Page last updated: 2024-11-07

4'-(9-acridinylamino)methanesulfon-o-anisidide

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

4'-(9-acridinylamino)methanesulfon-o-anisidide: 30-90 times less potent in killing L1210 cells & 200 times less potent in producing single-strand breaks in DNA than m-AMSA; RN given refers to parent cpd; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID107747
CHEMBL ID287889
MeSH IDM0102781

Synonyms (19)

Synonym
2-amsa
4'-(9-acridinylamino)methanesulfon-o-anisidide
methanesulfon-o-anisidide, 4'-(9-acridinylamino)-
4-(9-acridinylamino)methanesulfon-o-anisidine
ccris 1634
o-amsa
brn 0452140
methanesulfonanilide, 4'-(9-acridinylamino)-2'-methoxy-
4'-(9-acridinylamino)-2'-methoxymethanesulfonanilide
NCI60_001124
CHEMBL287889
o-amsacrine
unii-82kv3k1waj
82kv3k1waj ,
51264-17-6
methanesulfonamide, n-(4-(9-acridinylamino)-2-methoxyphenyl)-
n-(4-(9-acridinylamino)-2-methoxyphenyl)methanesulfonamide
DTXSID50965554
n-{4-[(acridin-9(10h)-ylidene)amino]-2-methoxyphenyl}methanesulfonamide

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Quantifying the embryotoxic effects of these drugs revealed that the no observed adverse effect level (NOAEL) for m-AMSA is 10 nM, the embryotoxic concentration range is 50-500 nM, and complete lethality is observed at 1 microM."( Embryotoxicity of the intercalating agents m-AMSA and o-AMSA and the epipodophyllotoxin VP-16 in postimplantation rat embryos in vitro.
Mirkes, PE; Zwelling, LA, 1990
)
0.28
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (15)

Assay IDTitleYearJournalArticle
AID98819Drug concentration in mole/kg/day providing 50% extension of life in intraperitoneally implanted leukemia L1210 mice.1982Journal of medicinal chemistry, Mar, Volume: 25, Issue:3
Potential antitumor agents. 36. Quantitative relationships between experimental antitumor activity, toxicity, and structure for the general class of 9-anilinoacridine antitumor agents.
AID139094Drug dose in (mg/kg)/day to provide an increase in life span of 40% was determined; nr refers to Particular level of biological response required not reached before drug toxicity supervened1980Journal of medicinal chemistry, Mar, Volume: 23, Issue:3
Potential antitumor agents. 33. Quantitative structure--activity relationships for mutagenic activity and antitumor activity of substituted 4'-(9-acridinylamino)methanesulfonanilide derivatives.
AID20524Relative measure (Rm) of lipophilic/hydrophilic balance from partition chromatography1980Journal of medicinal chemistry, Mar, Volume: 23, Issue:3
Potential antitumor agents. 33. Quantitative structure--activity relationships for mutagenic activity and antitumor activity of substituted 4'-(9-acridinylamino)methanesulfonanilide derivatives.
AID201226The mutagenic effectiveness, lowest molar concentration required for a constant proportion of revertant colonies (chosen as 50 per 10E8 bacteria)1980Journal of medicinal chemistry, Mar, Volume: 23, Issue:3
Potential antitumor agents. 33. Quantitative structure--activity relationships for mutagenic activity and antitumor activity of substituted 4'-(9-acridinylamino)methanesulfonanilide derivatives.
AID158039Inhibitory concentration IC50 against Plasmodium falciparum K1 by [3H]hypoxanthine uptake over 24 hr1994Journal of medicinal chemistry, May-13, Volume: 37, Issue:10
Synthesis and in vitro evaluation of 9-anilino-3,6-diaminoacridines active against a multidrug-resistant strain of the malaria parasite Plasmodium falciparum.
AID201364Mutagenic efficiency, measured as the concentration providing 50% inhibition of Salmonella Typhimurium strain TA 1537 growth in drug induced-mutant colonies1980Journal of medicinal chemistry, Mar, Volume: 23, Issue:3
Potential antitumor agents. 33. Quantitative structure--activity relationships for mutagenic activity and antitumor activity of substituted 4'-(9-acridinylamino)methanesulfonanilide derivatives.
AID235013In vitro therapeutic index value is the ratio between IC50 values of [J] and [P]1994Journal of medicinal chemistry, May-13, Volume: 37, Issue:10
Synthesis and in vitro evaluation of 9-anilino-3,6-diaminoacridines active against a multidrug-resistant strain of the malaria parasite Plasmodium falciparum.
AID679780TP_TRANSPORTER: increase in Calcein-AM intracellular accumulation (Calcein-AM: 0.5 uM, o-Amsacrine: 5 uM) in MDR1-expressing NIH-3T3 cells2004Biochemical and biophysical research communications, Mar-19, Volume: 315, Issue:4
Distinct groups of multidrug resistance modulating agents are distinguished by competition of P-glycoprotein-specific antibodies.
AID134224In vivo toxicity (qd 1-5), determined using the intraperitoneal implantation of L1210 leukemia cells in mice1980Journal of medicinal chemistry, Mar, Volume: 23, Issue:3
Potential antitumor agents. 33. Quantitative structure--activity relationships for mutagenic activity and antitumor activity of substituted 4'-(9-acridinylamino)methanesulfonanilide derivatives.
AID26064Ionization constant (pKa)1980Journal of medicinal chemistry, Mar, Volume: 23, Issue:3
Potential antitumor agents. 33. Quantitative structure--activity relationships for mutagenic activity and antitumor activity of substituted 4'-(9-acridinylamino)methanesulfonanilide derivatives.
AID210614Compound concentration in mole/kg/day lethal to 10% of mice1982Journal of medicinal chemistry, Mar, Volume: 25, Issue:3
Potential antitumor agents. 36. Quantitative relationships between experimental antitumor activity, toxicity, and structure for the general class of 9-anilinoacridine antitumor agents.
AID139101Percent increase in life span in L1210 assay at the LD10 dose1980Journal of medicinal chemistry, Mar, Volume: 23, Issue:3
Potential antitumor agents. 33. Quantitative structure--activity relationships for mutagenic activity and antitumor activity of substituted 4'-(9-acridinylamino)methanesulfonanilide derivatives.
AID201229Concentration of drug needed to kill Salmonella Typhimurium strain TA 1537 grown on histidine-enriched medium1980Journal of medicinal chemistry, Mar, Volume: 23, Issue:3
Potential antitumor agents. 33. Quantitative structure--activity relationships for mutagenic activity and antitumor activity of substituted 4'-(9-acridinylamino)methanesulfonanilide derivatives.
AID25559Ionization constant (pKa)1982Journal of medicinal chemistry, Mar, Volume: 25, Issue:3
Potential antitumor agents. 36. Quantitative relationships between experimental antitumor activity, toxicity, and structure for the general class of 9-anilinoacridine antitumor agents.
AID95454Concentration required to reduce growth of human jurkat leukemia cells to 50% of control cultures, determined using a 72 hr continuous exposure1994Journal of medicinal chemistry, May-13, Volume: 37, Issue:10
Synthesis and in vitro evaluation of 9-anilino-3,6-diaminoacridines active against a multidrug-resistant strain of the malaria parasite Plasmodium falciparum.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (22)

TimeframeStudies, This Drug (%)All Drugs %
pre-199014 (63.64)18.7374
1990's6 (27.27)18.2507
2000's2 (9.09)29.6817
2010's0 (0.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 10.94

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index10.94 (24.57)
Research Supply Index3.14 (2.92)
Research Growth Index4.08 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (10.94)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other22 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]