Compound: nicardipine
SMILES: O=[N+]([O-])c1cc(ccc1)C2C(=C(NC(=C2C(=O)OC)C)C)C(=O)OCCN(Cc3ccccc3)C
InChIKey: ZBBHBTPTTSWHBA-UHFFFAOYSA-N
Synonyms: nicardipine, 55985-32-5, Nicardipino, Nicardipinum, Perpidine, Nicardipine (stn), CHEBI:7550, 5-O-[2-[benzyl(methyl)amino]ethyl] 3-O-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate, DTXSID6023363, CZ5312222S, DTXCID903363, 3-(2-(benzyl(methyl)amino)ethyl) 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate, 3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, methyl 2-(methyl(phenylmethyl)amino)ethyl ester, 3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, methyl 2-[methyl(phenylmethyl)amino]ethyl ester, 3-{2-[benzyl(methyl)amino]ethyl} 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate, nicardipina, LA, Nicardipine, 5-O-(2-(benzyl(methyl)amino)ethyl) 3-O-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate, O5-methyl O3-(2-(methyl-(phenylmethyl)amino)ethyl) 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate, O5-methyl O3-[2-(methyl-(phenylmethyl)amino)ethyl] 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate, RefChem:56587, Hydrochloride, Nicardipine, C08CA04, 259-932-3, Nicardipinum [INN-Latin], Nicardipino [INN-Spanish], Cardene, Nicardipine (INN), YC-93 (free base), Cardene (TN), MFCD00216027, 2-(Benzylmethylamino)ethyl methyl 1,4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)pyridine-3,5-dicarboxylate, 3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, 2-(benzylmethylamino)ethyl methyl ester, NCGC00015747-03, NICARDIPINE [INN], Nicardipine [INN:BAN], Methyl 2-(benzyl-methyl-amino)ethyl2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate, 2-[benzyl(methyl)amino]ethyl methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate, CAS-55985-32-5, (+/-)-Nicardipine, EINECS 259-932-3, BRN 0504321, UNII-CZ5312222S, (R,S)-nicardipine, Spectrum_001372, NICARDIPINE [MI], Prestwick0_000383, Prestwick1_000383, Prestwick2_000383, Prestwick3_000383, Spectrum2_001415, Spectrum3_001452, Spectrum4_000422, Spectrum5_001320, NICARDIPINE [VANDF], CHEMBL1484, CBiol_001802, Lopac0_000809, Oprea1_436998, SCHEMBL34277, BSPBio_000565, BSPBio_001389, BSPBio_002943, KBioGR_000109, KBioGR_000744, KBioSS_000109, KBioSS_001852, NICARDIPINE [WHO-DD], BIDD:GT0621, DivK1c_000540, SPBio_001490, SPBio_002486, BPBio1_000623, GTPL2559, orb1306351, CHEMBL3302409, SCHEMBL29430153, KBio1_000540, KBio2_000109, KBio2_001852, KBio2_002677, KBio2_004420, KBio2_005245, KBio2_006988, KBio3_000217, KBio3_000218, KBio3_002443, CHEBI:180905, NINDS_000540, Bio1_000088, Bio1_000577, Bio1_001066, Bio2_000109, Bio2_000589, HMS1791F11, HMS1989F11, HMS2089C09, HMS3886G17, HMS5084P19, EX-A4680, MSK10213, Tox21_110211, BDBM50101815, EBC-27206, s5255, AKOS001637090, AKOS040744847, Tox21_110211_1, CCG-204893, CS-3685, DB00622, FN65103, SDCCGSBI-0050786.P004, IDI1_000540, IDI1_033859, NCGC00015747-02, NCGC00015747-04, NCGC00015747-05, NCGC00015747-06, NCGC00015747-07, NCGC00015747-09, NCGC00015747-11, NCGC00015747-18, NCGC00162262-01, NCGC00162262-02, NCGC00162262-03, NCGC00162262-04, AC-19947, AC-36578, AS-56335, HY-12515, methyl 2-[methyl(phenylmethyl)amino]ethyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate, O5-[2-[benzyl(methyl)amino]ethyl] O3-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate, PD033077, PD156023, SY284542, SBI-0050786.P003, DB-052833, AB00514658, NS00002168, A12641, C07264, D08270, EN300-708781, AB00053604-03, AB00053604_04, AB00053604_05, L000715, Q729213, BRD-A26711594-001-02-7, BRD-A26711594-003-05-6, BRD-A26711594-003-06-4, BRD-A26711594-003-08-0, BRD-A26711594-003-10-6, 106664-28-2, 2,6-dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-5-[ 2-(N-benzyl-N-methylamino)ethoxycarbonyl]-1,4-dihydropyridine, 2-(Benzylmethylamino) ethyl methyl 1,4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)-3,5-pyridinedicarboxylate, 2-(Benzylmethylamino)ethyl methyl 1.4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)-3,5-pyridinedicarboxylate, 2-(N-benzyl-N-methylamino)ethyl methyl 2,6-dimethyl-4(m-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate, 3,5-PYRIDINEDICARBOXYLIC ACID, 1,4-DIHYDRO-2,6-DIMETHYL-4-(3-NITROPHENYL)-, 3-METHYL 5-(2-(METHYL(PHENYLMETHYL)AMINO)ETHYL) ESTER, 3,5_Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, methyl 2-(methyl(phenylmethyl)amino)ethyl ester, 3-(2-[Benzyl(methyl)amino]ethyl) 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydro-3,5-pyridinedicarboxylate #, 5-O-[2-[Benzyl(methyl)amino]ethyl] 3-O-methyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
Theoretical properties:
molecular_formula: C26H29N3O6
molecular_weight: 479.5 g/mol
exact_mass: 479.20563565 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 8
rotatable_bond_count: 10
heavy_atom_count: 35
topological_polar_surface_area: 114 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: 136-138 °C
Descriptions:
pubchem: Nicardipine is a racemate comprising equimolar amounts of (R)- and (S)-nicardipine. It is a calcium channel blocker which is used to treat hypertension. It has a role as a vasodilator agent, an antihypertensive agent, a calcium channel blocker and an autophagy inhibitor. It contains a (S)-nicardipine and a (R)-nicardipine.
chebi: A dihydropyridine that is 1,4-dihydropyridine substituted by a methyl, {2-[benzyl(methyl)amino]ethoxy}carbonyl, 3-nitrophenyl, methoxycarbonyl and methyl groups at positions 2, 3, 4, 5 and 6, respectively.
chembl: NICARDIPINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Nicardipine (Cardene) is a medication used to treat angina and hypertension, especially for hemorrhagic stroke patients. It belongs to the dihydropyridine class of calcium channel blockers (CCBs). It is also used for Raynaud's phenomenon. It is available in by mouth and intravenous formulations. It has been used in percutaneous coronary intervention.
Its mechanism of action and clinical effects closely resemble those of nifedipine and the other dihydropyridine calcium channel blockers (amlodipine, felodipine), except that nicardipine is more selective for cerebral and coronary blood vessels. It is primarily a peripheral arterial vasodilator, thus unlike the nitrovasodilators (nitroglycerin and nitroprusside), cardiac preload is minimally affected. It has the longest duration among parenteral CCBs. As its use may lead to reflex tachycardia, it is advisable to use it in conjunction with a beta-blocker. In the setting of a ruptured brain aneurysm, nicardipine may be used (if nimodipine is unavailable) to reduce blood pressure and as prevention or treatment against cerebral vasospasm.
It was patented in 1973 and approved for medical use in 1981. Nicardipine was approved by the FDA in December 1988. The patent for both Cardene and Cardene SR expired in October 1995.