Compounds > hydroxyaniline mustard
Page last updated: 2024-12-06

hydroxyaniline mustard

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

Description

hydroxyaniline mustard: structure; RN given refers to parent cpd [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID71000
CHEMBL ID12995
SCHEMBL ID905253
MeSH IDM0040922

Synonyms (17)

Synonym
4-(bis(2-chloroethyl)amino)phenol
brn 2212728
hydroxyaniline mustard
p-hydroxyanilinlost [german]
p-(bis(2-chloroethyl)amino)phenol
phenol, p-(bis(2-chloroethyl)amino)-
NCIOPEN2_004170
CHEMBL12995
4-[bis(2-chloroethyl)amino]phenol
1204-69-9
p-hydroxyanilinlost
4-[bis(2-chloroethyl)amino]-phenol
WRVLEDLJKOSANT-UHFFFAOYSA-N
SCHEMBL905253
DTXSID40152850
p-di(2-chloroethyl)aminophenol
EN300-1704792

Research Excerpts

Toxicity

ExcerptReferenceRelevance
"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)		0.52

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)		0.27
" 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
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (16)

Assay IDTitleYearJournalArticle
AID1130928Antitumor activity against mouse B16 cells allografted in BDF mouse assessed as increase in life span at 8 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.
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.
AID1132018Ratio of LD50 for rat allografted with rat Walker 256 cells to ED90 for rat Walker 256 cells allografted in rat1978Journal of medicinal chemistry, Jan, Volume: 21, Issue:1
Structure-activity relationships in antitumor aniline mustards.
AID1152459Induction of [32P]-labeled 49-mer oligonucleotide duplex DNA 12 interstrand cross-linking (unknown origin) at purine nucleotide site using compound radiolabeled at 5' of 12b in phosphate buffer at pH 7 at 90 degC after 30 mins by PAGE2014Journal of medicinal chemistry, Jun-12, Volume: 57, Issue:11
Reactive oxygen species (ROS) inducible DNA cross-linking agents and their effect on cancer cells and normal lymphocytes.
AID101151Cytotoxicity was evaluated against LS174T-stCPG2(Q)3-expressing cell clone1998Journal of medicinal chemistry, Dec-17, Volume: 41, Issue:26
Self-immolative nitrogen mustard prodrugs for suicide gene therapy.
AID1584812Induction of DNA cross-linking activity in human CLL-derived lymphocytes assessed as increase in gammaH2AX formation at 5 to 20 uM after 24 hrs by flow cytometry2018Journal 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.
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.
AID23577Kinetic parameter (half-life) was evaluated1998Journal of medicinal chemistry, Dec-17, Volume: 41, Issue:26
Self-immolative nitrogen mustard prodrugs for suicide gene therapy.
AID1152463Induction of [32P]-labeled 49-mer oligonucleotide duplex DNA 12 interstrand cross-linking (unknown origin) at purine nucleotide site using compound radiolabeled at 3' of 12a at 90 deg C after 30 mins by PAGE in presence of piperidine2014Journal of medicinal chemistry, Jun-12, Volume: 57, Issue:11
Reactive oxygen species (ROS) inducible DNA cross-linking agents and their effect on cancer cells and normal lymphocytes.
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.
AID1152460Induction of [32P]-labeled 49-mer oligonucleotide duplex DNA 12 interstrand cross-linking (unknown origin) at purine nucleotide site using compound radiolabeled at 3' of 12a in phosphate buffer at pH 7 at 90 degC after 30 mins by PAGE2014Journal of medicinal chemistry, Jun-12, Volume: 57, Issue:11
Reactive oxygen species (ROS) inducible DNA cross-linking agents and their effect on cancer cells and normal lymphocytes.
AID1152458Induction of [32P]-labeled 49-mer oligonucleotide duplex DNA 12 interstrand cross-linking (unknown origin) at purine nucleotide site using compound radiolabeled at 5' of 12a in phosphate buffer at pH 7 at 90 degC after 30 mins by PAGE2014Journal of medicinal chemistry, Jun-12, Volume: 57, Issue:11
Reactive oxygen species (ROS) inducible DNA cross-linking agents and their effect on cancer cells and normal lymphocytes.
AID1132021Toxicity in rat allografted with rat Walker 256 cells1978Journal of medicinal chemistry, Jan, Volume: 21, Issue:1
Structure-activity relationships in antitumor aniline mustards.
AID1152462Induction of [32P]-labeled 49-mer oligonucleotide duplex DNA 12 interstrand cross-linking (unknown origin) at purine nucleotide site using compound radiolabeled at 5' of 12b at 90 deg C after 30 mins by PAGE in presence of piperidine2014Journal of medicinal chemistry, Jun-12, Volume: 57, Issue:11
Reactive oxygen species (ROS) inducible DNA cross-linking agents and their effect on cancer cells and normal lymphocytes.
AID1152461Induction of [32P]-labeled 49-mer oligonucleotide duplex DNA 12 interstrand cross-linking (unknown origin) at purine nucleotide site using compound radiolabeled at 5' of 12a at 90 deg C after 30 mins by PAGE in presence of piperidine2014Journal of medicinal chemistry, Jun-12, Volume: 57, Issue:11
Reactive oxygen species (ROS) inducible DNA cross-linking agents and their effect on cancer cells and normal lymphocytes.
AID102183Inhibitory concentration was evaluated against colorectal tumar cell line LoVo1996Journal of medicinal chemistry, Mar-01, Volume: 39, Issue:5
New mustard prodrugs for antibody-directed enzyme prodrug therapy: alternatives to the amide link.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (17)

TimeframeStudies, This Drug (%)All Drugs %
pre-19906 (35.29)18.7374
1990's7 (41.18)18.2507
2000's2 (11.76)29.6817
2010's2 (11.76)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: 11.41

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 Index11.41 (24.57)
Research Supply Index3.00 (2.92)
Research Growth Index4.41 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.41)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (5.56%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other17 (94.44%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
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
sarkolysin
[no description available]		2.3620monocarboxylic acid
pinacol
pinacol : A glycol that is ethylene glycol in which all four methylene hydrogens have been replaced by methyl groups.		2.110glycol
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
aniline mustard
Aniline Mustard: Alkylating anti-neoplastic agent.		5.38141
4-n-bis(2-chloroethyl)aminobenzoic acid
4-N-bis(2-chloroethyl)aminobenzoic acid: structure given in first source		2.3720
phenacid
phenacid: RN given refers to parent cpd; structure		2.3720
phenylenediamine mustard
phenylenediamine mustard: RN given refers to parent cpd		2.8840
4-((2-chloroethyl) (2-mesyloxyethyl)amino)benzoic acid
4-((2-chloroethyl) (2-mesyloxyethyl)amino)benzoic acid: structure given in first source		2.420
4-((2-chloroethyl)(2-mesyloxyethyl)amino)benzoylglutamic acid
4-((2-chloroethyl)(2-mesyloxyethyl)amino)benzoylglutamic acid: structure in first source		1.9910
4-n-bis(2-chloroethyl)aminobenzoylglutamic acid
4-N-bis(2-chloroethyl)aminobenzoylglutamic acid: structure given in first source		1.9910
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.		2.1710L-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
ConditionIndicatedRelationship StrengthStudiesTrials
Malignant Melanoma
[description not available]		02.3820
Experimental Neoplasms
[description not available]		02.3820
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)		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)		02.3620
Leukemia L 1210
[description not available]		02.3620
Experimental Leukemia
[description not available]		01.9510
Colorectal Cancer
[description not available]		04.341
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.		04.341
B-Cell Chronic Lymphocytic Leukemia
[description not available]		02.110
Leukemia, Lymphocytic, Chronic, B-Cell
A chronic leukemia characterized by abnormal B-lymphocytes and often generalized lymphadenopathy. In patients presenting predominately with blood and bone marrow involvement it is called chronic lymphocytic leukemia (CLL); in those predominately with enlarged lymph nodes it is called small lymphocytic lymphoma. These terms represent spectrums of the same disease.		02.110
Sarcoma 180
An experimental sarcoma of mice.		01.9610
Carcinoma, Anaplastic
[description not available]		01.9910
Cancer of Colon
[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
Colonic Neoplasms
Tumors or cancer of the COLON.		01.9910
Experimental Hepatoma
[description not available]		0210