Omeprazole sulfide
(Synonyms: 奥美拉唑硫醚,Ufiprazole) 目录号 : GC44509
An intermediate for omeprazole synthesis
Cas No.:73590-85-9
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Omeprazole sulfide is an intermediate used in the production of the gastric proton pump inhibitors, omeprazole and esomeprazole . As a degradation product, it is reported to be a direct-acting inhibitor of cytochrome P450 2C19 in pooled human liver microsomes (IC50 = 9.7 µM).
| Cas No. | 73590-85-9 | SDF | |
| 别名 | 奥美拉唑硫醚,Ufiprazole | ||
| Canonical SMILES | COC1=CC=C2C(N=C(SCC3=C(C)C(OC)=C(C)C=N3)N2)=C1 | ||
| 分子式 | C17H19N3O2S | 分子量 | 329.4 |
| 溶解度 | DMF: 30 mg/ml,DMF:PBS(pH 7.2)(1:1): 0.5 mg/ml,DMSO: 30 mg/ml,Ethanol: 25 mg/ml | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 3.0358 mL | 15.1791 mL | 30.3582 mL |
| 5 mM | 0.6072 mL | 3.0358 mL | 6.0716 mL |
| 10 mM | 0.3036 mL | 1.5179 mL | 3.0358 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Engineering of a Baeyer-Villiger monooxygenase reveals key residues for the asymmetric oxidation of Omeprazole sulfide
Chem Commun (Camb) 2022 Nov 29;58(95):13246-13249.PMID:36354966DOI:10.1039/d2cc04161h.
The structure-guided engineering of a BVMO from Rhodococcus aetherivorans (RaBVMO) was performed for its asymmetric sulfoxidation activity toward Omeprazole sulfide. Based on the structural model of RaBVMO, key residues that line the substrate entrance tunnel and the binding pocket were identified, and variants were interrogated with sulfides of varied sizes. The best mutant MT2 (F442A/R337P) was obtained with a specific activity of 2.54 U g-1 and excellent enantioselectivity (≥99%, S) toward Omeprazole sulfide, while wild-type RaBVMO exhibited no activity. Further structural analysis reveals that both mutations, F442A and R337P, could render an expanded substrate tunnel and an enlarged substrate binding pocket to enable easier access to the catalytic center for Omeprazole sulfide. This work provides valuable guidance for engineering-related BVMOs for improved activity and enantio-preference toward bulky substrates.
Regioselective C-H hydroxylation of Omeprazole sulfide by Bacillus megaterium CYP102A1 to produce a human metabolite
Biotechnol Lett 2017 Jan;39(1):105-112.PMID:27640009DOI:10.1007/s10529-016-2211-3.
Objectives: To find a simple enzymatic strategy for the efficient synthesis of the expensive 5'-hydroxyomeprazole sulfide, a recently identified minor human metabolite, from Omeprazole sulfide, which is an inexpensive substrate. Results: The practical synthetic strategy for the 5'-OH Omeprazole sulfide was accomplished with a set of highly active CYP102A1 mutants, which were obtained by blue colony screening from CYP102A1 libraries with a high conversion yield. The mutant and even the wild-type enzyme of CYP102A1 catalyzed the high regioselective (98 %) C-H hydroxylation of Omeprazole sulfide to 5'-OH Omeprazole sulfide with a high conversion yield (85-90 %). Conclusions: A highly efficient synthesis of 5'-OH Omeprazole sulfide was developed using CYP102A1 from Bacillus megaterium as a biocatalyst.
Solubility of Omeprazole sulfide in Different Solvents at the Range of 280.35-319.65 K
J Solution Chem 2013;42(12):2342-2353.PMID:24319302DOI:10.1007/s10953-013-0110-y.
Solubility data were measured for Omeprazole sulfide in ethanol, 95 mass-% ethanol, ethyl acetate, isopropanol, methanol, acetone, n-butanol and n-propanol in the temperature range from 280.35 to 319.65 K by employing the gravimetric method. The solubilities increase with temperature and they are in good agreement with the calculated solubility of the modified Apelblat equation and the λh equation. The experimental solubility and correlation equation in this work can be used as essential data and model in the purification process of Omeprazole sulfide. The thermodynamic properties of the solution process, including the Gibbs energy, enthalpy, and entropy were calculated using the van't Hoff equation.
Whole-cell oxidation of Omeprazole sulfide to enantiopure esomeprazole with Lysinibacillus sp. B71
Bioresour Technol 2011 Sep;102(17):7621-6.PMID:21683578DOI:10.1016/j.biortech.2011.05.052.
Production of enantiopure esomeprazole by biocatalysis is of great demand by pharmaceutical industry. A Gram-positive bacterium oxidizing Omeprazole sulfide 1a (5-methoxy-2-[((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)thio]-1H-benzoimidazole) to (S)-sulfoxide esomeprazole 2a (S)-5-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl) methylsulfinyl]-3H-benzoimidazole was isolated from soil polluted with elemental sulfur. The strain exhibited the highest identity with the genus Lysinibacillus and catalyzed oxidation of 1a into enantiopure esomeprazole with conversion of 77% in a stirred bioreactor, fed-batch culture. No consecutive oxidation of (S)-sulfoxide to sulfone was observed during whole-cell catalysis. The unique characteristics of the catalyst provide a solid basis for further improvement and development of sustainable green bioprocess.
Omeprazole, a specific inhibitor of gastric (H+-K+)-ATPase, is a H+-activated oxidizing agent of sulfhydryl groups
J Biol Chem 1985 Apr 25;260(8):4591-7.PMID:2985559doi
Omeprazole (5-methoxy-2-[[(4-methoxy-3,5- dimethylpyridinyl)methyl]sulfinyl]-1H-benzimidazole) appeared to inhibit gastric (H+-K+)-ATPase by oxidizing its essential sulfhydryl groups, since the gastric ATPase inactivated by the drug in vivo or in vitro recovered its K+-dependent ATP hydrolyzing activity upon incubation with mercaptoethanol. Biological reducing agents like cysteine or glutathione, however, were unable to reverse the inhibitory effect of omeprazole. Moreover, acidic environments enhanced the potency of omeprazole. For example, in vivo pretreatment of rats with carbachol, a secretagogue, enhanced the activity of omeprazole to inhibit gastric (H+-K+)-ATPase, while pretreatment with cimetidine, an antisecretory agent, reduced its potency. In vitro, lowering pH of incubation media from 7.4 to 5.0 improved the ability of omeprazole to inhibit hog gastric (H+-K+)-ATPase almost 60-fold. The inhibitory effect of the drug was accompanied by a dose-dependently decreased amount of free sulfhydryl groups in the isolated hog gastric membranes. The chemical reactivity of omeprazole with mercaptans is also consistent with the biological action of omeprazole. The drug, only under acidic conditions, reacted with a stoichiometric amount of ethyl mercaptan (or beta-mercaptoethanol) to produce regio-isomers of N-sulfenylated Omeprazole sulfide (5-methoxy-2[[(4-methoxy-3,5- dimethyl-2-pyridinyl)methyl]thio]-1- or 3-(ethylthio)benzimidazole). The N-sulfenylated compound reacted at neutral pH with another stoichiometric amount of ethyl mercaptan to produce Omeprazole sulfide quantitatively. The gastric polypeptides of 100 kilodaltons representing (H+-K+)-ATPase in the rat gastric mucosa or isolated hog gastric membranes were covalently labeled with [14C]omeprazole. The radioactive label bound to the ATPase, however, could not be displaced by mercaptoethanol under the identical conditions where the ATPase activity was fully restored. These observations suggest that the essential sulfhydryl groups which reacted with omeprazole did not form a stable covalent bond with the drug, but rather that they further reacted with adjacent sulfhydryl groups to form disulfides which could be reduced by mercaptoethanol.