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
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Physico-chemical Properties
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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
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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
Bioactivity Comments
Aranidipine inhibits CaCl2-induced contractions in rabbit aorta with IC50 ~5.4 nM [4]. For (S)-aranidipine the IC50 is 3.3 nM.