Synonym
AG-1777, EC 600-451-9, H 225/18, K-1252, Lansoprazole impurity C , Lansoprazole sulfide
IUPAC/Chemical Name
1H-Benzimidazole, 2-(((3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl)methyl)thio)-
InChi Key
CCHLMSUZHFPSFC-UHFFFAOYSA-N
InChi Code
1S/C16H14F3N3OS/c1-10-13(20-7-6-14(10)23-9-16(17,18)19)8-24-15-21-11-4-2-3-5-12(11)22-15/h2-7H,8-9H2,1H3,(H,21,22)
SMILES Code
Cc1c(ccnc1CSc2[nH]c3ccccc3n2)OCC(F)(F)F
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
2934.99.9001
Biological target:
Lansoprazole (AG 1749) is a potent brain penetrant neutral sphingomyelinase (N-SMase) inhibitor (exosome inhibitor).
In vitro activity:
Lansoprazole induced the expression of heme oxygenase-1 (HO-1) on rat gastric epithelial cells (RGM-1 cells), and exerted anti-inflammatory effect on the dependent of HO-1 expression.
Reference: J Clin Biochem Nutr. 2009 Jul;45(1):9-13. https://pubmed.ncbi.nlm.nih.gov/19590701/
In vivo activity:
The present study investigates the potential of lansoprazole (a proton pump inhibitor and agonist of liver x receptors) in experimental dementia of AD type. Streptozotocin [STZ, 3 mg/kg, injected intracerebroventricular (i.c.v), and high fat diet (HFD, administered for 90 days)] were used to induce dementia in separate groups of Swiss mice. Lansoprazole treatment significantly attenuated STZ and HFD -induced memory deficits, biochemical and histopathological alterations. It also prevented HFD-induced rise in the cholesterol level.
Reference: PLoS One. 2013 Jul 31;8(7):e70487. https://pubmed.ncbi.nlm.nih.gov/23936214/
Preparing Stock Solutions
The following data is based on the
product
molecular weight
353.36
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.
| 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. Cheng Z, Liu Y, Ma M, Sun S, Ma Z, Wang Y, Yu L, Qian X, Sun L, Zhang X, Liu Y, Wang Y. Lansoprazole-induced osteoporosis via the IP3R- and SOCE-mediated calcium signaling pathways. Mol Med. 2022 Feb 19;28(1):21. doi: 10.1186/s10020-022-00448-x. PMID: 35183103; PMCID: PMC8858482.
2. Takagi T, Naito Y, Yoshikawa T. The expression of heme oxygenase-1 induced by lansoprazole. J Clin Biochem Nutr. 2009 Jul;45(1):9-13. doi: 10.3164/jcbnSR09-28. Epub 2009 Jun 30. PMID: 19590701; PMCID: PMC2704331.
3. Sodhi RK, Singh N. Defensive effect of lansoprazole in dementia of AD type in mice exposed to streptozotocin and cholesterol enriched diet. PLoS One. 2013 Jul 31;8(7):e70487. doi: 10.1371/journal.pone.0070487. PMID: 23936214; PMCID: PMC3729942.
4. Matsukawa J, Hori Y, Nishida H, Kajino M, Inatomi N. A comparative study on the modes of action of TAK-438, a novel potassium-competitive acid blocker, and lansoprazole in primary cultured rabbit gastric glands. Biochem Pharmacol. 2011 May 1;81(9):1145-51. doi: 10.1016/j.bcp.2011.02.009. Epub 2011 Mar 1. PMID: 21371447.
In vitro protocol:
1. Cheng Z, Liu Y, Ma M, Sun S, Ma Z, Wang Y, Yu L, Qian X, Sun L, Zhang X, Liu Y, Wang Y. Lansoprazole-induced osteoporosis via the IP3R- and SOCE-mediated calcium signaling pathways. Mol Med. 2022 Feb 19;28(1):21. doi: 10.1186/s10020-022-00448-x. PMID: 35183103; PMCID: PMC8858482.
2. Takagi T, Naito Y, Yoshikawa T. The expression of heme oxygenase-1 induced by lansoprazole. J Clin Biochem Nutr. 2009 Jul;45(1):9-13. doi: 10.3164/jcbnSR09-28. Epub 2009 Jun 30. PMID: 19590701; PMCID: PMC2704331.
In vivo protocol:
1. Sodhi RK, Singh N. Defensive effect of lansoprazole in dementia of AD type in mice exposed to streptozotocin and cholesterol enriched diet. PLoS One. 2013 Jul 31;8(7):e70487. doi: 10.1371/journal.pone.0070487. PMID: 23936214; PMCID: PMC3729942.
2. Matsukawa J, Hori Y, Nishida H, Kajino M, Inatomi N. A comparative study on the modes of action of TAK-438, a novel potassium-competitive acid blocker, and lansoprazole in primary cultured rabbit gastric glands. Biochem Pharmacol. 2011 May 1;81(9):1145-51. doi: 10.1016/j.bcp.2011.02.009. Epub 2011 Mar 1. PMID: 21371447.
1: Mdanda S, Baijnath S, Shobo A, Singh SD, Maguire GEM, Kruger HG, Arvidsson PI, Naicker T, Govender T. Lansoprazole-sulfide, pharmacokinetics of this promising anti-tuberculous agent. Biomed Chromatogr. 2017 Dec;31(12). doi: 10.1002/bmc.4035. Epub 2017 Jul 13. PubMed PMID: 28623874.
2: Rybniker J, Vocat A, Sala C, Busso P, Pojer F, Benjak A, Cole ST. Lansoprazole is an antituberculous prodrug targeting cytochrome bc1. Nat Commun. 2015 Jul 9;6:7659. doi: 10.1038/ncomms8659. PubMed PMID: 26158909; PubMed Central PMCID: PMC4510652.
3: Pearce RE, Rodrigues AD, Goldstein JA, Parkinson A. Identification of the human P450 enzymes involved in lansoprazole metabolism. J Pharmacol Exp Ther. 1996 May;277(2):805-16. PubMed PMID: 8627562.
4: Landes BD, Petite JP, Flouvat B. Clinical pharmacokinetics of lansoprazole. Clin Pharmacokinet. 1995 Jun;28(6):458-70. Review. PubMed PMID: 7656504.
