ISRADIPINE

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Trade Names
Synonyms
Status
Molecule Category UNKNOWN
ATC C08CA03
UNII YO1UK1S598
EPA CompTox DTXSID4023179

Structure

InChI Key HMJIYCCIJYRONP-UHFFFAOYSA-N
Smiles COC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)C)C1c1cccc2nonc12
InChI
InChI=1S/C19H21N3O5/c1-9(2)26-19(24)15-11(4)20-10(3)14(18(23)25-5)16(15)12-7-6-8-13-17(12)22-27-21-13/h6-9,16,20H,1-5H3

Physicochemical Descriptors

Property Name Value
Molecular Formula C19H21N3O5
Molecular Weight 371.39
AlogP 2.58
Hydrogen Bond Acceptor 8.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 4.0
Polar Surface Area 103.55
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 27.0

Bioactivity

Mechanism of Action Action Reference
Voltage-gated L-type calcium channel blocker BLOCKER Wikipedia Wikipedia Wikipedia Wikipedia DailyMed
Protein: Voltage-gated L-type calcium channel
Description: Voltage-dependent L-type calcium channel subunit alpha-1F
Organism : Homo sapiens
O60840 ENSG00000102001
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(%)
Enzyme Cytochrome P450 Cytochrome P450 family 1 Cytochrome P450 family 1A Cytochrome P450 1A2
- 28300 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C8
- 5000 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C9
- 3660 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2D Cytochrome P450 2D6
- 4790 - - -
Ion channel Voltage-gated ion channel Voltage-gated calcium channel
- 107 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 12
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 28000 - - -
Assay Description Organism Bioactivity Reference
Inhibition of human liver OATP1B1 expressed in HEK293 Flp-In cells assessed as reduction in E17-betaG uptake at 20 uM by scintillation counting Homo sapiens 47.5 %
Inhibition of human liver OATP1B3 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E17-betaG uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 7.7 %
Inhibition of human liver OATP2B1 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E3S uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 12.0 %
Antagonist activity at rabbit voltage-dependent L-type calcium channel Cav1.2alpha-1C expressed in HEK293 cells by FLIPR assay Oryctolagus cuniculus 107.0 nM
Antagonist activity at rat voltage-dependent L-type calcium channel Cav1.3alpha-1D expressed in HEK293 cells by FLIPR assay Rattus norvegicus 221.0 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 2.2 nM
AntiOnchocerca activity O. gutturosa adult males: EC50 (uM) Onchocerca gutturosa 890.0 nM
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 14.31 % 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 3.78 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli -0.09 % Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli -1.04 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 7.21 % Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 6.29 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 14.96 % Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 2.23 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 18.51 % Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 4.46 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 4.43 % Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 4.19 %
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 -5.25 % 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 -10.15 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 5.45 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.57 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.57 %
Growth inhibiting activity of Naegleria gruberi in vitro Naegleria gruberi 48.7 %

Cross References

Resources Reference
ChEBI 6073
ChEMBL CHEMBL1648
DrugBank DB00270
DrugCentral 1511
FDA SRS YO1UK1S598
Human Metabolome Database HMDB0014415
Guide to Pharmacology 4488
KEGG D00349
PharmGKB PA450131
PubChem 3784
SureChEMBL SCHEMBL34555
ZINC ZINC22001248
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