NIMODIPINE

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Trade Names
Synonyms
Status
Molecule Category UNKNOWN
ATC C08CA06
UNII 57WA9QZ5WH
EPA CompTox DTXSID5023370

Structure

InChI Key UIAGMCDKSXEBJQ-UHFFFAOYSA-N
Smiles COCCOC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)C)C1c1cccc([N+](=O)[O-])c1
InChI
InChI=1S/C21H26N2O7/c1-12(2)30-21(25)18-14(4)22-13(3)17(20(24)29-10-9-28-5)19(18)15-7-6-8-16(11-15)23(26)27/h6-8,11-12,19,22H,9-10H2,1-5H3

Physicochemical Descriptors

Property Name Value
Molecular Formula C21H26N2O7
Molecular Weight 418.45
AlogP 2.97
Hydrogen Bond Acceptor 8.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 8.0
Polar Surface Area 117.0
Molecular species NEUTRAL
Aromatic Rings 1.0
Heavy Atoms 30.0

Bioactivity

Mechanism of Action Action Reference
Mineralocorticoid receptor antagonist ANTAGONIST PubMed
Protein: Voltage-gated L-type calcium channel
Description: Voltage-dependent L-type calcium channel subunit alpha-1F
Organism : Homo sapiens
O60840 ENSG00000102001
Protein: Mineralocorticoid receptor
Description: Mineralocorticoid receptor
Organism : Homo sapiens
P08235 ENSG00000151623
Protein: Voltage-gated L-type calcium channel
Description: Voltage-dependent L-type calcium channel subunit alpha-1D
Organism : Homo sapiens
Q01668 ENSG00000157388
Protein: Voltage-gated L-type calcium channel
Description: Voltage-dependent L-type calcium channel subunit alpha-1S
Organism : Homo sapiens
Q13698 ENSG00000081248
Protein: Voltage-gated L-type calcium channel
Description: Voltage-dependent L-type calcium channel subunit alpha-1C
Organism : Homo sapiens
Q13936 ENSG00000151067
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Auxiliary transport protein Calcium channel auxiliary subunit alpha2delta family
- 14000 - - 25
Auxiliary transport protein Calcium channel auxiliary subunit beta family
- 14000 - - 25
Auxiliary transport protein Calcium channel auxiliary subunit gamma family
- 14000 - - 25
Enzyme Cytochrome P450 Cytochrome P450 family 1 Cytochrome P450 family 1A Cytochrome P450 1A2
- 7200 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C19
- 2170 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C9
- 1690 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2D Cytochrome P450 2D6
- 18300 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A4
- 1780 - - 85
Enzyme
- 1690 - - 85
Ion channel Voltage-gated ion channel Transient receptor potential channel
800 - - - -
Ion channel Voltage-gated ion channel Voltage-gated calcium channel
- 110 - - 46-50
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Nucleotide-like receptor (family A GPCR) Adenosine receptor
- - - 20100 -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group H Nuclear hormone receptor subfamily 1 group H member 4
- 8960 - - 68
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group I Nuclear hormone receptor subfamily 1 group I member 2
390 - - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 38
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 10100 - - -
Assay Description Organism Bioactivity Reference
Equilibrium dissociation constant based on membrane concentration in rat smooth muscle Rattus norvegicus 690.0 nM
Calcium channel antagonist activity against carbachol-induced contractile response in guinea pig ileal longitudinal smooth muscle Cavia porcellus 14.9 nM
Compound was tested for percent of fraction inhibition by anti-P-450 NF. None 85.0 %
Antagonist activity at calcium channel expressed in SH-SY5Y cells assessed as blockade of potassium-induced calcium influx increase at 0.3 uM relative to control Homo sapiens 45.5 %
Antagonist activity at voltage-dependent L-type calcium channel in human SH-SY5Y cells assessed as inhibition of KCl-induced increase in cytosolic calcium concentration at 0.3 uM pretreated for 10 mins before KCl challenge relative to control Homo sapiens 45.5 %
Inhibition of potassium chloride-induced cytosolic calcium levels in human SH-SY5Y cells at 0.3 uM by fluorescence method relative to control Homo sapiens 45.5 %
Agonist activity at mouse TRPA1 channel expressed in CHO cells assessed as increase in intracellular calcium influx Mus musculus 800.0 nM
Antagonist activity at VGCC in Sprague-Dawley rat brain synaptoneurosomes assessed as inhibition of Kcl-induced calcium flux at 100 uM after 5 mins using FURA-2AM by fluorescent spectrometer analysis relative to control Rattus norvegicus 12.29 %
Antagonist activity at voltage gated calcium channel in Sprague-Dawley rat striatal synaptoneurosomes assessed as inhibition of KCl-induced calcium flux at 100 uM by spectrofluorimetric analysis relative to control Rattus norvegicus 12.29 %
DRUGMATRIX: Sodium/nucleoside co-transporter radioligand binding (ligand: nitrobenzylthioinosine) Cavia porcellus 433.0 nM
DRUGMATRIX: Calcium Channel Type L, Benzothiazepine radioligand binding (ligand: [3H] Diltiazem) Rattus norvegicus 2.093 nM DRUGMATRIX: Calcium Channel Type L, Benzothiazepine radioligand binding (ligand: [3H] Diltiazem) Rattus norvegicus 1.86 nM
DRUGMATRIX: Calcium Channel Type L, Dihydropyridine radioligand binding (ligand: [3H] Nitrendipine) Rattus norvegicus 0.242 nM DRUGMATRIX: Calcium Channel Type L, Dihydropyridine radioligand binding (ligand: [3H] Nitrendipine) Rattus norvegicus 0.156 nM
Inhibition of mouse Ido2 transfected in HEK293T cells using L-tryptophan as substrate assessed as kynurenine formation at 20 uM after 45 mins by spectrophotometric analysis relative to control Mus musculus 55.0 %
Agonist activity at PXR (unknown origin) expressed in human HepG2 cells assessed as induction of CYP3A4 transactivation after 16 hrs by luciferase reporter gene assay Homo sapiens 390.0 nM
Antagonist activity at human GTS-tagged FXR at 15 uM after 20 mins by TR-FRET assay Homo sapiens 67.5 %
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 64.8 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 37.85 %
Inhibition of voltage gated calcium channel in Wistar rat brain synaptoneurosomes homogenate assessed as intracellular calcium at 100 uM after 30 mins incubation by Fura-2/AM assay Rattus norvegicus 100.0 %
Inhibition of L-type calcium channel measured using whole-cell patch clamp in guinea pig ventricular myocytes Cavia porcellus 300.0 nM
Inhibition of L-type calcium channel measured using 2-electrode voltage-clamp in human embryonic kidney cells heterologically expressing alpha-1C subunit Homo sapiens 110.0 nM
Inhibition of voltage-gated calcium channel in mouse synaptoneurosomes assessed as reduction of KCl-induced calcium influx at 100 uM after 30 mins using Fura-2 AM by fluorescence assay relative to control Mus musculus 100.0 %
Inhibition of voltage-gated calcium channel in Wistar rat synaptoneurosomes after 30 mins by fluorescent ratiometric indicator method Rattus norvegicus 8.0 nM
Induction of mitochondrial dysfunction in Sprague-Dawley rat liver mitochondria assessed as inhibition of mitochondrial respiration per mg mitochondrial protein measured for 20 mins by A65N-1 oxygen probe based fluorescence assay Rattus norvegicus 100.0 nM
Antagonist activity at New Zealand rabbit L-type calcium channel assessed as dilation of K+-depolarization induced basilary artery contraction measured after 20 mins Oryctolagus cuniculus 520.0 nM
Inhibition of L-type voltage gated calcium channel in human SH-SY5Y cells assessed as blockade of K+-evoked calcium uptake at 1 uM pretreated for 10 mins followed by KCl/CaCl2 addition and measured for 55 secs by Fluo-4AM dye based fluorescence assay relative to control Homo sapiens 49.62 %
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600) Staphylococcus aureus subsp. aureus 7.57 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli 4.2 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 1.9 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 19.21 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 9.05 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 5.34 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570) Cryptococcus neoformans -7.18 %
Anti-anoxic activity in rat PC12 cells reduction in assessed as sodium hydrosulfite-induced cell injury Rattus norvegicus 1.29 ug.mL-1
Inhibition of K+-induced voltage gated calcium channel opening in human SH-SY5Y cells assessed as decrease in Ca2+ level at 10 uM after 10 mins by Fluo-4 dye-based fluorescence assay relative to control Homo sapiens 25.0 %
Blockade of VGCC in human SH-SY5Y cells assessed as inhibition of membrane depolarisation-induced calcium influx at 10 uM by Fura-2AM dye based fluorescence analysis relative to control Homo sapiens 34.07 %
Inhibition of Ca2+ channel in mouse microglial cells assessed as inhibition of Abeta-stimulated NLRP3 inflammasome activation-mediated IL-1beta release at 36 nM by ELISA Mus musculus 48.0 %

Related Entries

Cross References

Resources Reference
ChEBI 7575
ChEMBL CHEMBL1428
DrugBank DB00393
DrugCentral 1937
FDA SRS 57WA9QZ5WH
Human Metabolome Database HMDB0014537
Guide to Pharmacology 2523
KEGG C07267
PharmGKB PA450633
PubChem 4497
SureChEMBL SCHEMBL34041
ZINC ZINC19632718
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