Carprofen

Base Information

• Chemical Name: Carprofen
• CAS No.: 53716-49-7
• Deprecated CAS: 52263-47-5
• Molecular Formula: C15H12ClNO2
• Molecular Weight: 273.719
• Hs Code.: 29339900
• European Community (EC) Number: 258-712-4
• NSC Number: 758154,297935
• UNII: FFL0D546HO
• DSSTox Substance ID: DTXSID1045871
• Nikkaji Number: J291.247C,J291.248A,J68.117B
• Wikipedia: Carprofen
• Wikidata: Q905755
• NCI Thesaurus Code: C65290
• RXCUI: 20343
• Pharos Ligand ID: H5QXSQKN9H1S
• Metabolomics Workbench ID: 145553
• ChEMBL ID: CHEMBL1316
• Mol file: 53716-49-7.mol

Synonyms:(+-)-isomer of carprofen;(R)-isomer of carprofen;(S)-isomer of carprofen;C 5720;carprofen;carprofen, (+-)-isomer;carprofen, (R)-isomer;carprofen, (S)-isomer;Ro 20-5720;Ro 205720

Chemical Property of Carprofen

Chemical Property:

• Appearance/Colour: Off-white crystalline solid
• Vapor Pressure: 3.45E-11mmHg at 25°C
• Melting Point: 186-188 °C
• Refractive Index: 1.731
• Boiling Point: 509.1 °C at 760 mmHg
• PKA: 4.84±0.30(Predicted)
• Flash Point: 261.7 °C
• PSA: 53.09000
• Density: 1.42 g/cm³
• LogP: 4.16260
• Storage Temp.: 0-6°C
• Solubility.: DMSO: soluble20mg/mL, clear
• XLogP3: 4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 273.0556563
• Heavy Atom Count: 19
• Complexity: 362

Purity/Quality:

98%min ^*data from raw suppliers

racCarprofen ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T, Xn
• Hazard Codes: T,Xn
• Statements: 25-36/37/38-20/21/22
• Safety Statements: 45-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C1=CC2=C(C=C1)C3=C(N2)C=CC(=C3)Cl)C(=O)O
• Description: Carprofen 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 .
• Uses: Carprofen 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 . antiinflammatory, analgesic Carprofen 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.
• Therapeutic Function: Antiinflammatory

Technology Process of Carprofen

There total 63 articles about Carprofen which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

methyl 9-benzoyl-2-(6-chlorocarbazol-2-yl)propanoate → 2-(6-chloro-carbazol-2-yl)-propionic acid (53716-49-7,52263-83-9)

Guidance literature:

With sodium hydroxide; In methanol; at 80 ℃; for 1.5h;

DOI:10.1002/chem.202003430

Reference yield: 91.0%

2-(3-((4-chlorophenyl)amino)-4-chlorophenyl)propanoic acid → 2-(6-chloro-carbazol-2-yl)-propionic acid (53716-49-7,52263-83-9)

Guidance literature:

With triphenylphosphine; palladium dichloride; sodium t-butanolate; In N,N-dimethyl-formamide; at 100 ℃; for 10h; Reagent/catalyst; Inert atmosphere;

Reference yield: 91.0%

ethyl 2-(6-chloro-9H-carbazol-2-yl)propanoate (52262-89-2) → 2-(6-chloro-carbazol-2-yl)-propionic acid (53716-49-7,52263-83-9)

Guidance literature:

With water; sodium hydroxide; In methanol; at 20 ℃; for 8h; Inert atmosphere; Schlenk technique;

upstream raw materials:

methyl (2RS)-2-(6-chloro-9H-carbazol-2-yl)propanoate

2-(1-cyanoethyl)-6-chlorocarbazole

2-(6-Chloro-9H-carbazol-2-yl)-2-trimethylsilanyloxy-propionitrile

(6-chloro-2-carbazolyl)methylmalonic acid diethyl ester

Downstream raw materials:

(S)-carprofen

(R)-6-chloro-α-methyl-carbazole-2-acetic acid

Refernces

• 1、 Bhatthula, Bharath kumar goud,Kanchani, Janardhan reddy,Arava, Veera reddy,Subha. "Total synthesis of carbazole alkaloids". . p. 874 - 887. Retrieved 2019/01/11.
• 2、 -. "Carprofen and its intermediate synthesis method". . . Retrieved 2019/06/05.