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Compound Detail

CHEMBL513

CARMUSTINE
💊 Approved Drug
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💊 Approved Drug
O=NN(CCCl)C(=O)NCCCl
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL513
Name CARMUSTINE
Phase Approved
Structure Type MOL
InChI Key DLGOEMSEDOSKAD-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

BCNU Becenun Bicnu Bischloroethyl nitrosourea Camustine Carmubris Carmustina Carmustine Carmustine medac (previously carmustine obvius) Carmustine obvius DTI-015 FDA-0345 +4 more
34
Targets
55
Activities
2
Assay Types
7
PK Parameters
20
Publications
16
Known Names
20
Indications
3
Mechanisms

Molecular Properties

214.1
MW (Da)
1.16
ALogP
3
HBA
1
HBD
61.8
PSA (Ų)
0.42
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1977
Availability Prescription
Chirality Achiral

Routes of Administration

Parenteral

Flags

Natural Product
USAN Stem -mustine
USAN Year 1970

Extended Properties

Molecular Formula C5H9Cl2N3O2
MW 214.05
Aromatic Rings 0
Heavy Atoms 12
NP-Likeness -0.42

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Glutathione reductase inhibitor INHIBITOR Glutathione reductase, mitochondrial ✓ ✓
DNA inhibitor INHIBITOR DNA ✓ ✓
RNA inhibitor INHIBITOR RNA ✓ ✓

Indications

Astrocytoma Astrocytoma Ependymoma Glioblastoma Glioma Glioma Glioma Hodgkin Disease Hodgkin Disease Lymphoma, Non-Hodgkin Medulloblastoma Multiple Myeloma Neoplasms Breast Neoplasms Breast Neoplasms Central Nervous System Neoplasms Leukemia Lymphoma Lymphoma, Follicular Lymphoma, Follicular

ATC Classification

L01AD01
carmustine
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ANTINEOPLASTIC AGENTS

Activity Summary

IC50 53 meas. best 5.85
EC50 2 meas. best 5.32

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
U-87 MG
CHEMBL614247
 IC50 5.85 5.85 1420.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.62 4.4867 2370.0 9
Unchecked
CHEMBL612545
 IC50 5.41 5.41 3900.0 1
L1210
CHEMBL386
 IC50 5.35 5.35 4500.0 1
MCF7
CHEMBL387
 IC50 5.35 5.35 4500.0 1
C6
CHEMBL614657
 EC50 5.32 5.32 4800.0 1
NCI-H23
CHEMBL614997
 IC50 5.3 5.3 5000.0 1
P388
CHEMBL389
 IC50 5.23 5.23 5900.0 1
LOX IMVI
CHEMBL614096
 IC50 5.16 5.16 7000.0 1
MDA-MB-231
CHEMBL400
 IC50 5.13 5.13 7400.0 1
A-427
CHEMBL614515
 IC50 5.1 5.1 8000.0 1
Glutathione reductase, mitochondrial
CHEMBL2755
 IC50 5.09 5.09 8100.0 1
CHO
CHEMBL613853
 IC50 5.09 5.09 8200.0 1
NCI-H125
CHEMBL614159
 IC50 5.05 5.05 9000.0 1
K562
CHEMBL385
 IC50 5.05 5.05 9000.0 1
C6
CHEMBL614657
 IC50 5.03 5.03 9300.0 1
U-937
CHEMBL612794
 IC50 4.91 4.91 12300.0 1
U-251
CHEMBL615022
 IC50 4.82 4.82 15000.0 1
OVCAR-3
CHEMBL614213
 IC50 4.82 4.82 15000.0 1
HT-29
CHEMBL384
 IC50 4.77 4.77 17000.0 1
A 172
CHEMBL614512
 IC50 4.75 4.75 18000.0 1
OVCAR-4
CHEMBL614051
 IC50 4.75 4.75 18000.0 1
Malme-3M
CHEMBL614021
 IC50 4.7 4.7 20000.0 1
NCI-H520
CHEMBL614099
 IC50 4.7 4.7 20000.0 1
NCI/ADR-RES
CHEMBL613829
 IC50 4.7 4.7 20000.0 1
TE-671
CHEMBL615012
 IC50 4.6 4.6 25000.0 1
SK-MEL-5
CHEMBL614922
 IC50 4.57 4.57 27000.0 1
HL-60
CHEMBL383
 IC50 4.52 4.52 30500.0 1
DOD-1
CHEMBL614483
 IC50 4.43 4.43 37000.0 1
ADMET
CHEMBL612558
 EC50 4.26 4.26 54800.0 1
NCI-H322M
CHEMBL614803
 IC50 4.22 4.22 60000.0 1
NCI-H460
CHEMBL396
 IC50 4.1 4.1 80000.0 1
A549
CHEMBL392
 IC50 4.05 4.05 90000.0 1
NCI-H358
CHEMBL614135
 IC50 4.01 4.01 98000.0 1
Bile salt export pump
CHEMBL6020
 IC50 4.01 4.01 97210.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 78.0 mL.min-1.kg-1 Homo sapiens
Fu 0.23 - Homo sapiens
MRT 0.26 hr Homo sapiens
T1/2 1.5 hr Rattus norvegicus
T1/2 0.8333 hr -
T1/2 0.37 hr Homo sapiens
T1/2 0.25 hr -

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
U-87 MG IC50 = 1420.0 nM 5.85 In vitro inhibitory concentration against growth of U87MG glioblastoma cell line... 15603970
NON-PROTEIN TARGET IC50 = 2370.0 nM 5.62 In vitro inhibitory concentration against growth of SNB19 glioblastoma cell line... 15603970
Unchecked IC50 = 3900.0 nM 5.41 Antiproliferative activity against human U87 cells 33421712
L1210 IC50 = 4500.0 nM 5.35 Dose required to inhibit cell growth was determined against L1210 cell line of m... 11262080
MCF7 IC50 = 4500.0 nM 5.35 Evaluated for the inhibitory concentration required to cause growth inhibition o... 2391696
C6 EC50 = 4800.0 nM 5.32 Cytotoxicity against Rattus norvegicus (rat) C6 cells after 4 days by cresylecth... -
NCI-H23 IC50 = 5000.0 nM 5.3 Evaluated for the inhibitory concentration required to cause growth inhibition o... 2391696
P388 IC50 = 5900.0 nM 5.23 Dose required to inhibit cell growth was determined against P388D1 cell line of ... 11262080
LOX IMVI IC50 = 7000.0 nM 5.16 Evaluated for the inhibitory concentration required to cause growth inhibition o... 2391696
MDA-MB-231 IC50 = 7400.0 nM 5.13 Dose required to inhibit cell growth was determined against MDA-MB-231 cell line... 11262080
A-427 IC50 = 8000.0 nM 5.1 Evaluated for the inhibitory concentration required to cause growth inhibition o... 2391696
CHO IC50 = 8200.0 nM 5.09 Dose required to inhibit cell growth was determined against CHO cell line 11262080
Glutathione reductase, mitochondrial IC50 = 8100.0 nM 5.09 Inhibition of human recombinant glutathione reductase using glutathione as subst... 24321832
K562 IC50 = 9000.0 nM 5.05 Dose required to inhibit cell growth was determined against K562 cell line of ch... 11262080
NCI-H125 IC50 = 9000.0 nM 5.05 Evaluated for the inhibitory concentration required to cause growth inhibition o... 2391696
C6 IC50 = 9300.0 nM 5.03 Cytotoxicity against rat C6 glioma cell line 16970409
U-937 IC50 = 12300.0 nM 4.91 Cytotoxicity against Homo sapiens (human) U937 cells after 96 hr by MTT assay -
U-251 IC50 = 15000.0 nM 4.82 Evaluated for the inhibitory concentration required to cause growth inhibition o... 2391696
OVCAR-3 IC50 = 15000.0 nM 4.82 Evaluated for the inhibitory concentration required to cause growth inhibition o... 2391696
HT-29 IC50 = 17000.0 nM 4.77 Dose required to inhibit cell growth was determined against HT-29 cell line of h... 11262080

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 687
423215 10.1021/jm00189a019 L1210 23
2909727 10.1021/jm00121a005 Mus musculus 18
16472241 10.2174/1570163043334794 Hepatotoxicity 18
11356111 10.1021/jm0005149 Mus musculus 14
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
7401113 10.1021/jm00182a007 Mus musculus 12
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
28197307 10.1021/acsmedchemlett.6b00358 NON-PROTEIN TARGET 6
27041398 10.1016/j.bmc.2016.03.041 NON-PROTEIN TARGET 6
2909727 10.1021/jm00121a005 Unchecked 6
836501 10.1021/jm00212a020 NON-PROTEIN TARGET 5
18426954 10.1124/dmd.108.020479 ADMET 4
6226795 10.1021/jm00365a022 ADMET 3
20014752 10.1021/tx900326k Hepatotoxicity 3
22268526 10.1021/jm201428a ADMET 3
2939245 10.1021/jm00155a044 L1210 3
27041398 10.1016/j.bmc.2016.03.041 Unchecked 3
7365750 10.1021/jm00177a024 Mus musculus 3

Data from ChEMBL 36 via Core Engine