Droxicam
Identification
- Generic Name
- Droxicam
- DrugBank Accession Number
- DB09215
- Background
Droxicam is an oxicam non-steroidal anti-inflammatory drug and a prodrug of Piroxicam. It is used to reduce pain and inflammation in musculoskeletal disorders such as rheumatoid arthritis and osteoarthritis.
- Type
- Small Molecule
- Groups
- Withdrawn
- Structure
- Weight
- Average: 357.34
Monoisotopic: 357.04194164 - Chemical Formula
- C16H11N3O5S
- Synonyms
- Droxicam
Pharmacology
- Indication
Droxicam is an NSAID previously used for the treatment of inflammation and rheumatoid arthritis 4.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
- Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API
- Pharmacodynamics
Droxicam is a prodrug of Piroxicam 1. Droxicam administration produces anti-inflammatory, antirheumatic, analgesic, and antipyretic effects similar to Piroxicam.
- Mechanism of action
Droxicam is converted to Piroxicam via hydrolysis of the ester group in the intestine 2. Droxicam administration inhibits the synthesis of prostaglandins by cyclooxygenase enzymes 1.
Target Actions Organism AProstaglandin G/H synthase 1 inhibitorHumans AProstaglandin G/H synthase 2 inhibitorHumans - Absorption
Tmax of 7 h. Bioavailability equivalent to Piroxicam which is thought to be completely absorbed in humans based on data from rabbits 2.
- Volume of distribution
Data not available for prodrug. See Piroxicam for information on the active compound.
- Protein binding
Data not available for prodrug. See Piroxicam for information on the active compound.
- Metabolism
Converted to Piroxicam via ester hydrolysis 2.
Hover over products below to view reaction partners
- Route of elimination
Data not available for prodrug. See Piroxicam for information on the active compound.
- Half-life
Data not available for prodrug. See Piroxicam for information on the active compound.
- Clearance
Data not available for prodrug. See Piroxicam for information on the active compound.
- 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
Exposure to Droxicam is associated with significantly increased risk of hepatic toxicity resulting in its withdrawal from the market 3.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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 Droxicam 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 Droxicam is combined with Abciximab. Acebutolol Droxicam may decrease the antihypertensive activities of Acebutolol. Aceclofenac The risk or severity of adverse effects can be increased when Aceclofenac is combined with Droxicam. Acemetacin The risk or severity of adverse effects can be increased when Droxicam is combined with Acemetacin. - Food Interactions
- Not Available
Categories
- ATC Codes
- M01AC04 — Droxicam
- Drug Categories
- Agents causing hyperkalemia
- Agents that produce hypertension
- Analgesics
- Analgesics, Non-Narcotic
- Anti-Inflammatory Agents
- Anti-Inflammatory Agents, Non-Steroidal
- Anti-Inflammatory Agents, Non-Steroidal (Non-Selective)
- Antiinflammatory and Antirheumatic Products
- Antiinflammatory and Antirheumatic Products, Non-Steroids
- Antirheumatic Agents
- Musculo-Skeletal System
- Nephrotoxic agents
- Non COX-2 selective NSAIDS
- Oxicams
- Peripheral Nervous System Agents
- Sensory System Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as benzothiazines. These are organic compounds containing a benzene fused to a thiazine ring (a six-membered ring with four carbon atoms, one nitrogen atom and one sulfur atom).
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Benzothiazines
- Sub Class
- Not Available
- Direct Parent
- Benzothiazines
- Alternative Parents
- Pyridines and derivatives / Organosulfonamides / Benzenoids / Heteroaromatic compounds / Lactams / Oxacyclic compounds / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds show 2 more
- Substituents
- Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Benzothiazine / Heteroaromatic compound / Hydrocarbon derivative / Lactam / Organic nitrogen compound / Organic oxide / Organic oxygen compound show 8 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- organic heterotricyclic compound, pyridines, ring assembly (CHEBI:76133)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- F24ADO1E2D
- CAS number
- 90101-16-9
- InChI Key
- OEHFRZLKGRKFAS-UHFFFAOYSA-N
- InChI
- InChI=1S/C16H11N3O5S/c1-18-13-14(10-6-2-3-7-11(10)25(18,22)23)24-16(21)19(15(13)20)12-8-4-5-9-17-12/h2-9H,1H3
- IUPAC Name
- 8-methyl-5-(pyridin-2-yl)-3-oxa-9λ⁶-thia-5,8-diazatricyclo[8.4.0.0²,⁷]tetradeca-1(14),2(7),10,12-tetraene-4,6,9,9-tetrone
- SMILES
- CN1C2=C(OC(=O)N(C2=O)C2=CC=CC=N2)C2=CC=CC=C2S1(=O)=O
References
- General References
- Esteve J, Farre AJ, Roser R: Pharmacological profile of droxicam. Gen Pharmacol. 1988;19(1):49-54. [Article]
- Olkkola KT, Brunetto AV, Mattila MJ: Pharmacokinetics of oxicam nonsteroidal anti-inflammatory agents. Clin Pharmacokinet. 1994 Feb;26(2):107-20. [Article]
- Lapeyre-Mestre M, de Castro AM, Bareille MP, Del Pozo JG, Requejo AA, Arias LM, Montastruc JL, Carvajal A: Non-steroidal anti-inflammatory drug-related hepatic damage in France and Spain: analysis from national spontaneous reporting systems. Fundam Clin Pharmacol. 2006 Aug;20(4):391-5. doi: 10.1111/j.1472-8206.2006.00416.x. [Article]
- WHO: Droxicam [Link]
- External Links
- KEGG Drug
- D07267
- PubChem Compound
- 65679
- PubChem Substance
- 310265122
- ChemSpider
- 59108
- 23687
- ChEBI
- 76133
- ChEMBL
- CHEMBL1213420
- ZINC
- ZINC000000597502
- PharmGKB
- PA166049182
- Wikipedia
- Droxicam
- MSDS
- Download (263 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0319 mg/mL ALOGPS logP 1.75 ALOGPS logP 1.23 Chemaxon logS -4 ALOGPS pKa (Strongest Basic) 0.92 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 96.88 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 88.19 m3·mol-1 Chemaxon Polarizability 33.9 Å3 Chemaxon Number of Rings 4 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 splash10-0006-2933000000-5f186fed75038151cdf4 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-0009000000-91550487eceb97eba160 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-0090000000-f19d9e45e3aad522345c Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-0009000000-48a4b1e99e0b6c5f9169 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0gbc-0192000000-80c5fdfbbf0330f8080b Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-052f-0094000000-6dd766e9c3938f50c1ca Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-014i-1974000000-f6d51294151a177b0dcd 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]- 188.4340837 predictedDarkChem Lite v0.1.0 [M-H]- 169.82092 predictedDeepCCS 1.0 (2019) [M+H]+ 189.4874837 predictedDarkChem Lite v0.1.0 [M+H]+ 172.17892 predictedDeepCCS 1.0 (2019) [M+Na]+ 188.9678837 predictedDarkChem Lite v0.1.0 [M+Na]+ 178.48854 predictedDeepCCS 1.0 (2019)
Targets
![](https://go.drugbank.com/assets/locked/DrugTargets2-682eb846d210ae4bf33ca03febccfb57bb1c61318e699b729e5df4dfab2c5b67.png)
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- Curator comments
- Droxicam is converted to Piroxicam which acts on the target.
- General Function
- Prostaglandin-endoperoxide synthase activity
- Specific Function
- Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gas...
- Gene Name
- PTGS1
- Uniprot ID
- P23219
- Uniprot Name
- Prostaglandin G/H synthase 1
- Molecular Weight
- 68685.82 Da
References
- Esteve J, Farre AJ, Roser R: Pharmacological profile of droxicam. Gen Pharmacol. 1988;19(1):49-54. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- Curator comments
- Droxicam is converted to Piroxicam which acts on the target.
- General Function
- Prostaglandin-endoperoxide synthase activity
- Specific Function
- Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and...
- Gene Name
- PTGS2
- Uniprot ID
- P35354
- Uniprot Name
- Prostaglandin G/H synthase 2
- Molecular Weight
- 68995.625 Da
References
- Esteve J, Farre AJ, Roser R: Pharmacological profile of droxicam. Gen Pharmacol. 1988;19(1):49-54. [Article]
Drug created at October 21, 2015 16:02 / Updated at February 21, 2021 18:52