Compound Detail

CHEMBL43

AMSACRINE

💊 Approved Drug

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💊 Approved Drug

COc1cc(NS(C)(=O)=O)ccc1Nc1c2ccccc2nc2ccccc12

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL43
Name	AMSACRINE
Phase	Approved
Structure Type	MOL
InChI Key	XCPGHVQEEXUHNC-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

Acridinylanisidide Amekrin Amsacrina Amsacrine Amsidil Amsidine Amsidyl CI-880 Lamasine M-AMSA NCI-249992 NSC-156303 +3 more

Targets

163

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

393.5

MW (Da)

4.51

ALogP

HBA

HBD

80.3

PSA (Å²)

0.49

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1987
Availability	Unknown
Chirality	Achiral

Routes of Administration

Parenteral

Flags

Natural Product

USAN Stem	-crine
USAN Year	1980

Extended Properties

Molecular Formula	C21H19N3O3S
MW	393.47
Aromatic Rings	4
Heavy Atoms	28
NP-Likeness	-1.11

Mechanism of Action

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

Indications

Neoplasms Leukemia Leukemia, Myeloid, Acute Myelodysplastic Syndromes

ATC Classification

L01XX01

amsacrine

Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS

Level 2: ANTINEOPLASTIC AGENTS

Activity Summary

IC50 150 meas. best 9.22

EC50 10 meas. best 6.14

Ki 3 meas. best 7.22

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
CHO-AA8 CHEMBL614555	IC50	9.22	9.22	0.6	1
DC3F CHEMBL612702	IC50	8.4	8.4	4.0	1
HL-60 CHEMBL383	IC50	8.29	7.2717	5.1	6
NON-PROTEIN TARGET CHEMBL3879801	IC50	7.92	6.7967	12.0	9
LLTC cell line CHEMBL614093	IC50	7.92	7.92	12.0	1
Lewis lung carcinoma cell line CHEMBL614088	IC50	7.92	7.92	12.0	2
P388 CHEMBL389	IC50	7.92	7.099	12.0	10
HeLa CHEMBL399	IC50	7.92	6.1783	12.0	6
Jurkat CHEMBL397	IC50	7.7	7.2983	20.0	6
K562 CHEMBL385	IC50	7.64	5.685	23.0	6
CCRF-CEM CHEMBL382	IC50	7.52	7.005	30.0	4
A549 CHEMBL392	IC50	7.52	5.71	30.0	4
L1210 CHEMBL386	IC50	7.48	7.42	33.0	3
F460pv8/eto CHEMBL614493	IC50	7.4	7.4	40.0	1
DC3F/AD-II CHEMBL614283	IC50	7.33	7.33	47.0	1
NCI-H460 CHEMBL396	IC50	7.22	7.0467	60.0	3
SK-BR-3 CHEMBL613834	IC50	7.22	7.22	60.0	1
Aldehyde oxidase 1 CHEMBL1641356	Ki	7.22	7.22	60.0	1
NCI-H647 CHEMBL614999	IC50	7.16	7.16	70.0	1
MCF7 CHEMBL387	IC50	7.12	5.565	75.0	8
U-937 CHEMBL612794	IC50	7.1	6.5067	80.0	3
DLD-1 CHEMBL614285	IC50	7.1	6.67	80.0	2
A2780 CHEMBL614004	IC50	7.0	6.73	100.0	2
HCT-8 CHEMBL613510	IC50	6.92	6.7867	120.0	3
MDA-MB-231 CHEMBL400	IC50	6.85	5.925	140.0	2
NCI-H358 CHEMBL614135	IC50	6.82	6.82	150.0	1
A-431 CHEMBL614069	IC50	6.77	6.0	170.0	2
ZR-75-1 CHEMBL614393	IC50	6.75	6.75	180.0	1
NCI-H322M CHEMBL614803	IC50	6.68	6.68	210.0	1
Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240	IC50	6.68	6.68	208.9	2
T47D CHEMBL614361	IC50	6.66	6.345	220.0	2
ADMET CHEMBL612558	IC50	6.62	5.7025	240.0	4
XRS6 CHEMBL614060	IC50	6.62	6.62	240.0	1
SW-620 CHEMBL612262	IC50	6.52	5.36	300.0	3
DU-145 CHEMBL613508	IC50	6.52	6.52	300.0	1
HCT-15 CHEMBL612263	IC50	6.52	6.52	300.0	1
MDA-MB-468 CHEMBL614335	IC50	6.31	5.69	490.0	2
SF-295 CHEMBL614908	IC50	6.3	6.3	500.0	1
CEM-VLB CHEMBL614554	IC50	6.28	6.28	520.0	1
HT-29 CHEMBL384	IC50	6.25	6.25	559.0	1
Plasmodium falciparum CHEMBL364	IC50	6.22	6.22	600.0	1
HCT-116 CHEMBL394	IC50	6.16	5.4925	700.0	4
DNA topoisomerase II CHEMBL2094255	EC50	6.14	6.14	720.0	7
Lysine-specific histone demethylase 1A CHEMBL6136	IC50	6.06	6.06	880.0	1
J774 CHEMBL614123	IC50	6.04	6.04	900.6	1
DNA topoisomerase II CHEMBL2094255	IC50	6.0	6.0	1000.0	1
NCI-H226 CHEMBL614740	IC50	6.0	6.0	1010.0	1
COLO 205 CHEMBL614561	IC50	5.96	5.96	1100.0	1
NCI/ADR-RES CHEMBL613829	IC50	5.93	5.93	1165.0	1
J774.2 CHEMBL614484	IC50	5.87	5.85	1353.9	2

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	4.3	mL.min-1.kg-1	Homo sapiens
Fu	0.029	-	Homo sapiens
MRT	6.2	hr	Homo sapiens
T1/2	336.0	hr	-
T1/2	24.0	hr	-
T1/2	13.2	-	-
T1/2	0.03	hr	-
T1/2	4.7	hr	Homo sapiens
T1/2	1.767	hr	Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
CHO-AA8	IC50	=	0.6	nM	9.22	Inhibitory activity of compound for AA8 cells to reduce cell density by 50% (exp...	2909741
DC3F	IC50	=	4.0	nM	8.4	The compound was tested for the cytotoxicity DC-3F cell lines	7650675
HL-60	IC50	=	5.1	nM	8.29	Antiproliferative activity against human HL60 cells after 72 hrs by trypan blue ...	18077173
HL-60	IC50	=	6.0	nM	8.22	Growth inhibition in human HL60 cells after 72 hrs by trypan blue assay	21216603
HeLa	IC50	=	12.0	nM	7.92	Growth inhibition in human HeLa cells after 72 hrs by trypan blue assay	21216603
HeLa	IC50	=	12.0	nM	7.92	Antiproliferative activity against human HeLa cells after 72 hrs by trypan blue ...	18077173
LLTC cell line	IC50	=	12.0	nM	7.92	Inhibitory concentration required to reduce Lewis lung carcinoma cell number to ...	9191970
Lewis lung carcinoma cell line	IC50	=	12.0	nM	7.92	Inhibitory activity against Lewis lung carcinoma cells	11384245
Lewis lung carcinoma cell line	IC50	=	12.0	nM	7.92	Inhibitory activity of tested against Murine Lewis lung carcinoma	10395479
NON-PROTEIN TARGET	IC50	=	12.0	nM	7.92	Inhibitory concentration against Murine Lewis lung carcinoma (LLC) cell prolifer...	9207945
P388	IC50	=	12.0	nM	7.92	In vitro cell growth inhibitory activity against wild type P388 murine leukemia ...	2153829
P388	IC50	=	20.0	nM	7.7	Inhibitory activity against P388 murine leukemia cells	11384245
P388	IC50	=	20.0	nM	7.7	Inhibitory activity against Murine p38 leukemia	10395479
NON-PROTEIN TARGET	IC50	=	20.0	nM	7.7	Inhibitory concentration to reduce cell number to 50% of Murine P388 leukemia ce...	9207945
Jurkat	IC50	=	20.0	nM	7.7	Cytotoxicity against human Jurkat cells by Hoechst test	18656367
P388	IC50	=	20.0	nM	7.7	Inhibitory concentration required to reduce murine p388 leukemia cell number to ...	9191970
HL-60	IC50	=	21.0	nM	7.68	In vitro cytotoxicity against human leukemic HL-60 cell line.	7650675
K562	IC50	=	23.0	nM	7.64	Cytotoxicity against human K562 cells after 5 days by XTT assay	18076140
CCRF-CEM	IC50	=	30.0	nM	7.52	Antiproliferative against human CCRF-CEM cells incubated for 72 hrs by MTT assay	31635931
A549	IC50	=	30.0	nM	7.52	Inhibitory activity against A549 cell line using MTT assay(Wild type p53)	10780913

Literature References

PubMed	DOI	Target Context	# Activities
2157014	10.1021/jm00166a022	NON-PROTEIN TARGET	21
2362284	10.1021/jm00169a039	Nucleic Acid	20
10579838	10.1021/jm9901226	Mus musculus	19
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
2157014	10.1021/jm00166a022	L5178Y	12
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
184284	10.1021/jm00230a002	L1210	10
15646539	10.1016/s0399-8320(04)95062-2	NON-PROTEIN TARGET	8
7650675	10.1021/jm00017a006	Mus musculus	6
-	10.6019/CHEMBL4495565	SARS-CoV-2	6
2778449	10.1021/np50063a010	HT-29	5
2157014	10.1021/jm00166a022	Unchecked	5
-	10.6019/CHEMBL4808148	Histone deacetylase 6	5
33479643	10.1039/c9md00597h	A549	5
27594549	10.1016/j.bmc.2016.08.003	Unchecked	5
9733489	10.1021/jm9708083	Mus musculus	4
18426954	10.1124/dmd.108.020479	ADMET	4
7658436	10.1021/jm00018a009	Nucleic Acid	4
-	10.1016/0960-894X(96)00230-2	Mus musculus	4
18656367	10.1016/j.bmc.2008.07.015	NON-PROTEIN TARGET	4

Data from ChEMBL 36 via Core Engine