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Details

Stereochemistry ACHIRAL
Molecular Formula C21H19N3O3S
Molecular Weight 393.4607
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMSACRINE

SMILES

COc1cc(ccc1N=c2c3ccccc3[nH]c4ccccc42)NS(=O)(=O)C

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 393.4607
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
Targeting DNA through-covalent interactions of reversible binding drugs.
2001
DNA binding properties of the indolocarbazole antitumor drug NB-506.
2001 Apr-Jun
Effects of anticancer drugs on the metabolism of the anticancer drug 5,6-dimethylxanthenone-4-acetic (DMXAA) by human liver microsomes.
2001 Aug
Partial purification of mitochondrial DNA topoisomerase II from Plasmodium falciparum and its sensitivity to inhibitors.
2001 Dec
Hypophosphorylation of topoisomerase IIalpha in etoposide (VP-16)-resistant human carcinoma cell lines associated with carboxy-terminal truncation.
2001 Jul
Expression of drug resistance genes in VP-16 and mAMSA-selected human carcinoma cells.
2001 Jul
Novel pyrrolo[3,2-f]quinolines: synthesis and antiproliferative activity.
2001 Jul
Improved efficiency of remission induction facilitates autologous BMT harvesting and improves overall survival in adults with AML: 108 patients treated at a single institution.
2001 May
Catalytic inhibition of human DNA topoisomerase IIalpha by hypericin, a naphthodianthrone from St. John's wort (Hypericum perforatum).
2001 Oct 15
Altered topoisomerase IIalpha and multidrug resistance-associated protein levels during drug selection: adaptations to increasing drug pressure.
2001 Sep
Suppression of c-myc expression and c-Myc function in response to sustained DNA damage in MCF-7 breast tumor cells.
2001 Sep 1
Enhanced etoposide sensitivity following adenovirus-mediated human topoisomerase IIalpha gene transfer is independent of topoisomerase IIbeta.
2001 Sep 1
Inhibition of apoptotic proteins causes multidrug resistance in renal carcinoma cells.
2001 Sep-Oct
Favorable outcome with STI571 (imatinib mesylate) and allogeneic stem cell transplantation in a case of Ph+ chemorefractory acute lymphocytic leukaemia.
2002 Dec
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
Antitumor activity of ER-37328, a novel carbazole topoisomerase II inhibitor.
2002 Jan
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
Tetrakis-acridinyl peptide: a novel fluorometric reagent for nucleic acid analysis based on the fluorescence dequenching upon DNA binding.
2002 Jul
Point of attachment and sequence of immobilized peptide-acridine conjugates control affinity for nucleic acids.
2002 Jul 24
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
Antitumor triptycene bisquinones: a novel synthetic class of dual inhibitors of DNA topoisomerase I and II activities.
2003 Aug
Stem cell transplantation after salvage therapy with high-dose cytarabine and amsacrine in adults with high-risk leukaemia.
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
Mechanisms of action of DNA intercalating acridine-based drugs: how important are contributions from electron transfer and oxidative stress?
2003 Dec
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
Free radical scavengers can differentially modulate the genotoxicity of amsacrine in normal and cancer cells.
2003 Feb 5
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
Amino acid substitutions at position 43 of NaeI endonuclease. Evidence for changes in NaeI structure.
2003 Mar 14
[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
Intensive chemotherapy with idarubicin, cytarabine, etoposide, and G-CSF priming in patients with advanced myelodysplastic syndrome and high-risk acute myeloid leukemia.
2004 Aug
Comparison of BAVC to BuCy regimens in autologous stem cell transplantation for adult patients with acute myeloid leukemia.
2004 Jan
Increased susceptibility of poly(ADP-ribose) polymerase-1 knockout cells to antitumor triazoloacridone C-1305 is associated with permanent G2 cell cycle arrest.
2004 Jul 1
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
Mutation E522K in human DNA topoisomerase IIbeta confers resistance to methyl N-(4'-(9-acridinylamino)-phenyl)carbamate hydrochloride and methyl N-(4'-(9-acridinylamino)-3-methoxy-phenyl) methane sulfonamide but hypersensitivity to etoposide.
2004 Sep
Potent antitumor N-mustard derivatives of 9-anilinoacridine, synthesis and antitumor evaluation.
2004 Sep 20
Induction chemotherapy for acute myelogenous leukemia.
2005 Jan
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
E1A specifically enhances sensitivity to topoisomerase IIalpha targeting anticancer drug by up-regulating the promoter activity.
2005 May
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 Sat Jun 26 00:19:44 UTC 2021
Edited
by admin
on Sat Jun 26 00:19:44 UTC 2021
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
AMSACRINE [WHO-DD]
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
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 Sat Jun 26 00:19:44 UTC 2021 , Edited by admin on Sat Jun 26 00:19:44 UTC 2021
FDA ORPHAN DRUG 4584
Created by admin on Sat Jun 26 00:19:44 UTC 2021 , Edited by admin on Sat Jun 26 00:19:44 UTC 2021
NCI_THESAURUS C582
Created by admin on Sat Jun 26 00:19:44 UTC 2021 , Edited by admin on Sat Jun 26 00:19:44 UTC 2021
WHO-ATC L01XX01
Created by admin on Sat Jun 26 00:19:44 UTC 2021 , Edited by admin on Sat Jun 26 00:19:44 UTC 2021
Code System Code Type Description
ChEMBL
CHEMBL43
Created by admin on Sat Jun 26 00:19:44 UTC 2021 , Edited by admin on Sat Jun 26 00:19:44 UTC 2021
PRIMARY
NCI_THESAURUS
C240
Created by admin on Sat Jun 26 00:19:44 UTC 2021 , Edited by admin on Sat Jun 26 00:19:44 UTC 2021
PRIMARY
PUBCHEM
2179
Created by admin on Sat Jun 26 00:19:44 UTC 2021 , Edited by admin on Sat Jun 26 00:19:44 UTC 2021
PRIMARY
CAS
51264-14-3
Created by admin on Sat Jun 26 00:19:44 UTC 2021 , Edited by admin on Sat Jun 26 00:19:44 UTC 2021
PRIMARY
HSDB
7087
Created by admin on Sat Jun 26 00:19:44 UTC 2021 , Edited by admin on Sat Jun 26 00:19:44 UTC 2021
PRIMARY
MESH
D000677
Created by admin on Sat Jun 26 00:19:44 UTC 2021 , Edited by admin on Sat Jun 26 00:19:44 UTC 2021
PRIMARY
RXCUI
739
Created by admin on Sat Jun 26 00:19:44 UTC 2021 , Edited by admin on Sat Jun 26 00:19:44 UTC 2021
PRIMARY RxNorm
EPA CompTox
51264-14-3
Created by admin on Sat Jun 26 00:19:44 UTC 2021 , Edited by admin on Sat Jun 26 00:19:44 UTC 2021
PRIMARY
WIKIPEDIA
AMSACRINE
Created by admin on Sat Jun 26 00:19:44 UTC 2021 , Edited by admin on Sat Jun 26 00:19:44 UTC 2021
PRIMARY
DRUG BANK
DB00276
Created by admin on Sat Jun 26 00:19:44 UTC 2021 , Edited by admin on Sat Jun 26 00:19:44 UTC 2021
PRIMARY
INN
4864
Created by admin on Sat Jun 26 00:19:44 UTC 2021 , Edited by admin on Sat Jun 26 00:19:44 UTC 2021
PRIMARY
MERCK INDEX
M1859
Created by admin on Sat Jun 26 00:19:44 UTC 2021 , Edited by admin on Sat Jun 26 00:19:44 UTC 2021
PRIMARY Merck Index
ECHA (EC/EINECS)
257-094-3
Created by admin on Sat Jun 26 00:19:44 UTC 2021 , Edited by admin on Sat Jun 26 00:19:44 UTC 2021
PRIMARY
DRUG CENTRAL
203
Created by admin on Sat Jun 26 00:19:44 UTC 2021 , Edited by admin on Sat Jun 26 00:19:44 UTC 2021
PRIMARY
EVMPD
SUB05495MIG
Created by admin on Sat Jun 26 00:19:44 UTC 2021 , Edited by admin on Sat Jun 26 00:19:44 UTC 2021
PRIMARY
FDA UNII
00DPD30SOY
Created by admin on Sat Jun 26 00:19:44 UTC 2021 , Edited by admin on Sat Jun 26 00:19:44 UTC 2021
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