(S)-Lansoprazole
(Synonyms: 左旋兰索拉唑) 目录号 : GC41091
A proton pump inhibitor
Cas No.:138530-95-7
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
(S)-Lansoprazole is a proton pump inhibitor that irreversibly inhibits H+/K+-stimulated ATPase pumps in parietal cells (IC50 = 5.2 µM), inhibiting gastric acid secretion and increasing intragastric pH. It also inhibits acid formation in isolated canine parietal cells (IC50 = 82 µM). (S)-Lansoprazole is an enantiomerically pure form of lansoprazole . Both (S)- and (R)-lansoprazole are pharmacologically active with similar potencies.
| Cas No. | 138530-95-7 | SDF | |
| 别名 | 左旋兰索拉唑 | ||
| Canonical SMILES | CC1=C(C[S@@](C2=NC(C=CC=C3)=C3N2)=O)N=CC=C1OCC(F)(F)F | ||
| 分子式 | C16H14F3N3O2S | 分子量 | 369.4 |
| 溶解度 | DMF: 30 mg/ml,DMSO: 30 mg/ml,DMSO:PBS (pH 7.2) (1:1): 0.5 mg/ml,Ethanol: 5 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 | 2.7071 mL | 13.5355 mL | 27.0709 mL |
| 5 mM | 0.5414 mL | 2.7071 mL | 5.4142 mL |
| 10 mM | 0.2707 mL | 1.3535 mL | 2.7071 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。
Correlation between R/S enantiomer ratio of lansoprazole and CYP2C19 activity after single oral and enteral administration
Chirality 2010 Jul;22(7):635-40.PMID:20014035DOI:10.1002/chir.20810.
The purpose of this study was to investigate whether CYP2C19 activity can be estimated from plasma concentrations of lansoprazole enantiomers 4 h (C(4h)) after single administration by oral and enteral routes. Sixty-nine subjects, 22 homozygous extensive metabolizers (homEMs), 32 heterozygous EMs (hetEMs), and 15 poor metabolizers (PMs), participated in the study. After a single oral or enteral dose of racemic lansoprazole (30 mg), plasma concentrations of lansoprazole enantiomers were measured 4 h postdose. The R/S ratio of lansoprazole at 4 h differed significantly among the three groups (P < 0.0001) regardless of the administration route. The R/S ratio of lansoprazole in CYP2C19 PMs ranged from 3.0 to 13.7, whereas in homEMs and hetEMs the ratio ranged from 8.6 to 90 and 2.1 to 122, respectively. The relationship between (S)-Lansoprazole concentration and R/S ratio of lansoprazole at C(4h) is given by the following formula: log(10) [R/S ratio] = 2.2 - 0.64 x log(10) [C(4h) of (S)-Lansoprazole] (r = 0.867, P < 0.0001). Thus, phenotyping CYP2C19 using the R/S enantiomer ratio of lansoprazole seems unlikely. However, to obtain a pharmacological effect similar to that in CYP2C19 PMs, we can presume that lansoprazole has a sufficient effect in the patient with an R/S enantiomer ratio at 4 h < or = 13.70 and (S)-Lansoprazole concentration at 4 h > or = 50 ng/ml.
Enantioselective disposition of lansoprazole and rabeprazole in human plasma
Yakugaku Zasshi 2006 Jun;126(6):395-402.PMID:16755125DOI:10.1248/yakushi.126.395.
Lansoprazole is extensively metabolized by CYP2C19 and CYP3A4 in the liver, whereas rabeprazole is primarily converted non-enzymatically to rabeprazole-thioether, with only some being oxidized by CYP2C19 and CYP3A4. Lansoprazole and rabeprazole possess asymmetric sulfur in their chemical structure and have typically been used clinically as a racemic mixture. This article reviews the pharmacokinetic differences between enantiomers of lansoprazole and rabeprazole in relation to the CYP2C19 genotypes. In our studies in healthy Japanese subjects, the magnitude of contribution of each lansoprazole enantiomer for CYP2C19 was greater than that for CYP3A4. CYP2C19 influenced the disposition of (S)-Lansoprazole to a greater extent than the (R)-enantiomer. The R/S ratios for the AUC of lansoprazole in CYP2C19 homEMs, hetEMs and PMs was 12.7, 8.5 and 5.8, respectively. On the other hand, (R)-rabeprazole disposition was influenced to a greater degree by CYP2C19 genetic polymorphisms than (S)-rabeprazole. However, the R/S ratios for the AUC of rabeprazole in CYP2C19 homEMs, hetEMs and PMs was only 1.8, 2.2 and 2.4, respectively, suggesting a lesser effect of CYP2C19 polymorphisms on the stereoselective disposition of rabeprazole compared to lansoprazole. Such a difference in the AUC between rabeprazole enantiomers is likely to be dependent on stereoselectivity in the CYP3A4-mediated metabolic conversion from rabeprazole-thioether to rabeprazole. Both enantiomers of these PPIs have been reported to possess equal potency. Therefore, particularly with lansoprazole, the use of (R)-lansoprazole alone would be highly desirable for use in clinical applications.
Determination of R(+)- and S(-)-Lansoprazole using chiral stationary-phase liquid chromatography and their enantioselective pharmacokinetics in humans
Pharm Res 1996 Apr;13(4):611-5.PMID:8710755DOI:10.1023/a:1016062508580.
Purpose: Stereoselective and sensitive methods employing chiral stationary phase columns for HPLC determination of enantiomers of lansoprazole in the human serum were developed and pharmacokinetic behaviors of the enantiomers were evaluated in seven subjects. Methods: Five chiral stationary phase columns: Chiralcel OD (cellulose tris(3,5-dimethyl-phenylcarbamate)), OF (cellulose tris(4-chlorophenylcarbamate)), OG (cellulose tris(4-methylphenylcarbamate)) and OJ (cellulose tris(4-methylbenzoate)), and Chiralpak AS (amylose tris ((S)-1-phenylethylcarbamate)) were investigated. Results: Chiralcel OD and Chiralpak AS columns gave a good resolution of R(+)- and S(-)-enantiomers from racemic lansoprazole, but Chiralcel OF, OG, and OJ did not. The mean Cmax and the AUC values of R(+)-enantiomer were 3-5 times greater than those of S(-)-enantiomer following oral administration of 30 mg of racemic lansoprazole. The CLtot values of R(+)-enantiomer were significantly smaller than those of S(-)-enantiomer. Binding of R(+)-enantiomer to human serum proteins was significantly greater than that of S(-)-enantiomer. The mean metabolic ratio (metabolites/parent compound) in human liver microsomes of S(-)-enantiomer was significantly greater than that of R(+)-enantiomer. Conclusions: The stereoselective pharmacokinetics of lansoprazole enantiomers is likely due to its stereoselective protein binding and/or metabolism.
Determination of S-(-)-Lansoprazole in dexlansoprazole preparation by capillary zone electrophoresis
Arch Pharm Res 2017 Aug;40(8):962-971.PMID:28766240DOI:10.1007/s12272-017-0936-8.
Capillary zone electrophoresis was successfully applied to the enantiomeric purity determination of dexlansoprazole using sulfobutyl ether-β-cyclodextrin and methyl-β-cyclodextrin as chiral selectors. Separations were carried out in a 50 μm, 64/56 cm fused-silica capillary. The optimized conditions included 90 mM phosphate buffer, pH 6.0, containing 30 mM sulfobutyl ether-β-cyclodextrin, 20 mM methyl-β-cyclodextrin as background electrolyte, an applied voltage of 25 kV and a temperature of 16 °C, detection was at 280 nm. The assay was validated for the S-(-)-Lansoprazole in the range of 0.2-1.0%. The limit of detection was 0.07%, the limit of quantitation was 0.20%, relative to a total concentration of 4.0 mg mL-1. Intra-day precision varied between 1.72 and 2.07%. Relative standard deviations of inter-day precision ranged between 1.62 and 1.96% for peak area ratio. The assay was applied for the determination of the chiral purity of dexlansoprazole capsules. Recovery in capsules was ranged between 101.7 and 103.1%.
Enantioselective disposition of lansoprazole in relation to CYP2C19 genotypes in the presence of fluvoxamine
Br J Clin Pharmacol 2005 Jul;60(1):61-8.PMID:15963095DOI:10.1111/j.1365-2125.2005.02381.x.
Aims: Lansoprazole is affected by polymorphism of CYP2C19. The aim of this study was to examine the effects of fluvoxamine, a CYP2C19 inhibitor, on the pharmacokinetics of each lansoprazole enantiomer among three different CYP2C19 genotype groups. Methods: Eighteen healthy subjects, of whom six each were homozygous extensive metabolizers (homEMs), heterozygous extensive metabolizers (hetEMs), or poor metabolizers (PMs) for CYP2C19, participated in the study. Each subject received either placebo or fluvoxamine, 25 mg twice daily for 6 days, then a single oral dose of 60 mg of racemic lansoprazole. The plasma concentrations of lansoprazole enantiomers and lansoprazole sulphone were subsequently measured for 24 h post lansoprazole administration using liquid chromatography. Results: In the homEMs and hetEMs, fluvoxamine significantly increased the AUC(0, infinity) and C(max) and prolonged the elimination half-life of both (R)- and (S)-Lansoprazole, whereas in the PMs, the only statistically significant effect of fluvoxamine was on the AUC(0, infinity) for (R)-lansoprazole. The mean fluvoxamine-mediated percent increase in the AUC(0, infinity) of (R)-lansoprazole in the homEMs compared with the PMs was significant (P = 0.0117); however, C(max) did not differ among the three CYP2C19 genotypes. On the other hand, fluvoxamine induced a significant percent increase in both the AUC(0, infinity) and C(max) for (S)-Lansoprazole in the homEMs compared with the hetEMs (P = 0.0007 and P = 0.0125, respectively) as well as compared with the PMs (P < 0.0001 for each parameter). The mean R : S ratio for AUC(0, infinity) of lansoprazole in the homEMs was significantly different between the placebo and the fluvoxamine treatment groups (12.7 (9.1, 16.8) vs 6.4 (5.4, 7.4), respectively, P < 0.0001), though not in the PMs (5.5 (4.3, 6.7) vs 5.9 (5.3, 6.5), respectively). Conclusions: The magnitude of the contribution of CYP2C19 to the metabolism of (S)-Lansoprazole is much greater compared with that of the (R)-enantiomer. In extensive metabolizers, hepatic CYP2C19 plays an important role in the absorption and elimination of lansoprazole, particularly the (S)-enantiomer.