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Compound Detail

CHEMBL810

TEMOZOLOMIDE
💊 Approved Drug
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💊 Approved Drug
Cn1nnc2c(C(N)=O)ncn2c1=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL810
Name TEMOZOLOMIDE
Phase Approved
Structure Type MOL
InChI Key BPEGJWRSRHCHSN-UHFFFAOYSA-N
Therapeutic ✓ Yes
Active Moiety CHEMBL1442

Known Names

CCRG-81045 M&B 39831 M&B-39831 M-39831 Methazolastone Mk-7365 NSC-362856 SCH 52365 SCH-52365 Temodal Temodar Temomedac +7 more
20
Targets
86
Activities
2
Assay Types
30
PK Parameters
20
Publications
19
Known Names
20
Indications
1
Mechanisms

Molecular Properties

194.2
MW (Da)
-2.08
ALogP
7
HBA
1
HBD
108.2
PSA (Ų)
0.56
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1999
Availability Prescription
Chirality Achiral

Routes of Administration

Oral Parenteral

Flags

Black Box Warning Natural Product Prodrug
USAN Year 1999

Extended Properties

Molecular Formula C6H6N6O2
MW 194.15
Aromatic Rings 2
Heavy Atoms 14
NP-Likeness -1.63

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
DNA inhibitor INHIBITOR DNA ✓ ✓

Indications

Glioblastoma Glioblastoma Glioma Glioma Glioma Glioma Glioma Neoplasms Neoplasms Astrocytoma Astrocytoma Brain Neoplasms Brain Neoplasms Brain Neoplasms Carcinoma, Non-Small-Cell Lung Central Nervous System Neoplasms Choroid Plexus Neoplasms Diffuse Intrinsic Pontine Glioma Ganglioneuroblastoma Gliosarcoma

ATC Classification

L01AX03
temozolomide
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ANTINEOPLASTIC AGENTS

Drug Warnings

Black Box Warning
General Warning
Country: United States

Activity Summary

IC50 83 meas. best 5.36
EC50 3 meas. best 4.78

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
HCT-116
CHEMBL394
 IC50 5.36 5.36 4340.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.3 4.618 5000.0 5
TLX-5
CHEMBL615015
 IC50 5.3 5.3 5000.0 1
HepG2
CHEMBL395
 IC50 5.23 5.23 5900.0 1
U-251
CHEMBL615022
 IC50 5.19 4.7433 6426.0 6
GM892A cell line
CHEMBL614505
 IC50 5.12 5.12 7600.0 1
A2780
CHEMBL614004
 IC50 5.07 5.07 8500.0 1
MDA-MB-231
CHEMBL400
 IC50 4.84 4.84 14400.0 1
C6
CHEMBL614657
 EC50 4.78 4.5 16500.0 2
Unchecked
CHEMBL612545
 IC50 4.74 4.67 18200.0 3
C6
CHEMBL614657
 IC50 4.47 4.345 34000.0 2
A2058
CHEMBL613503
 IC50 4.45 4.45 35500.0 1
SNB-19
CHEMBL614164
 IC50 4.43 4.295 37000.0 2
Polyadenylate-binding protein 1
CHEMBL1293286
 IC50 4.36 4.36 43450.0 1
Hs 683
CHEMBL612596
 IC50 4.33 4.33 47180.0 1
H4
CHEMBL1075452
 IC50 4.32 4.32 47900.0 1
ADMET
CHEMBL612558
 EC50 4.29 4.29 51800.0 1
LN-229
CHEMBL4296459
 IC50 4.27 4.22 54080.0 2
NCI
CHEMBL614877
 IC50 4.1 4.0214 79000.0 7
carcinoma cell line
CHEMBL614380
 IC50 4.04 4.04 91000.0 1
Non-small cell lung cancer cell line
CHEMBL615002
 IC50 4.0 4.0 100000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 5660.37 ng.hr/g Rattus norvegicus
AUC 16853.7 ng.hr.mL-1 Rattus norvegicus
CL 3.6 mL.min-1.kg-1 Homo sapiens
CL 27.3 mL.min-1.g-1 Homo sapiens
CL 23.0 mL.min-1.g-1 Homo sapiens
CL 1.0 mL.min-1.g-1 Rattus norvegicus
CL 1.0 mL.min-1.g-1 Rattus norvegicus
F 100.0 % Homo sapiens
Fu 0.5 - Mus musculus
MRT 2.3 hr Homo sapiens
T1/2 8.25 hr -
T1/2 8.25 hr -
T1/2 0.4167 hr -
T1/2 1.833 hr -
T1/2 1.833 hr Homo sapiens
T1/2 1.5 hr Homo sapiens
T1/2 253.0 hr -
T1/2 1.38 hr -
T1/2 0.42 hr -
T1/2 1.24 hr -
T1/2 2.0 hr -
T1/2 1.83 hr -
T1/2 1.533 hr -
T1/2 1.667 hr -
T1/2 2.467 hr -
T1/2 4.022 hr -
T1/2 8.0 hr -
T1/2 0.33 hr Homo sapiens
T1/2 0.2983 hr Rattus norvegicus
T1/2 0.8483 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
HCT-116 IC50 = 4340.0 nM 5.36 Cytotoxicity against human HCT116 cells after 4 days 19800803
TLX-5 IC50 = 5000.0 nM 5.3 In vitro cytotoxicity against mouse TLX5 lymphoma cells 7739008
NON-PROTEIN TARGET IC50 = 5000.0 nM 5.3 In vitro cytotoxicity against mouse TLX5 lymphoma cells 12459014
HepG2 IC50 = 5900.0 nM 5.23 Cytotoxicity against human HepG2 cells assessed as reduction in cell viability b... 37335557
U-251 IC50 = 6426.0 nM 5.19 Cytotoxicity against cold atmospheric plasma (CAP)-treated human U-251MG cells a... 34384944
U-251 IC50 = 7284.0 nM 5.14 Cytotoxicity against cold atmospheric plasma (CAP)-treated human U-251MG cells a... 34384944
GM892A cell line IC50 = 7600.0 nM 5.12 In vitro cytotoxicity against human lymphoblast cell line (GM892 A). 7739008
A2780 IC50 = 8500.0 nM 5.07 Chemosensitization of human A2780 cells after 5 days by MTT assay in presence of... 23895620
U-251 IC50 = 12740.0 nM 4.89 Cytotoxicity against human U-251MG cells assessed as decrease in cell viability ... 34384944
MDA-MB-231 IC50 = 14400.0 nM 4.84 Cytotoxicity against human MDA-MB-231 cells assessed as reduction in cell viabil... 37335557
C6 EC50 = 16500.0 nM 4.78 Cytotoxicity against Rattus norvegicus (rat) C6 cells after 4 days by cresylecth... -
Unchecked IC50 = 18200.0 nM 4.74 Cytotoxicity against human Enzalutamide-resistant LNCaP C4-2 cells assessed as r... 37335557
NON-PROTEIN TARGET IC50 = 19380.0 nM 4.71 Cytotoxicity against human U87 cells assessed as growth inhibition after 72 hrs ... -
Unchecked IC50 = 20800.0 nM 4.68 Antiproliferative activity against human N13-1300 cells incubated for 72 hrs by ... 37449818
Unchecked IC50 = 25430.0 nM 4.59 Anticancer activity against patient-derived DB70 cells assessed as cell growth i... 37201660
NON-PROTEIN TARGET IC50 = 26000.0 nM 4.58 Cytotoxicity against human U138MG cells incubated for 48 hrs by MTT assay 23069682
C6 IC50 = 34000.0 nM 4.47 Cytotoxicity against rat C6 cells incubated for 48 hrs by MTT assay 23069682
A2058 IC50 = 35500.0 nM 4.45 Chemosensitization of human A2058 cells after 5 days by MTT assay 23895620
U-251 IC50 = 36400.0 nM 4.44 Cytotoxicity against human U251 cells incubated for 24 hrs by MTT assay 31891260
U-251 IC50 = 36400.0 nM 4.44 Cytotoxicity against human U-251 cells by MTT assay 33915258

Literature References

PubMed DOI Target Context # Activities
32960603 10.1021/acs.jnatprod.0c00580 DBTRG-05MG 40
32960603 10.1021/acs.jnatprod.0c00580 RG2 38
37262998 10.1016/j.ejmech.2023.115507 ADMET 21
32960603 10.1021/acs.jnatprod.0c00580 Unchecked 17
27614414 10.1016/j.bmcl.2016.08.064 ADMET 15
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
27218860 10.1016/j.ejmech.2016.05.004 NON-PROTEIN TARGET 12
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15615536 10.1021/jm049556d NCI 9
35044783 10.1021/acs.jnatprod.1c00595 U-87 MG 9
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
27823879 10.1016/j.ejmech.2016.10.037 MDCK 8
39136241 10.1021/acs.jmedchem.4c01304 U-87 MG 8
30925064 10.1021/acs.jmedchem.9b00282 Unchecked 7
26288699 10.1021/acsmedchemlett.5b00128 NON-PROTEIN TARGET 7
34656900 10.1016/j.ejmech.2021.113908 Unchecked 7
34091208 10.1016/j.ejmech.2021.113564 C6 7
37262998 10.1016/j.ejmech.2023.115507 Unchecked 6
24900418 10.1021/ml300132t No relevant target 6
30615449 10.1021/acs.jmedchem.8b01305 U-87 MG 6

Data from ChEMBL 36 via Core Engine