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

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

2

HS Code 

29333990

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.

OMEPRAZOLE RELATED COMPOUND A (15 MG) (OMEPRAZOLE SULFONE) (AS)(88546-55-8)Related Product Information

• 5-METHOXY-2-[(3,5-DIMETHYL-2-PYRIDINYL)-METHYLSULFINYL]-BENZIMIDAZOLE
• 8-Methoxy-1,3-dimethyl-12-thioxo-pyrido[123,4]imidazo[1,2-a]benzimidazol-2-(12H)-one
• 5-METHOXY-2-[((4-METHOXY-3,5-DIMETHYL-1-OXIDO-2-PYRIDINYL)METHYL)SULFINYL]-BENZIMIDAZOLE
• 4-Hydroxy Omeprazole Sulfide
• 2-[[(3,5-DiMethyl-2-pyridinyl)Methyl]thio]-6-Methoxy-1H-benziMidazole
• Ufiprazole
• (S)-4-Desmethoxy-4-chloro Omeprazole
• Omeprazole
• Ondansetron EP Impurity H
• ammonium 1-(5-methoxy-1H-benzo[d]imidazol-2-yl)-3,5-dimethyl-4-oxo-1,4-dihydropyridine-2-carboxylate
• 4-Hydroxy Omeprazole
• omeprazole acid
• 2-[(5-CARBOXY-4-METHOXY-3-METHYLPYRID-2-YL)-METHYLSULFO]-5-METHOXYBENZIMIDAZOLE
• 2-MERCAPTO-5-METHOXYBENZIMIDAZOLE
• Omeprazole EP Impurity G
• Omeprazole Sulfone N-Oxide
• OMEPRAZOLE IMP. C (EP): 5-METHOXY-2-[[(4-METHOXY-3,5-DIMETHYLPYRIDIN-2-YL)METHYL]SULPHANYL]-1H-BENZIMIDAZOLE (UFIPRAZOLE) MM STANDARD
• Omeprazole Impurity (2-[[(5-hydroxy-1H-benzimidazol-2-yl)sulfinyl]methyl]-3,5-dimethy-l-4(1H)-pyridone)
• Omeprazole Related Compound A