Synonym
Lercanidipine, Lercadip, Lerdip, Zanidip, REC-15-2375;
IUPAC/Chemical Name
3-(1-((3,3-diphenylpropyl)(methyl)amino)-2-methylpropan-2-yl) 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
InChi Key
ZDXUKAKRHYTAKV-UHFFFAOYSA-N
InChi Code
InChI=1S/C36H41N3O6/c1-24-31(34(40)44-6)33(28-18-13-19-29(22-28)39(42)43)32(25(2)37-24)35(41)45-36(3,4)23-38(5)21-20-30(26-14-9-7-10-15-26)27-16-11-8-12-17-27/h7-19,22,30,33,37H,20-21,23H2,1-6H3
SMILES Code
CC1=C(C(OC)=O)C(C2=CC([N+]([O-])=O)=CC=C2)C(C(OC(C)(CN(CCC(C3=CC=CC=C3)C4=CC=CC=C4)C)C)=O)=C(C)N1
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:
Lercanidipine is a lipophilic third-generation dihydropyridine-calcium channel blocker (DHP-CCB).
In vitro activity:
Lercanidipine and amlodipine were found to show an enhanced effect with doxorubicin in inhibiting the growth of gastric cancer cells. While doxorubicin was identified to activate the pathways TGF-β and ERK/MAPK, lercanidipine was found to inhibit these pathways.
Reference: Toxicol In Vitro. 2021 Aug;74:105152. https://pubmed.ncbi.nlm.nih.gov/33771646/
In vivo activity:
A total of 23 metabolites were altered significantly after cerebral ischaemic-reperfusion injury in MCAo control as compared to sham control rats. Lercanidipine significantly reduced the levels of valine, alanine, lactate, acetate and tyrosine, while N-acetylaspartate, glutamate, glutamine, aspartate, creatine/phosphocreatine, choline, glycerophosphorylcholine, taurine, myo-inositol and adenosine di-phosphate were elevated as compared to MCAo control.
Reference: J Pharm Pharmacol. 2020 Jun;72(6):816-825. https://pubmed.ncbi.nlm.nih.gov/32163186/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
55.0 |
89.91 |
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
611.73
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. Panneerpandian P, Rao DB, Ganesan K. Calcium channel blockers lercanidipine and amlodipine inhibit YY1/ERK/TGF-β mediated transcription and sensitize the gastric cancer cells to doxorubicin. Toxicol In Vitro. 2021 Aug;74:105152. doi: 10.1016/j.tiv.2021.105152. Epub 2021 Mar 24. PMID: 33771646.
2. Wu JR, Liou SF, Lin SW, Chai CY, Dai ZK, Liang JC, Chen IJ, Yeh JL. Lercanidipine inhibits vascular smooth muscle cell proliferation and neointimal formation via reducing intracellular reactive oxygen species and inactivating Ras-ERK1/2 signaling. Pharmacol Res. 2009 Jan;59(1):48-56. doi: 10.1016/j.phrs.2008.09.015. Epub 2008 Oct 5. PMID: 18973813.
3. Gupta S, Sharma U, Jagannathan NR, Gupta YK. 1 H NMR metabolomic profiling elucidated attenuation of neurometabolic alterations by lercanidipine in MCAo model in rats. J Pharm Pharmacol. 2020 Jun;72(6):816-825. doi: 10.1111/jphp.13249. Epub 2020 Mar 12. PMID: 32163186.
4. Elbaz EM, Helmy HS, El-Sahar AE, Saad MA, Sayed RH. Lercanidipine boosts the efficacy of mesenchymal stem cell therapy in 3-NP-induced Huntington's disease model rats via modulation of the calcium/calcineurin/NFATc4 and Wnt/β-catenin signalling pathways. Neurochem Int. 2019 Dec;131:104548. doi: 10.1016/j.neuint.2019.104548. Epub 2019 Sep 17. PMID: 31539560.
In vitro protocol:
1. Panneerpandian P, Rao DB, Ganesan K. Calcium channel blockers lercanidipine and amlodipine inhibit YY1/ERK/TGF-β mediated transcription and sensitize the gastric cancer cells to doxorubicin. Toxicol In Vitro. 2021 Aug;74:105152. doi: 10.1016/j.tiv.2021.105152. Epub 2021 Mar 24. PMID: 33771646.
2. Wu JR, Liou SF, Lin SW, Chai CY, Dai ZK, Liang JC, Chen IJ, Yeh JL. Lercanidipine inhibits vascular smooth muscle cell proliferation and neointimal formation via reducing intracellular reactive oxygen species and inactivating Ras-ERK1/2 signaling. Pharmacol Res. 2009 Jan;59(1):48-56. doi: 10.1016/j.phrs.2008.09.015. Epub 2008 Oct 5. PMID: 18973813.
In vivo protocol:
1. Gupta S, Sharma U, Jagannathan NR, Gupta YK. 1 H NMR metabolomic profiling elucidated attenuation of neurometabolic alterations by lercanidipine in MCAo model in rats. J Pharm Pharmacol. 2020 Jun;72(6):816-825. doi: 10.1111/jphp.13249. Epub 2020 Mar 12. PMID: 32163186.
2. Elbaz EM, Helmy HS, El-Sahar AE, Saad MA, Sayed RH. Lercanidipine boosts the efficacy of mesenchymal stem cell therapy in 3-NP-induced Huntington's disease model rats via modulation of the calcium/calcineurin/NFATc4 and Wnt/β-catenin signalling pathways. Neurochem Int. 2019 Dec;131:104548. doi: 10.1016/j.neuint.2019.104548. Epub 2019 Sep 17. PMID: 31539560.
1: Tabidze GA, Gezeli TD, Tsibadze TA, Dolidze NM. [Clinical efficacy of calcium channel blockers slow the third generation of lercanidipine in the treatment of patients with arterial hypertension and metabolic disorders (review)]. Georgian Med News. 2015 Feb;(239):51-6. Review. Russian. PubMed PMID: 25802450.
2: Pogosova GV, Ausheva AK, Karpova AV, Salbieva AO. [Third generation calcium antagonist lercanidipine: the evidence base for clinical decision]. Kardiologiia. 2014;54(2):43-6. Review. Russian. PubMed PMID: 24888200.
3: Burnier M. Renal protection with calcium antagonists: the role of lercanidipine. Curr Med Res Opin. 2013 Dec;29(12):1727-35. doi: 10.1185/03007995.2013.842891. Epub 2013 Sep 27. Review. PubMed PMID: 24069902.
4: Maksimov ML, Malykhina AI. [Clinical cfficacy of calcium channel blockers slow the third generation of lercanidipine in the treatment of patients with arterial hypertension]. Kardiologiia. 2013;53(6):85-90. Review. Russian. PubMed PMID: 23953051.
5: Striuk RI. [The place of lercanidipine in the treatment of cardiovascular diseases]. Kardiologiia. 2013;53(4):76-9. Review. Russian. PubMed PMID: 23952957.
6: Minushkina LO. [Treatment of arteril hypertension in patients with chronic kidney disease: a fixed combination of lercanidipine and enalapril]. Kardiologiia. 2013;53(12):64-9. Review. Russian. PubMed PMID: 24800484.
7: Minushkina LO, Iosava IK. [Lercanidipine in the treatment of arterial hypertension]. Kardiologiia. 2012;52(12):70-4. Review. Russian. PubMed PMID: 23237444.
8: Egan CG, Pontremoli R. Role of the fixed-dose combination lercanidipine-enalapril in renal protection. J Nephrol. 2011 Jul-Aug;24(4):428-37. doi: 10.5301/JN.2011.6271. Review. PubMed PMID: 21279953.
9: Borghi C, Cicero AF. Rationale for the use of a fixed-dose combination in the management of hypertension: efficacy and tolerability of lercanidipine/enalapril. Clin Drug Investig. 2010;30(12):843-54. doi: 10.2165/11584470-000000000-00000. Review. Erratum in: Clin Drug Investig. 2011;31(8):572. PubMed PMID: 20923243.
10: Chatzikyrkou C, Haller H, Menne J. The role of fixed-dose combinations in the management of hypertension: focus on lercanidipine-enalapril. Expert Opin Pharmacother. 2009 Aug;10(11):1833-40. doi: 10.1517/14656560903055087. Review. PubMed PMID: 19527194.
11: Burnier M, Pruijm M, Wuerzner G. Treatment of essential hypertension with calcium channel blockers: what is the place of lercanidipine? Expert Opin Drug Metab Toxicol. 2009 Aug;5(8):981-7. doi: 10.1517/17425250903085135. Review. PubMed PMID: 19619074.
12: Menne J, Haller H. Fixed-dose lercanidipine/enalapril for hypertension. Drugs Today (Barc). 2008 Apr;44(4):261-70. Review. PubMed PMID: 18536784.
13: Hair PI, Scott LJ, Perry CM. Fixed-dose combination lercanidipine/enalapril. Drugs. 2007;67(1):95-106; discussion 107-8. Review. PubMed PMID: 17209666.
14: Ram CV. Hypertension, possible vascular protection and lercanidipine. Expert Rev Cardiovasc Ther. 2006 Nov;4(6):783-8. Review. PubMed PMID: 17173495.
15: Epstein M. Lercanidipine: a novel dihydropyridine calcium-channel blocker. Heart Dis. 2001 Nov-Dec;3(6):398-407. Review. PubMed PMID: 11975824.
16: Tocci G, Palano F, Pagannone E, Chin D, Ferrucci A, Volpe M. Fixed-combination therapies in hypertension management: focus on enalapril/lercanidipine. Expert Rev Cardiovasc Ther. 2009 Feb;7(2):115-23. doi: 10.1586/14779072.7.2.115. Review. PubMed PMID: 19210207.
17: Barrios V, Escobar C, Echarri R. Fixed combinations in the management of hypertension: perspectives on lercanidipine-enalapril. Vasc Health Risk Manag. 2008;4(4):847-53. Review. PubMed PMID: 19066001; PubMed Central PMCID: PMC2597757.
18: Pruijm MT, Maillard MP, Burnier M. Patient adherence and the choice of antihypertensive drugs: focus on lercanidipine. Vasc Health Risk Manag. 2008;4(6):1159-66. Review. PubMed PMID: 19337529; PubMed Central PMCID: PMC2663443.
19: Beckey C, Lundy A, Lutfi N. Lercanidipine in the treatment of hypertension. Ann Pharmacother. 2007 Mar;41(3):465-73. Epub 2007 Mar 6. Review. PubMed PMID: 17341540.
20: Borghi C. Lercanidipine in hypertension. Vasc Health Risk Manag. 2005;1(3):173-82. Review. PubMed PMID: 17319103; PubMed Central PMCID: PMC1993952.
