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
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)
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 |
DescriptionSources: http://www.bccancer.bc.ca/drug-database-site/Drug%20Index/Amsacrine_monograph_1August2013_formatted.pdfCurator'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
Sources: http://www.bccancer.bc.ca/drug-database-site/Drug%20Index/Amsacrine_monograph_1August2013_formatted.pdf
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.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: DNA of tumor cells Sources: https://www.ncbi.nlm.nih.gov/pubmed/2602146 |
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Target ID: CHEMBL1806 Sources: http://www.ncbi.nlm.nih.gov/pubmed/10691026 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | AMSA PD Approved UseUnknown |
PubMed
Title | Date | PubMed |
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[Studies on programmed cell death induced by amsacrine and expression of bcl-2 in leukemia cell lines]. | 1997 Sep |
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Targeting DNA through-covalent interactions of reversible binding drugs. | 2001 |
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Analysis of cleavage complexes using reactive inhibitor derivatives. | 2001 |
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A phase I trial of amsalog (CI-921) administered by intravenous infusion using a 5-day schedule. | 2001 Apr |
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Bone marrow involvement by nasal NK cell lymphoma at diagnosis is uncommon. | 2001 Feb |
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Novel pyrrolo[3,2-f]quinolines: synthesis and antiproliferative activity. | 2001 Jul |
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Pretreatment leukaemia cell drug resistance is correlated to clinical outcome in acute myeloid leukaemia. | 2001 Mar |
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Paclitaxel sensitization of multidrug-resistant cells to chemotherapy is independent of the cell cycle. | 2001 Mar 1 |
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Repair of topoisomerase-mediated DNA damage in bacteriophage T4. | 2001 May |
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Design of new anti-cancer agents based on topoisomerase poisons targeted to specific DNA sequences. | 2001 Nov |
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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 |
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Amsacrine and cisplatin in poor prognosis patients with metastatic transitional cell carcinoma of the urothelium: a phase-II study. | 2001 Sep |
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Inhibition of apoptotic proteins causes multidrug resistance in renal carcinoma cells. | 2001 Sep-Oct |
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Phase I study of the combination of losoxantrone and cyclophosphamide in patients with refractory solid tumours. | 2002 Feb 12 |
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Mitotic arrest induced by XK469, a novel antitumor agent, is correlated with the inhibition of cyclin B1 ubiquitination. | 2002 Jan 1 |
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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 |
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A rare case of adenoviral fulminant hepatic necrosis after chemotherapy. | 2002 Jul-Aug |
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High-throughput measurement of the Tp53 response to anticancer drugs and random compounds using a stably integrated Tp53-responsive luciferase reporter. | 2002 Jun |
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Increased expression of beta 2-microglobulin in multidrug-resistant tumour cells. | 2002 Jun 17 |
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Synthesis and antiinflammatory evaluation of 9-anilinoacridine and 9-phenoxyacridine derivatives. | 2002 Oct 10 |
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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 |
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Intensive chemotherapy with idarubicin, cytarabine, etoposide, and G-CSF priming in patients with advanced myelodysplastic syndrome and high-risk acute myeloid leukemia. | 2004 Aug |
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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 |
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Dissecting the cell-killing mechanism of the topoisomerase II-targeting drug ICRF-193. | 2004 Jul 2 |
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A novel DNA-dependent protein kinase inhibitor, NU7026, potentiates the cytotoxicity of topoisomerase II poisons used in the treatment of leukemia. | 2004 Jun 15 |
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The antitumor triazoloacridone C-1305 is a topoisomerase II poison with unusual properties. | 2004 Oct |
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Cardiotoxicity of cancer chemotherapy: implications for children. | 2005 |
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Synthesis, antitumour activity and structure-activity relationships of 5H-benzo[b]carbazoles. | 2005 Feb 1 |
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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 |
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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 |
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Adaphostin and other anticancer drugs quench the fluorescence of mitochondrial potential probes. | 2006 Jan |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24122234
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
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QL01XX01
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FDA ORPHAN DRUG |
4584
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C582
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L01XX01
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CHEMBL43
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DTXSID4022604
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AMSACRINE
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BINDING
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Volume of Distribution | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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