Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1387)
Drug Name
Rabeprazole sodium
Synonyms
Rabeprazole sodium [USAN]; Rabeprazole sodium salt; Rebeprazole sodium; (S)-Rabeprazole Sodium Salt; 117976-90-6; 1H-Benzimidazole, 2-(((4-(3-methoxypropoxy)-3-methyl-2-pyridinyl)methyl)sulfinyl)-, sodium salt; 2-(((4-(3-Methoxypropoxy)-3-methyl-2-pyridyl)methyl)sulfinyl)benzimidazole sodium salt; AK-94764; Aciphex Sodium; C18H20N3NaO3S; CHEBI:8769; DSSTox_CID_24205; DSSTox_GSID_44205; DSSTox_RID_80118; E 3810; Habeprazole Sodium; LY 307640 sodium; LY-307640; Pariet; Q-201655; RABEPRAZOLE SODIUM
Indication Gastro-oesophageal reflux disease [ICD11: DA22] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 381.4 Topological Polar Surface Area 81.5
Heavy Atom Count 26 Rotatable Bond Count 8
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 7
Cross-matching ID
PubChem CID
14720269
ChEBI ID
CHEBI:8769
CAS Number
117976-90-6
TTD Drug ID
D0KL4J
Formula
C18H20N3NaO3S
Canonical SMILES
CC1=C(C=CN=C1CS(=O)C2=NC3=CC=CC=C3[N-]2)OCCCOC.[Na+]
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
InChIKey
KRCQSTCYZUOBHN-UHFFFAOYSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Desmethyl?rabeprazole?thioether DM015905
15166260
Unclear - Unclear 1 [3]
Desmethylrabeprazole DM015559
9906180
Unclear - Unclear 1 [4]
Rabeprazole?sulfone DM015781
11740183
Unclear - Unclear 1 [4]
Rabeprazole?thioether DM015574
9949996
Unclear - Unclear 1 [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR010025 Rabeprazole sodium Rabeprazole?thioether Unclear - Unclear Unclear [5]
MR010026 Rabeprazole sodium Desmethyl?rabeprazole?thioether Unclear - Unclear Unclear [3]
MR010027 Rabeprazole sodium Desmethylrabeprazole Unclear - Unclear CYP2C19 [4]
MR010028 Rabeprazole sodium Rabeprazole?sulfone Unclear - Unclear CYP3A4 [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
References
1 Rabeprazole Sodium was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Effects of clarithromycin and verapamil on rabeprazole pharmacokinetics between CYP2C19 genotypes. Eur J Clin Pharmacol. 2006 Aug;62(8):597-603.
3 Simultaneous determination of rabeprazole and its two active metabolites in human urine by liquid chromatography with tandem mass spectrometry and its application in a urinary excretion study
4 Determination of rabeprazole enantiomers and their metabolites by high-performance liquid chromatography with solid-phase extraction
5 Determination of rabeprazole and its active metabolite, rabeprazole thioether in human plasma by column-switching high-performance liquid chromatography and its application to pharmacokinetic study

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