Page last updated: 2024-12-06

oxamethacin

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

Description

oxamethacin: structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

oxametacin : A hydroxamic acid obtained by formal condensation of the carboxy group of indometacin with the amino group of 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 CID33675
CHEMBL ID295829
CHEBI ID76255
SCHEMBL ID24552
MeSH IDM0071125

Synonyms (52)

Synonym
indole-3-acetohydroxamic acid, 1-(p-chlorobenzoyl)-5-methoxy-2-methyl-
oxametacin [inn]
1-(4-chlorobenzoyl)-methyl-5-methoxy-3-indolylacetohydroxamic acid
oxametacinum [inn-latin]
acido indoxamico [italian]
flogar
oxametacina [inn-spanish]
einecs 248-179-6
1-(p-chlorobenzoyl)-5-methoxy-2-methylindole-3-acetohydroxamic acid
oxametacin
acido 1-(p-clorobenzoil)-5-metossi-2-metil-3-indolilacetoidrossamico [italian]
1-(4-chlorobenzoyl)-n-hydroxy-5-methoxy-2-methyl-1h-indole-3-acetamide
oxametacine
oxametacine [inn-french]
indoxamic acid
brn 0497721
oxamethacin
1-(p-chlorobenzoyl)-5-methoxy-2-methyl-3-indolylacetohydroxamic acid
1h-indole-3-acetamide, 1-(4-chlorobenzoyl)-n-hydroxy-5-methoxy-2-methyl-
abc 8/3
D07266
27035-30-9
oxametacin (inn)
CHEMBL295829 ,
2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]-n-hydroxyacetamide
2-[1-(4-chloro-benzoyl)-5-methoxy-2-methyl-1h-indol-3-yl]-n-hydroxy-acetamide
2-{1-[(4-chlorophenyl)carbonyl]-5-methoxy-2-methylindol-3-yl}ethanehydroxamic acid
bdbm50012893
2-[1-(4-chloro-benzoyl)-5-methoxy-2-methyl-1h-indol-3-yl]-n-hydroxy-acetamide(indomethacin series)
acido 1-(p-clorobenzoil)-5-metossi-2-metil-3-indolilacetoidrossamico
oxametacina
acido indoxamico
oxametacinum
unii-8g02rsw5cm
5-22-05-00243 (beilstein handbook reference)
8g02rsw5cm ,
oxametacine [mi]
oxametacin [mart.]
oxametacin [who-dd]
SCHEMBL24552
CHEBI:76255
2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1h-indol-3-yl]-n-hydroxyacetamide
AJRNYCDWNITGHF-UHFFFAOYSA-N
DTXSID70181517
Q3887768
1-p-chlorobenzoyl-5-methoxy-2-methyl-3-indoacetohydroxamic acid
2-(4-hydroxy-3-methoxy-phenyl)-1h-benzoimidazole-4-carboxylicacid
DB13308
dinulcid; flogar
EN300-7519408
AKOS040749103
Z59182177

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
"In a double-blind cross-over study 2 groups of 6 healthy volunteers were dosed with 2 x 75 mg and 3 x 75 mg/d oxametacin (1-p-chlorobenzoyl-2-methyl-5-methoxy-3-indolylacethydroxamic acid)."( [Pharmacokinetics of oxametacin in healthy volunteers following multiple administration (author's transl)].
Dittrich, P; Ferber, H; Kukovetz, WR; Vergin, H, 1981
)
0.26
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
non-steroidal anti-inflammatory drugAn anti-inflammatory drug that is not a steroid. In addition to anti-inflammatory actions, non-steroidal anti-inflammatory drugs have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins.
EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitorA compound or agent that combines with cyclooxygenases (EC 1.14.99.1) and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of icosanoids, prostaglandins, and thromboxanes.
non-narcotic analgesicA drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
[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 (4)

ClassDescription
organochlorine compoundAn organochlorine compound is a compound containing at least one carbon-chlorine bond.
N-acylindoleA carboxamide resulting from the formal condensation of a carboxylic acid with the nitrogen of an indole.
aromatic etherAny ether in which the oxygen is attached to at least one aryl substituent.
hydroxamic acidA compound, RkE(=O)lNHOH, derived from an oxoacid RkE(=O)l(OH) (l =/= 0) by replacing -OH with -NHOH, and derivatives thereof. Specific examples of hydroxamic acids are preferably named as N-hydroxy amides.
[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]

Protein Targets (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Polyunsaturated fatty acid 5-lipoxygenaseRattus norvegicus (Norway rat)IC50 (µMol)7.50000.00462.018210.0000AID6860
Prostaglandin G/H synthase 2 Rattus norvegicus (Norway rat)IC50 (µMol)1.10000.00291.786810.0000AID161005
Prostaglandin G/H synthase 1 Rattus norvegicus (Norway rat)IC50 (µMol)1.10000.00291.823210.0000AID161005
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (11)

Assay IDTitleYearJournalArticle
AID304232Inhibition of COX1 in human whole blood assessed as effect on A23187-induced thromboxane B2 production at 100 uM relative to control2007Journal of medicinal chemistry, Dec-13, Volume: 50, Issue:25
Structure-based design, synthesis, and biological evaluation of indomethacin derivatives as cyclooxygenase-2 inhibiting nitric oxide donors.
AID227084Relative binding affinity to 5-lipoxygenase and cyclooxygenase1990Journal of medicinal chemistry, Aug, Volume: 33, Issue:8
Nonsteroidal antiinflammatory drug hydroxamic acids. Dual inhibitors of both cyclooxygenase and 5-lipoxygenase.
AID304242Inhibition of COX2 in human whole blood assessed as effect on LPS-induced thromboxane B2 production at 1 uM relative to control2007Journal of medicinal chemistry, Dec-13, Volume: 50, Issue:25
Structure-based design, synthesis, and biological evaluation of indomethacin derivatives as cyclooxygenase-2 inhibiting nitric oxide donors.
AID304223Inhibition of COX1 in human whole blood assessed as effect on A23187-induced thromboxane B2 production2007Journal of medicinal chemistry, Dec-13, Volume: 50, Issue:25
Structure-based design, synthesis, and biological evaluation of indomethacin derivatives as cyclooxygenase-2 inhibiting nitric oxide donors.
AID161005Inhibition of Prostaglandin G/H synthase in intact RBL-1 cell line1990Journal of medicinal chemistry, Aug, Volume: 33, Issue:8
Nonsteroidal antiinflammatory drug hydroxamic acids. Dual inhibitors of both cyclooxygenase and 5-lipoxygenase.
AID179432In vivo percent inhibition of carrageenan foot-pad edema (CFE) after peroral administration was determined.1990Journal of medicinal chemistry, Aug, Volume: 33, Issue:8
Nonsteroidal antiinflammatory drug hydroxamic acids. Dual inhibitors of both cyclooxygenase and 5-lipoxygenase.
AID190152In vivo ulcerogenicity was determined after peroral administration in rat1990Journal of medicinal chemistry, Aug, Volume: 33, Issue:8
Nonsteroidal antiinflammatory drug hydroxamic acids. Dual inhibitors of both cyclooxygenase and 5-lipoxygenase.
AID304236Inhibition of COX1 in human whole blood assessed as effect on A23187-induced thromboxane B2 production at 1 uM relative to control2007Journal of medicinal chemistry, Dec-13, Volume: 50, Issue:25
Structure-based design, synthesis, and biological evaluation of indomethacin derivatives as cyclooxygenase-2 inhibiting nitric oxide donors.
AID6860Inhibition of 5-lipoxygenase in intact RBL-1 cell line1990Journal of medicinal chemistry, Aug, Volume: 33, Issue:8
Nonsteroidal antiinflammatory drug hydroxamic acids. Dual inhibitors of both cyclooxygenase and 5-lipoxygenase.
AID304234Inhibition of COX1 in human whole blood assessed as effect on A23187-induced thromboxane B2 production at 10 uM relative to control2007Journal of medicinal chemistry, Dec-13, Volume: 50, Issue:25
Structure-based design, synthesis, and biological evaluation of indomethacin derivatives as cyclooxygenase-2 inhibiting nitric oxide donors.
AID304244Inhibition of COX2 in human whole blood assessed as effect on LPS-induced thromboxane B2 production at 10 uM relative to control2007Journal of medicinal chemistry, Dec-13, Volume: 50, Issue:25
Structure-based design, synthesis, and biological evaluation of indomethacin derivatives as cyclooxygenase-2 inhibiting nitric oxide donors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (19)

TimeframeStudies, This Drug (%)All Drugs %
pre-199017 (89.47)18.7374
1990's1 (5.26)18.2507
2000's1 (5.26)29.6817
2010's0 (0.00)24.3611
2020's0 (0.00)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 (%)
Trials3 (15.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other17 (85.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]