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MedKoo Cat#: 598726 | Name: Levolansoprazole
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Levolansoprazole 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). Lansoprazole is an enantiomerically pure form of lansoprazole. Both (S)- and (R)-lansoprazole are pharmacologically active with similar potencies.

Chemical Structure

Levolansoprazole
CAS#138530-95-7

Theoretical Analysis

MedKoo Cat#: 598726

Name: Levolansoprazole

CAS#: 138530-95-7

Chemical Formula: C16H14F3N3O2S

Exact Mass: 369.0759

Molecular Weight: 369.36

Elemental Analysis: C, 52.03; H, 3.82; F, 15.43; N, 11.38; O, 8.66; S, 8.68

Price and Availability

Size Price Availability Quantity
1mg USD 350.00 2 Weeks
5mg USD 1,150.00 2 Weeks
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Related CAS #
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Synonym
Levolansoprazole; (S)-Lansoprazole; (-)-Lansoprazole;
IUPAC/Chemical Name
(S)-2-(((3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl)methyl)sulfinyl)-1H-benzo[d]imidazole
InChi Key
MJIHNNLFOKEZEW-VWLOTQADSA-N
InChi Code
1S/C16H14F3N3O2S/c1-10-13(20-7-6-14(10)24-9-16(17,18)19)8-25(23)15-21-11-4-2-3-5-12(11)22-15/h2-7H,8-9H2,1H3,(H,21,22)/t25-/m0/s1
SMILES Code
Cc1c(C[S@@](c([nH]2)nc3c2cccc3)=O)nccc1OCC(F)(F)F
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Levolansoprazole is a proton pump inhibitor that irreversibly inhibits H+/K+-stimulated ATPase pumps in parietal cells (IC50 = 5.2 µM).
In vitro activity:
This study demonstrated that the PPI Lpz (lansoprazole) played a tumor suppressive role in non-small cell lung cancer (NSCLC) A549 cells. Mechanistically, Lpz induced apoptosis and G0/G1 cell cycle arrest by inhibiting the activation of signal transducer and activator of transcription (Stat) 3 and the phosphoinositide 3-kinase (PI3K)/Akt and Raf/ERK pathways. In addition, Lpz inhibited autophagy by blocking the fusion of autophagosomes with lysosomes. Reference: . Front Cell Dev Biol. 2021 Apr 20;9:655559. https://pubmed.ncbi.nlm.nih.gov/33959611/
In vivo activity:
This study planned to examine the cardioprotective effect of LPZ (lansoprazole) against CIS (cisplatin)-induced cardiac injury. To achieve this goal, 32 male rats were randomly allocated into four groups. CIS, 7 mg/kg, was injected i.p. on the fifth day of the experiment. LPZ was administered via oral gavage at a dose of 50 mg/kg. CIS injection caused a significant inflammatory reaction mediated by alteration of cardiac NF-κB, STAT-3, p-STAT-3, and IκB expressions. In contrast, LPZ administration remarkably ameliorated these changes in the heart of CIS-intoxicated rats. Collectively, LPZ potently attenuated cardiac toxicity induced by CIS via regulation of Nrf2/HO-1, PPAR-γ, cytoglobin, IκB/NF-κB/STAT-3, and Ang-II/Ang 1-7 signals. Reference: Toxicol Mech Methods. 2022 Nov 3:1-11. https://pubmed.ncbi.nlm.nih.gov/36258671/
Solvent mg/mL mM comments
Solubility
DMF 30.0 81.22
DMSO 30.0 81.22
DMSO:PBS (pH 7.2) (1:1) 0.5 1.35
Ethanol 5.0 13.54
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 369.36 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Zhao X, Zhang N, Huang Y, Dou X, Peng X, Wang W, Zhang Z, Wang R, Qiu Y, Jin M, Kong D. Lansoprazole Alone or in Combination With Gefitinib Shows Antitumor Activity Against Non-small Cell Lung Cancer A549 Cells in vitro and in vivo. Front Cell Dev Biol. 2021 Apr 20;9:655559. doi: 10.3389/fcell.2021.655559. PMID: 33959611; PMCID: PMC8093516. 2. Nakatake R, Hishikawa H, Kotsuka M, Ishizaki M, Matsui K, Nishizawa M, Yoshizawa K, Kaibori M, Okumura T. The Proton Pump Inhibitor Lansoprazole Has Hepatoprotective Effects in In Vitro and In Vivo Rat Models of Acute Liver Injury. Dig Dis Sci. 2019 Oct;64(10):2854-2866. doi: 10.1007/s10620-019-05622-6. Epub 2019 Apr 15. PMID: 30989463. 3. Hassanein EHM, Ali FEM, Mohammedsaleh ZM, Atwa AM, Elfiky M. The involvement of Nrf2/HO-1/cytoglobin and Ang-II/NF-κB signals in the cardioprotective mechanism of lansoprazole against cisplatin-induced heart injury. Toxicol Mech Methods. 2022 Nov 3:1-11. doi: 10.1080/15376516.2022.2137870. Epub ahead of print. PMID: 36258671. 4. Bae HJ, Bae HJ, Kim JY, Park K, Yang X, Jung SY, Park SJ, Kim DH, Shin CY, Ryu JH. The effect of lansoprazole on MK-801-induced schizophrenia-like behaviors in mice. Prog Neuropsychopharmacol Biol Psychiatry. 2023 Jan 10;120:110646. doi: 10.1016/j.pnpbp.2022.110646. Epub 2022 Sep 30. PMID: 36191804.
In vitro protocol:
1. Zhao X, Zhang N, Huang Y, Dou X, Peng X, Wang W, Zhang Z, Wang R, Qiu Y, Jin M, Kong D. Lansoprazole Alone or in Combination With Gefitinib Shows Antitumor Activity Against Non-small Cell Lung Cancer A549 Cells in vitro and in vivo. Front Cell Dev Biol. 2021 Apr 20;9:655559. doi: 10.3389/fcell.2021.655559. PMID: 33959611; PMCID: PMC8093516. 2. Nakatake R, Hishikawa H, Kotsuka M, Ishizaki M, Matsui K, Nishizawa M, Yoshizawa K, Kaibori M, Okumura T. The Proton Pump Inhibitor Lansoprazole Has Hepatoprotective Effects in In Vitro and In Vivo Rat Models of Acute Liver Injury. Dig Dis Sci. 2019 Oct;64(10):2854-2866. doi: 10.1007/s10620-019-05622-6. Epub 2019 Apr 15. PMID: 30989463.
In vivo protocol:
1. Hassanein EHM, Ali FEM, Mohammedsaleh ZM, Atwa AM, Elfiky M. The involvement of Nrf2/HO-1/cytoglobin and Ang-II/NF-κB signals in the cardioprotective mechanism of lansoprazole against cisplatin-induced heart injury. Toxicol Mech Methods. 2022 Nov 3:1-11. doi: 10.1080/15376516.2022.2137870. Epub ahead of print. PMID: 36258671. 2. Bae HJ, Bae HJ, Kim JY, Park K, Yang X, Jung SY, Park SJ, Kim DH, Shin CY, Ryu JH. The effect of lansoprazole on MK-801-induced schizophrenia-like behaviors in mice. Prog Neuropsychopharmacol Biol Psychiatry. 2023 Jan 10;120:110646. doi: 10.1016/j.pnpbp.2022.110646. Epub 2022 Sep 30. PMID: 36191804.
1: Gellad WF, Choi P, Mizah M, Good CB, Kesselheim AS. Assessing the chiral switch: approval and use of single-enantiomer drugs, 2001 to 2011. Am J Manag Care. 2014 Mar 1;20(3):e90-7. PubMed PMID: 24773330. 2: Cao Z, Chen Q, Zhang W, Liang X, Liao J, Liu W, Xiao S, Lu H. Fourteen-day optimized levofloxacin-based therapy versus classical quadruple therapy for Helicobacter pylori treatment failures: a randomized clinical trial. Scand J Gastroenterol. 2015;50(10):1185-90. doi: 10.3109/00365521.2015.1037345. Epub 2015 Apr 16. PubMed PMID: 25881966.

View History

BMS-986144

BMS-986144