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 Source | ID |
|---|---|
| PubMed CID | 71000 |
| CHEMBL ID | 12995 |
| SCHEMBL ID | 905253 |
| MeSH ID | M0040922 |
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
| Excerpt | Reference | Relevance |
|---|---|---|
| "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
| Excerpt | Reference | Relevance |
|---|---|---|
| " 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
| Excerpt | Relevance | Reference |
|---|---|---|
| " 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 ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID1130928 | Antitumor 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 control | 1979 | Journal of medicinal chemistry, Oct, Volume: 22, Issue:10 | Structure-activity relationship of aniline mustards acting against B-16 melanoma in mice. |
| AID1132032 | Stability of the compound in acetone assessed as hydrolysis at 66 degC after 30 mins | 1978 | Journal of medicinal chemistry, Jan, Volume: 21, Issue:1 | Structure-activity relationships in antitumor aniline mustards. |
| AID1132018 | Ratio of LD50 for rat allografted with rat Walker 256 cells to ED90 for rat Walker 256 cells allografted in rat | 1978 | Journal of medicinal chemistry, Jan, Volume: 21, Issue:1 | Structure-activity relationships in antitumor aniline mustards. |
| AID1152459 | Induction 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 PAGE | 2014 | Journal 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. |
| AID101151 | Cytotoxicity was evaluated against LS174T-stCPG2(Q)3-expressing cell clone | 1998 | Journal of medicinal chemistry, Dec-17, Volume: 41, Issue:26 | Self-immolative nitrogen mustard prodrugs for suicide gene therapy. |
| AID1584812 | Induction 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 cytometry | 2018 | Journal 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. |
| AID1130920 | Antitumor activity against mouse B16 cells allografted in ip dosed BDF mouse assessed as 25% increase in life span administered for 9 days | 1979 | Journal of medicinal chemistry, Oct, Volume: 22, Issue:10 | Structure-activity relationship of aniline mustards acting against B-16 melanoma in mice. |
| AID23577 | Kinetic parameter (half-life) was evaluated | 1998 | Journal of medicinal chemistry, Dec-17, Volume: 41, Issue:26 | Self-immolative nitrogen mustard prodrugs for suicide gene therapy. |
| AID1152463 | Induction 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 piperidine | 2014 | Journal 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. |
| AID1132020 | Antitumor activity against rat Walker 256 cells allografted in rat | 1978 | Journal of medicinal chemistry, Jan, Volume: 21, Issue:1 | Structure-activity relationships in antitumor aniline mustards. |
| AID1152460 | Induction 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 PAGE | 2014 | Journal 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. |
| AID1152458 | Induction 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 PAGE | 2014 | Journal 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. |
| AID1132021 | Toxicity in rat allografted with rat Walker 256 cells | 1978 | Journal of medicinal chemistry, Jan, Volume: 21, Issue:1 | Structure-activity relationships in antitumor aniline mustards. |
| AID1152462 | Induction 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 piperidine | 2014 | Journal 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. |
| AID1152461 | Induction 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 piperidine | 2014 | Journal 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. |
| AID102183 | Inhibitory concentration was evaluated against colorectal tumar cell line LoVo | 1996 | Journal 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)
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 6 (35.29) | 18.7374 |
| 1990's | 7 (41.18) | 18.2507 |
| 2000's | 2 (11.76) | 29.6817 |
| 2010's | 2 (11.76) | 24.3611 |
| 2020's | 0 (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.
| This Compound (11.41) All Compounds (24.57) |
Study Types
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 1 (5.56%) | 5.53% |
| Reviews | 0 (0.00%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 17 (94.44%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||