OMEPRAZOLE RELATED COMPOUND A (15 MG) (OMEPRAZOLE SULFONE) (AS) CAS 88546-55-8

Introduction：Basic information about OMEPRAZOLE RELATED COMPOUND A (15 MG) (OMEPRAZOLE SULFONE) (AS) CAS 88546-55-8, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

OMEPRAZOLE RELATED COMPOUND A (15 MG) (OMEPRAZOLE SULFONE) (AS) Basic information

• Product Name: OMEPRAZOLE RELATED COMPOUND A (15 MG) (OMEPRAZOLE SULFONE) (AS)
• Synonyms: Esomeprazole sodium D(H168/66);Esomeprazole Sodium?CP Impurity Ⅰ;5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulfonyl]benzimidazole;EsoMeprazol iMpurity D;OMeprazole IMpurity-D(EP) (USP R C A);6-Methoxy-2-((4-Methoxy-3,5-diMethylpyridin-2-yl)Methylsulfonyl)-1H-benzo[d]iMidazole;OMeprazole EP IMpurity D;5-Methoxy-2-[[(4-Methxoy-3,5-diMethylpyridin-2-yl)Methyl]sulfonyl]-1H-benziMidazole
• CAS: 88546-55-8
• MF: C17H19N3O4S
• MW: 361.42
• Product Categories: Various Metabolites and Impurities;Intermediates & Fine Chemicals;Metabolites;Pharmaceuticals;Acid pump inhibitors;Isotopically Labeled Pharmaceutical Reference Standard
• Mol File: 88546-55-8.mol

OMEPRAZOLE RELATED COMPOUND A (15 MG) (OMEPRAZOLE SULFONE) (AS) Chemical Properties

• Melting point: 80-82°C
• Boiling point: 599.3±60.0 °C(Predicted)
• density: 1.331±0.06 g/cm3(Predicted)
• storage temp.: Inert atmosphere,2-8°C
• solubility: ≥40.6 mg/mL in DMSO,≥19.9 mg/mL in EtOH,insoluble in H2O
• form: Solid
• pka: 7.97±0.10(Predicted)
• color: White to off-white
• BRN: 8347309
• Major Application: pharmaceutical (small molecule)
• InChI: 1S/C17H19N3O4S/c1-10-8-18-15(11(2)16(10)24-4)9-25(21,22)17-19-13-6-5-12(23-3)7-14(13)20-17/h5-8H,9H2,1-4H3,(H,19,20)
• InChIKey: IXEQEYRTSRFZEO-UHFFFAOYSA-N
• SMILES: O=S(C1=NC2=CC(OC)=CC=C2N1)(CC3=NC=C(C)C(OC)=C3C)=O

Safety Information

• Hazard Codes: Xi
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 2
• HS Code: 29333990
• Storage Class: 11 - Combustible Solids
• Hazard Classifications: Acute Tox. 4 Oral Aquatic Chronic 2

OMEPRAZOLE RELATED COMPOUND A (15 MG) (OMEPRAZOLE SULFONE) (AS) Usage And Synthesis

Description

Omeprazole sulfone is the major metabolite of the gastric proton pump inhibitor, omeprazole . It is produced by cytochrome P450 (CYP)3A4 sulfoxidation of esomeprazole and is found in plasma. Omeprazole sulfone has been shown to act as a reversible direct-acting and metabolism-dependent inhibitor of CYP2C19 in pooled human liver microsomes (IC₅₀ = 18 μM).

Chemical Properties

Light Yellow Solid

Uses

A metabolite of Omeprazole.

Definition

ChEBI: Omeprazole sulfone is a sulfoxide and a member of benzimidazoles.

in vitro

omeprazole sulfone has been shown to act as a reversible direct-acting and metabolism-dependent inhibitor of cyp2c19 in pooled human liver microsomes with an ic50 of 18 μm [1].

in vivo

three hours after intake of 20 mg omeprazole only, the geometric mean plasma concentration of omeprazole sulfone were 106 nmol/l in 22 samples from subjects known to be extensive cyp2c19 metabolizers (em) and 672 nmol/l in the five subjects known to be poor cyp2c19 metabolizers (pm). the mean log10(omeprazole/omeprazole sulfone) ratio was 0.18 [4].

references

[1] nebert d w, russell d w. clinical importance of the cytochromes p450[j]. the lancet, 2002, 360(9340): 1155-1162.
[2] bel a, andersson t b, antonsson m, et al. stereoselective metabolism of omeprazole by human cytochrome p450 enzymes[j]. drug metabolism and disposition, 2000, 28(8): 966-972.
[3] nebert d w, russell d w. clinical importance of the cytochromes p450[j]. the lancet, 2002, 360(9340): 1155-1162.
[4] bttiger y. use of omeprazole sulfone in a single plasma sample as a probe for cyp3a4[j]. european journal of clinical pharmacology, 2006, 62(8): 621-625.