Amsacrine

Summary

Amsacrine (CHEMBL43) is an approved small-molecule antineoplastic agent (ATC L01XX01); indicated across 4 conditions including neoplasm and leukemia.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: L01XX01
• Indications: 4 conditions
• Clinical trials: 9
• Chemistry: 393.5 Da · C21H19N3O3S

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL43
Name	Amsacrine
Type	Small molecule
Max phase	4
FDA approved	no
PubChem CID	2179
ChEBI	CHEBI:2687
ATC	L01XX01
Molecular formula	C21H19N3O3S
Molecular weight	393.5
InChIKey	XCPGHVQEEXUHNC-UHFFFAOYSA-N

SMILES: COC1=C(C=CC(=C1)NS(=O)(=O)C)NC2=C3C=CC=CC3=NC4=CC=CC=C42

IUPAC name: N-[4-(acridin-9-ylamino)-3-methoxyphenyl]methanesulfonamide

ChEBI definition: A sulfonamide that is N-phenylmethanesulfonamide substituted by a methoxy group at position 3 and an acridin-9-ylamino group at position 4. It exhibits antineoplastic activity.

Pharmacological roles (ChEBI): antineoplastic agent, EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor.

Also known as: Acridinylanisidide, Amekrin, Amsacrina, Amsacrine, Amsidil, Amsidine, Amsidyl, CI-880, Lamasine, M-AMSA, NCI-249992, NSC-156303

Parent form; salt/anhydrous children: CHEMBL540070, CHEMBL1256655, CHEMBL3229103

Patent coverage: 20,243 distinct patent families (82,326 SureChEMBL compound mentions), from 3 matched compound structure(s). One matched structure accounts for 80,118 (97%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Broader ChEMBL bioactivity targets: 47 (assay-derived). Sample: Thrombopoietin, Ras-related protein Rab-9A, Aldehyde oxidase 1, Aldehyde oxidase 1, ATP-binding cassette sub-family C member 4, DNA topoisomerase 1, DNA topoisomerase 2-alpha, 5-hydroxytryptamine receptor 3A, Cholecystokinin receptor type A, Alpha-2C adrenergic receptor, Alpha-2B adrenergic receptor, Thyrotropin receptor, Equilibrative nucleoside transporter 1, Thromboxane A2 receptor, DNA topoisomerase II, Muscarinic acetylcholine receptor M1, D(2) dopamine receptor, Prostaglandin G/H synthase 2, Histamine H1 receptor, Delta-type opioid receptor.

Bioactivity

ChEMBL activities: 45 potent at pChembl ≥ 5 of 73 total. Top 100 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
P80456	7.22	Ki	60	nM	CHEMBL_ACT_5102830
MTOR	6.88	Potency	130.9	nM	CHEMBL_ACT_4787578
KCNH2	6.68	IC50	210	nM	CHEMBL_ACT_2191976
KCNH2	6.68	IC50	208.9	nM	CHEMBL_ACT_5218940
MTOR	6.28	Potency	521.2	nM	CHEMBL_ACT_4522759
TOP2A	6.14	EC50	720	nM	CHEMBL_ACT_1131941
TOP2A	6.14	EC50	720	nM	CHEMBL_ACT_1239796
TOP2A	6.14	EC50	720	nM	CHEMBL_ACT_158418
TOP2A	6.14	EC50	720	nM	CHEMBL_ACT_228045
TOP2A	6.14	EC50	720	nM	CHEMBL_ACT_268916
TOP2A	6.14	EC50	720	nM	CHEMBL_ACT_347146
TOP2A	6.14	EC50	720	nM	CHEMBL_ACT_736568
KDM1A	6.06	IC50	880	nM	CHEMBL_ACT_25563007
KCNH2	6.01	AC50	970	nM	CHEMBL_ACT_25118691
TOP2A	6	IC50	1000	nM	CHEMBL_ACT_1202773
TP53	6	Potency	1000	nM	CHEMBL_ACT_4878735
ADRA2B	5.89	AC50	1300	nM	CHEMBL_ACT_25144267
THPO	5.6	Potency	2512	nM	CHEMBL_ACT_4813373
THPO	5.6	Potency	2512	nM	CHEMBL_ACT_5074326
TOP2B	5.56	IC50	2760	nM	CHEMBL_ACT_18548570
ADRA2C	5.55	AC50	2800	nM	CHEMBL_ACT_25148461
PTGS2	5.54	AC50	2900	nM	CHEMBL_ACT_25166740
Q9Z0U5	5.52	Ki	3000	nM	CHEMBL_ACT_5102842
AOX1	5.5	IC50	3200	nM	CHEMBL_ACT_5102799
MTOR	5.43	Potency	3690	nM	CHEMBL_ACT_3919412
SLC22A1	5.3	IC50	5000	nM	CHEMBL_ACT_2364174
HIF1A	5.3	Potency	5012	nM	CHEMBL_ACT_4128826
HIF1A	5.3	Potency	5012	nM	CHEMBL_ACT_4520648
PDE4D	5.21	AC50	6200	nM	CHEMBL_ACT_25185911
P08482	5.2	Potency	6310	nM	CHEMBL_ACT_4811392
Q9Z0U5	5.19	IC50	6400	nM	CHEMBL_ACT_5102816
OPRK1	5.16	AC50	7000	nM	CHEMBL_ACT_25129957
DRD2	5.16	AC50	6900	nM	CHEMBL_ACT_25140912
ABCC4	5.13	IC50	7430	nM	CHEMBL_ACT_18130911
CYP2D6	5.12	Ki	7500	nM	CHEMBL_ACT_1473733
CHRM1	5.1	AC50	7900	nM	CHEMBL_ACT_25136042
HTR3A	5.1	AC50	8000	nM	CHEMBL_ACT_25149689
TP53	5.1	Potency	7943	nM	CHEMBL_ACT_4830390
CYP1A2	5.1	AC50	7943	nM	CHEMBL_ACT_6043079
CHRM3	5.07	AC50	8600	nM	CHEMBL_ACT_25137246
BDKRB2	5.05	AC50	8900	nM	CHEMBL_ACT_25170969
NPY1R	5.03	AC50	9300	nM	CHEMBL_ACT_25187037
HRH1	5.02	AC50	9500	nM	CHEMBL_ACT_25213094
TOP2A	5	IC50	9940	nM	CHEMBL_ACT_2637205
P08482	5	Potency	10000	nM	CHEMBL_ACT_4857919

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

4 approved indications. FDA phase 4, plus an anticancer drug’s labelled cancer uses (which ChEMBL often logs at phase 3).

Indication	Phase	MONDO	EFO
neoplasm	4	MONDO:0005070	EFO:0000616
leukemia	3	MONDO:0005059	EFO:0000565
acute myeloid leukemia	3	MONDO:0018874	EFO:0000222
myelodysplastic syndrome	3	MONDO:0018881	EFO:0000198

Clinical trials

Total trials: 9.

Phase distribution

Phase	Trials
PHASE3	5
PHASE1/PHASE2	2
PHASE4	1
PHASE2/PHASE3	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT00180102	PHASE4	COMPLETED	AML2003 - Standard-Therapy vs Intensified Therapy for Adult Acute Myeloid Leukemia Patients <= 60 Years
NCT00002658	PHASE3	UNKNOWN	Combination Chemotherapy, Biological Therapy, and Bone Marrow Transplantation in Treating Patients With Acute Myeloid Leukemia
NCT00002719	PHASE3	COMPLETED	Combination Chemotherapy With or Without G-CSF in Treating Older Patients With Acute Myeloid Leukemia
NCT00003436	PHASE3	COMPLETED	Combination Chemotherapy With or Without Bone Marrow Transplantation in Treating Children With Acute Myeloid Leukemia
NCT01228331	PHASE2/PHASE3	COMPLETED	Clofarabine or High-Dose Cytarabine and Pegaspargase in Children with ALL
NCT01324063	PHASE3	COMPLETED	A Randomized Phase III Study of Intensive Consolidation With High Dose Cytosine Arabinoside in Acute Myelogenous Leukemia (AML-8B)
NCT03765541	PHASE3	TERMINATED	Dexamethasone in Refractory or First Relapsed Acute Myeloid Leukemia
NCT05807932	PHASE1/PHASE2	RECRUITING	Venetoclax in Addition to Sequential Conditioning With Fludarabine / Amsacrine / Ara-C (FLAMSA) + Treosulfan for Allogeneic Blood Stem Cell Transplantation in Patients With MDS, CMML or sAML
NCT00840684	PHASE1/PHASE2	COMPLETED	Laromustine, Daunorubicin, and Cytarabine in Treating Patients With Acute Myeloid Leukemia

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.

Related molecules

Related molecules

No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).