Synonym
Lansoprazole, AG-1749, Prevacid, Zoton, Agopton, Bamalite, Opiren
IUPAC/Chemical Name
2-[[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylsulfinyl]-1H-benzimidazole
InChi Key
MJIHNNLFOKEZEW-UHFFFAOYSA-N
InChi Code
InChI=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)
SMILES Code
O=S(C1=NC2=CC=CC=C2N1)CC3=NC=CC(OCC(F)(F)F)=C3C
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, not in water
Shelf Life
>2 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/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMF |
30.0 |
81.22 |
| DMSO |
68.0 |
184.10 |
| DMSO:PBS (pH 7.2) (1:1) |
0.5 |
1.35 |
| Ethanol |
7.0 |
18.95 |
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.
| 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: Satoh H. Discovery of lansoprazole and its unique pharmacological properties independent from anti-secretory activity. Curr Pharm Des. 2013;19(1):67-75. Review. PubMed PMID: 22950496.
2: Capurso G, Marignani M, Attilia F, Milione M, Colarossi C, Zampaletta C, Di Giulio E, Delle Fave G. Lansoprazole-induced microscopic colitis: an increasing problem? Results of a prospecive case-series and systematic review of the literature. Dig Liver Dis. 2011 May;43(5):380-5. doi: 10.1016/j.dld.2010.11.015. Epub 2010 Dec 30. Review. PubMed PMID: 21195042.
3: Miura M. Enantioselective disposition of lansoprazole and rabeprazole in human plasma. Yakugaku Zasshi. 2006 Jun;126(6):395-402. Review. PubMed PMID: 16755125.
4: Asano M, Taniwaki H, Tsuji D, Sato Y, Shimizu T. [Cytochrome P450 2C19 genotype -based second line therapy with amoxicillin and lansoprazole after failure of initial helicobacter pylori eradication therapy]. Nihon Rinsho. 2005 Dec;63 Suppl 12:450-3. Review. Japanese. PubMed PMID: 16416832.
5: Fukuda Y, Tomita T, Koizuka H, Aoyama N. [Recent topics on important drugs for H. pylori eradication: Lansoprazole]. Nihon Rinsho. 2005 Nov;63 Suppl 11:338-49. Review. Japanese. PubMed PMID: 16363557.
6: Croom KF, Scott LJ. Lansoprazole: in the treatment of gastro-oesophageal reflux disease in children and adolescents. Drugs. 2005;65(15):2129-35; discussion 2136-7. Review. PubMed PMID: 16225368.
7: Dando TM, Plosker GL. Intravenous lansoprazole: in erosive oesophagitis. Drugs. 2004;64(18):2085-9; discussion 2090. Review. PubMed PMID: 15341501.
8: Curran MP, Wellington K. Delayed-release lansoprazole plus naproxen. Drugs. 2004;64(17):1915-9; discussion 1920-1. Review. PubMed PMID: 15329041.
9: Sugiyama T, Asaka M. [Eradication effect of lansoprazole-based triple therapy against H. pylori]. Nihon Rinsho. 2004 Mar;62(3):483-8. Review. Japanese. PubMed PMID: 15038091.
10: Raghunath AS, Green JR, Edwards SJ. A review of the clinical and economic impact of using esomeprazole or lansoprazole for the treatment of erosive esophagitis. Clin Ther. 2003 Jul;25(7):2088-101. Review. PubMed PMID: 12946553.
11: Scott LJ. Lansoprazole: in the management of gastroesophageal reflux disease in children. Paediatr Drugs. 2003;5(1):57-61; discussion 62. Review. PubMed PMID: 12513106.
12: Dobrilla G, Capurso L. [Lansoprazole: an analysis of the clinical trials in the 3 years of 1997-1999]. Recenti Prog Med. 2000 Apr;91(4):191-210. Review. Italian. PubMed PMID: 10804753.
13: Welage LS, Berardi RR. Evaluation of omeprazole, lansoprazole, pantoprazole, and rabeprazole in the treatment of acid-related diseases. J Am Pharm Assoc (Wash). 2000 Jan-Feb;40(1):52-62; quiz 121-3. Review. PubMed PMID: 10665250.
14: Sharma VK. Comparison of 24-hour intragastric pH using four liquid formulations of lansoprazole and omeprazole. Am J Health Syst Pharm. 1999 Dec 1;56(23 Suppl 4):S18-21. Review. Erratum in: Am J Health Syst Pharm 2000 Apr 1;57(7):699. PubMed PMID: 10597120.
15: Gisbert JP. [Lansoprazole: a review of its role in Helicobacter pylori eradication therapy]. Rev Esp Enferm Dig. 1999 Feb;91(2):133-43. Review. Spanish. PubMed PMID: 10231305.
16: Müller P, Simon B. [Helicobacter pylori eradication: modified triple therapy with lansoprazole]. Fortschr Med. 1996 Dec 20;114(35-36):497-9. Review. German. PubMed PMID: 9119351.
17: Blum RA. Lansoprazole and omeprazole in the treatment of acid peptic disorders. Am J Health Syst Pharm. 1996 Jun 15;53(12):1401-15. Review. PubMed PMID: 8781686.
18: Lamouliatte H. Adjuvant therapy for Helicobacter pylori eradication: role of lansoprazole in clinical studies. J Clin Gastroenterol. 1995;20 Suppl 1:S28-31. Review. PubMed PMID: 7673611.
19: Lockhart SP. Clinical review of lansoprazole. Br J Clin Pract Suppl. 1994 May-Jun;75:48-55; discussion 56-7. Review. PubMed PMID: 8060802.
20: Tamura K, Murai M, Tanaka M, Kawano S. [Activity of Lansoprazole (new proton pump inhibitor) against Helicobacter pylori and its therapeutic efficacy]. Nihon Rinsho. 1993 Dec;51(12):3261-6. Review. Japanese. PubMed PMID: 8283644.
