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Compound Detail

CHEMBL515

CHLORAMBUCIL
💊 Approved Drug
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💊 Approved Drug
O=C(O)CCCc1ccc(N(CCCl)CCCl)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL515
Name CHLORAMBUCIL
Phase Approved
Structure Type MOL
InChI Key JCKYGMPEJWAADB-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Ambochlorin CB-1348 Chlorambucil Chlorambucilum Clorambucilo Ecloril Leukeran Lympholysin NCI-3088 NSC-3088
61
Targets
184
Activities
3
Assay Types
20
PK Parameters
20
Publications
10
Known Names
12
Indications
1
Mechanisms

Molecular Properties

304.2
MW (Da)
3.38
ALogP
2
HBA
1
HBD
40.5
PSA (Ų)
0.71
QED
0
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1957
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Black Box Warning Natural Product

Extended Properties

Molecular Formula C14H19Cl2NO2
MW 304.22
Aromatic Rings 1
Heavy Atoms 19
NP-Likeness -0.31

Mechanism of Action

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

Indications

Hodgkin Disease Neoplasms Precursor Cell Lymphoblastic Leukemia-Lymphoma Glomerulonephritis, Membranous Glomerulosclerosis, Focal Segmental Leukemia Leukemia, Lymphocytic, Chronic, B-Cell Lymphoma Lymphoma, B-Cell, Marginal Zone Stomach Neoplasms Carcinoma, Pancreatic Ductal Lymphoma, Mantle-Cell

ATC Classification

L01AA02
chlorambucil
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ANTINEOPLASTIC AGENTS

Drug Warnings

Black Box Warning
carcinogenicity
Country: United States
Black Box Warning
teratogenicity
Country: United States
Black Box Warning
hematological toxicity
Country: United States

Activity Summary

IC50 182 meas. best 7.58
EC50 1 meas. best 4.49
Ki 1 meas. best 4.43

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
MCF7
CHEMBL387
 IC50 7.58 4.53 26.4 17
CHO-AA8
CHEMBL614555
 IC50 7.44 5.03 36.0 6
A549
CHEMBL392
 IC50 7.07 4.8238 85.7 8
MDA-MB-231
CHEMBL400
 IC50 6.28 4.3933 520.0 9
UV4
CHEMBL612800
 IC50 6.22 5.46 600.0 3
MDA-MB-468
CHEMBL614335
 IC50 6.19 4.9567 650.0 6
HeLa
CHEMBL399
 IC50 6.03 6.03 943.0 1
Unchecked
CHEMBL612545
 IC50 5.91 5.01 1244.6 5
Daoy
CHEMBL612519
 IC50 5.87 5.87 1360.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.82 4.6255 1500.0 11
MCF7S
CHEMBL614328
 IC50 5.77 5.77 1700.0 1
NCI-H460
CHEMBL396
 IC50 5.66 5.1 2190.0 2
Homo sapiens
CHEMBL372
 IC50 5.62 5.43 2400.0 2
A-375
CHEMBL613859
 IC50 5.59 4.6367 2580.0 3
PA-1
CHEMBL614949
 IC50 5.55 5.55 2800.0 2
L1210
CHEMBL386
 IC50 5.52 5.185 3000.0 2
HCT-15
CHEMBL612263
 IC50 5.51 4.905 3110.0 2
CH1
CHEMBL614455
 IC50 5.48 5.29 3300.0 2
B16
CHEMBL381
 IC50 5.29 5.29 5100.0 1
M4Beu cell line
CHEMBL612270
 IC50 5.29 5.29 5100.0 1
THP-1
CHEMBL614245
 IC50 5.28 5.28 5300.0 1
MOLT-4
CHEMBL614177
 IC50 5.2 5.2 6300.0 1
5637
CHEMBL612565
 IC50 5.18 5.18 6550.0 2
P388
CHEMBL389
 IC50 5.17 5.0367 6750.0 6
WiDr
CHEMBL614647
 IC50 5.15 5.15 7130.0 1
PC-9
CHEMBL614102
 IC50 5.14 5.14 7170.0 1
MV4-11
CHEMBL613835
 IC50 5.07 5.07 8550.0 1
LoVo
CHEMBL614721
 IC50 5.05 5.05 9000.0 1
Aldo-keto reductase family 1 member B1
CHEMBL2622
 IC50 5.03 5.03 9413.0 1
A-427
CHEMBL614515
 IC50 5.02 5.02 9500.0 1
Plasmodium falciparum
CHEMBL364
 IC50 5.0 4.98 10000.0 5
K562
CHEMBL385
 IC50 4.96 4.348 11000.0 5
ADMET
CHEMBL612558
 IC50 4.96 4.48 11000.0 2
HL-60
CHEMBL383
 IC50 4.93 4.7183 11630.0 6
A2780
CHEMBL614004
 IC50 4.92 4.6 12000.0 2
CCRF-CEM
CHEMBL382
 IC50 4.92 4.8 12025.0 2
2008
CHEMBL612818
 IC50 4.9 4.9 12500.0 1
B16-F10
CHEMBL612656
 IC50 4.9 4.9 12590.0 1
PC-3
CHEMBL390
 IC50 4.79 4.4875 16400.0 4
COLO 205
CHEMBL614561
 IC50 4.73 4.73 18800.0 1
IMR-32
CHEMBL614585
 IC50 4.73 4.73 18800.0 1
U-87 MG
CHEMBL614247
 IC50 4.73 4.73 18800.0 1
HEK293
CHEMBL614818
 IC50 4.6 4.6 25000.0 1
DAN-G
CHEMBL614033
 IC50 4.56 4.56 27800.0 1
NCI-H1975
CHEMBL614348
 IC50 4.55 4.55 28160.0 1
CHO
CHEMBL613853
 IC50 4.52 4.295 30000.0 2
Unchecked
CHEMBL612545
 EC50 4.49 4.49 32644.0 1
U-251
CHEMBL615022
 IC50 4.48 4.48 33110.0 1
SK-OV-3
CHEMBL614925
 IC50 4.46 4.46 35000.0 1
Solute carrier organic anion transporter family member 1B3
CHEMBL1743121
 Ki 4.43 4.43 37400.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 2.8 mL.min-1.kg-1 Homo sapiens
CL 2.8 mL.min-1.kg-1 Homo sapiens
CL 2.8 mL.min-1.kg-1 Homo sapiens
CL 2.8 mL.min-1.kg-1 Homo sapiens
F 80.0 % Homo sapiens
F 87.0 % Homo sapiens
Fu 0.01 - Homo sapiens
Fu 0.01 - Homo sapiens
MRT 1.5 hr Homo sapiens
T1/2 7.75 hr -
T1/2 4.5 hr Homo sapiens
T1/2 1.0 hr -
T1/2 1.1 hr Homo sapiens
T1/2 0.1083 hr -
T1/2 0.1083 hr -
T1/2 0.1083 hr -
T1/2 1.0 hr Mus musculus
T1/2 3.333 hr -
T1/2 3.333 hr -
T1/2 15.26 hr -

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
MCF7 IC50 = 26.4 nM 7.58 Cytotoxicity against human MCF7 cells assessed as cell viability after 5 days by... 26291039
CHO-AA8 IC50 = 36.0 nM 7.44 Inhibitory activity of compound for AA8 cells to reduce cell density by 50% (exp... 2909741
A549 IC50 = 85.7 nM 7.07 Cytotoxicity against human A549 cells assessed as cell viability after 5 days by... 26291039
MDA-MB-231 IC50 = 520.0 nM 6.28 Cytotoxicity against human MDA-MB-231 cells assessed as cell viability after 5 d... 26291039
UV4 IC50 = 600.0 nM 6.22 In vitro cytotoxicity against transformed chinese hamster fibroblast line UV4. 2319563
MDA-MB-468 IC50 = 650.0 nM 6.19 Cytotoxicity against human MDA-MB-468 cells expressing estrogen receptor after 5... 19121874
MDA-MB-468 IC50 = 790.0 nM 6.1 Cytotoxicity against human MDA-MB-468 cells transfected with NAD(P)H: quinone ox... 19121874
HeLa IC50 = 943.0 nM 6.03 Cytotoxicity against human HeLa cells assessed as cell viability after 5 days by... 26291039
UV4 IC50 = 1200.0 nM 5.92 Growth inhibition activity was measured in repair deficient UV4 cells under aero... 7707327
Unchecked IC50 = 1244.6 nM 5.91 PubChem BioAssay. VEGF stimulated ADSC/ECFC co-culture CD31-stained tube area de... -
Daoy IC50 = 1360.0 nM 5.87 Cytotoxicity against human DaOY cells after 5 days by MTT assay 19121874
NON-PROTEIN TARGET IC50 = 1500.0 nM 5.82 In vitro cytotoxicity activity against M4 Dau, by colony forming assay 11985479
MCF7S IC50 = 1700.0 nM 5.77 In vitro cytotoxic activity against MCF7, by colony forming assay 11985479
NCI-H460 IC50 = 2190.0 nM 5.66 Cytotoxicity against human H460 cells after 5 days by MTT assay 19121874
Unchecked IC50 = 2192.1 nM 5.66 PubChem BioAssay. Increased HeLa cells in S-phase-IC50. (Class of assay: confi... -
Homo sapiens IC50 = 2400.0 nM 5.62 Resistance factor (IC50 in the resistant cell line/IC50 in the parent cell line) 15027879
A-375 IC50 = 2580.0 nM 5.59 Cytotoxicity against human A375 cells after 5 days by MTT assay 19121874
PA-1 IC50 = 2800.0 nM 5.55 Cytotoxicity against human PA1 assessed as inhibition of cell growth incubated f... 28927903
PA-1 IC50 = 2800.0 nM 5.55 Cytotoxicity against human PA1 cells by resazurin reduction test 18424156
L1210 IC50 = 3000.0 nM 5.52 Dose required to inhibit cell growth was determined against L1210 cell line of m... 11262080

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 434
6876088 10.1021/jm00362a021 Mus musculus 25
28818449 10.1016/j.bmcl.2017.08.011 A-375 17
11354353 10.1016/s0960-894x(01)00157-3 Unchecked 16
30108928 10.1039/C7MD00476A A-375 15
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
28710962 10.1016/j.ejmech.2017.06.066 WM 266-4 13
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
28818459 10.1016/j.bmc.2017.08.003 Unchecked 9
20070106 10.1021/jm901371v Homo sapiens 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
11354353 10.1016/s0960-894x(01)00157-3 NON-PROTEIN TARGET 7
24147900 10.1021/jm4012438 NON-PROTEIN TARGET 6
218009 10.1021/jm00188a008 Mus musculus 6
24713308 10.1016/j.bmc.2014.03.029 MCF7 5
19734910 10.1038/nchembio.215 Plasmodium falciparum 5
24713308 10.1016/j.bmc.2014.03.029 MDA-MB-231 5
27823879 10.1016/j.ejmech.2016.10.037 MDCK 4
18426954 10.1124/dmd.108.020479 ADMET 4
2319563 10.1021/jm00166a015 P388 3

Data from ChEMBL 36 via Core Engine