Nicardipine

Details

• Internal ID: f9542499-6266-4629-8a9d-c9679fe759be
• Taxonomy: Organoheterocyclic compounds > Pyridines and derivatives > Hydropyridines > Dihydropyridines > Dihydropyridinecarboxylic acids and derivatives
• IUPAC Name: 5-O-[2-[benzyl(methyl)amino]ethyl] 3-O-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
• SMILES (Canonical): CC1=C(C(C(=C(N1)C)C(=O)OCCN(C)CC2=CC=CC=C2)C3=CC(=CC=C3)[N+](=O)[O-])C(=O)OC
• SMILES (Isomeric): CC1=C(C(C(=C(N1)C)C(=O)OCCN(C)CC2=CC=CC=C2)C3=CC(=CC=C3)[N+](=O)[O-])C(=O)OC
• InChI: InChI=1S/C26H29N3O6/c1-17-22(25(30)34-4)24(20-11-8-12-21(15-20)29(32)33)23(18(2)27-17)26(31)35-14-13-28(3)16-19-9-6-5-7-10-19/h5-12,15,24,27H,13-14,16H2,1-4H3
• InChI Key: ZBBHBTPTTSWHBA-UHFFFAOYSA-N
• Popularity: 6,862 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₂₉N₃O₆
• Molecular Weight: 479.50 g/mol
• Exact Mass: 479.20563565 g/mol
• Topological Polar Surface Area (TPSA): 114.00 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 3.68
• H-Bond Acceptor: 8
• H-Bond Donor: 1
• Rotatable Bonds: 9

Synonyms

• 55985-32-5
• Nicardipinum
• Nicardipinum [INN-Latin]
• Nicardipino [INN-Spanish]
• Nicardipino
• Perpidine
• Nicardipine [INN:BAN]
• Cardene
• Nicardipine LA
• Nicardipine (stn)
• Cardene (TN)
• Nicardipine (INN)
• CHEBI:7550
• (+/-)-Nicardipine
• C26H29N3O6
• YC-93 (free base)
• EINECS 259-932-3
• BRN 0504321
• 3-(2-(benzyl(methyl)amino)ethyl) 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
• 5-O-[2-[benzyl(methyl)amino]ethyl] 3-O-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
• DTXSID6023363
• UNII-CZ5312222S
• CZ5312222S
• 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
• 3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, methyl 2-(methyl(phenylmethyl)amino)ethyl ester
• NCGC00015747-03
• Y-93
• NICARDIPINE [INN]
• Cardene IV
• 3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, methyl 2-[methyl(phenylmethyl)amino]ethyl ester
• DTXCID903363
• 3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-,2-(benzylmethylamino)ethyl methyl ester
• 3-{2-[benzyl(methyl)amino]ethyl} 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
• methyl 2-[methyl(phenylmethyl)amino]ethyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
• CAS-55985-32-5
• Flusemide
• FlusemideNicardipine
• (R,S)-nicardipine
• Spectrum_001372
• NICARDIPINE [MI]
• Prestwick0_000383
• Prestwick1_000383
• Prestwick2_000383
• Prestwick3_000383
• Spectrum2_001415
• Spectrum3_001452
• Spectrum4_000422
• Spectrum5_001320
• D0T0KA
• 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
• CHEMBL3302409
• 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
• BCP21397
• EX-A4680
• Tox21_110211
• BDBM50101815
• s5255
• AKOS001637090
• AKOS040744847
• C26-H29-N3-O6
• Tox21_110211_1
• CCG-204893
• CS-3685
• CS-O-01985
• DB00622
• 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
• BN166182
• HY-12515
• PD033077
• PD156023
• SBI-0050786.P003
• LS-131263
• AB00514658
• FT-0630688
• C07264
• D08270
• EN300-708781
• AB00053604-03
• AB00053604_04
• AB00053604_05
• A924111
• L000715
• Q729213
• BRD-A26711594-001-02-7
• BRD-A26711594-003-05-6
• BRD-A26711594-003-06-4
• L-GLUTAMICACID,N-(1-DEOXY-D-FRUCTOS-1-YL)-
• 1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid methyl 2-[methy(phenyl-methyl)amino]ethyl ester
• 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-(Benzylmethylamino)ethylmethyl 1,4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)pyridine-3,5-dicarboxylate
• 2-(N-benzyl-N-methylamino)ethyl methyl 2,6-dimethyl-4(m-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
• 3,5-PYRIDINEDICARBOXYLIC ACID, 1,4-DIHYDRO-2,6-DIMETHYL-4-(3-NITROPHENYL)-, 3-METHYL 5-(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 #
• Methyl 2-(benzyl-methyl-amino)ethyl2,6-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

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8814	88.14%
Caco-2	-	0.6122	61.22%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7203	72.03%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9002	90.02%
OATP1B3 inhibitior	+	0.8561	85.61%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	+	0.7500	75.00%
BSEP inhibitior	+	0.9941	99.41%
P-glycoprotein inhibitior	+	0.9305	93.05%
P-glycoprotein substrate	+	0.7307	73.07%
CYP3A4 substrate	+	0.7865	78.65%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8822	88.22%
CYP3A4 inhibition	+	0.7959	79.59%
CYP2C9 inhibition	+	0.8948	89.48%
CYP2C19 inhibition	+	0.8994	89.94%
CYP2D6 inhibition	+	0.8932	89.32%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	+	0.9817	98.17%
CYP inhibitory promiscuity	+	0.8558	85.58%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7200	72.00%
Carcinogenicity (trinary)	Non-required	0.5167	51.67%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9699	96.99%
Skin irritation	-	0.7969	79.69%
Skin corrosion	-	0.9363	93.63%
Ames mutagenesis	-	0.8400	84.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7259	72.59%
Micronuclear	+	0.8900	89.00%
Hepatotoxicity	-	0.7750	77.50%
skin sensitisation	-	0.8476	84.76%
Respiratory toxicity	+	0.9556	95.56%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	1.0000	100.00%
Nephrotoxicity	-	0.9398	93.98%
Acute Oral Toxicity (c)	II	0.4326	43.26%
Estrogen receptor binding	+	0.6474	64.74%
Androgen receptor binding	+	0.8165	81.65%
Thyroid receptor binding	+	0.6533	65.33%
Glucocorticoid receptor binding	+	0.8198	81.98%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.8185	81.85%
Honey bee toxicity	-	0.8671	86.71%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	+	0.9852	98.52%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL256	P0DMS8	Adenosine A3 receptor	3250 nM	Ki	PMID: 8709132
CHEMBL5393	Q9UNQ0	ATP-binding cassette sub-family G member 2	16595.87 nM	IC50	PMID: 18678495
CHEMBL3356	P05177	Cytochrome P450 1A2	13300 nM	IC50	PMID: 23033255
CHEMBL3622	P33261	Cytochrome P450 2C19	560 nM; 3300 nM	IC50; IC50	PMID: 23033255; PMID: 22328583
CHEMBL3721	P10632	Cytochrome P450 2C8	1560 nM	IC50	PMID: 22328583
CHEMBL3397	P11712	Cytochrome P450 2C9	660 nM; 378 nM	IC50; IC50	PMID: 23033255; PMID: 22328583
CHEMBL289	P10635	Cytochrome P450 2D6	1780 nM; 1590 nM	IC50; IC50	PMID: 23033255; PMID: 22328583
CHEMBL3491	P51589	Cytochrome P450 2J2	1690 nM	IC50	PMID: 23033255
CHEMBL340	P08684	Cytochrome P450 3A4	380 nM; 420 nM	IC50; IC50	PMID: 23033255; PMID: 12699389
CHEMBL4040	P28482	MAP kinase ERK2	12.6 nM	Potency	via Super-PRED
CHEMBL1293224	P10636	Microtubule-associated protein tau	8912.5 nM; 19952.6 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4302	P08183	P-glycoprotein 1	3200 nM; 5600 nM; 6600 nM; 7100 nM; 4540 nM; 950 nM; 2300 nM; 2300 nM; 5128.61 nM; 4786.3 nM; 4786.3 nM	IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50; IC50	PMID: 11716514; PMID: 11716514; PMID: 11716514; PMID: 11716514; PMID: 12128170; PMID: 12699389; PMID: 12699389; PMID: 12699389; PMID: 17890094; PMID: 17890094; PMID: 18678495
CHEMBL1293235	P02545	Prelamin-A/C	1995.3 nM	Potency	via CMAUP
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	26121.6 nM; 18492.7 nM; 18492.7 nM; 23280.9 nM	Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP
CHEMBL1293232	Q16637	Survival motor neuron protein	35481.3 nM	Potency	via CMAUP
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	56234.1 nM; 44668.4 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1940	Q13936	Voltage-gated L-type calcium channel alpha-1C subunit	250 nM; 24100 nM; 9600 nM; 250 nM	IC50; IC50; IC50; IC50	PMID: 22761000; PMID: 22761000; PMID: 22761000; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.14%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.57%	86.33%
CHEMBL2581	P07339	Cathepsin D	96.75%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	94.57%	94.73%
CHEMBL221	P23219	Cyclooxygenase-1	94.40%	90.17%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.13%	99.17%
CHEMBL1255126	O15151	Protein Mdm4	91.57%	90.20%
CHEMBL5028	O14672	ADAM10	88.69%	97.50%
CHEMBL3902	P09211	Glutathione S-transferase Pi	88.55%	93.81%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.12%	97.09%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.40%	96.95%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	86.19%	89.67%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.86%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.84%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.83%	95.56%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.88%	95.89%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	82.51%	93.03%
CHEMBL340	P08684	Cytochrome P450 3A4	81.92%	91.19%
CHEMBL3231	Q13464	Rho-associated protein kinase 1	81.68%	95.55%
CHEMBL1287628	Q9Y5S8	NADPH oxidase 1	81.35%	95.48%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.45%	95.89%

Plants that contains it

• Cinnamomum aromaticum

Cross-Links

• PubChem: 4474
• NPASS: NPC36836
• ChEMBL: CHEMBL1484