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Compound Detail

CHEMBL371405

MARIZOMIB
🧪 Phase III
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🧪 Phase III
C[C@@]12OC(=O)[C@]1([C@@H](O)[C@@H]1C=CCCC1)NC(=O)[C@@H]2CCCl
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL371405
Name MARIZOMIB
Phase Phase III
Structure Type MOL
InChI Key NGWSFRIPKNWYAO-SHTIJGAHSA-N

Known Names

Marizomib NPI-0052 Salinosporamide a
10
Targets
38
Activities
3
Assay Types
2
PK Parameters
20
Publications
3
Known Names
7
Indications
1
Mechanisms

Molecular Properties

313.8
MW (Da)
1.13
ALogP
4
HBA
2
HBD
75.6
PSA (Ų)
0.46
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product
USAN Stem -zomib
USAN Year 2009

Extended Properties

Molecular Formula C15H20ClNO4
MW 313.78
Aromatic Rings 0
Heavy Atoms 21
NP-Likeness 2.87

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
20S proteasome inhibitor INHIBITOR 20S proteasome ✓ ✓

Indications

Glioblastoma Ependymoma Ependymoma Multiple Myeloma Paraganglioma Lymphoma Neoplasms

Activity Summary

IC50 35 meas. best 9.22
Ki 2 meas. best 7.64
EC50 1 meas. best 7.96

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Proteasome component C5
CHEMBL4208
 IC50 9.22 7.795 0.6 2
20S proteasome
CHEMBL3831201
 IC50 8.89 8.89 1.3 1
Unchecked
CHEMBL612545
 IC50 8.89 7.5845 1.3 20
Oryctolagus cuniculus
CHEMBL374
 IC50 8.59 7.5467 2.6 3
Proteasome Macropain subunit MB1
CHEMBL4662
 IC50 8.46 8.1933 3.5 3
RPMI-8226
CHEMBL614882
 IC50 8.09 8.025 8.2 2
Plasmodium falciparum
CHEMBL364
 EC50 7.96 7.96 11.0 1
HEK293
CHEMBL614818
 IC50 7.96 7.96 11.0 1
HCT-116
CHEMBL394
 IC50 7.8 7.63 16.0 2
Unchecked
CHEMBL612545
 Ki 7.64 7.325 23.0 2
Proteasome Macropain subunit
CHEMBL3492
 IC50 7.55 7.55 28.0 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 1.283 hr -
T1/2 0.9333 hr -

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Proteasome component C5 IC50 = 0.604 nM 9.22 Inhibition of 20S proteasome beta 1c (unknown origin) after 1 hr by fluorescence... 31521028
Unchecked IC50 = 1.3 nM 8.89 Irreversible inhibition of 20S proteasome 21835627
20S proteasome IC50 = 1.3 nM 8.89 Inhibition of 20S proteasome (unknown origin) by fluorescence based assay 35063731
Unchecked IC50 = 1.9 nM 8.72 Inhibition of chymotrypsin like activity of yeast 20S proteasome beta 5 subunit ... 19746976
Unchecked IC50 = 2.0 nM 8.7 Inhibition of chymotrypsin-like activity of yeast 20S proteasome 18939815
Unchecked IC50 = 2.5 nM 8.6 Inhibition of chymotrypsin-like activity of rabbit 20S proteasome 18939815
Oryctolagus cuniculus IC50 = 2.6 nM 8.59 Inhibition of chymotrypsin-like (CT-L) activity of rabbit 20S proteasome 15916417
Unchecked IC50 = 2.6 nM 8.59 Inhibition of chymotrypsin-like activity of 20S proteasome in rabbit erythrocyte... 23541650
Unchecked IC50 = 2.6 nM 8.59 Inhibition of 20s constitutive proteasome beta 5 subunit chymotrypsin-like activ... 24534487
Unchecked IC50 = 3.5 nM 8.46 Inhibition of chymotrypsin-like activity of human 20S proteasome 18939815
Proteasome Macropain subunit MB1 IC50 = 3.5 nM 8.46 Inhibition of 20S proteasome beta 5c (unknown origin) after 1 hr by fluorescence... 31521028
Proteasome Macropain subunit MB1 IC50 = 3.5 nM 8.46 Reversible inhibition of human erythrocyte derived 20S proteasome subunit beta5 ... 22978849
Unchecked IC50 = 4.0 nM 8.4 Inhibition of chymotrypsin-like activity of rabbit 20S proteasome 19133779
RPMI-8226 IC50 = 8.2 nM 8.09 Cytotoxic activity against RPMI 8226 cells 15916417
HEK293 IC50 = 11.0 nM 7.96 Inhibition of NF-kB activation in HEK293 cells 15916417
RPMI-8226 IC50 = 11.0 nM 7.96 Cytotoxicity against human RPMI8226 cells after 48 hrs by resazurin assay 19133779
Plasmodium falciparum EC50 = 11.0 nM 7.96 Antiplasmodial activity against Plasmodium falciparum by SYBR Green staining-bas... 23587422
HCT-116 IC50 = 16.0 nM 7.8 Cytotoxicity against human HCT116 cells after 72 hrs by MTS/PMS assay 19746976
Unchecked IC50 = 21.0 nM 7.68 Inhibition of trypsin-like activity of 20S proteasome in rabbit erythrocytes usi... 23541650
Unchecked IC50 = 21.0 nM 7.68 Inhibition of 20s constitutive proteasome beta 2 subunit trypsin-like activity i... 24534487

Literature References

PubMed DOI Target Context # Activities
18939815 10.1021/jm800548b Unchecked 21
24269479 10.1016/j.bmcl.2013.09.066 Proteasome Macropain subunit MB1 6
15916417 10.1021/jm048995+ Oryctolagus cuniculus 3
24534487 10.1016/j.bmcl.2014.01.072 Unchecked 3
23541650 10.1016/j.bmcl.2013.02.079 Unchecked 3
19133779 10.1021/np800578e Unchecked 3
19746976 10.1021/jm901098m HCT-116 1
23547757 10.1021/jm4002296 No relevant target 1
22978849 10.1021/jm300434z Proteasome Macropain subunit MB1 1
35063731 10.1016/j.ejmech.2022.114117 20S proteasome 1
22978849 10.1021/jm300434z Proteasome component C5 1
21835627 10.1016/j.bmc.2011.07.017 HCT-116 1
21835627 10.1016/j.bmc.2011.07.017 Unchecked 1
17108984 10.1038/nchembio841 Unchecked 1
15916417 10.1021/jm048995+ RPMI-8226 1
19746976 10.1021/jm901098m Unchecked 1
19133779 10.1021/np800578e RPMI-8226 1
19022674 10.1016/j.bmc.2008.10.075 NON-PROTEIN TARGET 1
19022674 10.1016/j.bmc.2008.10.075 HCT-116 1
18939815 10.1021/jm800548b No relevant target 1

Data from ChEMBL 36 via Core Engine