Page last updated: 2024-11-04

3,4-dihydroxybenzohydroxamic acid

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

3,4-Dihydroxybenzohydroxamic acid (DHBA) is a naturally occurring hydroxamic acid found in plants and has been investigated for its potential therapeutic properties. It exhibits diverse biological activities, including antioxidant, anti-inflammatory, anti-cancer, and anti-microbial effects. DHBA is known to act as a chelating agent, binding to metals like iron and copper. This property is linked to its antioxidant activity, as it can scavenge free radicals and prevent oxidative damage. In the context of cancer research, DHBA has shown promising results in inhibiting the growth and proliferation of cancer cells, particularly in leukemia and breast cancer. Its potential anti-inflammatory effects are attributed to its ability to suppress the production of pro-inflammatory cytokines. Further studies are ongoing to explore the mechanisms underlying its biological activities and evaluate its safety and efficacy for therapeutic use.'

Cross-References

ID SourceID
PubMed CID3045
CHEMBL ID367788
CHEBI ID184074
SCHEMBL ID171446
SCHEMBL ID18732059
SCHEMBL ID18346609
MeSH IDM0108563

Synonyms (40)

Synonym
3,4-dihydroxybenzenecarbohydroxamic acid
n,3,4-trihydroxybenzamide
NCI60_002815
3,4-dihydroxybenzohydroxamic acid
nsc324360
nsc-324360
3,4-dihydroxyphenylhydroxamic acid
didox ,
benzamide,3,4-trihydroxy-
69839-83-4
brn 2096682
vf 147
benzamide, n,3,4-trihydroxy-
ccris 7909
nsc 324360
EC-000.2085
CHEMBL367788
CHEBI:184074
n-3,4-tridhydroxybenzamide
AKOS006278180
unii-l106xfv0rq
l106xfv0rq ,
n-3,4-tridhydroxy-benzamide
SCHEMBL171446
HY-19387
CS-5292
DTXSID90220134
QJMCKEPOKRERLN-UHFFFAOYSA-N
SCHEMBL18732059
SCHEMBL18346609
dido
didox, >=98% (hplc)
DB12948
BCP16846
C76222
Q27282568
A937090
AS-55818
3,4,n-trihydroxy-benzamide
EX-A8014G

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" Pharmacokinetic studies showed that a peak level of didox was achieved within 5 minutes of injection."( A phase 1 and pharmacokinetic study of didox: a ribonucleotide reductase inhibitor.
Blackie, R; Cantwell, BM; Carmichael, J; Elford, HL; Harris, AL; Kaye, SB; Kerr, DJ; Veale, D, 1988
)
0.27

Compound-Compound Interactions

The new series of RRIs, 3,4-dihydroxybenzohydroxamic acid (Didox) and trimidox (Trimidox), were evaluated along with HU for anti-retroviral efficacy in LPBM5-induced retro-viral disease (MAIDS) Both as monotherapeutic regimens and in combination with the guanine containing NRTI abacavir (ABC)

ExcerptReferenceRelevance
" We examined a new series of RRIs, 3,4-dihydroxybenzohydroxamic acid (Didox) and 3,4,5-trihydroxybenzohydroxamidoxime (Trimidox) for their ability to alter disease progression in murine acquired immunodeficiency syndrome (MAIDS), both alone and in combination with 2',3'-dideoxyinosine (ddI)."( Effective use of ribonucleotide reductase inhibitors (Didox and Trimidox) alone or in combination with didanosine (ddI) to suppress disease progression and increase survival in murine acquired immunodeficiency syndrome (MAIDS).
Birch, NJ; Elford, HL; Gallicchio, VS; Hughes, NK; Mayhew, C; Oakley, O; Phillips, J; Piper, J, 1997
)
0.57
" We have examined the capacity of two novel RRIs, didox (DI) and trimidox (TRI), in combination with streptozotocin (STZ), to induce hemoglobin and F-cell production."( Enhancement of hemoglobin and F-cell production by targeting growth inhibition and differentiation of K562 cells with ribonucleotide reductase inhibitors (didox and trimidox) in combination with streptozotocin.
Adunyah, SE; Asakura, T; Elford, HL; Fasold, H; Horiuchi, K; Iyamu, WE; Turner, EA, 2000
)
0.31
" In this study, the novel RR inhibitors didox (DX; 3,4-dihydroxybenzohydroxamic acid), and trimidox (TX; 3,4,5-trihydroxybenzamidoxime) were evaluated along with HU for anti-retroviral efficacy in LPBM5-induced retro-viral disease (MAIDS) both as monotherapeutic regimens and in combination with the guanine containing NRTI abacavir (ABC)."( In vivo examination of hydroxyurea and the novel ribonucleotide reductase inhibitors trimidox and didox in combination with the reverse transcriptase inhibitor abacavir: suppression of retrovirus-induced immunodeficiency disease.
Duvall, W; Elford, HL; Gallicchio, VS; Hagan, E; Inayat, MS; Mayhew, CN; Sumpter, LR; Yost, EE, 2004
)
0.58
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
benzoic acidsAny aromatic carboxylic acid that consists of benzene in which at least a single hydrogen has been substituted by a carboxy group.
[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 (41)

Assay IDTitleYearJournalArticle
AID1079935Cytolytic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is > 5 (see ACUTE). Value is number of references indexed. [column 'CYTOL' in source]
AID1079948Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' in source]
AID1079945Animal toxicity known. [column 'TOXIC' in source]
AID1079938Chronic liver disease either proven histopathologically, or through a chonic elevation of serum amino-transferase activity after 6 months. Value is number of references indexed. [column 'CHRON' in source]
AID496819Antimicrobial activity against Plasmodium falciparum2010Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6
Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.
AID1124486Antitumor activity against mouse L1210 cells allografted in C6D2F1 mouse at 600 mg/kg, ip for 8 days starting from day 1 of challenge relative to control1979Journal of medicinal chemistry, May, Volume: 22, Issue:5
Synthesis of hydroxy- and amino-substituted benzohydroxamic acids: inhibition of ribonucleotide reductase and antitumor activity.
AID1079934Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source]
AID1693173Antiinflammatory activity against mouse RAW 264.7 cells assessed as inhibition of LPS-induced NO production at 50 uM incubated for 24 hrs by Griess assay relative to control2021Bioorganic & medicinal chemistry, 01-01, Volume: 29Synthesis of nature product kinsenoside analogues with anti-inflammatory activity.
AID1079932Highest frequency of moderate liver toxicity observed during clinical trials, expressed as a percentage. [column '% BIOL' in source]
AID1124478Antitumor activity against mouse L1210 cells allografted in C6D2F1 mouse at 10 to 1000 mg/kg, ip for 8 days starting from day 1 of challenge relative to control1979Journal of medicinal chemistry, May, Volume: 22, Issue:5
Synthesis of hydroxy- and amino-substituted benzohydroxamic acids: inhibition of ribonucleotide reductase and antitumor activity.
AID91562Percentage inhibition against strand transfer of HIV-1 integrase at 100 ug/mL1997Journal of medicinal chemistry, Mar-14, Volume: 40, Issue:6
Depsides and depsidones as inhibitors of HIV-1 integrase: discovery of novel inhibitors through 3D database searching.
AID1124493Antitumor activity against mouse L1210 cells allografted in C6D2F1 mouse at 800 mg/kg, ip for 8 days starting from day 1 of challenge relative to control1979Journal of medicinal chemistry, May, Volume: 22, Issue:5
Synthesis of hydroxy- and amino-substituted benzohydroxamic acids: inhibition of ribonucleotide reductase and antitumor activity.
AID1079944Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' in source]
AID1124492Antitumor activity against mouse L1210 cells allografted in C6D2F1 mouse at 400 mg/kg, ip for 8 days starting from day 1 of challenge relative to control1979Journal of medicinal chemistry, May, Volume: 22, Issue:5
Synthesis of hydroxy- and amino-substituted benzohydroxamic acids: inhibition of ribonucleotide reductase and antitumor activity.
AID1693185Antiinflammatory activity against mouse RAW 264.7 cells assessed as inhibition of LPS-induced IL-1alpha mRNA level at 50 uM preincubated for 1 hr followed by LPS addition measured after 16 hrs by RT-PCR analysis2021Bioorganic & medicinal chemistry, 01-01, Volume: 29Synthesis of nature product kinsenoside analogues with anti-inflammatory activity.
AID1693187Antiinflammatory activity against mouse RAW 264.7 cells assessed as inhibition of LPS-induced IL-6 mRNA level at 50 uM preincubated for 1 hr followed by LPS addition measured after 16 hrs by RT-PCR analysis2021Bioorganic & medicinal chemistry, 01-01, Volume: 29Synthesis of nature product kinsenoside analogues with anti-inflammatory activity.
AID1079939Cirrhosis, proven histopathologically. Value is number of references indexed. [column 'CIRRH' in source]
AID1404506Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-induced nitric oxide production measured after 24 hrs by Griess assay
AID1693183Antiinflammatory activity against mouse RAW 264.7 cells assessed as inhibition of LPS-induced iNOS production at 50 uM preincubated for 1 hr followed by LPS addition measured after 16 hrs by Western blot analysis2021Bioorganic & medicinal chemistry, 01-01, Volume: 29Synthesis of nature product kinsenoside analogues with anti-inflammatory activity.
AID1079942Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' in source]
AID1079941Liver damage due to vascular disease: peliosis hepatitis, hepatic veno-occlusive disease, Budd-Chiari syndrome. Value is number of references indexed. [column 'VASC' in source]
AID1079937Severe hepatitis, defined as possibly life-threatening liver failure or through clinical observations. Value is number of references indexed. [column 'MASS' in source]
AID1079940Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source]
AID1124498Toxicity in mouse L1210 cells allografted C6D2F1 mouse at 800 mg/kg, ip for 8 days measured on day 21979Journal of medicinal chemistry, May, Volume: 22, Issue:5
Synthesis of hydroxy- and amino-substituted benzohydroxamic acids: inhibition of ribonucleotide reductase and antitumor activity.
AID1124485Antitumor activity against mouse L1210 cells allografted in C6D2F1 mouse at 500 mg/kg, ip for 8 days starting from day 1 of challenge relative to control1979Journal of medicinal chemistry, May, Volume: 22, Issue:5
Synthesis of hydroxy- and amino-substituted benzohydroxamic acids: inhibition of ribonucleotide reductase and antitumor activity.
AID1079947Comments (NB not yet translated). [column 'COMMENTAIRES' in source]
AID1079933Acute liver toxicity defined via clinical observations and clear clinical-chemistry results: serum ALT or AST activity > 6 N or serum alkaline phosphatases activity > 1.7 N. This category includes cytolytic, choleostatic and mixed liver toxicity. Value is
AID1693182Antiinflammatory activity against mouse RAW 264.7 cells assessed as inhibition of LPS-induced COX2 production at 50 uM preincubated for 1 hr followed by LPS addition measured after 16 hrs by Western blot analysis2021Bioorganic & medicinal chemistry, 01-01, Volume: 29Synthesis of nature product kinsenoside analogues with anti-inflammatory activity.
AID1124489Antitumor activity against mouse L1210 cells allografted in C6D2F1 mouse at 300 mg/kg, ip for 8 days starting from day 1 of challenge relative to control1979Journal of medicinal chemistry, May, Volume: 22, Issue:5
Synthesis of hydroxy- and amino-substituted benzohydroxamic acids: inhibition of ribonucleotide reductase and antitumor activity.
AID91561Percentage inhibition of compound against 3'-processing of HIV-1 integrase at 100 ug/mL1997Journal of medicinal chemistry, Mar-14, Volume: 40, Issue:6
Depsides and depsidones as inhibitors of HIV-1 integrase: discovery of novel inhibitors through 3D database searching.
AID1079936Choleostatic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is < 2 (see ACUTE). Value is number of references indexed. [column 'CHOLE' in source]
AID1124476Inhibition of ribonucleotide reductase purified from rat Novikoff hepatoma assessed as inhibition of [3H]CDP to [3H]dCDP conversion after 40 mins1979Journal of medicinal chemistry, May, Volume: 22, Issue:5
Synthesis of hydroxy- and amino-substituted benzohydroxamic acids: inhibition of ribonucleotide reductase and antitumor activity.
AID1693188Antiinflammatory activity against mouse RAW 264.7 cells assessed as inhibition of LPS-induced TNF-alpha mRNA level at 50 uM preincubated for 1 hr followed by LPS addition measured after 16 hrs by RT-PCR analysis2021Bioorganic & medicinal chemistry, 01-01, Volume: 29Synthesis of nature product kinsenoside analogues with anti-inflammatory activity.
AID1693186Antiinflammatory activity against mouse RAW 264.7 cells assessed as inhibition of LPS-induced IL-1beta mRNA level at 50 uM preincubated for 1 hr followed by LPS addition measured after 16 hrs by RT-PCR analysis2021Bioorganic & medicinal chemistry, 01-01, Volume: 29Synthesis of nature product kinsenoside analogues with anti-inflammatory activity.
AID1079943Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' in source]
AID1079931Moderate liver toxicity, defined via clinical-chemistry results: ALT or AST serum activity 6 times the normal upper limit (N) or alkaline phosphatase serum activity of 1.7 N. Value is number of references indexed. [column 'BIOL' in source]
AID1079949Proposed mechanism(s) of liver damage. [column 'MEC' in source]
AID1124479Antitumor activity against ip dosed mouse L1210 cells allografted in C6D2F1 mouse assessed as dose to achieve maximum life span administered for 8 days starting from day 1 of challenge1979Journal of medicinal chemistry, May, Volume: 22, Issue:5
Synthesis of hydroxy- and amino-substituted benzohydroxamic acids: inhibition of ribonucleotide reductase and antitumor activity.
AID1079946Presence of at least one case with successful reintroduction. [column 'REINT' in source]
AID1693184Antiinflammatory activity against mouse RAW 264.7 cells assessed as inhibition of LPS-induced translocation into nucleus at 50 uM by preincubated for 1 hr followed by LPS addition measured after 16 hrs by immunofluorescence assay2021Bioorganic & medicinal chemistry, 01-01, Volume: 29Synthesis of nature product kinsenoside analogues with anti-inflammatory activity.
AID1124491Antitumor activity against mouse L1210 cells allografted in C6D2F1 mouse at 100 mg/kg, ip for 8 days starting from day 1 of challenge relative to control1979Journal of medicinal chemistry, May, Volume: 22, Issue:5
Synthesis of hydroxy- and amino-substituted benzohydroxamic acids: inhibition of ribonucleotide reductase and antitumor activity.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (49)

TimeframeStudies, This Drug (%)All Drugs %
pre-19905 (10.20)18.7374
1990's15 (30.61)18.2507
2000's14 (28.57)29.6817
2010's13 (26.53)24.3611
2020's2 (4.08)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 10.78

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

MetricThis Compound (vs All)
Research Demand Index10.78 (24.57)
Research Supply Index4.03 (2.92)
Research Growth Index4.80 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (10.78)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials2 (3.77%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other51 (96.23%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]