U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C21H19N3O3S
Molecular Weight 393.459
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMSACRINE

SMILES

COC1=C(NC2=C3C=CC=CC3=NC4=C2C=CC=C4)C=CC(NS(C)(=O)=O)=C1

InChI

InChIKey=XCPGHVQEEXUHNC-UHFFFAOYSA-N
InChI=1S/C21H19N3O3S/c1-27-20-13-14(24-28(2,25)26)11-12-19(20)23-21-15-7-3-5-9-17(15)22-18-10-6-4-8-16(18)21/h3-13,24H,1-2H3,(H,22,23)

HIDE SMILES / InChI

Molecular Formula C21H19N3O3S
Molecular Weight 393.459
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/2602146 https://www.ncbi.nlm.nih.gov/pubmed/16330449

Aminoacridine derivative that is a potent intercalating antineoplastic agent. It is effective in the treatment of acute leukemias and malignant lymphomas, but has poor activity in the treatment of solid tumors. It is frequently used in combination with other antineoplastic agents in chemotherapy protocols. It produces consistent but acceptable myelosuppression and cardiotoxic effects. Although its mechanism of action is incompletely defined, amsacrine inhibits DNA synthesis by binding to and intercalating with DNA. Amsacrine also inhibits topoisomerase II activity and may exert an effect on cell membranes. This agent also possesses immunosuppressive and antiviral properties. While amsacrine is not cell cycle phase-specific, cytotoxicity is maximal during the G2 and S phases.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: DNA of tumor cells
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
AMSA PD

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Partial purification of mitochondrial DNA topoisomerase II from Plasmodium falciparum and its sensitivity to inhibitors.
2001 Dec
FAB M4 and high CD14 surface expression is associated with high cellular resistance to Ara-C and daunorubicin: implications for clinical outcome in acute myeloid leukaemia.
2001 Oct
Co-amplification of dhfr and a homologue of hmsh3 in a Chinese hamster methotrexate-resistant cell line correlates with resistance to a range of chemotherapeutic drugs.
2001 Oct
Incidence of mutation and deletion in topoisomerase II alpha mRNA of etoposide and mAMSA-resistant cell lines.
2001 Oct
Amsacrine and cisplatin in poor prognosis patients with metastatic transitional cell carcinoma of the urothelium: a phase-II study.
2001 Sep
Inhibition of apoptotic proteins causes multidrug resistance in renal carcinoma cells.
2001 Sep-Oct
Phase I study of the combination of losoxantrone and cyclophosphamide in patients with refractory solid tumours.
2002 Feb 12
The modulation of the DNA-damaging effect of polycyclic aromatic agents by xanthines. Part I. Reduction of cytostatic effects of quinacrine mustard by caffeine.
2002 Feb 15
A study of amsalog (CI-921) administered orally on a 5-day schedule, with bioavailability and pharmacokinetically guided dose escalation.
2002 Jan
Mitotic arrest induced by XK469, a novel antitumor agent, is correlated with the inhibition of cyclin B1 ubiquitination.
2002 Jan 1
Different drug sensitivity profiles of acute myeloid and lymphoblastic leukemia and normal peripheral blood mononuclear cells in children with and without Down syndrome.
2002 Jan 1
Point of attachment and sequence of immobilized peptide-acridine conjugates control affinity for nucleic acids.
2002 Jul 24
A rare case of adenoviral fulminant hepatic necrosis after chemotherapy.
2002 Jul-Aug
High-throughput measurement of the Tp53 response to anticancer drugs and random compounds using a stably integrated Tp53-responsive luciferase reporter.
2002 Jun
Impact of addition of maintenance therapy to intensive induction and consolidation chemotherapy for childhood acute myeloblastic leukemia: results of a prospective randomized trial, LAME 89/91. Leucámie Aiqüe Myéloïde Enfant.
2002 Jun 15
Increased expression of beta 2-microglobulin in multidrug-resistant tumour cells.
2002 Jun 17
A unique type II topoisomerase mutant that is hypersensitive to a broad range of cleavage-inducing antitumor agents.
2002 Jun 25
Cytotoxicity of rhein, the active metabolite of sennoside laxatives, is reduced by multidrug resistance-associated protein 1.
2002 May 6
Compatibility and stability of 5-HT3 receptor antagonists: a pharmacology review.
2002 Nov-Dec
Synthesis and antiinflammatory evaluation of 9-anilinoacridine and 9-phenoxyacridine derivatives.
2002 Oct 10
Luteolin, an emerging anti-cancer flavonoid, poisons eukaryotic DNA topoisomerase I.
2002 Sep 1
[Effect of etoposide and amsacrine on mitotic progression of GM-130 and Hep-2 cell lines. The flow cytometry assay].
2003
Acute pericarditis and pleural effusion complicating cytarabine chemotherapy.
2003 Aug
Antitumor triptycene bisquinones: a novel synthetic class of dual inhibitors of DNA topoisomerase I and II activities.
2003 Aug
More efficient mobilisation of peripheral blood stem cells with HiDAC+AMSA+G-CSF than with mini-ICE+G-CSF in patients with AML.
2003 Dec
A feasibility study of simultaneous administration of gemtuzumab ozogamicin with intensive chemotherapy in induction and consolidation in younger patients with acute myeloid leukemia.
2003 Dec 15
Factors influencing outcome and incidence of long-term complications in children who underwent autologous stem cell transplantation for acute myeloid leukemia in first complete remission.
2003 Feb 15
Crystallization and preliminary X-ray analysis of anti-cancer agent 3-(9-acridinylamino)-5-(hydroxymethyl)aniline complexed with the DNA hexamer d(CGTACG)2.
2003 Jan 3
In vitro chemosensitivity testing of selected myeloid cells in acute myeloid leukemia.
2003 May
Dinucleoside monophosphates containing AZT and 1-methyladenosine or 7-methylguanosine.
2003 May-Aug
[Topotecan-based combined chemotherapy for refractory or relapsed hematologic malignancies].
2003 Nov
Investigations into the biological relevance of in vitro clastogenic and aneugenic activity.
2004
Maintenance therapy in childhood acute myeloid leukemia.
2004
Rescue therapy combining intermediate-dose cytarabine with amsacrine and etoposide in relapsed adult acute lymphoblastic leukemia.
2004
Intensive chemotherapy with idarubicin, cytarabine, etoposide, and G-CSF priming in patients with advanced myelodysplastic syndrome and high-risk acute myeloid leukemia.
2004 Aug
Characterisation of cytotoxicity and DNA damage induced by the topoisomerase II-directed bisdioxopiperazine anti-cancer agent ICRF-187 (dexrazoxane) in yeast and mammalian cells.
2004 Dec 2
Differences in the longevity of topo IIalpha and topo IIbeta drug-stabilized cleavable complexes and the relationship to drug sensitivity.
2004 Feb
Topoisomerase I and II inhibitors control caspase-2 pre-messenger RNA splicing in human cells.
2004 Jan
Dissecting the cell-killing mechanism of the topoisomerase II-targeting drug ICRF-193.
2004 Jul 2
Inhibition of cardiac HERG currents by the DNA topoisomerase II inhibitor amsacrine: mode of action.
2004 Jun
Risk-adapted induction and consolidation therapy in adults with de novo AML aged
2004 Jun
The antitumor triazoloacridone C-1305 is a topoisomerase II poison with unusual properties.
2004 Oct
Translocation t(12;21) is related to in vitro cellular drug sensitivity to doxorubicin and etoposide in childhood acute lymphoblastic leukemia.
2004 Oct 15
Cardiotoxicity of cancer chemotherapy: implications for children.
2005
Synthesis, antitumour activity and structure-activity relationships of 5H-benzo[b]carbazoles.
2005 Feb 1
Highly sensitive analysis of the anti-tumor agent 1-[4-(furo[2,3-b]-quinolin-4-ylamino)phenyl]ethanone in rat plasma by high-performance liquid chromatography using electrochemical detection.
2005 Jul 1
Potent antitumor 9-anilinoacridines bearing an alkylating N-mustard residue on the anilino ring: synthesis and biological activity.
2005 Jun 2
[Disseminated cutaneous and visceral fusariosis in an aplastic patient: an unusual digestive entry].
2005 Mar
E1A specifically enhances sensitivity to topoisomerase IIalpha targeting anticancer drug by up-regulating the promoter activity.
2005 May
In vitro activity of the flt3-inhibitor su5614 and standard cytotoxic agents in tumour cells from patients with wild type and mutated flt3 acute myeloid leukaemia.
2005 Sep
Patents

Sample Use Guides

Adults: Cycle Length 3-4 weeks, induction: 75-125 mg/m2 IV once daily for 5 consecutive days starting on day 1 (total dose per cycle 375-625 mg/m2) dose should be increased by 20% in the second and each subsequent cycle if marrow hypoplasia has not been achieved and the patient has had no significant toxicity in the preceding cycle. 4-8 weeks, maintenance: approximately half of the induction dose dependant on blood counts
Route of Administration: Intravenous
Amsacrine attenuated cell invasion with decreased MMP-2/MMP-9 protein expression and mRNA levels in U937, Jurkat, HL-60, K562, KU812, and MEG-01 cells. Moreover, amsacrine reduced both MMP-2/MMP-9 promoter luciferase activity and MMP-2/MMP-9 mRNA stability in leukemia cells.
Substance Class Chemical
Created
by admin
on Wed Jul 05 22:54:07 UTC 2023
Edited
by admin
on Wed Jul 05 22:54:07 UTC 2023
Record UNII
00DPD30SOY
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AMSACRINE
HSDB   INN   MART.   MI   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
N-(4-(9-ACRIDINYLAMINO)-3-METHOXYPHENYL)METHANESULFONAMIDE
Systematic Name English
METHANESULFONAMIDE, N-(4-(9-ACRIDINYLAMINO)-3-METHOXYPHENYL)-
Systematic Name English
amsacrine [INN]
Common Name English
AMSACRINE [IARC]
Common Name English
AMSACRINE [VANDF]
Common Name English
AMSACRINE [HSDB]
Common Name English
AMSIDINE
Brand Name English
ACRIDINYLANISIDIDE
Common Name English
AMSIDYL
Brand Name English
M-AMSA
Code English
SN-11841
Code English
AMSACRINE [MART.]
Common Name English
NCI-249992
Code English
SN-21429
Code English
AMSACRINE [USAN]
Common Name English
CI-880
Code English
Amsacrine [WHO-DD]
Common Name English
AMEKRIN
Brand Name English
NSC-156303
Code English
AMSACRINE [MI]
Common Name English
NSC-249992
Code English
LAMASINE
Brand Name English
AMSIDIL
Brand Name English
4'-(9-ACRIDINYLAMINO)METHANESULFON-M-ANISIDIDE
Systematic Name English
Classification Tree Code System Code
WHO-VATC QL01XX01
Created by admin on Wed Jul 05 22:54:07 UTC 2023 , Edited by admin on Wed Jul 05 22:54:07 UTC 2023
FDA ORPHAN DRUG 4584
Created by admin on Wed Jul 05 22:54:07 UTC 2023 , Edited by admin on Wed Jul 05 22:54:07 UTC 2023
NCI_THESAURUS C582
Created by admin on Wed Jul 05 22:54:07 UTC 2023 , Edited by admin on Wed Jul 05 22:54:07 UTC 2023
WHO-ATC L01XX01
Created by admin on Wed Jul 05 22:54:07 UTC 2023 , Edited by admin on Wed Jul 05 22:54:07 UTC 2023
Code System Code Type Description
NSC
156303
Created by admin on Wed Jul 05 22:54:07 UTC 2023 , Edited by admin on Wed Jul 05 22:54:07 UTC 2023
PRIMARY
ChEMBL
CHEMBL43
Created by admin on Wed Jul 05 22:54:07 UTC 2023 , Edited by admin on Wed Jul 05 22:54:07 UTC 2023
PRIMARY
NCI_THESAURUS
C240
Created by admin on Wed Jul 05 22:54:07 UTC 2023 , Edited by admin on Wed Jul 05 22:54:07 UTC 2023
PRIMARY
PUBCHEM
2179
Created by admin on Wed Jul 05 22:54:07 UTC 2023 , Edited by admin on Wed Jul 05 22:54:07 UTC 2023
PRIMARY
CAS
51264-14-3
Created by admin on Wed Jul 05 22:54:07 UTC 2023 , Edited by admin on Wed Jul 05 22:54:07 UTC 2023
PRIMARY
HSDB
7087
Created by admin on Wed Jul 05 22:54:07 UTC 2023 , Edited by admin on Wed Jul 05 22:54:07 UTC 2023
PRIMARY
SMS_ID
100000091914
Created by admin on Wed Jul 05 22:54:07 UTC 2023 , Edited by admin on Wed Jul 05 22:54:07 UTC 2023
PRIMARY
MESH
D000677
Created by admin on Wed Jul 05 22:54:07 UTC 2023 , Edited by admin on Wed Jul 05 22:54:07 UTC 2023
PRIMARY
RXCUI
739
Created by admin on Wed Jul 05 22:54:07 UTC 2023 , Edited by admin on Wed Jul 05 22:54:07 UTC 2023
PRIMARY RxNorm
EPA CompTox
DTXSID4022604
Created by admin on Wed Jul 05 22:54:07 UTC 2023 , Edited by admin on Wed Jul 05 22:54:07 UTC 2023
PRIMARY
WIKIPEDIA
AMSACRINE
Created by admin on Wed Jul 05 22:54:07 UTC 2023 , Edited by admin on Wed Jul 05 22:54:07 UTC 2023
PRIMARY
DRUG BANK
DB00276
Created by admin on Wed Jul 05 22:54:07 UTC 2023 , Edited by admin on Wed Jul 05 22:54:07 UTC 2023
PRIMARY
INN
4864
Created by admin on Wed Jul 05 22:54:07 UTC 2023 , Edited by admin on Wed Jul 05 22:54:07 UTC 2023
PRIMARY
MERCK INDEX
M1859
Created by admin on Wed Jul 05 22:54:07 UTC 2023 , Edited by admin on Wed Jul 05 22:54:07 UTC 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
257-094-3
Created by admin on Wed Jul 05 22:54:07 UTC 2023 , Edited by admin on Wed Jul 05 22:54:07 UTC 2023
PRIMARY
DRUG CENTRAL
203
Created by admin on Wed Jul 05 22:54:07 UTC 2023 , Edited by admin on Wed Jul 05 22:54:07 UTC 2023
PRIMARY
CHEBI
2687
Created by admin on Wed Jul 05 22:54:07 UTC 2023 , Edited by admin on Wed Jul 05 22:54:07 UTC 2023
PRIMARY
NSC
249992
Created by admin on Wed Jul 05 22:54:07 UTC 2023 , Edited by admin on Wed Jul 05 22:54:07 UTC 2023
PRIMARY
EVMPD
SUB05495MIG
Created by admin on Wed Jul 05 22:54:07 UTC 2023 , Edited by admin on Wed Jul 05 22:54:07 UTC 2023
PRIMARY
FDA UNII
00DPD30SOY
Created by admin on Wed Jul 05 22:54:07 UTC 2023 , Edited by admin on Wed Jul 05 22:54:07 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
BINDER->LIGAND
BINDING
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC