Carprofen
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Basic information
- CAS
53716-49-7- Standard SMILES
CC(C(=O)O)c1ccc2c(c1)[nH]c1ccc(Cl)cc12- InChIKey
PUXBGTOOZJQSKH-UHFFFAOYSA-N- Molecular formula
- C15H12ClNO2
- Average molar mass
- 273.71 g/mol
- Monoisotopic mass
- 273.0556563
Overview
Carprofen is propanoic acid in which one of the methylene hydrogens is substituted by a 6-chloro-9H-carbazol-2-yl group. A non-steroidal anti-inflammatory drug, it is no longer used in human medicine but is still used for treatment of arthritis in elderly dogs. It has a role as a non-steroidal anti-inflammatory drug, an EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor and a photosensitizing agent. It is an organochlorine compound and a member of carbazoles.
Names & identifiers
- Preferred name
- Carprofen
- IUPAC
- 2-(6-chloro-9H-carbazol-2-yl)propanoic acid
- English name
- Carprofen
- Molecular formula
- C15H12ClNO2
- Molecular weight
- 273.71
Names & synonyms
carprofen53716-49-72-(6-Chloro-9H-carbazol-2-yl)propanoic acidRimadylCarprofeno6-Chloro-alpha-methyl-9H-carbazole-2-acetic acidCarprofeneCarprofenumCarprodyl6-Chloro-alpha-methylcarbazole-2-acetic acidRo 20-5720/000DTXSID1045871
Show more names
rac Carprofenc5720imadylRidamylCarolinekanujofen
Ro-20-5720/000Rimadyl Caplets(+-)-6-Chloro-alpha-methylcarbazole-2-acetic acidCarprofen for veterinary useFFL0D546HONSC-2979352-(6-Chloro-9H-carbazol-2-yl)-propionic acidRimadyl Chewable Tablets
Database identifiers
- CAS
53716-49-7- PubChem CID
- 2581
- DTXSID
DTXSID1045871- ChEMBL
CHEMBL1316- ChEBI
CHEBI:364453- UNII
- FFL0D546HO
- EC Number
- 258-712-4
- Nikkaji
- J68.117B
Properties
Computed structural propertiesFilling in
- XLogP
- 4
- Topological polar surface area
- 53.1 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 2
- Heavy atoms
- 19
- Formal charge
- 0
- Complexity
- 362
Experimental & physicochemical properties
LogP
3.8
4.04
Solubility
Practically insoluble at 25 °C
3.79e-03 g/L
>41.1 [ug/mL] (The mean of the results at pH 7.4)
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Animal Drugs
EMA approved medicines: Veterinary medicine
Active Ingredients (Carprofen) -> FDA Greenbook
Pharmaceuticals -> UK Veterinary Medicines Directorate List
Pharmaceuticals -> Animal Drugs -> Approved in Taiwan
Melting Point
195-199
197.5 °C
Physical DescriptionSolid
Collision Cross Section
156.1 Ų [M+H]+ [CCS Type: TW]
161.46 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 186 · 186-1880C
- Boiling point
- 509.1 · 509.1±35.0 °C(Predicted)
- Density
- 1.2011 · 1.2011 (rough estimate)
- refractive index
- 1.52 · 1.5200 (estimate)
- storage temp.
- 2 · Sealed in dry,2-8°C
- solubility
- 20 mg/mL, · DMSO: soluble20mg/mL, clear
- form
- powder
- pka
- 4.84 · 4.84±0.30(Predicted)
- color
- white to beige
- Merck
- 14 · 14,1862
- Major Application
- forensics and toxicologypharmaceutical (small molecule)
- 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)
- InChIKey
- PUXBGTOOZJQSKH-UHFFFAOYSA-N
- SMILES
- N1C2=C(C=C(Cl)C=C2)C2=C1C=C(C(C)C(O)=O)C=C2
- CAS DataBase Reference
- 53716 · 53716-49-7(CAS DataBase Reference)
- FDA UNII
- 0 D546HO · FFL0D546HO
- EPA Substance Registry System
- 9 H-Carbazole-2-acetic · 9H-Carbazole-2-acetic acid, 6-chloro-.alpha.-methyl- (53716-49-7)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 6 · GHS06
- Signal word
- Danger
- Hazard statements
- 301 · H301
- Precautionary statements
- 301 · P301+P330+P331+P310
- PPE
- 2 · Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
- Hazard Codes
- T,Xn
- Risk Statements
- 25 · 25-36/37/38-20/21/22
- Safety Statements
- 45 · 45-36-26
- RIDADR
- 2811 · UN 2811
- WGK Germany
- 3 · 3
- RTECS
- 3180000 · FE3180000
- HazardClass
- 6.1 · 6.1
- PackingGroup
- III
- HS Code
- 29339900 · 29339900
- Storage Class
- 6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard Classifications
- 3 Oral · Acute Tox. 3 Oral
- Toxicity
- 50 orally · LD50 orally in mice: 400 mg/kg (Berger, Corraz)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 2% (1 of 50) of reports.
Danger
H301 (98%): Toxic if swallowed [Danger Acute toxicity, oral]
P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 50 reports by companies from 4 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory InformationCarprofen: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Other Safety InformationIMAP assessments - 9H-Carbazole-2-acetic acid, 6-chloro-.alpha.-methyl-, (.+-.)-: Environment tier I assessment
Hazard Classes and CategoriesAcute Tox. 3 (98%)
Safety data
- PPE
- Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
- wgk
- 3
- rtecs
- FE3180000
- ridadr
- UN 2811
- hs_code
- 29339900
- Toxicity
- LD50 orally in mice: 400 mg/kg (Berger, Corraz)
- risk_code
- 25-36/37/38-20/21/22
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- hazard_code
- T,Xn
- safety_code
- 45-36-26
- hazard_class
- 6.1
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- packing_group
- III
- Hazard statements
- H301
- Hazard Classifications
- Acute Tox. 3 Oral
- Precautionary statements
- P301+P330+P331+P310
Chemistry & industry
Pharmacology
ATC CodeQM - Musculo-skeletal system
Protein BindingHigh (99%)
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 <i>in vitro</i> study using canine cell cultures, carprofen demonstrated selective inhibition of COX-2 versus COX-1.
Biological Half-LifeApproximately 8 hours (range 4.5–9.8 hours) in dogs.
Metabolism/MetabolitesHepatic.
MeSH Pharmacological Classification
Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects.
Drugs that are pharmacologically inactive but when exposed to ultraviolet radiation or sunlight are converted to their active metabolite to produce a beneficial reaction affecting the diseased tissue. These compounds can be administered topically or systemically and have been used therapeutically to treat psoriasis and various types of neoplasms.
Absorption, Distribution and ExcretionRapidly and nearly completely absorbed (more than 90% bioavailable) when administered orally.
Cellular LocationsCytoplasm
Metabolite PathwaysCarprofen Action Pathway
Uses & manufacturing
Use Classification
Animal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients
Pharmaceuticals -> Animal Drugs -> Approved in Taiwan
Applications
DescriptionCarprofen is a non-steroidal anti-inflammatory drug (NSAID) commonly used in animals to combat pain and inflammation, particularly as associated with osteoarthritis. Like many NSAIDs, carprofen inhibits both cyclooxygenases COX-1 and COX-2 (IC50s = 22.3 and 3.9 μM, respectively). It also inhibits fatty acid amide hydrolase (IC50 = 74 μM), blocking the metabolism of the cannabinoid receptor ligand, arachidonoyl ethanolamide .
HistoryCarprofen has strong anti-inflammatory and analgesic activity. It has been used in human medicine for more than 10 years at doses of 150 to 600 mg per day. In human clinical trials, Carprofen was generally well tolerated. Most adverse reactions were transient and mild, such as gastrointestinal discomfort or pain and nausea. The incidence of side effects in humans is similar to that of aspirin and other NSAIDs. However, for commercial reasons, carprofen has been withdrawn from the market and is no longer available for human use.
UsesCarprofen is a non-steroidal anti-inflammatory drug (NSAID) commonly used in animals to combat pain and inflammation, particularly as associated with osteoarthritis. Like many NSAIDs, carprofen inhibits both cyclooxygenases COX-1 and COX-2 (IC50s = 22.3 and 3.9 μM, respectively). It also inhibits fatty acid amide hydrolase (IC50 = 74 μM), blocking the metabolism of the cannabinoid receptor ligand, arachidonoyl ethanolamide .
Usesantiinflammatory, analgesic
UsesCarprofen is a non steroidal anti-inflammatory that is used by veterinarians for the relief of arthritic systems in dogs. It can be used for joint pain or post operative inflammation. Carprofen, is al so used for the relief from pain and inflammation associated with osteoarthritis, hip dysplasia and other joint issues.
Upstream & downstream products
Upstream raw materials
Additional notes
DefinitionChEBI: Propanoic acid in which one of the methylene hydrogens is substituted by a 6-chloro-9H-carbazol-2-yl group. A non-steroidal anti-inflammatory drug, it is no longer used in human medicine but is still used for treatment of arthritis in elderly dogs.
Related reactions
4 records
Compound notes
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