Compounds > nitracrine
Page last updated: 2024-12-06

nitracrine

Description

Nitracrine: Acridine antineoplastic agent used in mammary and ovarian tumors. It inhibits RNA synthesis. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID20628
CHEMBL ID26291
CHEBI ID135384
SCHEMBL ID8807
MeSH IDM0014872

Synonyms (31)

Synonym
1-nitro-9-(3'-dimethylaminopropylamino)-acridine
nitracrina [inn-spanish]
ccris 1973
acridine, 9-(3-(dimethylamino)propylamino)-1-nitro-
1-nitro-9-(dimethylaminopropylamino)acridine
nitracrine [inn]
1,3-propanediamine, n,n-dimethyl-n'-(1-nitro-9-acridinyl)-
nitracrinum [inn-latin]
9-((3-(dimethylamino)propyl)amino)-1-nitroacridine
nitracrine
1,3-propanediamine, n,n-dimethyl-n'-(1-nitro-9-acridinyl)-, dihydrochloride
9-((3-(dimethylamino)propyl)amino)-1-(hydroxy(oxido)amino)acridine
ledacrine
n',n'-dimethyl-n-(1-nitroacridin-9-yl)propane-1,3-diamine
nsc247561
NCI60_001977
CHEBI:135384
CHEMBL26291
4533-39-5
nitracrina
nitracrinum
712mlz30sb ,
unii-712mlz30sb
nitracrine [mi]
SCHEMBL8807
DTXSID90196481
CS-7229
HY-U00279
Q27265916
n,n-dimethyl-n'-(1-nitro-acridin-9-yl)-propane-1,3-diamine
AKOS040742305

Research Excerpts

Overview

Nitracrine (Ledakrin) is an antitumor drug which is activated by cellular enzymes and binds covalently to DNA. Nitracrine is an electron affinic DNA intercalating agent and a potent hypoxia-selective cytotoxin and radiosensitizer in cell culture.

ExcerptReferenceRelevance
"Nitracrine (Ledakrin) is an antitumor drug which is activated by cellular enzymes and binds covalently to DNA. "( Modulation of G(2) arrest enhances cell death induced by the antitumor 1-nitroacridine derivative, Nitracrine.
Skladanowski, A, 2002)		1.97
"Nitracrine (NC) is an electron affinic DNA intercalating agent and a potent hypoxia-selective cytotoxin and radiosensitizer in cell culture. "( The reaction between nitracrine and glutathione: implications for hypoxic cell radiosensitization and cytotoxicity.
Anderson, RF; Wilson, WR, 1989)		2.04

Treatment

ExcerptReferenceRelevance
"Nitracrine treatment with biologically relevant concentrations (0.1-3.0 microM, 1 hr, 37 degrees) induced only DPCs."( Are lethal effects of nitracrine on L5178Y cell sublines associated with DNA-protein crosslinks?
Ciesielska, E; Gradzka, I; Szmigiero, L; Walicka, M, 1993)		1.32

Toxicity

ExcerptReferenceRelevance
" We have found nitracrine to be selectively toxic to the Chinese hamster ovary cell line AA8 under hypoxic conditions in culture, with a potency approximately 100,000 times higher than that of misonidazole."( Selective toxicity of nitracrine to hypoxic mammalian cells.
Baguley, BC; Denny, WA; Probert, JC; Twigden, SJ; Wilson, WR, 1984)		0.94
"Some N-oxide derivatives of DNA intercalators are bioreductive prodrugs that are selectively toxic under hypoxic conditions."( Comparison of aromatic and tertiary amine N-oxides of acridine DNA intercalators as bioreductive drugs. Cytotoxicity, DNA binding, cellular uptake, and metabolism.
Denny, WA; Hicks, KO; Pullen, SM; Siim, BG; van Zijl, PL; Wilson, WR, 2000)		0.31
" General toxic effect was calculated as a direct cell kill and a cell proliferation arrest."( Cytotoxicity of nitroheterocyclic compounds, quinifuryl and nitracrine, towards leukaemic and normal cells on the dark and under illumination with visible light.
Borissevitch, IE; Daghastanli, NA; Degterev, IA; Rossa, MM; Selistre-De-Araujo, HS; Tedesco, AC, 2004)		0.57

Compound-Compound Interactions

ExcerptReferenceRelevance
" The present studies aimed to know its biotransformation with phase II enzymes - UDP-glucuronosyltransferases (UGTs) and its potential to be engaged in drug-drug interactions arising from the modulation of UGT activity."( Drug-drug interaction potential of antitumor acridine agent C-1748: The substrate of UDP-glucuronosyltransferases 2B7, 2B17 and the inhibitor of 1A9 and 2B7.
Bejrowska, A; Mazerska, Z; Mróz, A; Ryska, I; Sominko, H, 2018)		0.48
"The observed UGT-mediated metabolism of C-1748 and its ability to inhibit UGT activity should be considered as the potency for drug resistance and drug-drug interactions in the prospective multidrug therapy."( Drug-drug interaction potential of antitumor acridine agent C-1748: The substrate of UDP-glucuronosyltransferases 2B7, 2B17 and the inhibitor of 1A9 and 2B7.
Bejrowska, A; Mazerska, Z; Mróz, A; Ryska, I; Sominko, H, 2018)		0.48
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
acridines
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (52)

Assay IDTitleYearJournalArticle
AID25229Extrapolated fraction of biological activity remaining at time zero of hypoxic AA8 suspension cultures1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Hypoxia-selective antitumor agents. 2. Electronic effects of 4-substituents on the mechanisms of cytotoxicity and metabolic stability of nitracrine derivatives.
AID25358Compound was evaluated for quinoline pKa value in aqueous solution at 25 degree Celsius by spectrophotometry1992Journal of medicinal chemistry, Dec-25, Volume: 35, Issue:26
Hypoxia-selective antitumor agents. 6. 4-(Alkylamino)nitroquinolines: a new class of hypoxia-selective cytotoxins.
AID231784Ratio of concentration required to reduce cell (AA8) survival by 10% under aerobic to hypoxic (air/N2) conditions.1992Journal of medicinal chemistry, Dec-25, Volume: 35, Issue:26
Hypoxia-selective antitumor agents. 6. 4-(Alkylamino)nitroquinolines: a new class of hypoxia-selective cytotoxins.
AID45253Ratio of cytotoxicity determined in air to that of cytotoxicity determined in N2 was measured under aerobic conditions to hypoxic conditions by the clonogenic assay against Chinese hamster ovary (subline AA8) cells1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Hypoxia-selective antitumor agents. 1. Relationships between structure, redox properties and hypoxia-selective cytotoxicity for 4-substituted derivatives of nitracrine.
AID215282Inhibitory concentration required to reduce cell density in UV-4 cells to 50% of controls (cells were exposed to compound for 4 days continuously)1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Hypoxia-selective antitumor agents. 2. Electronic effects of 4-substituents on the mechanisms of cytotoxicity and metabolic stability of nitracrine derivatives.
AID115154Maximum tolerated ip dose for male C3H/HeN mice.1996Journal of medicinal chemistry, Jun-21, Volume: 39, Issue:13
Hypoxia-selective antitumor agents. 13. Effects of acridine substitution on the hypoxia-selective cytotoxicity and metabolic reduction of the bis-bioreductive agent nitracrine N-oxide.
AID25329Acridine pKa values were determined in aqueous solution at 25 degrees Centigrade by spectrophotometric method.1990Journal of medicinal chemistry, May, Volume: 33, Issue:5
Hypoxia-selective antitumor agents. 4. Relationships between structure, physicochemical properties, and hypoxia-selective cytotoxicity for nitracrine analogues with varying side chains: the "iminoacridan hypothesis".
AID55130Logarithm of association constant for binding to poly[d(A-T)], determined by ethidium displacement1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Hypoxia-selective antitumor agents. 1. Relationships between structure, redox properties and hypoxia-selective cytotoxicity for 4-substituted derivatives of nitracrine.
AID232184Ratio of concentrations inhibiting AA8 cell growth (18 hr exposure) under aerobic (air) and hypoxic (air/N2) conditions1992Journal of medicinal chemistry, Dec-25, Volume: 35, Issue:26
Hypoxia-selective antitumor agents. 6. 4-(Alkylamino)nitroquinolines: a new class of hypoxia-selective cytotoxins.
AID9675CT10 (air/N2) ratio of the product of the drug concentration to the exposure time needed to reduce cell survival to 10% of controls using AA8 cells at 10 E 6 /mL in the clonogenic assay1990Journal of medicinal chemistry, May, Volume: 33, Issue:5
Hypoxia-selective antitumor agents. 4. Relationships between structure, physicochemical properties, and hypoxia-selective cytotoxicity for nitracrine analogues with varying side chains: the "iminoacridan hypothesis".
AID9837Growth inhibitory activity against CHO subline AA8 cells exposed for 18 hr under aerobic conditions1992Journal of medicinal chemistry, Dec-25, Volume: 35, Issue:26
Hypoxia-selective antitumor agents. 6. 4-(Alkylamino)nitroquinolines: a new class of hypoxia-selective cytotoxins.
AID215156Trypanocidal activity against Trypanosoma brucei, exposure of parasites to compound prior to injection into mice at 10 e-5 M concentration in presence of light1984Journal of medicinal chemistry, Jul, Volume: 27, Issue:7
Identification of an acridine photoaffinity probe for trypanocidal action.
AID25570Dissociation constant of the compound1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Hypoxia-selective antitumor agents. 1. Relationships between structure, redox properties and hypoxia-selective cytotoxicity for 4-substituted derivatives of nitracrine.
AID215159Trypanocidal activity against Trypanosoma brucei, exposure of parasites to compound prior to injection into mice at 10 e-6 M concentration in dark conditions1984Journal of medicinal chemistry, Jul, Volume: 27, Issue:7
Identification of an acridine photoaffinity probe for trypanocidal action.
AID9650Inhibitory activity against aerobic growth of AA8 cells.1996Journal of medicinal chemistry, Jun-21, Volume: 39, Issue:13
Hypoxia-selective antitumor agents. 13. Effects of acridine substitution on the hypoxia-selective cytotoxicity and metabolic reduction of the bis-bioreductive agent nitracrine N-oxide.
AID45746Inhibitory activity to reduce cell density by 50% of AA8 cells under aerobic conditions1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Hypoxia-selective antitumor agents. 2. Electronic effects of 4-substituents on the mechanisms of cytotoxicity and metabolic stability of nitracrine derivatives.
AID226471Hypersensitivity factor, IC50 (AA8) air /IC50 (UV4) in N21990Journal of medicinal chemistry, May, Volume: 33, Issue:5
Hypoxia-selective antitumor agents. 4. Relationships between structure, physicochemical properties, and hypoxia-selective cytotoxicity for nitracrine analogues with varying side chains: the "iminoacridan hypothesis".
AID228707Compound's one-electron reduction potential (E(1)) has been measured by radiolysis at pK11989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Hypoxia-selective antitumor agents. 1. Relationships between structure, redox properties and hypoxia-selective cytotoxicity for 4-substituted derivatives of nitracrine.
AID214997Trypanocidal activity against Trypanosoma brucei, exposure of parasites to compound prior to injection into mice at 10 e-4 M concentration in presence of light1984Journal of medicinal chemistry, Jul, Volume: 27, Issue:7
Identification of an acridine photoaffinity probe for trypanocidal action.
AID226472Hypersensitivity factor, IC50 (AA8) air /IC50 (UV4) in air1990Journal of medicinal chemistry, May, Volume: 33, Issue:5
Hypoxia-selective antitumor agents. 4. Relationships between structure, physicochemical properties, and hypoxia-selective cytotoxicity for nitracrine analogues with varying side chains: the "iminoacridan hypothesis".
AID9477Concentration needed to reduce cell survival to 10% of control values, using 1 hour exposure of plateau phase AA8 cells at 10e6 cells/ml1996Journal of medicinal chemistry, Jun-21, Volume: 39, Issue:13
Hypoxia-selective antitumor agents. 13. Effects of acridine substitution on the hypoxia-selective cytotoxicity and metabolic reduction of the bis-bioreductive agent nitracrine N-oxide.
AID215158Compound is evaluated for trypanocidal activity against Trypanosoma brucei, by exposing the parasites directly to compound prior to injection to mice at 10 e-6 M concentration (pre) in presence of light.1984Journal of medicinal chemistry, Jul, Volume: 27, Issue:7
Identification of an acridine photoaffinity probe for trypanocidal action.
AID47694Inhibitory activity of compound for AA8 cells to reduce cell density by 50% (exposed to compound for 4 hours)1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Hypoxia-selective antitumor agents. 2. Electronic effects of 4-substituents on the mechanisms of cytotoxicity and metabolic stability of nitracrine derivatives.
AID27042Half life of extracellular bioactivity assessed by bioassay of culture supernatant against hypoxic UV-4 cells1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Hypoxia-selective antitumor agents. 2. Electronic effects of 4-substituents on the mechanisms of cytotoxicity and metabolic stability of nitracrine derivatives.
AID215154Trypanocidal activity against Trypanosoma brucei, exposure of parasites to compound prior to injection into mice at 10 e-5 M concentration in dark conditions1984Journal of medicinal chemistry, Jul, Volume: 27, Issue:7
Identification of an acridine photoaffinity probe for trypanocidal action.
AID232183Ratio of growth inhibitory concentrations against AA8 cells and UV4 cells exposed to the compound for 18 hr under aerobic(air) conditions1992Journal of medicinal chemistry, Dec-25, Volume: 35, Issue:26
Hypoxia-selective antitumor agents. 6. 4-(Alkylamino)nitroquinolines: a new class of hypoxia-selective cytotoxins.
AID9838Tested for the concentration of the drug to reduce cell numbers to 50 percent of controls against AA8 cells in the microassay1990Journal of medicinal chemistry, May, Volume: 33, Issue:5
Hypoxia-selective antitumor agents. 4. Relationships between structure, physicochemical properties, and hypoxia-selective cytotoxicity for nitracrine analogues with varying side chains: the "iminoacridan hypothesis".
AID230206Inhibitory activity against aerobic growth of UV4cells, Hypersensitivity factor is the ratio of IC50(AA8) to IC50(UV4).1996Journal of medicinal chemistry, Jun-21, Volume: 39, Issue:13
Hypoxia-selective antitumor agents. 13. Effects of acridine substitution on the hypoxia-selective cytotoxicity and metabolic reduction of the bis-bioreductive agent nitracrine N-oxide.
AID229914Spheroid resistance factor which is defined as the ratio C10 (intact)/ C10 (dissociated) EMT6 cells1996Journal of medicinal chemistry, Jun-21, Volume: 39, Issue:13
Hypoxia-selective antitumor agents. 13. Effects of acridine substitution on the hypoxia-selective cytotoxicity and metabolic reduction of the bis-bioreductive agent nitracrine N-oxide.
AID16679Equilibrium constant measured by the pulse radiolysis at pH 71989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Hypoxia-selective antitumor agents. 1. Relationships between structure, redox properties and hypoxia-selective cytotoxicity for 4-substituted derivatives of nitracrine.
AID215162Compound is evaluated for trypanocidal activity against Trypanosoma brucei, by exposing the parasites directly to compound prior to injection to mice at 10 e-7 M concentration in dark conditions1984Journal of medicinal chemistry, Jul, Volume: 27, Issue:7
Identification of an acridine photoaffinity probe for trypanocidal action.
AID9674Tested for the product of the drug concentration to the exposure time needed to reduce cell survival to 10% of controls using AA8 cells at 10 E 6 /mL in the clonogenic assay1990Journal of medicinal chemistry, May, Volume: 33, Issue:5
Hypoxia-selective antitumor agents. 4. Relationships between structure, physicochemical properties, and hypoxia-selective cytotoxicity for nitracrine analogues with varying side chains: the "iminoacridan hypothesis".
AID228706Compound''s one-electron reduction potential (E(1)) has been measured by radiolysis at pH 71989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Hypoxia-selective antitumor agents. 1. Relationships between structure, redox properties and hypoxia-selective cytotoxicity for 4-substituted derivatives of nitracrine.
AID9672Concentration required to reduce AA8 cell survival by 10%1992Journal of medicinal chemistry, Dec-25, Volume: 35, Issue:26
Hypoxia-selective antitumor agents. 6. 4-(Alkylamino)nitroquinolines: a new class of hypoxia-selective cytotoxins.
AID27040Half life of extracellular bioactivity assessed by bioassay of culture supernatant against aerobic UV-4 cells1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Hypoxia-selective antitumor agents. 2. Electronic effects of 4-substituents on the mechanisms of cytotoxicity and metabolic stability of nitracrine derivatives.
AID25230Extrapolated fraction of biological activity remaining at time zero of stirred aerobic AA8 suspension cultures1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Hypoxia-selective antitumor agents. 2. Electronic effects of 4-substituents on the mechanisms of cytotoxicity and metabolic stability of nitracrine derivatives.
AID215160Trypanocidal activity against Trypanosoma brucei, exposur of parasites to compound prior to injection into mice at 10 e-6 M concentration in presence of light1984Journal of medicinal chemistry, Jul, Volume: 27, Issue:7
Identification of an acridine photoaffinity probe for trypanocidal action.
AID229743Hypersensitivity factor (HF) of IC50 (AA8) / IC50 (UV-5) of compound for repair deffective mutants1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Hypoxia-selective antitumor agents. 2. Electronic effects of 4-substituents on the mechanisms of cytotoxicity and metabolic stability of nitracrine derivatives.
AID27864Total compound concentration in AA8 suspension cultures at zero time1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Hypoxia-selective antitumor agents. 2. Electronic effects of 4-substituents on the mechanisms of cytotoxicity and metabolic stability of nitracrine derivatives.
AID67616Concentration resulting in 10% survival in dissociated EMT6 spheroid cell suspension1996Journal of medicinal chemistry, Jun-21, Volume: 39, Issue:13
Hypoxia-selective antitumor agents. 13. Effects of acridine substitution on the hypoxia-selective cytotoxicity and metabolic reduction of the bis-bioreductive agent nitracrine N-oxide.
AID214996Trypanocidal activity against Trypanosoma brucei, exposure of parasites to compound prior to injection into mice at 10 e-4 M concentration in dark conditions1984Journal of medicinal chemistry, Jul, Volume: 27, Issue:7
Identification of an acridine photoaffinity probe for trypanocidal action.
AID232180Ratio of growth inhibition of compound to reduce cell density by 50% of AA8 cells under aerobic and hypoxic conditions (air/N2)1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Hypoxia-selective antitumor agents. 2. Electronic effects of 4-substituents on the mechanisms of cytotoxicity and metabolic stability of nitracrine derivatives.
AID229742Hypersensitivity factor (HF) of IC50 (AA8) / IC50 (UV-4) of compound for repair deffective mutants1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Hypoxia-selective antitumor agents. 2. Electronic effects of 4-substituents on the mechanisms of cytotoxicity and metabolic stability of nitracrine derivatives.
AID211493Cytotoxicity was measured under aerobic conditions by the clonogenic assay against Chinese hamster ovary (subline AA8) cells1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Hypoxia-selective antitumor agents. 1. Relationships between structure, redox properties and hypoxia-selective cytotoxicity for 4-substituted derivatives of nitracrine.
AID229741Hypersensitivity factor (HF) of IC50 (AA8) / IC50 (EM-9) of compound for repair deffective mutants1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Hypoxia-selective antitumor agents. 2. Electronic effects of 4-substituents on the mechanisms of cytotoxicity and metabolic stability of nitracrine derivatives.
AID215281Inhibitory ativity to reduce cell density by 50% of repair deffective mutant UV-4 cells in 96-well cultures under aerobic conditions1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Hypoxia-selective antitumor agents. 2. Electronic effects of 4-substituents on the mechanisms of cytotoxicity and metabolic stability of nitracrine derivatives.
AID231942Ratio for hypoxic AA8/ hypoxic UV-4, expressed as hypersensitivity factor under aerobic conditions1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Hypoxia-selective antitumor agents. 2. Electronic effects of 4-substituents on the mechanisms of cytotoxicity and metabolic stability of nitracrine derivatives.
AID215163Compound is evaluated for trypanocidal activity against Trypanosoma brucei, by exposing the parasites directly to compound prior to injection to mice at 10 e-7 M concentration in presence of light1984Journal of medicinal chemistry, Jul, Volume: 27, Issue:7
Identification of an acridine photoaffinity probe for trypanocidal action.
AID232181Ratio of growth inhibition of compound to reduce cell density by 50% of repair deffective mutant UV-4 cells in 96-well cultures under aerobic and hypoxic conditions (air/N2)1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Hypoxia-selective antitumor agents. 2. Electronic effects of 4-substituents on the mechanisms of cytotoxicity and metabolic stability of nitracrine derivatives.
AID20518Relative lipophilicity of the compound1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
Hypoxia-selective antitumor agents. 1. Relationships between structure, redox properties and hypoxia-selective cytotoxicity for 4-substituted derivatives of nitracrine.
AID233733Air/N2 ratio = C10(air)/C10(nitrogen)1996Journal of medicinal chemistry, Jun-21, Volume: 39, Issue:13
Hypoxia-selective antitumor agents. 13. Effects of acridine substitution on the hypoxia-selective cytotoxicity and metabolic reduction of the bis-bioreductive agent nitracrine N-oxide.
AID9840IC50 (air/N2) ratio of the drug to reduce cell numbers to 50 percent of controls using AA8 cells in the microassay1990Journal of medicinal chemistry, May, Volume: 33, Issue:5
Hypoxia-selective antitumor agents. 4. Relationships between structure, physicochemical properties, and hypoxia-selective cytotoxicity for nitracrine analogues with varying side chains: the "iminoacridan hypothesis".
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (109)

TimeframeStudies, This Drug (%)All Drugs %
pre-199062 (56.88)18.7374
1990's23 (21.10)18.2507
2000's14 (12.84)29.6817
2010's9 (8.26)24.3611
2020's1 (0.92)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 18.60

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index18.60 (24.57)
Research Supply Index4.93 (2.92)
Research Growth Index4.23 (4.65)
Search Engine Demand Index18.60 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (18.60)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials2 (1.48%)5.53%
Reviews2 (1.48%)6.00%
Case Studies1 (0.74%)4.05%
Observational0 (0.00%)0.25%
Other130 (96.30%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
urea
pseudourea: clinical use; structure. isourea : A carboximidic acid that is the imidic acid tautomer of urea, H2NC(=NH)OH, and its hydrocarbyl derivatives.		210isourea;
monocarboxylic acid amide;
one-carbon compound		Daphnia magna metabolite;
Escherichia coli metabolite;
fertilizer;
flour treatment agent;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
mercaptoethanol
Mercaptoethanol: A water-soluble thiol derived from hydrogen sulfide and ethanol. It is used as a reducing agent for disulfide bonds and to protect sulfhydryl groups from oxidation.		1.9610alkanethiol;
primary alcohol		geroprotector
amsacrine
Amsacrine: An aminoacridine derivative that intercalates into DNA and is used as an antineoplastic agent.. amsacrine : A sulfonamide that is N-phenylmethanesulfonamide substituted by a methoxy group at position 3 and an acridin-9-ylamino group at position 4. It exhibits antineoplastic activity.		7.6630acridines;
aromatic ether;
sulfonamide		antineoplastic agent;
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor
diminazene
Diminazene: An effective trypanocidal agent.. diminazene : A triazene derivative that is triazene in which each of the terminal nitrogens is substituted by a 4-carbamimidoylphenyl group.		1.9610carboxamidine;
triazene derivative		antiparasitic agent;
trypanocidal drug
beta-naphthoflavone
beta-Naphthoflavone: A polyaromatic hydrocarbon inducer of P4501A1 and P4501A2 cytochromes. (Proc Soc Exp Biol Med 1994 Dec:207(3):302-308). beta-naphthoflavone : An extended flavonoid resulting from the formal fusion of a benzene ring with the f side of flavone.		1.9910extended flavonoid;
naphtho-gamma-pyrone;
organic heterotricyclic compound		aryl hydrocarbon receptor agonist
chlorambucil
Chlorambucil: A nitrogen mustard alkylating agent used as antineoplastic for chronic lymphocytic leukemia, Hodgkin's disease, and others. Although it is less toxic than most other nitrogen mustards, it has been listed as a known carcinogen in the Fourth Annual Report on Carcinogens (NTP 85-002, 1985). (Merck Index, 11th ed). chlorambucil : A monocarboxylic acid that is butanoic acid substituted at position 4 by a 4-[bis(2-chloroethyl)amino]phenyl group. A chemotherapy drug that can be used in combination with the antibody obinutuzumab for the treatment of chronic lymphocytic leukemia.		1.9710aromatic amine;
monocarboxylic acid;
nitrogen mustard;
organochlorine compound;
tertiary amino compound		alkylating agent;
antineoplastic agent;
carcinogenic agent;
drug allergen;
immunosuppressive agent
ethidium
Ethidium: A trypanocidal agent and possible antiviral agent that is widely used in experimental cell biology and biochemistry. Ethidium has several experimentally useful properties including binding to nucleic acids, noncompetitive inhibition of nicotinic acetylcholine receptors, and fluorescence among others. It is most commonly used as the bromide.. ethidium : The fluorescent compound widely used in experimental cell biology and biochemistry to reveal double-stranded DNA and RNA.		1.9510phenanthridinesfluorochrome;
intercalator
hydroxyurea
[no description available]		1.9610one-carbon compound;
ureas		antimetabolite;
antimitotic;
antineoplastic agent;
DNA synthesis inhibitor;
EC 1.17.4.1 (ribonucleoside-diphosphate reductase) inhibitor;
genotoxin;
immunomodulator;
radical scavenger;
teratogenic agent
methoxsalen
Methoxsalen: A naturally occurring furocoumarin compound found in several species of plants, including Psoralea corylifolia. It is a photoactive substance that forms DNA ADDUCTS in the presence of ultraviolet A irradiation.. methoxsalen : A member of the class of psoralens that is 7H-furo[3,2-g]chromen-7-one in which the 9 position is substituted by a methoxy group. It is a constituent of the fruits of Ammi majus. Like other psoralens, trioxsalen causes photosensitization of the skin. It is administered topically or orally in conjunction with UV-A for phototherapy treatment of vitiligo and severe psoriasis.		2.6630aromatic ether;
psoralens		antineoplastic agent;
cross-linking reagent;
dermatologic drug;
photosensitizing agent;
plant metabolite
phenobarbital
Phenobarbital: A barbituric acid derivative that acts as a nonselective central nervous system depressant. It potentiates GAMMA-AMINOBUTYRIC ACID action on GABA-A RECEPTORS, and modulates chloride currents through receptor channels. It also inhibits glutamate induced depolarizations.. phenobarbital : A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by ethyl and phenyl groups.		1.9910barbituratesanticonvulsant;
drug allergen;
excitatory amino acid antagonist;
sedative
mitomycin
Mitomycin: An antineoplastic antibiotic produced by Streptomyces caespitosus. It is one of the bi- or tri-functional ALKYLATING AGENTS causing cross-linking of DNA and inhibition of DNA synthesis.. mitomycin : A family of aziridine-containing natural products isolated from Streptomyces caespitosus or Streptomyces lavendulae.		2.3720mitomycinalkylating agent;
antineoplastic agent
thymidine
[no description available]		2.3720pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
metabolite;
mouse metabolite
4-nitroquinoline-1-oxide
4-nitroquinoline N-oxide : A quinoline N-oxide carrying a nitro substituent at position 4.		1.9710C-nitro compound;
quinoline N-oxide		carcinogenic agent
ethyl methanesulfonate
Ethyl Methanesulfonate: An antineoplastic agent with alkylating properties. It also acts as a mutagen by damaging DNA and is used experimentally for that effect.. ethyl methanesulfonate : A methanesulfonate ester resulting from the formal condensation of methanesulfonic acid with ethanol.		1.9710methanesulfonate esteralkylating agent;
antineoplastic agent;
carcinogenic agent;
genotoxin;
mutagen;
teratogenic agent
acriflavine chloride
3,6-diamino-10-methylacridinium chloride : The 10-methochloride salt of 3,6-diaminoacridine. Note that a mixture of this compound with 3,6-diaminoacridine (proflavine) is known as acriflavine or neutral acriflavine.		1.9610organic chloride saltantibacterial agent;
antiseptic drug;
carcinogenic agent;
histological dye;
intercalator
aminacrine
Aminacrine: A highly fluorescent anti-infective dye used clinically as a topical antiseptic and experimentally as a mutagen, due to its interaction with DNA. It is also used as an intracellular pH indicator.. 9-aminoacridine : An aminoacridine that is acridine in which the hydrogen at position 9 is replaced by an amino group. A fluorescent dyd and topical antiseptic agent, it is used (usually as the hydrochloride salt) in eye drops for the treatment of superficial eye infections.		2.3720aminoacridines;
primary amino compound		acid-base indicator;
antiinfective agent;
antiseptic drug;
fluorescent dye;
MALDI matrix material;
mutagen
proflavine
Proflavine: Topical antiseptic used mainly in wound dressings.. 3,6-diaminoacridine : An aminoacridine that is acridine that is substituted by amino groups at positions 3 and 6. A slow-acting bacteriostat that is effective against many Gram-positive bacteria (but ineffective against spores), its salts were formerly used for treatment of burns and infected wounds.		1.9610aminoacridinesantibacterial agent;
antiseptic drug;
carcinogenic agent;
chromophore;
intercalator
xanthenes
Xanthenes: Compounds with three aromatic rings in linear arrangement with an OXYGEN in the center ring.		2.4120xanthene
acridines
Acridines: Compounds that include the structure of acridine.. acridine : A polycyclic heteroarene that is anthracene in which one of the central CH groups is replaced by a nitrogen atom.		6.15321acridines;
mancude organic heterotricyclic parent;
polycyclic heteroarene		genotoxin
hydrazine
diamine : Any polyamine that contains two amino groups.		210azane;
hydrazines		EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor
c 137
C 137: RN given refers to parent cpd		3.4980
dithiothreitol
1,4-dimercaptobutane-2,3-diol : A glycol that is butane-2,3-diol in which a hydrogen from each of the methyl groups is replaced by a thiol group.. 1,4-dithiothreitol : The threo-diastereomer of 1,4-dimercaptobutane-2,3-diol.		3.08501,4-dimercaptobutane-2,3-diol;
butanediols;
dithiol;
glycol;
thiol		chelator;
human metabolite;
reducing agent
n-methylaspartate
N-Methylaspartate: An amino acid that, as the D-isomer, is the defining agonist for the NMDA receptor subtype of glutamate receptors (RECEPTORS, NMDA).. N-methyl-D-aspartic acid : An aspartic acid derivative having an N-methyl substituent and D-configuration.		2.0210amino dicarboxylic acid;
D-alpha-amino acid;
D-aspartic acid derivative;
secondary amino compound		neurotransmitter agent
platinum
Platinum: A heavy, soft, whitish metal, resembling tin, with atomic number 78, atomic weight 195.084, symbol Pt. It is used in manufacturing equipment for laboratory and industrial use. It occurs as a black powder (platinum black) and as a spongy substance (spongy platinum) and may have been known in Pliny's time as alutiae.		2.0110elemental platinum;
nickel group element atom;
platinum group metal atom
camptothecin
NSC 100880: carboxylate (opened lactone) form of camptothecin; RN refers to (S)-isomer; structure given in first source		2.0110delta-lactone;
pyranoindolizinoquinoline;
quinoline alkaloid;
tertiary alcohol		antineoplastic agent;
EC 5.99.1.2 (DNA topoisomerase) inhibitor;
genotoxin;
plant metabolite
misonidazole
Misonidazole: A nitroimidazole that sensitizes normally radio-resistant hypoxic cells to radiation. It may also be directly cytotoxic to hypoxic cells and has been proposed as an antineoplastic.		2.3720
daunorubicin
Daunorubicin: A very toxic anthracycline aminoglycoside antineoplastic isolated from Streptomyces peucetius and others, used in treatment of LEUKEMIA and other NEOPLASMS.. anthracycline : Anthracyclines are polyketides that have a tetrahydronaphthacenedione ring structure attached by a glycosidic linkage to the amino sugar daunosamine.. daunorubicin : A natural product found in Actinomadura roseola.		1.9610aminoglycoside antibiotic;
anthracycline;
p-quinones;
tetracenequinones		antineoplastic agent;
bacterial metabolite
4-(9-acridinylamino)aniline
4-(9-acridinylamino)aniline: RN given refers to parent cpd		1.9610
triazoles
Triazoles: Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3.. triazoles : An azole in which the five-membered heterocyclic aromatic skeleton contains three N atoms and two C atoms.		2.49201,2,3-triazole
cobalt
Cobalt: A trace element that is a component of vitamin B12. It has the atomic symbol Co, atomic number 27, and atomic weight 58.93. It is used in nuclear weapons, alloys, and pigments. Deficiency in animals leads to anemia; its excess in humans can lead to erythrocytosis.. cobalt(1+) : A monovalent inorganic cation obtained from cobalt.. cobalt atom : A cobalt group element atom that has atomic number 27.		1.9510cobalt group element atom;
metal allergen		micronutrient
n-(2'-(dimethylamino)ethyl)acridine-4-carboxamide
[no description available]		2.420
vadimezan
vadimezan : A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is replaced by a 5,6-dimethyl-9-oxoxanthen-4-yl group.		1.9910monocarboxylic acid;
xanthones		antineoplastic agent
1-nitro-9-aminoacridine
[no description available]		2.6630
4-methoxynitracrine
4-methoxynitracrine: structure given in first source		3.0850
thioacetamide
Thioacetamide: A crystalline compound used as a laboratory reagent in place of HYDROGEN SULFIDE. It is a potent hepatocarcinogen.. thioacetamide : A thiocarboxamide consiting of acetamide having the oxygen replaced by sulfur.		1.9610thiocarboxamidehepatotoxic agent
nadp
[no description available]		1.9510
lobeline
Lobeline: An alkaloid that has actions similar to NICOTINE on nicotinic cholinergic receptors but is less potent. It has been proposed for a variety of therapeutic uses including in respiratory disorders, peripheral vascular disorders, insomnia, and smoking cessation.		1.9510
aq4n
AQ4N: structure given in first source		6.9910
thromboplastin
Thromboplastin: Constituent composed of protein and phospholipid that is widely distributed in many tissues. It serves as a cofactor with factor VIIa to activate factor X in the extrinsic pathway of blood coagulation.		2.0210
9-(2'-hydroxyethylamino)-4-methyl-1-nitroacridine
9-(2'-hydroxyethylamino)-4-methyl-1-nitroacridine: anti-cancer agent; structure in first source		3.6890
deoxyguanosine triphosphate
[no description available]		1.9610deoxyguanosine phosphate;
guanyl deoxyribonucleotide;
purine 2'-deoxyribonucleoside 5'-triphosphate		Arabidopsis thaliana metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
plant metabolite;
Saccharomyces cerevisiae metabolite
allopurinol
Allopurinol: A XANTHINE OXIDASE inhibitor that decreases URIC ACID production. It also acts as an antimetabolite on some simpler organisms.. allopurinol : A bicyclic structure comprising a pyrazole ring fused to a hydroxy-substituted pyrimidine ring.		210nucleobase analogue;
organic heterobicyclic compound		antimetabolite;
EC 1.17.3.2 (xanthine oxidase) inhibitor;
gout suppressant;
radical scavenger
phosphorus radioisotopes
Phosphorus Radioisotopes: Unstable isotopes of phosphorus that decay or disintegrate emitting radiation. P atoms with atomic weights 28-34 except 31 are radioactive phosphorus isotopes.		2.6730
ConditionIndicatedRelationship StrengthStudiesTrials
Cancer of Pancreas
[description not available]		02.1510
Pancreatic Neoplasms
Tumors or cancer of the PANCREAS. Depending on the types of ISLET CELLS present in the tumors, various hormones can be secreted: GLUCAGON from PANCREATIC ALPHA CELLS; INSULIN from PANCREATIC BETA CELLS; and SOMATOSTATIN from the SOMATOSTATIN-SECRETING CELLS. Most are malignant except the insulin-producing tumors (INSULINOMA).		02.1510
Anoxemia
[description not available]		02.4120
Hypoxia
Sub-optimal OXYGEN levels in the ambient air of living organisms.		07.4120
Sensitivity and Specificity
Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)		02.4220
Cancer of Colon
[description not available]		02.0510
Colonic Neoplasms
Tumors or cancer of the COLON.		02.0510
Necrosis
The death of cells in an organ or tissue due to disease, injury or failure of the blood supply.		02.0510
Leukemia P388
An experimental lymphocytic leukemia originally induced in DBA/2 mice by painting with methylcholanthrene.		02.4220
Benign Neoplasms
[description not available]		02.0110
Neoplasms
New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.		02.0110
Body Weight
The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.		02.0310
Leukocytopenia
[description not available]		02.0310
Thrombopenia
[description not available]		02.0310
Emesis
[description not available]		02.3820
Leukopenia
A decrease in the number of LEUKOCYTES in a blood sample below the normal range (LEUKOCYTE COUNT less than 4000).		02.0310
Thrombocytopenia
A subnormal level of BLOOD PLATELETS.		02.0310
Vomiting
The forcible expulsion of the contents of the STOMACH through the MOUTH.		02.3820
Cancer of Prostate
[description not available]		02.4420
Prostatic Neoplasms
Tumors or cancer of the PROSTATE.		02.4420
Bone Marrow Diseases
Diseases involving the BONE MARROW.		01.9610
Carcinoma, Ehrlich Tumor
A transplantable, poorly differentiated malignant tumor which appeared originally as a spontaneous breast carcinoma in a mouse. It grows in both solid and ascitic forms.		03.2160
Carcinoma, Epidermoid
[description not available]		01.9510
Cancer of Lung
[description not available]		02.6530
Carcinoma, Squamous Cell
A carcinoma derived from stratified SQUAMOUS EPITHELIAL CELLS. It may also occur in sites where glandular or columnar epithelium is normally present. (From Stedman, 25th ed)		01.9510
Lung Neoplasms
Tumors or cancer of the LUNG.		02.6530
Germinoblastoma
[description not available]		01.9510
Experimental Neoplasms
[description not available]		03.0750
Lymphoma
A general term for various neoplastic diseases of the lymphoid tissue.		01.9510
Leukemia L 1210
[description not available]		03.2260
Experimental Mammary Neoplasms
[description not available]		02.420
Cancer of Ovary
[description not available]		01.9510
Ascites
Accumulation or retention of free fluid within the peritoneal cavity.		01.9510
Ovarian Neoplasms
Tumors or cancer of the OVARY. These neoplasms can be benign or malignant. They are classified according to the tissue of origin, such as the surface EPITHELIUM, the stromal endocrine cells, and the totipotent GERM CELLS.		01.9510
Herpes Simplex Virus Infection
[description not available]		01.9510
Herpes Simplex
A group of acute infections caused by herpes simplex virus type 1 or type 2 that is characterized by the development of one or more small fluid-filled vesicles with a raised erythematous base on the skin or mucous membrane. It occurs as a primary infection or recurs due to a reactivation of a latent infection. (Dorland, 27th ed.)		01.9510
Furrow Keratitis
[description not available]		01.9510
Remission, Spontaneous
A spontaneous diminution or abatement of a disease over time, without formal treatment.		01.9510
Breast Cancer
[description not available]		01.9510
Breast Neoplasms
Tumors or cancer of the human BREAST.		01.9510
Pleural Effusion
Presence of fluid in the pleural cavity resulting from excessive transudation or exudation from the pleural surfaces. It is a sign of disease and not a diagnosis in itself.		01.9510
Cancer of Liver
[description not available]		01.9510
Liver Neoplasms
Tumors or cancer of the LIVER.		01.9510
Sarcoma 180
An experimental sarcoma of mice.		02.3620
Leukemia L5178
An experimental lymphocytic leukemia of mice.		01.9810
Abnormalities, Autosome
[description not available]		02.3820
Carcinoma 256, Walker
A transplantable carcinoma of the rat that originally appeared spontaneously in the mammary gland of a pregnant albino rat, and which now resembles a carcinoma in young transplants and a sarcoma in older transplants. (Stedman, 25th ed)		02.3720
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