This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Robenacoxib
Accession Number
DB11455
Type
Small Molecule
Groups
Experimental, Vet approved
Description

Robenacoxib is a non-steroidal anti-inflammatory drug used in veterinary medicine for the relief of pain and inflammation in cats and dogs.

Structure
Thumb
Synonyms
  • Robénacoxib
  • Robenacoxib
  • Robenacoxibum
Categories
UNII
Z588009C7C
CAS number
220991-32-2
Weight
Average: 327.279
Monoisotopic: 327.088241315
Chemical Formula
C16H13F4NO2
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

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UCyclooxygenase 2
inhibitor
Canis 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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe risk or severity of bleeding and hemorrhage can be increased when Robenacoxib is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding and hemorrhage can be increased when Robenacoxib is combined with (S)-Warfarin.
1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic AcidThe risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Robenacoxib is combined with 1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid.
1-benzylimidazoleThe risk or severity of hypertension can be increased when 1-benzylimidazole is combined with Robenacoxib.
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of hypertension can be increased when 2,5-Dimethoxy-4-ethylamphetamine is combined with Robenacoxib.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of hypertension can be increased when Robenacoxib is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,4-MethylenedioxyamphetamineThe risk or severity of hypertension can be increased when 3,4-Methylenedioxyamphetamine is combined with Robenacoxib.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of hypertension can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Robenacoxib.
4-hydroxycoumarinThe risk or severity of bleeding and hemorrhage can be increased when Robenacoxib is combined with 4-hydroxycoumarin.
4-MethoxyamphetamineThe risk or severity of hypertension can be increased when 4-Methoxyamphetamine is combined with Robenacoxib.
Food Interactions
Not Available

References

General References
  1. 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. [PubMed:21736587]
  2. 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. [PubMed:19161454]
  3. 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. [PubMed:23434263]
  4. 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. [PubMed:19161453]
  5. 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. [PubMed:20004922]
  6. 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. [PubMed:21480932]
  7. 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. [PubMed:21767277]
  8. 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. [PubMed:23438125]
  9. 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. [PubMed:23726662]
  10. 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. [PubMed:20444036]
  11. 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. [PubMed:19161451]
  12. 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. [PubMed:19161452]
  13. 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. [PubMed:20594071]
  14. 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. [PubMed:20840388]
  15. 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. [PubMed:20922466]
  16. 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. [PubMed:21281192]
  17. 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. [PubMed:21281197]
  18. 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. [PubMed:21492194]
  19. 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. [PubMed:22227226]
  20. 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. [PubMed:22430026]
  21. 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. [PubMed:22673598]
  22. 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. [PubMed:23106460]
  23. 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. [PubMed:23452411]
  24. 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. [PubMed:23638669]
  25. 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. [PubMed:23738129]
  26. 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. [PubMed:23782347]
  27. 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. [PubMed:24004933]
External Links
ChemSpider
4938295
ChEBI
76269
ChEMBL
CHEMBL2107774
Wikipedia
Robenacoxib

Clinical Trials

Clinical Trials
Not Available

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
PropertyValueSource
Water Solubility0.00411 mg/mLALOGPS
logP4.68ALOGPS
logP4.58ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)3.65ChemAxon
pKa (Strongest Basic)-2.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.33 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity76.36 m3·mol-1ChemAxon
Polarizability28.89 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
Aniline or substituted anilines / Fluorobenzene / Halobenzene / Aryl fluoride / Aryl halide / Amino acid or derivatives / Amino acid / Carboxylic acid derivative / Carboxylic acid / Secondary amine
show 13 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
organofluorine compound, monocarboxylic acid, secondary amino compound, aromatic amino acid (CHEBI:76269)

Targets

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 on February 25, 2016 11:53 / Updated on December 14, 2018 05:46