Page last updated: 2024-12-06

benzamidoxime

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

Description

benzamidoxime: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

benzamidoxime : A member of the class of amidoximes obtained by formal condensation of the carbonyl group of benzamide with hydroxylamine. [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]

Cross-References

ID SourceID
PubMed CID7259353
CHEMBL ID335598
CHEBI ID83354
SCHEMBL ID30242
MeSH IDM0151695

Synonyms (45)

Synonym
benzenecarboximidamide, n-hydroxy-
benzamide oxime
n-hydroxybenzenecarboximidamide
phenylhydroxamidine
n-hydroxybenzamidine
nsc 13999
benzohydroxamamide
einecs 210-361-8
ccris 2953
nsc13999
613-92-3
nsc-13999
benzamidoxime
n'-hydroxybenzenecarboximidamide
STK298698
B0015
n-hydroxy-benzamidine
chebi:83354 ,
n'-hydroxybenzimidamide
n'-hydroxybenzamidine
CHEMBL335598
AKOS000310179
inchi=1/c7h8n2o/c8-7(9-10)6-4-2-1-3-5-6/h1-5,10h,(h2,8,9)
mxoqnvmdkhlycz-uhfffaoysa-
A833199
BBL005528
ec 210-361-8
n'-pydroxybenzenecarboximidamide
AKOS022299864
(e)-n'-hydroxybenzimidamide
SCHEMBL30242
J-502062
n'-hydroxybenzenecarboximidamide #
benzamidoxime, aldrichcpr
mfcd00031485
AS-37894
F2147-0550
(z)-n'-hydroxybenzenecarboximidamide
DTXSID10976787
69289-27-6
CS-W017758
EN300-03997
benzenecarboximidamide, n'-hydroxy-, (z)-
n'~1~-hydroxy-1-benzenecarboximidamide
Z56827052

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
"N, N'-dihydroxybenzamdine represents a model compound for a new prodrug principle to improve the oral bioavailability of drugs containing amidine functions."( N,N'-dihydroxyamidines: a new prodrug principle to improve the oral bioavailability of amidines.
Clement, B; Reeh, C; Wundt, J, 2007
)
0.34
" These substances are amidoxime/N-hydroxyguanidine prodrugs, leading to improved bioavailability compared to the active amidines/guanidines."( The fourth molybdenum containing enzyme mARC: cloning and involvement in the activation of N-hydroxylated prodrugs.
Bittner, F; Clement, B; Gruenewald, S; Hungeling, H; Kanzow, S; Kotthaus, J; Mendel, RR; Schwering, U; Wahl, B, 2008
)
0.35
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
genotoxinA role played by a chemical compound to induce direct or indirect DNA damage. Such damage can potentially lead to the formation of a malignant tumour, but DNA damage does not lead inevitably to the creation of cancerous cells.
bacterial metaboliteAny prokaryotic metabolite produced during a metabolic reaction in bacteria.
mammalian metaboliteAny animal metabolite produced during a metabolic reaction in mammals.
[role 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]

Drug Classes (1)

ClassDescription
amidoximeAmidines of general formula RC(=NOH)NR(1)R(2), in which the imino nitrogen is substituted by a hydroxy 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 (16)

Assay IDTitleYearJournalArticle
AID1653806Substrate activity at human mARC2 expressed in Escherichia coli assessed as turnover rates at 3 mM pre-incubated for 3 mins followed by NADH addition and measured after 15 mins by LC-MS analysis based assay2020Journal of medicinal chemistry, 06-25, Volume: 63, Issue:12
Drug Metabolism by the Mitochondrial Amidoxime Reducing Component (mARC): Rapid Assay and Identification of New Substrates.
AID548100Antioxidant activity assessed as DPPH free radical scavenging activity at 100 uM after 60 mins2010European journal of medicinal chemistry, Dec, Volume: 45, Issue:12
Convenient synthesis and biological profile of 5-amino-substituted 1,2,4-oxadiazole derivatives.
AID1653796Substrate activity at human mARC2 expressed in Escherichia coli assessed as turnover rates at 3 mM pre-incubated for 3 mins followed by NADH addition and measured after 15 mins by UV-Visible spectroscopy based NADH assay2020Journal of medicinal chemistry, 06-25, Volume: 63, Issue:12
Drug Metabolism by the Mitochondrial Amidoxime Reducing Component (mARC): Rapid Assay and Identification of New Substrates.
AID412956Specific activity at molybdenum cofactor/metal-free precursor molybopterin bound human recombinant mARC1 expressed in Escherichia coli TP1000 assessed as reduction to benzamidine in complete reconstituted system containing microsomal cyt b5, NADH and micr2008Journal of medicinal chemistry, Dec-25, Volume: 51, Issue:24
The fourth molybdenum containing enzyme mARC: cloning and involvement in the activation of N-hydroxylated prodrugs.
AID548106Induction of NO release in phosphate buffer pH 7.4 containing 0.5 mM L-cysteine assessed as nitrite level at 100 uM after 60 mins by Griess assay2010European journal of medicinal chemistry, Dec, Volume: 45, Issue:12
Convenient synthesis and biological profile of 5-amino-substituted 1,2,4-oxadiazole derivatives.
AID304873Plasma concentration in pig at 10 mg/kg, po2007Journal of medicinal chemistry, Dec-27, Volume: 50, Issue:26
N,N'-dihydroxyamidines: a new prodrug principle to improve the oral bioavailability of amidines.
AID1653801Substrate activity at human mARC1 expressed in Escherichia coli assessed as turnover rates at 3 mM pre-incubated for 3 mins followed by NADH addition and measured after 15 mins by LC-MS analysis based assay2020Journal of medicinal chemistry, 06-25, Volume: 63, Issue:12
Drug Metabolism by the Mitochondrial Amidoxime Reducing Component (mARC): Rapid Assay and Identification of New Substrates.
AID1653791Substrate activity at human mARC1 expressed in Escherichia coli assessed as turnover rates at 3 mM pre-incubated for 3 mins followed by NADH addition and measured after 15 mins by UV-Visible spectroscopy based NADH assay2020Journal of medicinal chemistry, 06-25, Volume: 63, Issue:12
Drug Metabolism by the Mitochondrial Amidoxime Reducing Component (mARC): Rapid Assay and Identification of New Substrates.
AID548098Antioxidant activity assessed as DPPH free radical scavenging activity at 100 uM after 20 mins2010European journal of medicinal chemistry, Dec, Volume: 45, Issue:12
Convenient synthesis and biological profile of 5-amino-substituted 1,2,4-oxadiazole derivatives.
AID548097Antioxidant activity assessed as DPPH free radical scavenging activity at 50 uM after 20 mins2010European journal of medicinal chemistry, Dec, Volume: 45, Issue:12
Convenient synthesis and biological profile of 5-amino-substituted 1,2,4-oxadiazole derivatives.
AID143528Nitric oxide (NO) formation during oxidation of NADPH and O2, catalyzed by NOS II detected spectrophotometrically using hemoglobin assay.2002Journal of medicinal chemistry, Feb-14, Volume: 45, Issue:4
N-Aryl N'-hydroxyguanidines, a new class of NO-donors after selective oxidation by nitric oxide synthases: structure-activity relationship.
AID412954Specific activity at molybdenum cofactor/metal-free precursor molybopterin bound human recombinant mARC1 expressed in Escherichia coli TP1000 assessed as reduction to benzamidine in reconstituted system containing microsomal cyt b5 and NADH without micros2008Journal of medicinal chemistry, Dec-25, Volume: 51, Issue:24
The fourth molybdenum containing enzyme mARC: cloning and involvement in the activation of N-hydroxylated prodrugs.
AID412955Specific activity at molybdenum cofactor/metal-free precursor molybopterin bound human recombinant mARC1 expressed in Escherichia coli TP1000 assessed as reduction to benzamidine in reconstituted system containing NADH and microsomal NADH cyt b5 reductase2008Journal of medicinal chemistry, Dec-25, Volume: 51, Issue:24
The fourth molybdenum containing enzyme mARC: cloning and involvement in the activation of N-hydroxylated prodrugs.
AID548107Induction of NO release in phosphate buffer pH 7.4 containing 0.5 mM thiophenol assessed as nitrite level at 100 uM after 60 mins by Griess assay2010European journal of medicinal chemistry, Dec, Volume: 45, Issue:12
Convenient synthesis and biological profile of 5-amino-substituted 1,2,4-oxadiazole derivatives.
AID775062Cytotoxicity against human HuH7 cells expressing luc/neo after 72 hrs by MTT assay2013Bioorganic & medicinal chemistry letters, Nov-01, Volume: 23, Issue:21
Benzohydroxamic acids as potent and selective anti-HCV agents.
AID775063Antiviral activity against HCV in human Huh-luc/neo7 cells after 72 hrs by luciferase reporter gene assay2013Bioorganic & medicinal chemistry letters, Nov-01, Volume: 23, Issue:21
Benzohydroxamic acids as potent and selective anti-HCV agents.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (32)

TimeframeStudies, This Drug (%)All Drugs %
pre-19903 (9.38)18.7374
1990's6 (18.75)18.2507
2000's10 (31.25)29.6817
2010's10 (31.25)24.3611
2020's3 (9.38)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other32 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]