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
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
AMSA PD

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
[Studies on programmed cell death induced by amsacrine and expression of bcl-2 in leukemia cell lines].
1997 Sep
Targeting DNA through-covalent interactions of reversible binding drugs.
2001
Analysis of cleavage complexes using reactive inhibitor derivatives.
2001
A phase I trial of amsalog (CI-921) administered by intravenous infusion using a 5-day schedule.
2001 Apr
Bone marrow involvement by nasal NK cell lymphoma at diagnosis is uncommon.
2001 Feb
Novel pyrrolo[3,2-f]quinolines: synthesis and antiproliferative activity.
2001 Jul
Pretreatment leukaemia cell drug resistance is correlated to clinical outcome in acute myeloid leukaemia.
2001 Mar
Paclitaxel sensitization of multidrug-resistant cells to chemotherapy is independent of the cell cycle.
2001 Mar 1
Repair of topoisomerase-mediated DNA damage in bacteriophage T4.
2001 May
Design of new anti-cancer agents based on topoisomerase poisons targeted to specific DNA sequences.
2001 Nov
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
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
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
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
Increased expression of beta 2-microglobulin in multidrug-resistant tumour cells.
2002 Jun 17
Synthesis and antiinflammatory evaluation of 9-anilinoacridine and 9-phenoxyacridine derivatives.
2002 Oct 10
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
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
Dissecting the cell-killing mechanism of the topoisomerase II-targeting drug ICRF-193.
2004 Jul 2
A novel DNA-dependent protein kinase inhibitor, NU7026, potentiates the cytotoxicity of topoisomerase II poisons used in the treatment of leukemia.
2004 Jun 15
The antitumor triazoloacridone C-1305 is a topoisomerase II poison with unusual properties.
2004 Oct
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
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
Adaphostin and other anticancer drugs quench the fluorescence of mitochondrial potential probes.
2006 Jan
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 Fri Dec 15 15:23:44 GMT 2023
Edited
by admin
on Fri Dec 15 15:23:44 GMT 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 Fri Dec 15 15:23:45 GMT 2023 , Edited by admin on Fri Dec 15 15:23:45 GMT 2023
FDA ORPHAN DRUG 4584
Created by admin on Fri Dec 15 15:23:45 GMT 2023 , Edited by admin on Fri Dec 15 15:23:45 GMT 2023
NCI_THESAURUS C582
Created by admin on Fri Dec 15 15:23:45 GMT 2023 , Edited by admin on Fri Dec 15 15:23:45 GMT 2023
WHO-ATC L01XX01
Created by admin on Fri Dec 15 15:23:45 GMT 2023 , Edited by admin on Fri Dec 15 15:23:45 GMT 2023
Code System Code Type Description
NSC
156303
Created by admin on Fri Dec 15 15:23:45 GMT 2023 , Edited by admin on Fri Dec 15 15:23:45 GMT 2023
PRIMARY
ChEMBL
CHEMBL43
Created by admin on Fri Dec 15 15:23:45 GMT 2023 , Edited by admin on Fri Dec 15 15:23:45 GMT 2023
PRIMARY
NCI_THESAURUS
C240
Created by admin on Fri Dec 15 15:23:45 GMT 2023 , Edited by admin on Fri Dec 15 15:23:45 GMT 2023
PRIMARY
PUBCHEM
2179
Created by admin on Fri Dec 15 15:23:45 GMT 2023 , Edited by admin on Fri Dec 15 15:23:45 GMT 2023
PRIMARY
CAS
51264-14-3
Created by admin on Fri Dec 15 15:23:45 GMT 2023 , Edited by admin on Fri Dec 15 15:23:45 GMT 2023
PRIMARY
HSDB
7087
Created by admin on Fri Dec 15 15:23:45 GMT 2023 , Edited by admin on Fri Dec 15 15:23:45 GMT 2023
PRIMARY
SMS_ID
100000091914
Created by admin on Fri Dec 15 15:23:45 GMT 2023 , Edited by admin on Fri Dec 15 15:23:45 GMT 2023
PRIMARY
MESH
D000677
Created by admin on Fri Dec 15 15:23:45 GMT 2023 , Edited by admin on Fri Dec 15 15:23:45 GMT 2023
PRIMARY
RXCUI
739
Created by admin on Fri Dec 15 15:23:45 GMT 2023 , Edited by admin on Fri Dec 15 15:23:45 GMT 2023
PRIMARY RxNorm
EPA CompTox
DTXSID4022604
Created by admin on Fri Dec 15 15:23:45 GMT 2023 , Edited by admin on Fri Dec 15 15:23:45 GMT 2023
PRIMARY
WIKIPEDIA
AMSACRINE
Created by admin on Fri Dec 15 15:23:45 GMT 2023 , Edited by admin on Fri Dec 15 15:23:45 GMT 2023
PRIMARY
DRUG BANK
DB00276
Created by admin on Fri Dec 15 15:23:45 GMT 2023 , Edited by admin on Fri Dec 15 15:23:45 GMT 2023
PRIMARY
INN
4864
Created by admin on Fri Dec 15 15:23:45 GMT 2023 , Edited by admin on Fri Dec 15 15:23:45 GMT 2023
PRIMARY
MERCK INDEX
m1859
Created by admin on Fri Dec 15 15:23:45 GMT 2023 , Edited by admin on Fri Dec 15 15:23:45 GMT 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
257-094-3
Created by admin on Fri Dec 15 15:23:45 GMT 2023 , Edited by admin on Fri Dec 15 15:23:45 GMT 2023
PRIMARY
DRUG CENTRAL
203
Created by admin on Fri Dec 15 15:23:45 GMT 2023 , Edited by admin on Fri Dec 15 15:23:45 GMT 2023
PRIMARY
CHEBI
2687
Created by admin on Fri Dec 15 15:23:45 GMT 2023 , Edited by admin on Fri Dec 15 15:23:45 GMT 2023
PRIMARY
NSC
249992
Created by admin on Fri Dec 15 15:23:45 GMT 2023 , Edited by admin on Fri Dec 15 15:23:45 GMT 2023
PRIMARY
EVMPD
SUB05495MIG
Created by admin on Fri Dec 15 15:23:45 GMT 2023 , Edited by admin on Fri Dec 15 15:23:45 GMT 2023
PRIMARY
FDA UNII
00DPD30SOY
Created by admin on Fri Dec 15 15:23:45 GMT 2023 , Edited by admin on Fri Dec 15 15:23:45 GMT 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