Nicardipine Hydrochloride

Details

• Internal ID: 5dcb2d61-d394-4179-a30c-ba017d9e665f
• 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;hydrochloride
• InChI: InChI=1S/C26H29N3O6.ClH/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;1H
• InChI Key: AIKVCUNQWYTVTO-UHFFFAOYSA-N
• Popularity: 2,836 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₀ClN₃O₆
• Molecular Weight: 516.00 g/mol
• Exact Mass: 515.1823134 g/mol
• Topological Polar Surface Area (TPSA): 114.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): 4.10
• H-Bond Acceptor: 8
• H-Bond Donor: 1
• Rotatable Bonds: 9

Synonyms

• 54527-84-3
• Nicardipine HCl
• Perdipine
• Nicodel
• Loxen
• Perdipina
• YC-93
• Cardene SR
• Barizin
• Cardepine
• Dacarel
• Lecibra
• Lecibral
• Lescodil
• Nerdipina
• Nicapress
• Nicardal
• Nicarpin
• Nimicor
• Rycarden
• Vasodin
• Vasonase
• Nicant
• Ranvil
• Ridene
• Rydene
• RS-69216
• RS-69216-XX-07-0
• NSC-757855
• DTXSID9046992
• K5BC5011K3
• RS-69216XX07-0
• DTXCID7026992
• Cardene In 4.8% Dextrose In Plastic Container
• Cardene In 5.0% Dextrose In Plastic Container
• Cardene In 0.83% Sodium Chloride In Plastic Container
• Cardene In 0.86% Sodium Chloride In Plastic Container
• 3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, methyl 2-(methyl(phenylmethyl)amino)ethyl ester, monohydrochloride
• Cardene IV
• 3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, methyl 2-[methyl(phenylmethyl)amino]ethyl ester, monohydrochloride
• RefChem:56588
• NICARDIPINE HYDROCHLORIDE IN 0.9% SODIUM CHLORIDE
• 2-(Benzyl(methyl)amino)ethyl methyl (4RS)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate monohydrochloride
• 259-198-4
• 5-O-(2-(benzyl(methyl)amino)ethyl) 3-O-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate;hydron;chloride
• Cardene
• Nicardipine (Hydrochloride)
• Nicardipinehydrochloride
• MFCD00057327
• YC-93 hydrochloride
• 3-{2-[benzyl(methyl)amino]ethyl} 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate hydrochloride
• 69441-18-5
• MLS000069782
• 2-(Benzylmethylamino)ethyl methyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylatemonohydrochloride
• C26H30ClN3O6
• s4181
• 2-(Benzylmethylamino)ethyl methyl 1,4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)-3,5-pyridinedicarboxylate monohydrochloride
• 3-(2-(benzyl(methyl)amino)ethyl) 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate hydrochloride
• 5-O-[2-[benzyl(methyl)amino]ethyl] 3-O-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate;hydrochloride
• Angioglebil
• Bionicard
• Nicardil
• SMR000058487
• Lincil
• Dafil
• Dagan
• Cardene (TN)
• 1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)methyl-2-[methyl(phenylmethyl)amino]-3,5-pyridinedicarboxylic acid ethyl ester hydrochloride
• 3,5-pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, 3-methyl 5-[2-[methyl(phenylmethyl)amino]ethyl] ester, hydrochloride (1:1)
• YC 93
• SR-01000075333
• EINECS 259-198-4
• Nicardipine hydrochloride [USAN:JAN]
• Nerdipine
• UNII-K5BC5011K3
• CCRIS 8508
• 1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid methyl 2-[methyl(phenylmethyl)amino]ethyl ester hydrochlori de;RS-69216;YC-93
• Prestwick_590
• EINECS 274-007-4
• Opera_ID_357
• CAS-54527-84-3
• SCHEMBL41845
• MLS001146898
• MLS002153279
• MLS002153794
• SPECTRUM1501135
• AC1Q67X4
• CHEBI:7551
• orb1309370
• CHEMBL1200326
• CHEMBL3199626
• SCHEMBL29465066
• HMS1569M07
• HMS1921H21
• HMS5082J06
• HY-12515AR
• Pharmakon1600-01501135
• BCP05610
• Tox21_301832
• Tox21_500809
• CCG-39033
• HY-12515A
• Nicardipine HCl - Bio-X trade mark
• NSC757855
• TN-901
• NICARDIPINE HYDROCHLORIDE [MI]
• AKOS015994734
• BCP9000988
• CS-3684
• FN26189
• KS-1276
• LP00809
• NC00578
• Nicardipine (hydrochloride) (Standard)
• NICARDIPINE HYDROCHLORIDE [JAN]
• NSC 757855
• RS-69216-XX-07-O
• Nicardipine hydrochloride (JP17/USAN)
• NICARDIPINE HYDROCHLORIDE [USAN]
• NCGC00094142-01
• NCGC00094142-02
• NCGC00094142-03
• NCGC00094142-04
• NCGC00094142-05
• NCGC00256289-01
• NCGC00261494-01
• NICARDIPINE HYDROCHLORIDE [MART.]
• NICARDIPINE HYDROCHLORIDE [VANDF]
• 2-(Benzyl(methyl)amino)ethyl methyl 1,4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)pyridine-3,5-dicarboxylate hydrochloride
• 3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)-, 2-(benzylmethylamino)ethyl methyl ester, monohydrochloride
• AC-36579
• BN166182
• NICARDIPINE HYDROCHLORIDE [USP-RS]
• NICARDIPINE HYDROCHLORIDE [WHO-DD]
• PD003063
• Nicardipine hydrochloride, powder, >=98%
• DB-052598
• EU-0100809
• N0635
• NS00090982
• SW196762-3
• D00617
• D91754
• EN300-123533
• N 7510
• NICARDIPINE HYDROCHLORIDE [EP MONOGRAPH]
• NICARDIPINE HYDROCHLORIDE [ORANGE BOOK]
• SBI-0050786.0001
• NICARDIPINE HYDROCHLORIDE [USP MONOGRAPH]
• 527N843
• SR-01000075333-1
• SR-01000075333-5
• Q27281986
• 12-(7-NITROBENZOFURAZAN-4-YLAMINO)DODECANOICACID
• Z1551967349
• Nicardipine hydrochloride, European Pharmacopoeia (EP) Reference Standard
• Nicardipine for system suitability, European Pharmacopoeia (EP) Reference Standard
• Nicardipine hydrochloride, United States Pharmacopeia (USP) Reference Standard
• 1,4-Dihydro-2,6-dimethyl-4-[3-nitrophenyl]methyl-2-[methyl-(phenyl-methl)amino]-3,5-pyridinedicarboxylic acid ethyl ester
• 2,6-Dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-[2-(N-benzyl-N-methylamino)]-ethyl ester 5-methyl ester hydrochloride
• 2-(N-benzyl-N-methylamino)ethyl methyl 2,6-dimethyl-4-(m-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate hydrochloride
• 2-[benzyl(methyl)amino]ethyl-methyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridin-3,5-dicarboxylathydrochlorid
• 3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-,?methyl 2-[methyl(phenylmethyl)amino]ethyl ester, hydrochloride (1:1)
• O5-[2-[benzyl(methyl)amino]ethyl] O3-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate;hydrochloride

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8860	88.60%
Caco-2	-	0.6122	61.22%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7782	77.82%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8994	89.94%
OATP1B3 inhibitior	+	0.8956	89.56%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	+	0.6500	65.00%
BSEP inhibitior	+	0.9941	99.41%
P-glycoprotein inhibitior	+	0.9305	93.05%
P-glycoprotein substrate	+	0.7400	74.00%
CYP3A4 substrate	+	0.7851	78.51%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8822	88.22%
CYP3A4 inhibition	+	0.9161	91.61%
CYP2C9 inhibition	+	0.7865	78.65%
CYP2C19 inhibition	+	0.8360	83.60%
CYP2D6 inhibition	+	0.7321	73.21%
CYP1A2 inhibition	+	0.8217	82.17%
CYP2C8 inhibition	+	0.9809	98.09%
CYP inhibitory promiscuity	+	0.8646	86.46%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7400	74.00%
Carcinogenicity (trinary)	Non-required	0.5110	51.10%
Eye corrosion	-	0.9842	98.42%
Eye irritation	-	0.9699	96.99%
Skin irritation	-	0.7845	78.45%
Skin corrosion	-	0.9265	92.65%
Ames mutagenesis	-	0.8400	84.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7259	72.59%
Micronuclear	+	0.9100	91.00%
Hepatotoxicity	-	0.7750	77.50%
skin sensitisation	-	0.8360	83.60%
Respiratory toxicity	+	0.9556	95.56%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	-	0.9388	93.88%
Acute Oral Toxicity (c)	III	0.4875	48.75%
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	-	0.8602	86.02%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	+	0.9900	99.00%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293237	P54132	Bloom syndrome protein	28183.8 nM; 28183.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	1000 nM; 1000 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293278	O75496	Geminin	22387.2 nM	Potency	via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	39810.7 nM; 39810.7 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	14125.4 nM; 14125.4 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL5162	Q6W5P4	Neuropeptide S receptor	5011.9 nM	Potency	via CMAUP
CHEMBL1293298	Q01453	Peripheral myelin protein 22	47754.8 nM	Potency	via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	5623.4 nM; 19952.6 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	44668.4 nM; 17782.8 nM	Potency; Potency	via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.17%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.57%	86.33%
CHEMBL2581	P07339	Cathepsin D	96.35%	98.95%
CHEMBL1940	Q13936	Voltage-gated L-type calcium channel alpha-1C subunit	95.28%	86.00%
CHEMBL221	P23219	Cyclooxygenase-1	94.78%	90.17%
CHEMBL3401	O75469	Pregnane X receptor	94.57%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.26%	99.17%
CHEMBL1255126	O15151	Protein Mdm4	91.57%	90.20%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.83%	97.09%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	89.62%	96.95%
CHEMBL5028	O14672	ADAM10	88.82%	97.50%
CHEMBL3902	P09211	Glutathione S-transferase Pi	88.55%	93.81%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.46%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.30%	95.56%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	86.19%	89.67%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.86%	94.45%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.88%	95.89%
CHEMBL1287628	Q9Y5S8	NADPH oxidase 1	83.39%	95.48%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	82.34%	93.03%
CHEMBL340	P08684	Cytochrome P450 3A4	81.92%	91.19%
CHEMBL3231	Q13464	Rho-associated protein kinase 1	80.92%	95.55%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.45%	95.89%

Plants that contains it

• Cinnamomum aromaticum

Cross-Links

• PubChem: 41114
• NPASS: NPC63370
• ChEMBL: CHEMBL1200326