Amlodipine maleate (Amvaz; Norvasc), the maleate salt of Amlodipine, is an antihypertensive medication of the dihydropyridine (DHP) class used for lowering blood pressure, angina pectoris and preventing chest pain. It acts as a long-acting L-type calcium channel blocker (CCB).
Physicochemical Properties
| Molecular Formula | C₂₄H₂₉CLN₂O₉ |
| Molecular Weight | 524.95 |
| Exact Mass | 524.156 |
| CAS # | 88150-47-4 |
| Related CAS # | Amlodipine;88150-42-9;Amlodipine besylate;111470-99-6;Amlodipine-d4 maleate;2714486-25-4;Amlodipine mesylate;246852-12-0 |
| PubChem CID | 6435922 |
| Appearance | Light yellow to yellow solid powder |
| Boiling Point | 527.2ºC at 760 mmHg |
| Flash Point | 272.6ºC |
| LogP | 3.007 |
| Hydrogen Bond Donor Count | 4 |
| Hydrogen Bond Acceptor Count | 11 |
| Rotatable Bond Count | 12 |
| Heavy Atom Count | 36 |
| Complexity | 766 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | CCOC(=O)C1=C(NC(=C(C1C2=CC=CC=C2Cl)C(=O)OC)C)COCCN.C(=C\C(=O)O)\C(=O)O |
| InChi Key | TZNOWAJJWCGILX-BTJKTKAUSA-N |
| InChi Code | 1S/C20H25ClN2O5.C4H4O4/c1-4-28-20(25)18-15(11-27-10-9-22)23-12(2)16(19(24)26-3)17(18)13-7-5-6-8-14(13)215-3(6)1-2-4(7)8/h5-8,17,23H,4,9-11,22H2,1-3H31-2H,(H,5,6)(H,7,8)/b2-1- |
| Chemical Name | 3,5-Pyridinedicarboxylic acid, 2-((2-aminoethoxy)methyl)-4-(2-chlorophenyl)-1,4-dihydro-6-methyl-, 3-ethyl 5-methyl ester, (+-)-, (Z)-2-butenedioate (1 |
| Synonyms | Amlodipine (+-)-form maleate, Amvaz |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| ln Vitro | BrdU incorporation rates in A431 cells were lowered by amlodipine maleate (20–40 μM; 48 hours) to 68.6% and 26.3%, respectively, at doses of 20 and 30 μM [3]. The increase in [Ca2+]i in A431 cells caused by uridine 5'-triphosphate (UTP) was greatly reduced by amlodipine maleate (30 μM) one hour before treatment [3]. In Fluo-3-loaded cells, amlodipine maleate (30 μM) suppresses Thapsigargin-induced store-operated Ca2+ influx [3]. |
| ln Vivo | In VSMC ATP2B1 KO mice, amlodipine maleate (5 mg/kg/day; subcutaneous injection for 2 weeks) can dramatically lower systolic blood pressure (SBP) [4]. Amlodipine maleate (10 mg/kg; intraperitoneally given once daily for 20 days) can prolong the survival of A431 tumor-bearing mice and considerably delay the formation of tumors [3]. |
| Animal Protocol |
Animal/Disease Models: ATP2B1loxP/loxP mice [4] Doses: 5 mg/kg/day Route of Administration: subcutaneously (sc) (sc) implanted osmotic pump for 2 weeks Experimental Results: Dramatically lowered blood pressure. |
| References |
[1]. Antitumor effects of amlodipine, a Ca2+ channel blocker, on human epidermoid carcinoma A431 cells in vitro and in vivo. Eur J Pharmacol. 2004 May 25;492(2-3):103-12. [2]. The effects of anti-hypertensive drugs and the mechanism of hypertension in vascular smooth muscle cell-specific ATP2B1 knockout mice. Hypertens Res. 2018 Feb;41(2):80-87. [3]. Amlodipine. [4]. Amlodipine. A reappraisal of its pharmacological properties and therapeutic use in cardiovascular disease [published correction appears in Drugs 1995 Nov;50(5):896]. Drugs. 1995;50(3):560-586. |
| Additional Infomation |
Amlodipine Maleate is the maleate salt of amlodipine, a synthetic phenylpyridine vasodilator with antihypertensive and antianginal effects. Amlodipine inhibits the influx of extracellular calcium ions into myocardial and peripheral vascular smooth muscle cells, thereby preventing vascular and myocardial contraction. Furthermore, decreased myocardial contractility and dilation of the main coronary and systemic arteries lead to increased blood flow and oxygen delivery to the myocardial tissue and decreases total peripheral resistance. This agent may also modulate multi-drug resistance (MDR) activity through inhibition of the p-glycoprotein efflux pump. A long-acting dihydropyridine calcium channel blocker. It is effective in the treatment of ANGINA PECTORIS and HYPERTENSION. See also: Amlodipine (has active moiety); Amlodipine maleate; benazepril hydrochloride (component of). |
Solubility Data
| Solubility (In Vitro) | DMSO : ~120 mg/mL (~228.59 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 1.71 mg/mL (3.26 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 17.1 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 1.71 mg/mL (3.26 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 17.1 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 1.71 mg/mL (3.26 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 17.1 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.9049 mL | 9.5247 mL | 19.0494 mL | |
| 5 mM | 0.3810 mL | 1.9049 mL | 3.8099 mL | |
| 10 mM | 0.1905 mL | 0.9525 mL | 1.9049 mL |