Compounds > aniline mustard
Page last updated: 2024-12-05

aniline mustard

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

Description

Aniline Mustard: Alkylating anti-neoplastic agent. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID11108
CHEMBL ID19336
SCHEMBL ID121635
MeSH IDM0001217

Synonyms (56)

Synonym
beta,beta'-dichlorodiethylaniline
ai3-31838
brn 0880463
n,n,-di(2-chloroethyl)aniline
anilinlost [german]
n,n-bis(2-chloroethyl)benzenamine
benzenamine, n,n-bis(2-chloroethyl)-
aniline, n,n-bis(2-chloroethyl)-
553-27-5
cb 1074
sk 592
lymphoquin
mesylerythrol
lymphocin
n,n-di(2-chloroethyl)aniline
wln: g2nr&2g
aniline mustard
phenylbis(2-chloroethylamine)
lymphchin
tl 476
lymphoquine
nsc18429
ncs-18429
n,n-bis(2-chloroethyl)aniline
lymphochin
a 14489
.beta.,.beta.'-dichlorodiethylaniline
nsc-18429
nn-bis(2-chloroethyl)aniline
CHEMBL19336
NCGC00186318-01
n,n-bis(2-chloroethyl)-n-phenylamine
AE-641/02429030
AKOS016003020
FT-0675950
unii-cuj6745z9j
anilinlost
cuj6745z9j ,
4-12-00-00253 (beilstein handbook reference)
SCHEMBL121635
aniline mustard [mi]
n,n-bis(2'-chloroethyl)aniline
ROSJKFFLIXTTAW-UHFFFAOYSA-N
n,n-bis(dichloroethyl)aniline
DTXSID30203820
mfcd00013689
n,n-bis(2-chloroethyl)-benzenamine
n,n-bis(2-chloroethyl) aniline
O12001
Q27275806
2-bromo-4,5-dimethoxycinnamicacid
A870221
SB78920
AS-75665
CS-0083103
SY317373

Research Excerpts

Effects

ExcerptReferenceRelevance
"Aniline mustard, which has the same alkylating group as does benzoquinone mustard but no quinone function, produced lower levels of DNA-DNA cross-links and no DNA strand breaks."( Quinone-induced DNA damage and its relationship to antitumor activity in L5178Y lymphoblasts.
Begleiter, A; Blair, GW, 1984)		0.99

Toxicity

Aniline mustard is 80 times more toxic than its glucuronide. Half-mustard is much less toxic than the full mustard in the uvrB- strain TA100.

ExcerptReferenceRelevance
" -450 mV by cyclic voltammetry) and were more toxic to hypoxic than aerobic UV4 cells."( Hypoxia-selective antitumor agents. 5. Synthesis of water-soluble nitroaniline mustards with selective cytotoxicity for hypoxic mammalian cells.
Cliffe, S; Denny, WA; Palmer, BD; Wilson, WR, 1992)		0.52
" The 4-methyl aniline mustard N,N-bis(2-chloroethyl)-4-methylaniline and its corresponding half-mustard N-(2-chloroethyl)-4-methylaniline showed widely different effects in the various bacterial strains, with the half-mustard being much less toxic than the full mustard in the uvrB- strain TA100."( Relationships between structure, toxicity and genetic effects in Salmonella typhimurium and Saccharomyces cerevisiae for substituted aniline mustards.
Denny, WA; Ferguson, LR; Palmer, BD, 1989)		0.84
"The effect of aniline mustard glucuronide (AMG), p-hydroxyaniline mustard (HAM), and aniline mustard (AM), on Walker ascites tumour cells in vitro showed that AM in about 80 times more toxic than its glucuronide but HAM is at least 800 times more toxic."( Cytotoxicity of aniline mustard glucuronide alone or in a combination with glucose in Walker cells in culture and sarcoma-180 tumour bearing animals.
Deliconstantinos, G; Ramantanis, G; Todorou, DK, 1983)		0.97
" Importantly, there was a highly significant linear relationship between cytotoxic potency and alkylating reactivity in both the aziridine and the mustard series, with the notable exception of 4, the 4-hydroxylamine of 1, which was 300-fold more toxic than predicted by this relationship."( Effect of nitroreduction on the alkylating reactivity and cytotoxicity of the 2,4-dinitrobenzamide-5-aziridine CB 1954 and the corresponding nitrogen mustard SN 23862: distinct mechanisms of bioreductive activation.
Denny, WA; Helsby, NA; Palmer, BD; Pruijn, FB; Wheeler, SJ; Wilson, WR; Yang, S, 2003)		0.32
" The metabolites that obtained from the reduction of nitro benzamide prodrugs (1-4) by Ssap-NtrB, showed differential cytotoxic effects, with none toxic for HUVEC cells, moderate toxic for Hep3B cells, but highly toxic for PC3 cells."( Prodrugs for Nitroreductase Based Cancer Therapy- 1: Metabolite Profile, Cell Cytotoxicity and Molecular Modeling Interactions of Nitro Benzamides with Ssap-NtrB.
Ay, M; Celik, A; Gungor, T; Kockar, F; Onder, FC; Tok, TT; Tokay, E; Yetis, G, 2018)		0.48
"Amongst all metabolites of prodrugs after Ssap-NtrB reduction, N-(2,4- dinitrophenyl)-4-nitrobenzamide (3) was efficient and toxic in PC3 cells as comparable as CB1954."( Prodrugs for Nitroreductase Based Cancer Therapy- 1: Metabolite Profile, Cell Cytotoxicity and Molecular Modeling Interactions of Nitro Benzamides with Ssap-NtrB.
Ay, M; Celik, A; Gungor, T; Kockar, F; Onder, FC; Tok, TT; Tokay, E; Yetis, G, 2018)		0.48

Pharmacokinetics

ExcerptReferenceRelevance
"3-betaG-PEG) localized to a peak concentration in LS174T xenografts within 48 h after injection, but enzyme activity persisted in plasma such that prodrug administration had to be delayed for at least 4 days to avoid systemic prodrug activation and associated toxicity."( Efficient clearance of poly(ethylene glycol)-modified immunoenzyme with anti-PEG monoclonal antibody for prodrug cancer therapy.
Chen, BM; Cheng, TL; Chern, JW; Roffler, SR; Wu, MF, )		0.13

Compound-Compound Interactions

ExcerptReferenceRelevance
" The administration of AMG in combination with glucose to animals bearing the highly resistant to alkylating agents Sarcoma-180 tumour, increased the toxicity of the glucuronide but produced a slight effect on tumour growth."( Cytotoxicity of aniline mustard glucuronide alone or in a combination with glucose in Walker cells in culture and sarcoma-180 tumour bearing animals.
Deliconstantinos, G; Ramantanis, G; Todorou, DK, 1983)		0.61
" These prodrugs have been evaluated for utility in ADEPT when used in combination with a conjugate of CPG2 and the F(ab')2 fragment of the anti-CEA monoclonal antibody, A5B7."( Anti-tumour effects of an antibody-carboxypeptidase G2 conjugate in combination with phenol mustard prodrugs.
Blakey, DC; Burke, PJ; Davies, DH; Dowell, RI; East, SJ; Mauger, AB; Melton, RG; Sharma, SK; Springer, CJ, 1995)		0.29

Dosage Studied

ExcerptRelevanceReference
" Significant survival times were produced at four dosage levels for the butyl, decyl, and dodecyl derivatives, three dosage levels for the octyl and tetradecyl derivatives, and one dosage level for the ethyl derivative."( Synthesis and bioevaluation of a series of alkyl ethers of p-N,N-bis(2-chloroethyl)aminophenol.
Bauguess, CT; Beamer, RL; Wise, JW; Wynn, JE, 1982)		0.26
" The palmitate and stearate derivatives produced significant survival at five and four dosage levels, respectively."( Synthesis and bioevaluation of a series of fatty acid esters of p-[N,N-bis(2-chloroethyl)amino]phenol.
Bauguess, CT; Beamer, RL; Caldwell, ML; Robinson, JR; Wynn, JE, 1982)		0.26
" S-9 activation was required in the Ames test using TA-100, and the dose-response curve, prior to toxicity, appeared biphasic."( A comparison of mutagenic and carcinogenic activities of aniline mustards.
Andrews, AW; Hansch, C; Leo, A; Panthananickal, A; Shimkin, M; Theiss, J, 1981)		0.51
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (2)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
thioredoxin reductaseRattus norvegicus (Norway rat)Potency44.66840.100020.879379.4328AID588453
TDP1 proteinHomo sapiens (human)Potency1.33570.000811.382244.6684AID686978; AID686979
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (26)

Assay IDTitleYearJournalArticle
AID1132020Antitumor activity against rat Walker 256 cells allografted in rat1978Journal of medicinal chemistry, Jan, Volume: 21, Issue:1
Structure-activity relationships in antitumor aniline mustards.
AID229477Evaluated for hypersensitivity factor (HF) (HF = IC50 AA8 / IC50 UV-4) values are intra experiment ratios1990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
Hypoxia-selective antitumor agents. 3. Relationships between structure and cytotoxicity against cultured tumor cells for substituted N,N-bis(2-chloroethyl)anilines.
AID22549Half-life in culture medium was determined at 37 degrees Celsius in alpha MEM with 10% fetal calf-serum (FCS)1990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
Hypoxia-selective antitumor agents. 3. Relationships between structure and cytotoxicity against cultured tumor cells for substituted N,N-bis(2-chloroethyl)anilines.
AID123958Compound was evaluated for low level mutagenicity1981Journal of medicinal chemistry, Jul, Volume: 24, Issue:7
A comparison of mutagenic and carcinogenic activities of aniline mustards.
AID215290Evaluated for inhibitory concentration against UV-4 cells under aerobic conditions with a compound exposure of 1 h1990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
Hypoxia-selective antitumor agents. 3. Relationships between structure and cytotoxicity against cultured tumor cells for substituted N,N-bis(2-chloroethyl)anilines.
AID1132022Antitumor activity against mouse L1210 cells assessed as dose required to produce T/C of 125% administered for 15 days1978Journal of medicinal chemistry, Jan, Volume: 21, Issue:1
Structure-activity relationships in antitumor aniline mustards.
AID1180048Antitumor activity against human LNCAP cells xenografted in immunocompromised mouse assessed as tumor growth inhibition at 30 mg/kg, ip for 5 days a week for 7 consecutive weeks relative to vehicle-treated control2014Journal of medicinal chemistry, Oct-23, Volume: 57, Issue:20
Targeting the androgen receptor with steroid conjugates.
AID215286Evaluated for cytotoxicity under aerobic conditions against UV4 cells using microassay1990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
Hypoxia-selective antitumor agents. 3. Relationships between structure and cytotoxicity against cultured tumor cells for substituted N,N-bis(2-chloroethyl)anilines.
AID215285Evaluated for (CF10) the concentration x time to reduce the surviving fraction to 10% of controls in the stirred suspension assay (SSC) in UV-4 cells under aerobic conditions1990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
Hypoxia-selective antitumor agents. 3. Relationships between structure and cytotoxicity against cultured tumor cells for substituted N,N-bis(2-chloroethyl)anilines.
AID1584823Drug level in DMSO-d6/PBS buffer treated with 4-(bis(2-chloroethyl)amino)phenylboronic acid assessed as compound formation after 10 days in presence of GSH by IT-TOF mass analysis2018Journal of medicinal chemistry, 10-25, Volume: 61, Issue:20
Discovery and Optimization of Novel Hydrogen Peroxide Activated Aromatic Nitrogen Mustard Derivatives as Highly Potent Anticancer Agents.
AID215291Evaluated for inhibitory concentration against UV-4 cells under aerobic conditions with a compound exposure of 18 h1990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
Hypoxia-selective antitumor agents. 3. Relationships between structure and cytotoxicity against cultured tumor cells for substituted N,N-bis(2-chloroethyl)anilines.
AID1132021Toxicity in rat allografted with rat Walker 256 cells1978Journal of medicinal chemistry, Jan, Volume: 21, Issue:1
Structure-activity relationships in antitumor aniline mustards.
AID215292IC50 value determined against UV-4 cells with an 18 hr exposure under either aerobic or hypoxic conditions (Ratio = aerobic IC50 / hypoxic IC50)1990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
Hypoxia-selective antitumor agents. 3. Relationships between structure and cytotoxicity against cultured tumor cells for substituted N,N-bis(2-chloroethyl)anilines.
AID1132023Antitumor activity against mouse P388 cells allografted in mouse assessed as dose required to produce T/C of 125% administered for 9 days1978Journal of medicinal chemistry, Jan, Volume: 21, Issue:1
Structure-activity relationships in antitumor aniline mustards.
AID22569Half-life was determined in culture medium at 37 degrees Celsius in alpha MEM1990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
Hypoxia-selective antitumor agents. 3. Relationships between structure and cytotoxicity against cultured tumor cells for substituted N,N-bis(2-chloroethyl)anilines.
AID124078Compound was evaluated for Carcinogenicity to produce 0.5 tumors per mouse (B.5)1981Journal of medicinal chemistry, Jul, Volume: 24, Issue:7
A comparison of mutagenic and carcinogenic activities of aniline mustards.
AID124081Compound was evaluated for mutagenicity after threshold range1981Journal of medicinal chemistry, Jul, Volume: 24, Issue:7
A comparison of mutagenic and carcinogenic activities of aniline mustards.
AID123956Compound was evaluated for Carcinogenicity based on concentration necessary to produce one tumor per mouse (Strain A)1981Journal of medicinal chemistry, Jul, Volume: 24, Issue:7
A comparison of mutagenic and carcinogenic activities of aniline mustards.
AID1130920Antitumor activity against mouse B16 cells allografted in ip dosed BDF mouse assessed as 25% increase in life span administered for 9 days1979Journal of medicinal chemistry, Oct, Volume: 22, Issue:10
Structure-activity relationship of aniline mustards acting against B-16 melanoma in mice.
AID9830Evaluated for cytotoxicity under aerobic conditions against AA8 cells using microassay1990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
Hypoxia-selective antitumor agents. 3. Relationships between structure and cytotoxicity against cultured tumor cells for substituted N,N-bis(2-chloroethyl)anilines.
AID1132032Stability of the compound in acetone assessed as hydrolysis at 66 degC after 30 mins1978Journal of medicinal chemistry, Jan, Volume: 21, Issue:1
Structure-activity relationships in antitumor aniline mustards.
AID1130926Antitumor activity against mouse B16 cells allografted in BDF mouse assessed as increase in life span at 12.5 mg/kg, ip administered for 9 days relative to untreated control1979Journal of medicinal chemistry, Oct, Volume: 22, Issue:10
Structure-activity relationship of aniline mustards acting against B-16 melanoma in mice.
AID1180047Binding affinity to progesterone receptor (unknown origin) by radiometric competitive assay2014Journal of medicinal chemistry, Oct-23, Volume: 57, Issue:20
Targeting the androgen receptor with steroid conjugates.
AID229489Evaluated for ratio of CT10 value. (CT10 = aerobic CT10 / hypoxic CT10)1990Journal of medicinal chemistry, Jan, Volume: 33, Issue:1
Hypoxia-selective antitumor agents. 3. Relationships between structure and cytotoxicity against cultured tumor cells for substituted N,N-bis(2-chloroethyl)anilines.
AID1132026Antitumor activity against mouse P388 cells allografted in mouse assessed as dose required to produce T/C of 180% administered for 9 days1978Journal of medicinal chemistry, Jan, Volume: 21, Issue:1
Structure-activity relationships in antitumor aniline mustards.
AID1180046Binding affinity to androgen receptor (unknown origin) by radiometric competitive assay2014Journal of medicinal chemistry, Oct-23, Volume: 57, Issue:20
Targeting the androgen receptor with steroid conjugates.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (88)

TimeframeStudies, This Drug (%)All Drugs %
pre-199024 (27.27)18.7374
1990's40 (45.45)18.2507
2000's14 (15.91)29.6817
2010's8 (9.09)24.3611
2020's2 (2.27)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 15.09

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 Index15.09 (24.57)
Research Supply Index4.56 (2.92)
Research Growth Index4.47 (4.65)
Search Engine Demand Index10.37 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (15.09)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (1.06%)5.53%
Reviews5 (5.32%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other88 (93.62%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
acetaldehyde
Acetaldehyde: A colorless, flammable liquid used in the manufacture of acetic acid, perfumes, and flavors. It is also an intermediate in the metabolism of alcohol. It has a general narcotic action and also causes irritation of mucous membranes. Large doses may cause death from respiratory paralysis.. acetaldehyde : The aldehyde formed from acetic acid by reduction of the carboxy group. It is the most abundant carcinogen in tobacco smoke.. aldehyde : A compound RC(=O)H, in which a carbonyl group is bonded to one hydrogen atom and to one R group.. acetyl group : A group, formally derived from acetic acid by dehydroxylation, which is fundamental to the biochemistry of all forms of life. When bound to coenzyme A, it is central to the metabolism of carbohydrates and fats.		2.0210aldehydecarcinogenic agent;
EC 3.5.1.4 (amidase) inhibitor;
electron acceptor;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
mutagen;
oxidising agent;
Saccharomyces cerevisiae metabolite;
teratogenic agent
adenine
[no description available]		6.98106-aminopurines;
purine nucleobase		Daphnia magna metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
carbamates
[no description available]		2.0110amino-acid anion
melatonin
[no description available]		3.110acetamides;
tryptamines		anticonvulsant;
central nervous system depressant;
geroprotector;
hormone;
human metabolite;
immunological adjuvant;
mouse metabolite;
radical scavenger
thiosulfates
Thiosulfates: Inorganic salts of thiosulfuric acid possessing the general formula R2S2O3.. thiosulfate(2-) : A divalent inorganic anion obtained by removal of both protons from thiosulfuric acid.		1.9910divalent inorganic anion;
sulfur oxide;
sulfur oxoanion		human metabolite
toluene
methylbenzene : Any alkylbenzene that is benzene substituted with one or more methyl groups.		3.110methylbenzene;
toluenes;
volatile organic compound		cholinergic antagonist;
fuel additive;
neurotoxin;
non-polar solvent
urea
pseudourea: clinical use; structure. isourea : A carboximidic acid that is the imidic acid tautomer of urea, H2NC(=NH)OH, and its hydrocarbyl derivatives.		2.0410isourea;
monocarboxylic acid amide;
one-carbon compound		Daphnia magna metabolite;
Escherichia coli metabolite;
fertilizer;
flour treatment agent;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
altretamine
Altretamine: A hexamethyl-2,4,6-triamine derivative of 1,3,5-triazine.		1.9610triamino-1,3,5-triazine
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.		7.4220acridines;
aromatic ether;
sulfonamide		antineoplastic agent;
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor
bisbenzimidazole
Bisbenzimidazole: A benzimidazole antifilarial agent; it is fluorescent when it binds to certain nucleotides in DNA, thus providing a tool for the study of DNA replication; it also interferes with mitosis.		1.9810bibenzimidazole;
N-methylpiperazine		anthelminthic drug;
fluorochrome
verapamil
Verapamil: A calcium channel blocker that is a class IV anti-arrhythmia agent.. verapamil : A racemate comprising equimolar amounts of dexverapamil and (S)-verapamil. An L-type calcium channel blocker of the phenylalkylamine class, it is used (particularly as the hydrochloride salt) in the treatment of hypertension, angina pectoris and cardiac arrhythmia, and as a preventive medication for migraine.. 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile : A tertiary amino compound that is 3,4-dimethoxyphenylethylamine in which the hydrogens attached to the nitrogen are replaced by a methyl group and a 4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexyl group.		2.1710aromatic ether;
nitrile;
polyether;
tertiary amino compound
carbamazepine
Carbamazepine: A dibenzazepine that acts as a sodium channel blocker. It is used as an anticonvulsant for the treatment of grand mal and psychomotor or focal SEIZURES. It may also be used in the management of BIPOLAR DISORDER, and has analgesic properties.. carbamazepine : A dibenzoazepine that is 5H-dibenzo[b,f]azepine carrying a carbamoyl substituent at the azepine nitrogen, used as an anticonvulsant.		2.1710dibenzoazepine;
ureas		analgesic;
anticonvulsant;
antimanic drug;
drug allergen;
EC 3.5.1.98 (histone deacetylase) inhibitor;
environmental contaminant;
glutamate transporter activator;
mitogen;
non-narcotic analgesic;
sodium channel blocker;
xenobiotic
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.		2.6730aromatic amine;
monocarboxylic acid;
nitrogen mustard;
organochlorine compound;
tertiary amino compound		alkylating agent;
antineoplastic agent;
carcinogenic agent;
drug allergen;
immunosuppressive agent
stallimycin
[no description available]		210
fluorouracil
Fluorouracil: A pyrimidine analog that is an antineoplastic antimetabolite. It interferes with DNA synthesis by blocking the THYMIDYLATE SYNTHETASE conversion of deoxyuridylic acid to thymidylic acid.. 5-fluorouracil : A nucleobase analogue that is uracil in which the hydrogen at position 5 is replaced by fluorine. It is an antineoplastic agent which acts as an antimetabolite - following conversion to the active deoxynucleotide, it inhibits DNA synthesis (by blocking the conversion of deoxyuridylic acid to thymidylic acid by the cellular enzyme thymidylate synthetase) and so slows tumour growth.		2.1510nucleobase analogue;
organofluorine compound		antimetabolite;
antineoplastic agent;
environmental contaminant;
immunosuppressive agent;
radiosensitizing agent;
xenobiotic
mechlorethamine
nitrogen mustard : Compounds having two beta-haloalkyl groups bound to a nitrogen atom, as in (X-CH2-CH2)2NR.		2.1310nitrogen mustard;
organochlorine compound		alkylating agent
sarkolysin
[no description available]		2.3620monocarboxylic acid
temozolomide
[no description available]		1.9610imidazotetrazine;
monocarboxylic acid amide;
triazene derivative		alkylating agent;
antineoplastic agent;
prodrug
cytarabine
[no description available]		1.9910beta-D-arabinoside;
monosaccharide derivative;
pyrimidine nucleoside		antimetabolite;
antineoplastic agent;
antiviral agent;
immunosuppressive agent
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.		1.9810aminoacridines;
primary amino compound		acid-base indicator;
antiinfective agent;
antiseptic drug;
fluorescent dye;
MALDI matrix material;
mutagen
xanthenes
Xanthenes: Compounds with three aromatic rings in linear arrangement with an OXYGEN in the center ring.		2.3920xanthene
4-nitroaniline
[no description available]		1.9810nitroanilinebacterial xenobiotic metabolite
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.		2.420acridines;
mancude organic heterotricyclic parent;
polycyclic heteroarene		genotoxin
oxazoles
Oxazoles: Five-membered heterocyclic ring structures containing an oxygen in the 1-position and a nitrogen in the 3-position, in distinction from ISOXAZOLES where they are at the 1,2 positions.. 1,3-oxazole : A five-membered monocyclic heteroarene that is an analogue of cyclopentadiene with O in place of CH2 at position 1 and N in place of CH at position 3.. oxazole : An azole based on a five-membered heterocyclic aromatic skeleton containing one N and one O atom.		2.02101,3-oxazoles;
mancude organic heteromonocyclic parent;
monocyclic heteroarene
chlornaphazin
chlornaphazin: structure		1.9510naphthalenes
azomycin
azomycin: RN given refers to parent cpd with specified locant; structure		1.9910C-nitro compound;
imidazoles		antitubercular agent
acetylcysteine
N-acetyl-L-cysteine : An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.		2.0610acetylcysteine;
L-cysteine derivative;
N-acetyl-L-amino acid		antidote to paracetamol poisoning;
antiinfective agent;
antioxidant;
antiviral drug;
ferroptosis inhibitor;
geroprotector;
human metabolite;
mucolytic;
radical scavenger;
vulnerary
4-n-bis(2-chloroethyl)aminobenzoic acid
4-N-bis(2-chloroethyl)aminobenzoic acid: structure given in first source		1.9510
d-alpha tocopherol
Vitamin E: A generic descriptor for all TOCOPHEROLS and TOCOTRIENOLS that exhibit ALPHA-TOCOPHEROL activity. By virtue of the phenolic hydrogen on the 2H-1-benzopyran-6-ol nucleus, these compounds exhibit varying degree of antioxidant activity, depending on the site and number of methyl groups and the type of ISOPRENOIDS.. tocopherol : A collective name for a group of closely related lipids that contain a chroman-6-ol nucleus substituted at position 2 by a methyl group and by a saturated hydrocarbon chain consisting of three isoprenoid units. They are designated as alpha-, beta-, gamma-, and delta-tocopherol depending on the number and position of additional methyl substituents on the aromatic ring. Tocopherols occur in vegetable oils and vegetable oil products, almost exclusively with R,R,R configuration. Tocotrienols differ from tocopherols only in having three double bonds in the hydrocarbon chain.. vitamin E : Any member of a group of fat-soluble chromanols that exhibit biological activity against vitamin E deficiency. The vitamers in this class consists of a chroman-6-ol core which is substituted at position 2 by a methyl group and (also at position 2) either a saturated or a triply-unsaturated hydrocarbon chain consisting of three isoprenoid units. The major function of vitamin E is to act as a natural antioxidant by scavenging free radicals and molecular oxygen.. (R,R,R)-alpha-tocopherol : An alpha-tocopherol that has R,R,R configuration. The naturally occurring stereoisomer of alpha-tocopherol, it is found particularly in sunflower and olive oils.		2.0610alpha-tocopherolalgal metabolite;
antiatherogenic agent;
anticoagulant;
antioxidant;
antiviral agent;
EC 2.7.11.13 (protein kinase C) inhibitor;
immunomodulator;
micronutrient;
nutraceutical;
plant metabolite
9-anilinoacridine
[no description available]		2.0410
vidarabine
adenine arabinoside : A purine nucleoside in which adenine is attached to arabinofuranose via a beta-N(9)-glycosidic bond.		1.9910beta-D-arabinoside;
purine nucleoside		antineoplastic agent;
bacterial metabolite;
nucleoside antibiotic
phenacid
phenacid: RN given refers to parent cpd; structure		1.9510
levamisole
Levamisole: An antihelminthic drug that has been tried experimentally in rheumatic disorders where it apparently restores the immune response by increasing macrophage chemotaxis and T-lymphocyte function. Paradoxically, this immune enhancement appears to be beneficial in rheumatoid arthritis where dermatitis, leukopenia, and thrombocytopenia, and nausea and vomiting have been reported as side effects. (From Smith and Reynard, Textbook of Pharmacology, 1991, p435-6). levamisole : A 6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole that has S configuration. It is used (generally as the monohydrochloride salt) to treat parasitic worm infections in pigs, sheep and cattle and was formerly used in humans as an adjuvant to chemotherapy for the treatment of various cancers. It is also widely used as an adulterant to coccaine.		6.95106-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazoleantinematodal drug;
antirheumatic drug;
EC 3.1.3.1 (alkaline phosphatase) inhibitor;
immunological adjuvant;
immunomodulator
glutamic acid
Glutamic Acid: A non-essential amino acid naturally occurring in the L-form. Glutamic acid is the most common excitatory neurotransmitter in the CENTRAL NERVOUS SYSTEM.. glutamic acid : An alpha-amino acid that is glutaric acid bearing a single amino substituent at position 2.		2.4220glutamic acid;
glutamine family amino acid;
L-alpha-amino acid;
proteinogenic amino acid		Escherichia coli metabolite;
ferroptosis inducer;
micronutrient;
mouse metabolite;
neurotransmitter;
nutraceutical
flavone acetic acid
flavone acetic acid: structure given in first source		1.9810
nitroaniline
nitroaniline: RN given refers to cpd with unspecified locant for nitro moiety. nitroaniline : A substituted aniline that carries one or more nitro groups.		1.9710
trazodone hydrochloride
Triticum: A plant genus of the family POACEAE that is the source of EDIBLE GRAIN. A hybrid with rye (SECALE CEREALE) is called TRITICALE. The seed is ground into FLOUR and used to make BREAD, and is the source of WHEAT GERM AGGLUTININS.. trazodone hydrochloride : A hydrochloride salt prepared from equimolar amounts of trazodone and hydrogen chloride.		1.9510hydrochlorideadrenergic antagonist;
antidepressant;
H1-receptor antagonist;
sedative;
serotonin uptake inhibitor
hydroxyaniline mustard
hydroxyaniline mustard: structure; RN given refers to parent cpd		5.38141
phenylenediamine mustard
phenylenediamine mustard: RN given refers to parent cpd		2.6530
2-(bis(2-hydroxyethyl)amino)-1,4-benzoquinone
2-(bis(2-hydroxyethyl)amino)-1,4-benzoquinone: induces DNA damage; structure given in first source		1.9610
tretazicar
tretazicar: minor descriptor (75-84); on-line & Index Medicus search AZIRIDINES (75-84)		3.5280
arginyl-glycyl-aspartic acid
arginyl-glycyl-aspartic acid: amino acid sequence of basic unit of widespread cellular recognition system		2.1510oligopeptide
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.		2.3920monocarboxylic acid;
xanthones		antineoplastic agent
sn 23862
5-(N,N-bis(2-chloroethyl)amino)-2,4-dinitrobenzamide: RN & structure given in first source		4.08150
n-((n,n-dimethylamino)ethyl)-5-(n,n-bis(2-chloroethyl)amino)-2,4-dinitrobenzamide
N-((N,N-dimethylamino)ethyl)-5-(N,N-bis(2-chloroethyl)amino)-2,4-dinitrobenzamide: RN & structure given in first source		1.9810
aflatoxin b1
Aflatoxin B1: A potent hepatotoxic and hepatocarcinogenic mycotoxin produced by the Aspergillus flavus group of fungi. It is also mutagenic, teratogenic, and causes immunosuppression in animals. It is found as a contaminant in peanuts, cottonseed meal, corn, and other grains. The mycotoxin requires epoxidation to aflatoxin B1 2,3-oxide for activation. Microsomal monooxygenases biotransform the toxin to the less toxic metabolites aflatoxin M1 and Q1.. aflatoxin B1 : An aflatoxin having a tetrahydrocyclopenta[c]furo[3',2':4,5]furo[2,3-h]chromene skeleton with oxygen functionality at positions 1, 4 and 11.		1.9610aflatoxin;
aromatic ether;
aromatic ketone		carcinogenic agent;
human metabolite
tretinoin
Tretinoin: An important regulator of GENE EXPRESSION during growth and development, and in NEOPLASMS. Tretinoin, also known as retinoic acid and derived from maternal VITAMIN A, is essential for normal GROWTH; and EMBRYONIC DEVELOPMENT. An excess of tretinoin can be teratogenic. It is used in the treatment of PSORIASIS; ACNE VULGARIS; and several other SKIN DISEASES. It has also been approved for use in promyelocytic leukemia (LEUKEMIA, PROMYELOCYTIC, ACUTE).. retinoic acid : A retinoid consisting of 3,7-dimethylnona-2,4,6,8-tetraenoic acid substituted at position 9 by a 2,6,6-trimethylcyclohex-1-en-1-yl group (geometry of the four exocyclic double bonds is not specified).. all-trans-retinoic acid : A retinoic acid in which all four exocyclic double bonds have E- (trans-) geometry.		1.9910retinoic acid;
vitamin A		anti-inflammatory agent;
antineoplastic agent;
antioxidant;
AP-1 antagonist;
human metabolite;
keratolytic drug;
retinoic acid receptor agonist;
retinoid X receptor agonist;
signalling molecule
melphalan
Melphalan: An alkylating nitrogen mustard that is used as an antineoplastic in the form of the levo isomer - MELPHALAN, the racemic mixture - MERPHALAN, and the dextro isomer - MEDPHALAN; toxic to bone marrow, but little vesicant action; potential carcinogen.. melphalan : A phenylalanine derivative comprising L-phenylalanine having [bis(2-chloroethyl)amino group at the 4-position on the phenyl ring.		7.730L-phenylalanine derivative;
nitrogen mustard;
non-proteinogenic L-alpha-amino acid;
organochlorine compound		alkylating agent;
antineoplastic agent;
carcinogenic agent;
drug allergen;
immunosuppressive agent
oxazolone
Oxazolone: Immunologic adjuvant and sensitizing agent.		2.0210
ranitidine
Ranitidine: A non-imidazole blocker of those histamine receptors that mediate gastric secretion (H2 receptors). It is used to treat gastrointestinal ulcers.. ranitidine : A member of the class of furans used to treat peptic ulcer disease (PUD) and gastroesophageal reflux disease.		2.1710C-nitro compound;
furans;
organic sulfide;
tertiary amino compound		anti-ulcer drug;
drug allergen;
environmental contaminant;
H2-receptor antagonist;
xenobiotic
nitrofurazone
Nitrofurazone: A topical anti-infective agent effective against gram-negative and gram-positive bacteria. It is used for superficial WOUNDS AND INJURIES and skin infections. Nitrofurazone has also been administered orally in the treatment of TRYPANOSOMIASIS.. nitrofurazone : A semicarbazone resulting from the formal condensation of semicarbazide with 5-nitrofuraldehyde. A broad spectrum antibacterial drug, although with little activity against Pseudomonas species, it is used as a local application for burns, ulcers, wounds and skin infections.		2.0710
acid phosphatase
Acid Phosphatase: An enzyme that catalyzes the conversion of an orthophosphoric monoester and water to an alcohol and orthophosphate. EC 3.1.3.2.		2.3620
dicumarol
Dicumarol: An oral anticoagulant that interferes with the metabolism of vitamin K. It is also used in biochemical experiments as an inhibitor of reductases.		2.0110hydroxycoumarinanticoagulant;
EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor;
Hsp90 inhibitor;
vitamin K antagonist
nitrophenols
Nitrophenols: PHENOLS carrying nitro group substituents.		1.9510
flavin mononucleotide
Flavin Mononucleotide: A coenzyme for a number of oxidative enzymes including NADH DEHYDROGENASE. It is the principal form in which RIBOFLAVIN is found in cells and tissues.		2.4420
guanine
[no description available]		6.98102-aminopurines;
oxopurine;
purine nucleobase		algal metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
dacarbazine
(E)-dacarbazine : A dacarbazine in which the N=N double bond adopts a trans-configuration.		1.9610dacarbazine
tirapazamine
Tirapazamine: A triazine derivative that introduces breaks into DNA strands in hypoxic cells, sensitizing tumor cells to the cytotoxic activity of other drugs and radiation.. tirapazamine : A member of the class of benzotriazines that is 1,2,4-benzotriazine carrying an amino substituent at position 3 and two oxido substituents at positions 1 and 4.		1.9810aromatic amine;
benzotriazines;
N-oxide		antibacterial agent;
antineoplastic agent;
apoptosis inducer
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.		1.9810
ConditionIndicatedRelationship StrengthStudiesTrials
Malignant Melanoma
[description not available]		02.3820
Experimental Neoplasms
[description not available]		03.5890
Melanoma
A malignant neoplasm derived from cells that are capable of forming melanin, which may occur in the skin of any part of the body, in the eye, or, rarely, in the mucous membranes of the genitalia, anus, oral cavity, or other sites. It occurs mostly in adults and may originate de novo or from a pigmented nevus or malignant lentigo. Melanomas frequently metastasize widely, and the regional lymph nodes, liver, lungs, and brain are likely to be involved. The incidence of malignant skin melanomas is rising rapidly in all parts of the world. (Stedman, 25th ed; from Rook et al., Textbook of Dermatology, 4th ed, p2445)		07.3820
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)		02.3620
Leukemia L 1210
[description not available]		02.8740
Experimental Leukemia
[description not available]		03.9850
Benign Neoplasms
[description not available]		03.580
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.		03.580
Adenoma, Basal Cell
[description not available]		01.9610
Cancer of Lung
[description not available]		01.9610
Adenoma
A benign epithelial tumor with a glandular organization.		01.9610
Lung Neoplasms
Tumors or cancer of the LUNG.		01.9610
Cancer of Prostate
[description not available]		03.3120
Prostatic Neoplasms
Tumors or cancer of the PROSTATE.		03.3120
Anoxemia
[description not available]		02.4520
Hypoxia
Sub-optimal OXYGEN levels in the ambient air of living organisms.		02.4520
Leukemia P388
An experimental lymphocytic leukemia originally induced in DBA/2 mice by painting with methylcholanthrene.		02.9140
Breast Cancer
[description not available]		02.940
Breast Neoplasms
Tumors or cancer of the human BREAST.		02.940
Colorectal Cancer
[description not available]		04.0831
Colorectal Neoplasms
Tumors or cancer of the COLON or the RECTUM or both. Risk factors for colorectal cancer include chronic ULCERATIVE COLITIS; FAMILIAL POLYPOSIS COLI; exposure to ASBESTOS; and irradiation of the CERVIX UTERI.		04.0831
Hepatocellular Carcinoma
[description not available]		02.3820
Cancer of Liver
[description not available]		02.3820
Carcinoma, Hepatocellular
A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.		02.3820
Liver Neoplasms
Tumors or cancer of the LIVER.		02.3820
Leukemia L5178
An experimental lymphocytic leukemia of mice.		01.9610
Sarcoma 180
An experimental sarcoma of mice.		01.9610
Adenocarcinoma, Basal Cell
[description not available]		01.9610
Cancer of Colon
[description not available]		02.6730
Adenocarcinoma
A malignant epithelial tumor with a glandular organization.		01.9610
Colonic Neoplasms
Tumors or cancer of the COLON.		02.6730
Experimental Mammary Neoplasms
[description not available]		01.9810
Carcinoma, Anaplastic
[description not available]		01.9910
Carcinoma
A malignant neoplasm made up of epithelial cells tending to infiltrate the surrounding tissues and give rise to metastases. It is a histological type of neoplasm and not a synonym for cancer.		01.9910
Cancer of Ovary
[description not available]		02.3720
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.		02.3720
Experimental Hepatoma
[description not available]		02.9140
Ascites
Accumulation or retention of free fluid within the peritoneal cavity.		01.9910
Plasma Cell Tumor
[description not available]		01.9510
Plasmacytoma
Any discrete, presumably solitary, mass of neoplastic PLASMA CELLS either in BONE MARROW or various extramedullary sites.		06.9510
Cancer of Mouth
[description not available]		01.9510
Mouth Neoplasms
Tumors or cancer of the MOUTH.		01.9510
Emesis
[description not available]		01.9610
Nausea
An unpleasant sensation in the stomach usually accompanied by the urge to vomit. Common causes are early pregnancy, sea and motion sickness, emotional stress, intense pain, food poisoning, and various enteroviruses.		01.9610
Vomiting
The forcible expulsion of the contents of the STOMACH through the MOUTH.		01.9610