Rabeprazole (CED0004199)

Record Information

Version

1.0

Creation Date

2016-05-26 06:42:52 UTC

Update Date

2026-08-20 00:37:06 UTC

Accession Number

CHEM035842

Identification

Common Name

Rabeprazole

Class

Small Molecule

Description

Rabeprazole is an organic compound with the chemical formula C18H21N3O3S and an average molecular weight of 359.44 g/mol. Rabeprazole belongs to the sulfinylbenzimidazoles, a subclass of benzimidazoles within the organic compounds. It is categorized as an organoheterocyclic compound. The compound is found in or released from ten recorded sources. These include healthcare, pharmaceuticals and veterinary products, specifically drugs for acid related disorders, and food, food processing and cookware for food preservation. It is also associated with household cleaning and consumer products, specifically other smoking requisites, and electrical and electronic equipment, including electrodes, magnets, amplifiers, conductors or conductive bodies characterised by the conductive materials, and electrically stimulated smoking devices, among two others. The recorded route of exposure for this compound is oral. In terms of its biological activity, rabeprazole acts on one recorded protein target, functioning as an inhibitor of Potassium-transporting ATPase alpha chain 1 (ATP4A).

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Clofezone	ChEBI
Eraloc	Kegg
Aciphex	HMDB, MeSH
Habeprazole	HMDB
Pariet	HMDB, MeSH
Pariets	HMDB
Rabeprazole sodium	HMDB, MeSH
Sodium rabeprazole	HMDB
Dexrabeprazole	MeSH, HMDB
1H-Benzimidazole, 2-(((4-(3-methoxypropoxy)-3-methyl-2-pyridinyl)methyl)sulfinyl)-, sodium salt	MeSH, HMDB
2-((4-(3-Methoxypropoxy)-3-methylpyridin-2-yl)methylsulfinyl)-1H-benzimidazole	MeSH, HMDB
Sodium, rabeprazole	MeSH, HMDB

Chemical Formula

C₁₈H₂₁N₃O₃S

Average Molecular Mass

359.443 g/mol

Monoisotopic Mass

359.130 g/mol

CAS Registry Number

117976-89-3

IUPAC Name

2-{[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methanesulfinyl}-1H-1,3-benzodiazole

Traditional Name

rabeprazole

SMILES

COCCCOC1=C(C)C(CS(=O)C2=NC3=CC=CC=C3N2)=NC=C1

InChI Identifier

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)

InChI Key

YREYEVIYCVEVJK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sulfinylbenzimidazoles. These are polycyclic aromatic compounds containing a sulfinyl group attached at the position 2 of a benzimidazole moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzimidazoles

Sub Class

Sulfinylbenzimidazoles

Direct Parent

Sulfinylbenzimidazoles

Alternative Parents

Substituents

Sulfinylbenzimidazole
Alkyl aryl ether
Methylpyridine
Pyridine
Benzenoid
Azole
Imidazole
Heteroaromatic compound
Sulfoxide
Sulfinyl compound
Ether
Dialkyl ether
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

sulfoxide (CHEBI:8768 )
pyridines (CHEBI:8768 )
benzimidazoles (CHEBI:8768 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.34 g/L	ALOGPS
logP	2.04	ALOGPS
logP	2.09	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	9.35	ChemAxon
pKa (Strongest Basic)	4.24	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	77.1 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	98.07 m³·mol⁻¹	ChemAxon
Polarizability	39.64 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-009e-9843000000-7b2764dc90023b55c85c	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03dl-2159000000-f97510bdc8045ab08ca6	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-006x-5792000000-af268bb77b35247f0f41	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00dl-9800000000-6bea6647768de1869c4d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-066r-1938000000-25678fb8a17be5befc29	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0900000000-c503bc067607aca1451e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-2910000000-aa7552fe843abc4a67e6	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0119000000-c5f221b3ffcf7b5cc55c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0900000000-3214248b0f4d9b60f153	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0900000000-9c4b8759dd61ba097216	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-0093000000-14b0419adbad3c76149e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0229-1950000000-ce8b99f657880db6f1d0	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-08ml-2910000000-2fbee5190b8417e0ac8a	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
1085.0	Log mg/kg	[610:1900]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
242	Drugs for acid related disorders	Healthcare, pharmaceuticals & veterinary products	Not Available
505	Amplifiers	Electrical & Electronic Equipment	Not Available
511	Conductors Or Conductive Bodies Characterised By The Conductive Materials	Electrical & Electronic Equipment	Not Available
518	Electrically Stimulated Smoking Devices	Electrical & Electronic Equipment	Not Available
519	Electrodes	Electrical & Electronic Equipment	Not Available
527	Magnets	Electrical & Electronic Equipment	Not Available
530	Radio Transmission Systems	Electrical & Electronic Equipment	Not Available
531	Relays	Electrical & Electronic Equipment	Not Available
545	Food Preservation	Food, food processing & cookware	Not Available
560	Other Smoking Requisites	Household cleaning & consumer products	Not Available
580	Manufacture Preparation Of Tobacco Products	Industrial manufacturing & chemical processing	Not Available
596	Acaricides	Agriculture & land management	Not Available
611	Anti Perspirants Or Body Deoderants	Personal care & cosmetics	Not Available
613	Depilatories	Personal care & cosmetics	Not Available
614	Essential Oils Or Perfumes	Personal care & cosmetics	Not Available
615	Eye Makeup Products	Personal care & cosmetics	Not Available
617	Lip Care Products	Personal care & cosmetics	Not Available
618	Lip Makeup Products	Personal care & cosmetics	Not Available
632	Apparel	Textiles, leather & furnishings	Not Available

Pathways

4 pathways

Rabeprazole Action Pathway

Rabeprazole Metabolism Pathway

Rabeprazole Antacid Action Pathway

Rabeprazole Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Fatty acid synthase	P49327	Humans	Predicted (SEA)	6.69503
Click to view 3D structure	D(3) dopamine receptor	P35462	Humans	Predicted (SEA)	355.849
Click to view 3D structure	Broad substrate specificity ATP-binding cassette transporter ABCG2	Q9UNQ0	Humans	Predicted (SEA)	176.796
Click to view 3D structure	Alpha-2B adrenergic receptor	P18089	Humans	Predicted (SEA)	294.27
Click to view 3D structure	Cytochrome P450 2C19	P33261	Humans	Predicted (SEA)	1015.78
Click to view 3D structure	Adenosine receptor A3	P0DMS8	Humans	Predicted (SEA)	375.622
Click to view 3D structure	Cytochrome P450 2D6	P10635	Humans	Predicted (SEA)	1619.96
Click to view 3D structure	Luciferin 4-monooxygenase	P08659	Photinus pyralis	Predicted (SEA)	224.284
Click to view 3D structure	Cytochrome P450 1A2	P05177	Humans	Predicted (SEA)	1456.56
Click to view 3D structure	Cytochrome P450 2C8	P10632	Humans	Predicted (SEA)	481.887
Click to view 3D structure	Cytochrome P450 3A4	P08684	Humans	Predicted (SEA)	3482.58
Click to view 3D structure	Ferroportin	Q9JHI9	Mus musculus	Predicted (SEA)	8.40772
Click to view 3D structure	Pup--protein ligase	Q8NQE1	Corynebacterium glutamicum	Predicted (SEA)	2.02408
Click to view 3D structure	Replicase polyprotein 1ab	P0DTD1	SARS-CoV-2	Predicted (SEA)	441.483
Click to view 3D structure	D(2) dopamine receptor	P14416	Humans	Predicted (SEA)	2221.35
Click to view 3D structure	Vascular endothelial growth factor receptor 2	P35968	Humans	Predicted (SEA)	3440.94
Click to view 3D structure	Photoreceptor-specific nuclear receptor	Q9Y5X4	Humans	Predicted (SEA)	274.263
Click to view 3D structure	Aurora kinase B	Q96GD4	Humans	Predicted (SEA)	3126.81
Click to view 3D structure	Voltage-dependent T-type calcium channel subunit alpha-1H	O95180	Humans	Predicted (SEA)	436.812
Click to view 3D structure	Vascular endothelial growth factor receptor 1	P17948	Humans	Predicted (SEA)	2725.11
Click to view 3D structure	Aurora kinase A	O14965	Humans	Predicted (SEA)	3177.65
Click to view 3D structure	Short transient receptor potential channel 4	Q9QUQ5	Mus musculus	Predicted (SEA)	630.89
Click to view 3D structure	Fibroblast growth factor receptor 1	P11362	Humans	Predicted (SEA)	3237.67
Click to view 3D structure	NAD(+) hydrolase SARM1	Q6SZW1	Humans	Predicted (SEA)	0.389246
Click to view 3D structure	Methionine aminopeptidase	P0AE18	Escherichia coli (strain K12)	Predicted (SEA)	25.6902