Robenacoxib
Star1
This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
Identification
- Generic Name
- Robenacoxib
- DrugBank Accession Number
- DB11455
- Background
Robenacoxib is a non-steroidal anti-inflammatory drug used in veterinary medicine for the relief of pain and inflammation in cats and dogs.
- Type
- Small Molecule
- Groups
- Experimental, Vet approved
- Structure
- Weight
- Average: 327.279
Monoisotopic: 327.088241315 - Chemical Formula
- C16H13F4NO2
- Synonyms
- Robénacoxib
- Robenacoxib
- Robenacoxibum
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UCyclooxygenase 2 inhibitorCanis lupus familiaris - 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 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 Robenacoxib 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 Robenacoxib is combined with Abciximab. Acebutolol Robenacoxib may decrease the antihypertensive activities of Acebutolol. Aceclofenac The risk or severity of adverse effects can be increased when Aceclofenac is combined with Robenacoxib. Acemetacin The risk or severity of adverse effects can be increased when Robenacoxib is combined with Acemetacin. - Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as aniline and substituted anilines. These are organic compounds containing an aminobenzene moiety.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Aniline and substituted anilines
- Direct Parent
- Aniline and substituted anilines
- Alternative Parents
- Fluorobenzenes / Aryl fluorides / Amino acids / Secondary amines / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds / Organofluorides / Organic oxides / Hydrocarbon derivatives show 1 more
- Substituents
- Amine / Amino acid / Amino acid or derivatives / Aniline or substituted anilines / Aromatic homomonocyclic compound / Aryl fluoride / Aryl halide / Carbonyl group / Carboxylic acid / Carboxylic acid derivative show 13 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- organofluorine compound, monocarboxylic acid, secondary amino compound, aromatic amino acid (CHEBI:76269)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Z588009C7C
- CAS number
- 220991-32-2
- InChI Key
- ZEXGDYFACFXQPF-UHFFFAOYSA-N
- InChI
- InChI=1S/C16H13F4NO2/c1-2-8-3-4-12(9(5-8)6-13(22)23)21-16-14(19)10(17)7-11(18)15(16)20/h3-5,7,21H,2,6H2,1H3,(H,22,23)
- IUPAC Name
- 2-{5-ethyl-2-[(2,3,5,6-tetrafluorophenyl)amino]phenyl}acetic acid
- SMILES
- CCC1=CC(CC(O)=O)=C(NC2=C(F)C(F)=CC(F)=C2F)C=C1
References
- General References
- King JN, Hotz R, Reagan EL, Roth DR, Seewald W, Lees P: Safety of oral robenacoxib in the cat. J Vet Pharmacol Ther. 2012 Jun;35(3):290-300. doi: 10.1111/j.1365-2885.2011.01320.x. Epub 2011 Jul 8. [Article]
- Jung M, Lees P, Seewald W, King JN: Analytical determination and pharmacokinetics of robenacoxib in the dog. J Vet Pharmacol Ther. 2009 Feb;32(1):41-8. doi: 10.1111/j.1365-2885.2008.01035.x. [Article]
- Staffieri F, Centonze P, Gigante G, De Pietro L, Crovace A: Comparison of the analgesic effects of robenacoxib, buprenorphine and their combination in cats after ovariohysterectomy. Vet J. 2013 Aug;197(2):363-7. doi: 10.1016/j.tvjl.2013.01.018. Epub 2013 Feb 21. [Article]
- Giraudel JM, Toutain PL, King JN, Lees P: Differential inhibition of cyclooxygenase isoenzymes in the cat by the NSAID robenacoxib. J Vet Pharmacol Ther. 2009 Feb;32(1):31-40. doi: 10.1111/j.1365-2885.2008.01031.x. [Article]
- King JN, Rudaz C, Borer L, Jung M, Seewald W, Lees P: In vitro and ex vivo inhibition of canine cyclooxygenase isoforms by robenacoxib: a comparative study. Res Vet Sci. 2010 Jun;88(3):497-506. doi: 10.1016/j.rvsc.2009.11.002. Epub 2009 Dec 11. [Article]
- Reymond N, Speranza C, Gruet P, Seewald W, King JN: Robenacoxib vs. carprofen for the treatment of canine osteoarthritis; a randomized, noninferiority clinical trial. J Vet Pharmacol Ther. 2012 Apr;35(2):175-83. doi: 10.1111/j.1365-2885.2011.01297.x. Epub 2011 Apr 12. [Article]
- Pelligand L, King JN, Toutain PL, Elliott J, Lees P: Pharmacokinetic/pharmacodynamic modelling of robenacoxib in a feline tissue cage model of inflammation. J Vet Pharmacol Ther. 2012 Feb;35(1):19-32. doi: 10.1111/j.1365-2885.2011.01288.x. Epub 2011 Jul 18. [Article]
- King JN, Jung M, Maurer MP, Schmid VB, Seewald W, Lees P: Effects of route of administration and feeding schedule on pharmacokinetics of robenacoxib in cats. Am J Vet Res. 2013 Mar;74(3):465-72. doi: 10.2460/ajvr.74.3.465. [Article]
- Fink M, Letellier I, Peyrou M, Mochel JP, Jung M, King JN, Gruet P, Giraudel JM: Population pharmacokinetic analysis of blood concentrations of robenacoxib in dogs with osteoarthritis. Res Vet Sci. 2013 Oct;95(2):580-7. doi: 10.1016/j.rvsc.2013.04.021. Epub 2013 May 31. [Article]
- Schmid VB, Spreng DE, Seewald W, Jung M, Lees P, King JN: Analgesic and anti-inflammatory actions of robenacoxib in acute joint inflammation in dog. J Vet Pharmacol Ther. 2010 Apr;33(2):118-31. doi: 10.1111/j.1365-2885.2009.01117.x. [Article]
- King JN, Dawson J, Esser RE, Fujimoto R, Kimble EF, Maniara W, Marshall PJ, O'Byrne L, Quadros E, Toutain PL, Lees P: Preclinical pharmacology of robenacoxib: a novel selective inhibitor of cyclooxygenase-2. J Vet Pharmacol Ther. 2009 Feb;32(1):1-17. doi: 10.1111/j.1365-2885.2008.00962.x. [Article]
- Giraudel JM, King JN, Jeunesse EC, Lees P, Toutain PL: Use of a pharmacokinetic/pharmacodynamic approach in the cat to determine a dosage regimen for the COX-2 selective drug robenacoxib. J Vet Pharmacol Ther. 2009 Feb;32(1):18-30. doi: 10.1111/j.1365-2885.2008.01016.x. [Article]
- Giraudel JM, Gruet P, Alexander DG, Seewald W, King JN: Evaluation of orally administered robenacoxib versus ketoprofen for treatment of acute pain and inflammation associated with musculoskeletal disorders in cats. Am J Vet Res. 2010 Jul;71(7):710-9. doi: 10.2460/ajvr.71.7.710. [Article]
- Schmid VB, Seewald W, Lees P, King JN: In vitro and ex vivo inhibition of COX isoforms by robenacoxib in the cat: a comparative study. J Vet Pharmacol Ther. 2010 Oct;33(5):444-52. doi: 10.1111/j.1365-2885.2010.01166.x. [Article]
- Silber HE, Burgener C, Letellier IM, Peyrou M, Jung M, King JN, Gruet P, Giraudel JM: Population pharmacokinetic analysis of blood and joint synovial fluid concentrations of robenacoxib from healthy dogs and dogs with osteoarthritis. Pharm Res. 2010 Dec;27(12):2633-45. doi: 10.1007/s11095-010-0262-z. Epub 2010 Oct 5. [Article]
- Gruet P, Seewald W, King JN: Evaluation of subcutaneous and oral administration of robenacoxib and meloxicam for the treatment of acute pain and inflammation associated with orthopedic surgery in dogs. Am J Vet Res. 2011 Feb;72(2):184-93. doi: 10.2460/ajvr.72.2.184. [Article]
- Marshall JF, Bhatnagar AS, Bowman SG, Howard CM, Morris NN, Skorich DA, Redding CD, Blikslager AT: Evaluation of the cyclooxygenase selectivity of robenacoxib and its effect on recovery of ischemia-injured jejunal mucosa in horses. Am J Vet Res. 2011 Feb;72(2):226-32. doi: 10.2460/ajvr.72.2.226. [Article]
- King JN, Arnaud JP, Goldenthal EI, Gruet P, Jung M, Seewald W, Lees P: Robenacoxib in the dog: target species safety in relation to extent and duration of inhibition of COX-1 and COX-2. J Vet Pharmacol Ther. 2011 Jun;34(3):298-311. doi: 10.1111/j.1365-2885.2010.01209.x. [Article]
- Kamata M, King JN, Seewald W, Sakakibara N, Yamashita K, Nishimura R: Comparison of injectable robenacoxib versus meloxicam for peri-operative use in cats: results of a randomised clinical trial. Vet J. 2012 Jul;193(1):114-8. doi: 10.1016/j.tvjl.2011.11.026. Epub 2012 Jan 9. [Article]
- Sano T, King JN, Seewald W, Sakakibara N, Okumura M: Comparison of oral robenacoxib and ketoprofen for the treatment of acute pain and inflammation associated with musculoskeletal disorders in cats: a randomised clinical trial. Vet J. 2012 Aug;193(2):397-403. doi: 10.1016/j.tvjl.2012.02.008. Epub 2012 Mar 18. [Article]
- Edamura K, King JN, Seewald W, Sakakibara N, Okumura M: Comparison of oral robenacoxib and carprofen for the treatment of osteoarthritis in dogs: a randomized clinical trial. J Vet Med Sci. 2012 Sep;74(9):1121-31. Epub 2012 May 17. [Article]
- Waldherr K, Zurbriggen A, Spreng DE, Forterre S: In vitro cytoprotective effects of acetylsalicylic acid, carprofen, meloxicam, or robenacoxib against apoptosis induced by sodium nitroprusside in canine cruciate ligament cells. Am J Vet Res. 2012 Nov;73(11):1752-8. doi: 10.2460/ajvr.73.11.1752. [Article]
- Bennett D, Eckersall PD, Waterston M, Marchetti V, Rota A, McCulloch E, Sbrana S: The effect of robenacoxib on the concentration of C-reactive protein in synovial fluid from dogs with osteoarthritis. BMC Vet Res. 2013 Mar 1;9:42. doi: 10.1186/1746-6148-9-42. [Article]
- Gruet P, Seewald W, King JN: Robenacoxib versus meloxicam for the management of pain and inflammation associated with soft tissue surgery in dogs: a randomized, non-inferiority clinical trial. BMC Vet Res. 2013 May 2;9:92. doi: 10.1186/1746-6148-9-92. [Article]
- King S, Roberts ES, Roycroft LM, King JN: Evaluation of oral robenacoxib for the treatment of postoperative pain and inflammation in cats: results of a randomized clinical trial. ISRN Vet Sci. 2012 Jul 1;2012:794148. doi: 10.5402/2012/794148. Print 2012. [Article]
- Monteiro-Steagall BP, Steagall PV, Lascelles BD: Systematic review of nonsteroidal anti-inflammatory drug-induced adverse effects in dogs. J Vet Intern Med. 2013 Sep-Oct;27(5):1011-9. doi: 10.1111/jvim.12127. Epub 2013 Jun 19. [Article]
- Tamura J, Itami T, Ishizuka T, Fukui S, Ooyama N, Miyoshi K, Sano T, Yamashita K: Sparing effect of robenacoxib on the minimum alveolar concentration for blunting adrenergic response (MAC-BAR) of sevoflurane in dogs. J Vet Med Sci. 2014 Jan;76(1):113-7. Epub 2013 Sep 4. [Article]
- External Links
- ChemSpider
- 4938295
- 1250203
- ChEBI
- 76269
- ChEMBL
- CHEMBL2107774
- ZINC
- ZINC000000007562
- Wikipedia
- Robenacoxib
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
- Not Available
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.00411 mg/mL ALOGPS logP 4.68 ALOGPS logP 4.58 Chemaxon logS -4.9 ALOGPS pKa (Strongest Acidic) 3.65 Chemaxon pKa (Strongest Basic) -2.5 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 49.33 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 76.36 m3·mol-1 Chemaxon Polarizability 28.89 Å3 Chemaxon Number of Rings 2 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 splash10-00lr-1974000000-5bc9e1cd610acca8a615 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-004i-0009000000-fd8e15a9d08b9392d3fa Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0a6r-0009000000-716733e6a067c7774cdf Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-00or-0069000000-927a690320db99e98138 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-07gi-7179000000-0f1fe8f2d008d8c6dc65 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0gb9-0190000000-2e4edb2517783018de05 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0j59-0390000000-8c8e22447b31a467131a 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]- 172.5197 predictedDeepCCS 1.0 (2019) [M+H]+ 174.8777 predictedDeepCCS 1.0 (2019) [M+Na]+ 182.55737 predictedDeepCCS 1.0 (2019)
Targets
![](https://go.drugbank.com/assets/locked/DrugTargets2-682eb846d210ae4bf33ca03febccfb57bb1c61318e699b729e5df4dfab2c5b67.png)
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1. DetailsCyclooxygenase 2
- Kind
- Protein
- Organism
- Canis lupus familiaris
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Not Available
- Specific Function
- Enzyme binding
- Gene Name
- PTGS2
- Uniprot ID
- Q8SPQ9
- Uniprot Name
- Cyclooxygenase 2
- Molecular Weight
- 68974.625 Da
Drug created at February 25, 2016 18:53 / Updated at February 21, 2021 18:53