

1.5 EINECS(EC#): 601-501-2

1.6 Molecular Formula: C18H21N3O3S (isomer)

1.7 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)

1.8 InChkey: YREYEVIYCVEVJK-UHFFFAOYSA-N

1.9 Canonical Smiles: CC1=C(C=CN=C1CS(=O)C2=NC3=CC=CC=C3N2)OCCCOC

1.10 Isomers Smiles: CC1=C(C=CN=C1CS(=O)C2=NC3=CC=CC=C3N2)OCCCOC

2. Properties

2.1 Density: 1.33

2.1 Melting point: 99 - 100

2.1 Refractive index: 1.505

2.1 Flash Point: 319.1 oC

2.1 Precise Quality: 359.13000

2.1 PSA: 96.31000

2.1 logP: 3.85510

2.1 Appearance: white to yellowish crystalline powder

2.2 Color/Form: White crystals from CH2Cl2/ether

2.3 pKa: 9.57±0.10(Predicted)

2.4 Water Solubility: Soluble Appearance:white to yellowish crystalline powder
Hazard Symbols:UN NO.

2.5 StorageTemp: Store in original container in a cool dark place.

3. Use and Manufacturing

3.1 Usage: antiulcerative;proton pump inhibitors

4. Safety and Handling

4.1 Hazard Codes: Xi

4.1 Risk Statements: R36/38

4.1 Safety Statements: S26;S37/39

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.

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin irritation, Category 2

Eye irritation, Category 2

Specific target organ toxicity \u2013 single exposure, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area.
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. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.
Storage	P403+P233 Store in a well-ventilated place. Keep container tightly closed. P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. Synthesis Route

117976-89-3Total: 8 Synthesis Route

117977-21-6 100 Suppliers

117976-89-3 139 Suppliers

Literatures:
US2009/5570 A1, ; Page/Page column 3-4 ;
Yield: ~90%

924663-40-1 3 Suppliers

117976-89-3 139 Suppliers

Literatures:
US2007/249662 A1, ; Page/Page column 5 ;
Yield: ~5%

924663-38-7 13 Suppliers

117976-89-3 139 Suppliers

Literatures:
EP1921075 A2, ; Page/Page column 8 ;
Yield: null

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7. Precursor and Product

precursor:

1080503-68-9

924663-40-1

408332-88-7

937-14-4

1080503-70-3

924663-38-7

117977-21-6

13811-71-7

product :

117976-90-6

8. Other Information

8.0 Uses: antiulcerative;proton pump inhibitors

8.1 Brand name: Aciphex (Eisai Medical Research) .

9. Computational chemical data

Molecular Weight: 359.44264g/mol
Molecular Formula: C₁₈H₂₁N₃O₃S
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 359.13036271
Monoisotopic Mass: 359.13036271
Complexity: 440
Rotatable Bond Count: 8
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 6
Topological Polar Surface Area: 96.3
Heavy Atom Count: 25
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: 1
CACTVS Substructure Key Fingerprint: AAADceB7MABAAAAAAAAAAAAAAAAAAWAAAAA8QAAAAAAAAFgB/AAAHgQQAAAADAzl3ga/1rbJlAqgAzRnZEDK2i3xMrAJ2SA+fJiMbuLkuZuWOCjvkBrI6CcQAAAOAAAAAAAAACAAAAAAAAAAQAAAAAAAAA==