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targets (2) transporters (1)
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Identification
Name Carprofen
Accession Number DB00821 (APRD00849)
Type small molecule
Groups approved
Description

Carprofen is a non-steroidal anti-inflammatory drug (NSAID) that is used by veterinarians as a supportive treatment for the relief of arthritic symptoms in geriatric dogs. Carprofen was previously used in human medicine for over 10 years (1985-1995). It was generally well tolerated, with the majority of adverse effects being mild, such as gastro-intestinal pain and nausea, similar to those recorded with aspirin and other non-steroidal anti-inflammatory drugs. It is no longer marketed for human usage, after being withdrawn on commercial grounds. [Wikipedia]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
2-(6-Chloro-9H-carbazol-2-yl)propanoic acid
6-Chloro-alpha-methyl-9H-carbazole-2-acetic acid
6-Chloro-alpha-methylcarbazole-2-acetic acid
Carprofene [inn-french]
Carprofeno [inn-spanish]
Carprofenum [inn-latin]
Salts Not Available
Brand names
Name Company
Ridamyl
Rimadyl
Brand mixtures Not Available
Categories
  • Photosensitizing Agents
CAS number 53716-49-7
Weight Average: 273.714
Monoisotopic: 273.05565634
Chemical Formula C15H12ClNO2
InChI Key InChIKey=PUXBGTOOZJQSKH-UHFFFAOYSA-N
InChI
InChI=1S/C15H12ClNO2/c1-8(15(18)19)9-2-4-11-12-7-10(16)3-5-13(12)17-14(11)6-9/h2-8,17H,1H3,(H,18,19)
Plain Text
IUPAC Name
2-(6-chloro-9H-carbazol-2-yl)propanoic acid
SMILES
CC(C(O)=O)C1=CC2=C(C=C1)C1=C(N2)C=CC(Cl)=C1
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Carbazoles
Substructures
  • Hydroxy Compounds
  • Acetates
  • Indoles and Indole Derivatives
  • Carboxylic Acids and Derivatives
  • Carbazoles
  • Pyrroles
  • Phenylacetates
  • Benzene and Derivatives
  • Aryl Halides
  • Halobenzenes
  • Heterocyclic compounds
  • Aromatic compounds
Pharmacology
Indication For use as a pain reliever in the treatment of joint pain and post-surgical pain.
Pharmacodynamics Carprofen is a non-steroidal anti-inflammatory drug (NSAID) of the propionic acid class that includes ibuprofen, naproxen, and ketoprofen. It is no longer used in the clinical setting, but is approved for use in dogs. Carprofen is non-narcotic and has characteristic analgesic and antipyretic activity approximately equipotent to indomethacin in animal models.
Mechanism of action The mechanism of action of carprofen, like that of other NSAIDs, is believed to be associated with the inhibition of cyclooxygenase activity. Two unique cyclooxygenases have been described in mammals. The constitutive cyclooxygenase, COX-1, synthesizes prostaglandins necessary for normal gastrointestinal and renal function. The inducible cyclooxygenase, COX-2, generates prostaglandins involved in inflammation. Inhibition of COX-1 is thought to be associated with gastrointestinal and renal toxicity while inhibition of COX-2 provides anti-inflammatory activity. In an in vitro study using canine cell cultures, carprofen demonstrated selective inhibition of COX-2 versus COX-1.
Absorption Rapidly and nearly completely absorbed (more than 90% bioavailable) when administered orally.
Volume of distribution Not Available
Protein binding High (99%)
Metabolism Hepatic.
Route of elimination Not Available
Half life Approximately 8 hours (range 4.5–9.8 hours) in dogs.
Clearance Not Available
Toxicity Symptoms of NSAID overdose include dizziness and nystagmus. Oral LD50 in mouse and rat is 282 mg/kg and 149 mg/kg, respectively.
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Hoffmann la roche inc
Packagers
Dosage forms
Form Route Strength
Tablet Oral
Prices Not Available
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 197.5 °C PhysProp
water solubility Practically insoluble at 25 °C Not Available
logP 3.8 Not Available
Predicted Properties
Property Value Source
water solubility 3.79e-03 g/l ALOGPS
logP 4.09 ALOGPS
logP 3.88 ChemAxon
logS -4.9 ALOGPS
pKa (strongest acidic) 4.42 ChemAxon
physiological charge -1 ChemAxon
hydrogen acceptor count 2 ChemAxon
hydrogen donor count 2 ChemAxon
polar surface area 53.09 ChemAxon
rotatable bond count 2 ChemAxon
refractivity 74.16 ChemAxon
polarizability 28.56 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
PubChem Compound 2581 Link_out
PubChem Substance 46505357 Link_out
ChemSpider 2483 Link_out
BindingDB 50097346 Link_out
ChEBI 364453 Link_out
ChEMBL 364453 Link_out
Therapeutic Targets Database DAP000975 Link_out
PharmGKB PA164781361 Link_out
Drug Product Database 2246557 Link_out
Wikipedia http://en.wikipedia.org/wiki/Carprofen Link_out
ATC Codes Not Available
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS show (24.5 KB)
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Prostaglandin G/H synthase 2

Pharmacological action: yes
Actions: inhibitor

May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity

Organism class: human
UniProt ID: P35354 Link_out
Gene: PTGS2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Kay-Mugford P, Benn SJ, LaMarre J, Conlon P: In vitro effects of nonsteroidal anti-inflammatory drugs on cyclooxygenase activity in dogs. Am J Vet Res. 2000 Jul;61(7):802-10. Pubmed
  2. Brideau C, Van Staden C, Chan CC: In vitro effects of cyclooxygenase inhibitors in whole blood of horses, dogs, and cats. Am J Vet Res. 2001 Nov;62(11):1755-60. Pubmed
  3. Wilson JE, Chandrasekharan NV, Westover KD, Eager KB, Simmons DL: Determination of expression of cyclooxygenase-1 and -2 isozymes in canine tissues and their differential sensitivity to nonsteroidal anti-inflammatory drugs. Am J Vet Res. 2004 Jun;65(6):810-8. Pubmed
  4. Beretta C, Garavaglia G, Cavalli M: COX-1 and COX-2 inhibition in horse blood by phenylbutazone, flunixin, carprofen and meloxicam: an in vitro analysis. Pharmacol Res. 2005 Oct;52(4):302-6. Pubmed
  5. Narlawar R, Perez Revuelta BI, Haass C, Steiner H, Schmidt B, Baumann K: Scaffold of the cyclooxygenase-2 (COX-2) inhibitor carprofen provides Alzheimer gamma-secretase modulators. J Med Chem. 2006 Dec 28;49(26):7588-91. Pubmed
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

2. Prostaglandin G/H synthase 1

Pharmacological action: unknown
Actions: inhibitor

May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells

Organism class: human
UniProt ID: P23219 Link_out
Gene: PTGS1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Beretta C, Garavaglia G, Cavalli M: COX-1 and COX-2 inhibition in horse blood by phenylbutazone, flunixin, carprofen and meloxicam: an in vitro analysis. Pharmacol Res. 2005 Oct;52(4):302-6. Pubmed
Transporters

1. Solute carrier family 22 member 6

Actions: inhibitor
UniProt ID: Q4U2R8 Link_out
Gene: hROAT1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Kuze K, Graves P, Leahy A, Wilson P, Stuhlmann H, You G: Heterologous expression and functional characterization of a mouse renal organic anion transporter in mammalian cells. J Biol Chem. 1999 Jan 15;274(3):1519-24. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19