aranidipine   Click here for help

GtoPdb Ligand ID: 11744

Synonyms: MPC-1304 | MPC1304 | Sapresta®
Approved drug
aranidipine is an approved drug (Japan (1996))
Compound class: Synthetic organic
Comment: Aranidipine (MPC-1304) is a long-acting, dihydropyridine-type Ca2+ channel blocker [1] that produces an hypotensive effect in vivo [2]. Activation of K+ channels may also be involved in aranidipine-induced vasodilation, as identified in a rat model [3]. We show the compound with no specified stereochemistry to represent the racemic mixture of enantiomers. It has been reported that the (S) enantiomer of aranidipine is responsible for most of the pharmacological activity of the racemate [4].
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 6
Hydrogen bond donors 1
Rotatable bonds 8
Topological polar surface area 124.84
Molecular weight 388.13
XLogP 2.95
No. Lipinski's rules broken 0
Click here for help
Canonical SMILES COC(=O)C1=C(C)NC(=C(C1c1ccccc1[N+](=O)[O-])C(=O)OCC(=O)C)C
Isomeric SMILES CC1=C(C(C(=C(N1)C)C(=O)OCC(=O)C)c1ccccc1[N+](=O)[O-])C(=O)OC
InChI InChI=1S/C19H20N2O7/c1-10(22)9-28-19(24)16-12(3)20-11(2)15(18(23)27-4)17(16)13-7-5-6-8-14(13)21(25)26/h5-8,17,20H,9H2,1-4H3
1. Masumiya H, Tanaka Y, Tanaka H, Shigenobu K. (2000)
Inhibition of T-type and L-type Ca(2+) currents by aranidipine, a novel dihydropyridine Ca(2+) antagonist.
Pharmacology, 61 (2): 57-61. [PMID:10940777]
2. Miyoshi K, Kanda A, Nozawa Y, Nakano M, Miyake H. (1996)
Regional vascular effects of MPC-1304, a novel dihydropyridine derivative, in conscious normotensive and spontaneously hypertensive rats.
J Pharmacol Exp Ther, 277 (3): 1328-36. [PMID:8667194]
3. Okumura K, Ichihara K, Nagasaka M. (1997)
Effects of aranidipine, a novel calcium channel blocker, on mechanical responses of the isolated rat portal vein: comparison with typical calcium channel blockers and potassium channel openers.
J Cardiovasc Pharmacol, 29 (2): 209-15. [PMID:9057070]
4. Okumura K, Ichihara K, Nagasaka M, Oda N, Tajima K. (1993)
Calcium entry blocking activities of MPC-1304 and of its enantiomers and metabolites.
Eur J Pharmacol, 235 (1): 69-74. [PMID:8519282]