Ibuproxam
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Identification
- Generic Name
- Ibuproxam
- DrugBank Accession Number
- DB08955
- Background
Ibuproxam is a non steroidal anti-inflammatory drug (NSAID).
- Type
- Small Molecule
- Groups
- Withdrawn
- Structure
- Weight
- Average: 221.2955
Monoisotopic: 221.141578857 - Chemical Formula
- C13H19NO2
- Synonyms
- Ibuproxam
- Ibuproxamum
- p-Isobutylhydratropohydroxamic acid
- External IDs
- G 277
- G-277
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism APolyunsaturated fatty acid 5-lipoxygenase inhibitorHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Ibuproxam may decrease the excretion rate of Abacavir which could result in a higher serum level. Abciximab The risk or severity of bleeding and hemorrhage can be increased when Ibuproxam is combined with Abciximab. Acebutolol Ibuproxam may decrease the antihypertensive activities of Acebutolol. Aceclofenac The risk or severity of adverse effects can be increased when Aceclofenac is combined with Ibuproxam. Acemetacin The risk or severity of adverse effects can be increased when Ibuproxam is combined with Acemetacin. - Food Interactions
- Not Available
Products
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- International/Other Brands
- Deflogon / Ibudros (Lucchini Laboratoire)
Categories
- ATC Codes
- M01AE13 — Ibuproxam
- Drug Categories
- Acetamides
- Agents causing hyperkalemia
- Agents that produce hypertension
- Amides
- Amines
- Analgesics
- Analgesics, Non-Narcotic
- Anti-Inflammatory Agents
- Anti-Inflammatory Agents, Non-Steroidal
- Antiinflammatory and Antirheumatic Products
- Antiinflammatory and Antirheumatic Products, Non-Steroids
- Antirheumatic Agents
- Benzene Derivatives
- Hydroxy Acids
- Hydroxylamines
- Musculo-Skeletal System
- Nephrotoxic agents
- Non COX-2 selective NSAIDS
- Peripheral Nervous System Agents
- Propionates
- Sensory System Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Prenol lipids
- Sub Class
- Monoterpenoids
- Direct Parent
- Aromatic monoterpenoids
- Alternative Parents
- Monocyclic monoterpenoids / Phenylpropanes / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds / Hydrocarbon derivatives
- Substituents
- Aromatic homomonocyclic compound / Aromatic monoterpenoid / Benzenoid / Hydrocarbon derivative / Monocyclic benzene moiety / Monocyclic monoterpenoid / Organic nitrogen compound / Organic oxygen compound / Organonitrogen compound / Organooxygen compound
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- hydroxamic acid (CHEBI:76160)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- O3LD16O96Z
- CAS number
- 53648-05-8
- InChI Key
- BYPIURIATSUHDW-UHFFFAOYSA-N
- InChI
- InChI=1S/C13H19NO2/c1-9(2)8-11-4-6-12(7-5-11)10(3)13(15)14-16/h4-7,9-10,16H,8H2,1-3H3,(H,14,15)
- IUPAC Name
- N-hydroxy-2-[4-(2-methylpropyl)phenyl]propanamide
- SMILES
- CC(C)CC1=CC=C(C=C1)C(C)C(=O)NO
References
- Synthesis Reference
U.S. Patent 4,082,707.
- General References
- Orzalesi G, Mari F, Bertol E, Selleri R, Pisaturo G: Anti-inflammatory agents: determination of ibuproxam and its metabolite humans. Correlation between bioavailability, tolerance and chemico-physical characteristics. Arzneimittelforschung. 1980;30(9):1607-9. [Article]
- External Links
Clinical Trials
- Clinical Trials
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Suppository Tablet - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 119-121 U.S. Patent 4,082,707. - Predicted Properties
Property Value Source Water Solubility 0.073 mg/mL ALOGPS logP 2.77 ALOGPS logP 3.03 Chemaxon logS -3.5 ALOGPS pKa (Strongest Acidic) 8.83 Chemaxon pKa (Strongest Basic) -5.5 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 49.33 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 64.32 m3·mol-1 Chemaxon Polarizability 25.08 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-07vi-3900000000-1f77a4c97febd785dc71 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-05fr-1960000000-ca7832f2055bb8341606 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0fk9-0290000000-87c21e811b2abcd83cf8 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-01bc-2910000000-f10003d96f7d03307bd8 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-01qc-2900000000-49ffaed9464fde0689d7 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-014i-3900000000-fc06edd923ddabf45570 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-014l-6910000000-8486772c0b794f36e70a Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 152.0183 predictedDeepCCS 1.0 (2019) [M+H]+ 154.3763 predictedDeepCCS 1.0 (2019) [M+Na]+ 161.0135 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Catalyzes the oxygenation of arachidonate ((5Z,8Z,11Z,14Z)-eicosatetraenoate) to 5-hydroperoxyeicosatetraenoate (5-HPETE) followed by the dehydration to 5,6- epoxyeicosatetraenoate (Leukotriene A4/LTA4), the first two steps in the biosynthesis of leukotrienes, which are potent mediators of inflammation (PubMed:19022417, PubMed:21233389, PubMed:22516296, PubMed:23246375, PubMed:24282679, PubMed:24893149, PubMed:31664810, PubMed:8615788, PubMed:8631361). Also catalyzes the oxygenation of arachidonate into 8-hydroperoxyicosatetraenoate (8-HPETE) and 12-hydroperoxyicosatetraenoate (12-HPETE) (PubMed:23246375). Displays lipoxin synthase activity being able to convert (15S)-HETE into a conjugate tetraene (PubMed:31664810). Although arachidonate is the preferred substrate, this enzyme can also metabolize oxidized fatty acids derived from arachidonate such as (15S)-HETE, eicosapentaenoate (EPA) such as (18R)- and (18S)-HEPE or docosahexaenoate (DHA) which lead to the formation of specialized pro-resolving mediators (SPM) lipoxin and resolvins E and D respectively, therefore it participates in anti-inflammatory responses (PubMed:17114001, PubMed:21206090, PubMed:31664810, PubMed:32404334, PubMed:8615788). Oxidation of DHA directly inhibits endothelial cell proliferation and sprouting angiogenesis via peroxisome proliferator-activated receptor gamma (PPARgamma) (By similarity). It does not catalyze the oxygenation of linoleic acid and does not convert (5S)-HETE to lipoxin isomers (PubMed:31664810). In addition to inflammatory processes, it participates in dendritic cell migration, wound healing through an antioxidant mechanism based on heme oxygenase-1 (HO-1) regulation expression, monocyte adhesion to the endothelium via ITGAM expression on monocytes (By similarity). Moreover, it helps establish an adaptive humoral immunity by regulating primary resting B cells and follicular helper T cells and participates in the CD40-induced production of reactive oxygen species (ROS) after CD40 ligation in B cells through interaction with PIK3R1 that bridges ALOX5 with CD40 (PubMed:21200133). May also play a role in glucose homeostasis, regulation of insulin secretion and palmitic acid-induced insulin resistance via AMPK (By similarity). Can regulate bone mineralization and fat cell differentiation increases in induced pluripotent stem cells (By similarity)
- Specific Function
- arachidonate 12(S)-lipoxygenase activity
- Gene Name
- ALOX5
- Uniprot ID
- P09917
- Uniprot Name
- Polyunsaturated fatty acid 5-lipoxygenase
- Molecular Weight
- 77982.595 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Drug created at May 28, 2014 19:10 / Updated at August 26, 2024 19:22