88546-55-8 Usage
Description
OMEPRAZOLE RELATED COMPOUND A (15 MG) (OMEPRAZOLE SULFONE) (AS) 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). It is a light yellow solid.
Uses
Used in Pharmaceutical Industry:
OMEPRAZOLE RELATED COMPOUND A (15 MG) (OMEPRAZOLE SULFONE) (AS) is used as a metabolite of omeprazole for understanding the drug's metabolism and potential effects on the activity of other drugs metabolized by the same enzyme, CYP2C19. This information is crucial for drug interaction studies and optimizing therapeutic regimens.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 88546-55-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,8,5,4 and 6 respectively; the second part has 2 digits, 5 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 88546-55:
(7*8)+(6*8)+(5*5)+(4*4)+(3*6)+(2*5)+(1*5)=178
178 % 10 = 8
So 88546-55-8 is a valid CAS Registry Number.
InChI:InChI=1/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)
88546-55-8Relevant articles and documents
Omeprazole sodium related substance preparation method
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Paragraph 0044; 0048; 0050; 0052; 0054; 0056; 0057-0058; 006, (2018/09/12)
The invention provides a method for preparing two sulfone impurities of omeprazole sodium by a one-pot method. The method includes: 1) subjecting a compound 3 and a compound 4 to condensation reactionto generate omeprazole sulfide 5; 2) subjecting omeprazole sulfide 5 to oxidation reaction under the action of sodium hypochlorite to generate a sulfone impurity 1 and a sulfone impurity 2. The method has advantages that convenience in operation is achieved, and high yield and high purity in acquisition of the sulfone impurities 1 and 2 are realized.
Method for synthesizing esomeprazole sodium impurity I
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Paragraph 0042-0055, (2018/05/16)
The invention discloses a method for synthesizing an esomeprazole sodium impurity I. The method comprises the following steps: by taking omeprazole thioether as an initial raw material, performing low-temperature oxidation, quenching, extracting, performing low-temperature rotary evaporation so as to obtain a crude product of an esomeprazole sodium impurity I, and further performing a salting reaction, thereby obtaining an impurity I, namely a sodium salt. The method has the characteristics of being mild in reaction, simple and convenient to operate, high in product purity, and the like, the purity of the product is up to 99.5%, and the yield of the product is up to 80% or greater. After being calibrated, the product can be directly used as a reference substance of an impurity I, and the purchase cost of the impurity I at a quality study stage is reduced.
