Synonym
Lacidipine; Lacipil; Lacimen; Motens; GR 43659 X; GR-43659 X; GR43659 X;
IUPAC/Chemical Name
diethyl (E)-4-(2-(3-(tert-butoxy)-3-oxoprop-1-en-1-yl)phenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
InChi Key
GKQPCPXONLDCMU-CCEZHUSRSA-N
InChi Code
InChI=1S/C26H33NO6/c1-8-31-24(29)21-16(3)27-17(4)22(25(30)32-9-2)23(21)19-13-11-10-12-18(19)14-15-20(28)33-26(5,6)7/h10-15,23,27H,8-9H2,1-7H3/b15-14+
SMILES Code
O=C(C1=C(C)NC(C)=C(C(OCC)=O)C1C2=CC=CC=C2/C=C/C(OC(C)(C)C)=O)OCC
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
Biological target:
Lacidipine is an orally active and highly selective L-type calcium channel blocker that acts on smooth muscle calcium channels, primarily dilates peripheral arteries, reduces peripheral resistance, and has long-lasting anti-hypertensive activity.
In vitro activity:
Lacidipine, an L-type Ca(2+) channel blocker that also inhibits [Ca(2+)](ER) efflux, enhances folding, trafficking, and activity of degradation-prone GC variants. Lacidipine remodels mutated GC proteostasis by simultaneously activating a series of distinct molecular mechanisms, namely modulation of Ca(2+) homeostasis, upregulation of the ER chaperone BiP, and moderate induction of the unfolded protein response.
Reference: Chem Biol. 2011 Jun 24;18(6):766-76. https://pubmed.ncbi.nlm.nih.gov/21700212/
In vivo activity:
Both doses of lacidipine (1 and 3 mg/kg) also effectively increased calcium concentrations (P<0.01) significantly in ovariectomized rats.
Reference: Eur J Pharmacol. 2008 Jan 28;579(1-3):241-5. https://pubmed.ncbi.nlm.nih.gov/17936271/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMF |
25.0 |
54.88 |
| DMF:PBS (pH 7.2) (1:3) |
0.3 |
0.55 |
| DMSO |
53.7 |
117.81 |
| Ethanol |
13.5 |
29.63 |
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
455.55
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. Wang F, Chou A, Segatori L. Lacidipine remodels protein folding and Ca 2+ homeostasis in Gaucher's disease fibroblasts: a mechanism to rescue mutant glucocerebrosidase. Chem Biol. 2011 Jun 24;18(6):766-76. doi: 10.1016/j.chembiol.2011.04.008. PMID: 21700212.
2. Bernini F, Canavesi M, Bernardini E, Scurati N, Bellosta S, Fumagalli R. Effect of lacidipine on cholesterol esterification: in vivo and in vitro studies. Br J Pharmacol. 1997 Nov;122(6):1209-15. doi: 10.1038/sj.bjp.0701469. PMID: 9401788; PMCID: PMC1565031.
3. Halici Z, Borekci B, Ozdemir Y, Cadirci E, Suleyman H. Protective effects of amlodipine and lacidipine on ovariectomy-induced bone loss in rats. Eur J Pharmacol. 2008 Jan 28;579(1-3):241-5. doi: 10.1016/j.ejphar.2007.09.027. Epub 2007 Oct 3. PMID: 17936271.
4. Kyselovic J, Krenek P, Wibo M, Godfraind T. Effects of amlodipine and lacidipine on cardiac remodelling and renin production in salt-loaded stroke-prone hypertensive rats. Br J Pharmacol. 2001 Dec;134(7):1516-22. doi: 10.1038/sj.bjp.0704398. PMID: 11724758; PMCID: PMC1573087.
In vitro protocol:
1. Wang F, Chou A, Segatori L. Lacidipine remodels protein folding and Ca 2+ homeostasis in Gaucher's disease fibroblasts: a mechanism to rescue mutant glucocerebrosidase. Chem Biol. 2011 Jun 24;18(6):766-76. doi: 10.1016/j.chembiol.2011.04.008. PMID: 21700212.
2. Bernini F, Canavesi M, Bernardini E, Scurati N, Bellosta S, Fumagalli R. Effect of lacidipine on cholesterol esterification: in vivo and in vitro studies. Br J Pharmacol. 1997 Nov;122(6):1209-15. doi: 10.1038/sj.bjp.0701469. PMID: 9401788; PMCID: PMC1565031.
In vivo protocol:
1. Halici Z, Borekci B, Ozdemir Y, Cadirci E, Suleyman H. Protective effects of amlodipine and lacidipine on ovariectomy-induced bone loss in rats. Eur J Pharmacol. 2008 Jan 28;579(1-3):241-5. doi: 10.1016/j.ejphar.2007.09.027. Epub 2007 Oct 3. PMID: 17936271.
2. Kyselovic J, Krenek P, Wibo M, Godfraind T. Effects of amlodipine and lacidipine on cardiac remodelling and renin production in salt-loaded stroke-prone hypertensive rats. Br J Pharmacol. 2001 Dec;134(7):1516-22. doi: 10.1038/sj.bjp.0704398. PMID: 11724758; PMCID: PMC1573087.
1. Micheli, D., Collodel, A., Semeraro, C., et al. Lacidipine: A calcium antagonist with potent and long-lasting antihypertensive effects in animal studies. J. Cardiovasc. Parmacol. 15(4), 666-675 (1990).
2. Lupo, E., Locher, R., Weisser, B., et al. In vitro antioxidant activity of calcium antagonists against LDL oxidation compared with α-tocopherol. Biochem. Biophys. Res. Commun. 203(3), 1803-1808 (1994).
3. Kyselovic, J., Martinka, P., Batova, Z., et al. Calcium channel blocker inhibits Western-type diet-evoked atherosclerosis development in ApoE-deficient mice. J. Pharmacol. Exp. Ther. 315(1), 320-328 (2005).
