IRINOTECAN

/static/temp/default.svg Search structure
Synonyms
Status
Molecule Category Free-form
ATC L01CE02
UNII 7673326042
EPA CompTox DTXSID1041051

Structure

InChI Key UWKQSNNFCGGAFS-XIFFEERXSA-N
Smiles CCc1c2c(nc3ccc(OC(=O)N4CCC(N5CCCCC5)CC4)cc13)-c1cc3c(c(=O)n1C2)COC(=O)[C@]3(O)CC
InChI
InChI=1S/C33H38N4O6/c1-3-22-23-16-21(43-32(40)36-14-10-20(11-15-36)35-12-6-5-7-13-35)8-9-27(23)34-29-24(22)18-37-28(29)17-26-25(30(37)38)19-42-31(39)33(26,41)4-2/h8-9,16-17,20,41H,3-7,10-15,18-19H2,1-2H3/t33-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C33H38N4O6
Molecular Weight 586.69
AlogP 4.09
Hydrogen Bond Acceptor 9.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 4.0
Polar Surface Area 114.2
Molecular species BASE
Aromatic Rings 3.0
Heavy Atoms 43.0
Assay Description Organism Bioactivity Reference
Cytotoxic activity against human lymphoblast tumor cell line RPMI8402 after 4 days of treatment Homo sapiens 570.0 nM
Growth inhibition of human T24 cells after 4 days by MTT assay Homo sapiens 23.8 %
Inhibition of Torpedo californica AChE Torpedo californica 26.4 nM
Inhibition of human AChE Homo sapiens 50.5 nM
Cytotoxicity against human KB3-1 cells by MTT method Homo sapiens 680.0 nM
Antitumor activity against human SJSA1 cells xenografted in mouse assessed as tumor growth inhibition at 100 mg/kg, ip dosed once weekly for two weeks relative to untreated control Homo sapiens 0.0002 %
Cytotoxicity against human H460 cells after 72 hrs by alamar blue assay Homo sapiens 15.0 nM
Cytotoxicity against human PC3 cells after 72 hrs by alamar blue assay Homo sapiens 4.0 nM
Cytotoxicity against human HT-29 cells after 72 hrs by alamar blue assay Homo sapiens 220.0 nM
Cytotoxicity against human SK-MEL-2 cells after 72 hrs by alamar blue assay Homo sapiens 100.0 nM
Cytotoxicity against human A375 cells after 72 hrs by alamar blue assay Homo sapiens 4.0 nM
Cytotoxicity against human MALME-3M cells after 72 hrs by alamar blue assay Homo sapiens 200.0 nM
Cytotoxicity against human DU145 cells after 72 hrs by alamar blue assay Homo sapiens 200.0 nM
Cytotoxicity against human LNCAP cells after 72 hrs by alamar blue assay Homo sapiens 9.0 nM
Cytotoxicity against human IGROV1 cells after 72 hrs by alamar blue assay Homo sapiens 30.0 nM
Cytotoxicity against human H460 cells after 72 hrs by alamar blue assay in presence of 40 mg/ml HSA Homo sapiens 27.0 nM
Cytotoxicity against human MESSA cells after 72 hrs by alamar blue assay Homo sapiens 10.0 nM
Cytotoxicity against human MES-SA/Dx5 cells overexpressing MDR1 after 72 hrs by alamar blue assay Homo sapiens 22.0 nM
Cytotoxicity against human H69 cells after 72 hrs by alamar blue assay Homo sapiens 22.0 nM
Cytotoxicity against human H69AR cells overexpressing MDR1 after 72 hrs by alamar blue assay Homo sapiens 250.0 nM
Cytotoxicity against human bone marrow cell by CFU-GM assay Homo sapiens 110.0 nM
Cytotoxicity against mouse bone marrow cell by CFU-GM assay Mus musculus 1.0 nM
DRUGMATRIX: Muscarinic M4 radioligand binding (ligand: [3H] N-Methylscopolamine) None 217.0 nM
DRUGMATRIX: Adrenergic Alpha-2C radioligand binding (ligand: [3H] MK-912) None 461.0 nM
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 40.5 %
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 26.9 %
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 16.3 %
Inhibition of human MATE1-mediated ASP+ uptake expressed in HEK293 cells at 20 uM after 1.5 mins by fluorescence assay Homo sapiens 49.0 %
Inhibition of human OATP1B3-mediated [3H]CCK-8 at 100 uM after 5 mins relative to control Homo sapiens 34.3 %
Antiproliferative activity against human MCF7 cells assessed as cellular DNA content after 96 hrs by CyQUANT NF fluorescence assay Homo sapiens 900.0 nM
Antiproliferative activity against human PC3 cells assessed as cellular DNA content after 72 hrs by CyQUANT NF fluorescence assay Homo sapiens 800.0 nM
Cytotoxicity against human HepG2 cells assessed as reduction in cell viability after 24 hrs by MTS assay Homo sapiens 900.0 nM
Cytotoxicity against human A549 cells assessed as reduction in cell viability after 24 hrs by MTS assay Homo sapiens 800.0 nM
Cytotoxicity against human MCF7 cells assessed as reduction in cell viability after 24 hrs by MTS assay Homo sapiens 500.0 nM
Antiproliferative activity against human HepG2 cells at 10 uM after 24 hrs by MTS assay relative to control Homo sapiens 98.9 %
Antiproliferative activity against human A549 cells at 10 uM after 24 hrs by MTS assay relative to control Homo sapiens 91.8 %
Antiproliferative activity against human MCF7 cells at 10 uM after 24 hrs by MTS assay relative to control Homo sapiens 93.6 %
Antiproliferative activity against human SW480 cells at 10 uM after 24 hrs by MTS assay relative to control Homo sapiens 95.0 %
Antiproliferative activity against human Maver2 cells after 72 hrs by MTT assay Homo sapiens 740.0 nM
Antitumor activity against human MM473 cells xenografted in CD1 nude mouse assessed as inhibition of tumor volume at 20 mg/kg, iv administered every 4 days per week for 3 weeks measured 10 days post last dose by luciferase reporter assay relative to vehicle-treated control Homo sapiens 37.0 %
Cytotoxicity against human MCF7 cells incubated for 24 hrs by MTT assay Homo sapiens 800.0 nM
Antiproliferative activity against human HCT116 cells assessed as reduction in cell viability after 72 hrs by SRB assay Homo sapiens 498.0 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 121.15 %
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 0.01 % 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 0.01 %
Antiproliferative activity against human HeLa cells after 72 hrs by MTT assay Homo sapiens 32.0 nM
Antiproliferative activity against human A549 cells after 72 hrs by MTT assay Homo sapiens 32.0 nM
Antiproliferative activity against human HL60 cells after 72 hrs by MTT assay Homo sapiens 32.0 nM
Antitumor activity against human SK-OV-3 cells xenografted in BALB/c nude mouse assessed as reduction in tumor volume at 20 mg/kg, iv once a week for 3 weeks relative to control Homo sapiens 53.5 %
Anticancer activity against human HCT-116 cells assessed as inhibition of cell proliferation measured after 72 hrs by MTT assay Homo sapiens 4.4 nM
Anticancer activity against human SW-620 cells assessed as inhibition of cell proliferation measured after 72 hrs by MTT assay Homo sapiens 5.1 nM
Anticancer activity against human T84 cells assessed as inhibition of cell proliferation measured after 72 hrs by MTT assay Homo sapiens 6.9 nM
Cytotoxicity against human MCF7 cells by MTT assay Homo sapiens 800.0 nM
Cytotoxicity against human NCI-H526 cells assessed as reduction in cell viability incubated for 72 hrs by PrestoBlue reagent based assay Homo sapiens 490.0 nM

Related Entries

Cross References

Resources Reference
ChEBI 80630
ChEMBL CHEMBL481
DrugBank DB00762
DrugCentral 1482
FDA SRS 7673326042
Human Metabolome Database HMDB0014900
Guide to Pharmacology 6823
KEGG C16641
PDB CP0
PharmGKB PA450085
PubChem 60838
SureChEMBL SCHEMBL4034
ZINC ZINC000001612996
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