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Droxicam
Identification
- Name
- Droxicam
- Accession Number
- DB09215
- Description
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- Withdrawn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
Structure for Droxicam (DB09215)
- 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.
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- 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
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
Exposure to Droxicam is associated with significantly increased risk of hepatic toxicity resulting in its withdrawal from the market 3.
- Affected organisms
- 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 Unlock Additional DataAbacavir 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. Acarbose Droxicam may decrease the excretion rate of Acarbose which could result in a higher serum level. 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. Acenocoumarol The risk or severity of bleeding and hemorrhage can be increased when Droxicam is combined with Acenocoumarol. Acetaminophen The risk or severity of adverse effects can be increased when Acetaminophen is combined with Droxicam. Acetohexamide The protein binding of Acetohexamide can be decreased when combined with Droxicam. Acetylsalicylic acid The therapeutic efficacy of Acetylsalicylic acid can be decreased when used in combination with Droxicam. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Not Available
Products
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
- Central Nervous System 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)
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. [PubMed:3278945]
- Olkkola KT, Brunetto AV, Mattila MJ: Pharmacokinetics of oxicam nonsteroidal anti-inflammatory agents. Clin Pharmacokinet. 1994 Feb;26(2):107-20. [PubMed:8162655]
- 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. [PubMed:16867024]
- 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
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 Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
- 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. [PubMed:3278945]
- 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. [PubMed:3278945]
Drug created on October 21, 2015 10:02 / Updated on June 12, 2020 10:52
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