2-(6-chloro-9H-carbazol-2-yl)propanoic acid

• ChemBase ID: 700
• Molecular Formular: C15H12ClNO2
• Molecular Mass: 273.71428
• Monoisotopic Mass: 273.05565631
• SMILES: Clc1cc2c3c([nH]c2cc1)cc(C(C)C(=O)O)cc3
• Canonical SMILES: OC(=O)C(c1ccc2c(c1)[nH]c1c2cc(cc1)Cl)C
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(6-chloro-9H-carbazol-2-yl)propanoic acid
• IUPAC Traditional name: 2-(6-chloro-9H-carbazol-2-yl)propanoic acid; carprofen
• Brand Name: Rimadyl; Ridamyl
• Synonyms: 2-(6-chloro-9H-carbazol-2-yl)propanoic acid; (dl)-6-Chloro-α-methylcarbazole-2-acetic Acid; C 5720; Carprodyl; (+/-)-Carprofen; Imadyl; NSC 297935; Rimadyl; Ro 20-5720; rac Carprofen; Carprofene [inn-french]; Carprofeno [inn-spanish]; Carprofenum [inn-latin]; 6-Chloro-alpha-methylcarbazole-2-acetic acid; 6-Chloro-alpha-methyl-9H-carbazole-2-acetic acid; 2-(6-Chloro-9H-carbazol-2-yl)propanoic acid; Carprofen; 6-Chloro-α-methyl-9H-carbazole-2-acetic acid; Carprofen; 6-氯-α-甲基-9H-咔唑-2-乙酸; 卡洛芬

Database IDs

• CAS Number: 53716-49-7
• EC Number: 258-712-4
• MDL Number: MFCD00079028
• PubChem SID: 46505357; 160964163; 24860673
• PubChem CID: 2581

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.4157977
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 2.7586398
• LogD (pH = 7.4): 0.99989116
• Log P: 3.875665
• Molar Refractivity: 74.1591 cm^3
• Polarizability: 30.937445 Å^3
• Polar Surface Area: 53.09 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.09
• LOG S: -4.86
• Solubility (Water): 3.79e-03 g/l

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Practically insoluble at 25oC
• Apperance: Off-White Solid
• Melting Point: 186-188°C
• Hydrophobicity(logP): 3.8; 3.978

Safety Information

• Storage Condition: Refrigerator
• RTECS: FE3180000
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 25
• Safety Statements: 45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3

Pharmacology Properties

• Target: Others
• Gene Information: human ... IL8RA(3577)
• Mechanism of Action: Prostaglandin antagonist

Product Information

• Purity: 95%
• Grade: VETRANAL™, analytical standard
• Salt Data: Free Base
• Application(s): Analgesic; Antiinflammatory agent; Antipyretic
• Empirical Formula (Hill Notation): C15H12ClNO2

DETAILS

DrugBank - DB00821

• Drug 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]
• Indication: For use as a pain reliever in the treatment of joint pain and post-surgical pain.
• Pharmacology: 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.
• 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
• Biotransformation: Hepatic.
• Absorption: Rapidly and nearly completely absorbed (more than 90% bioavailable) when administered orally.
• Half Life: Approximately 8 hours (range 4.5–9.8 hours) in dogs.
• Protein Binding: High (99%)
• External Links: Wikipedia

Sigma Aldrich - 33975

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 33975.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - C184350

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 also used for the relief from pain and inflammation assoc

REFERENCES

• Randall, L.O., et al.: Arch. Int. Pharmacodyn., 220, 94 (1976)
• Yu, T.F., et al.: J. Clin. Pharmacol., 20, 347 (1976)
• O’Brien, W.M., et al.: Pharmacotherapy, 7, 16 (1976)
• Ger. Pat., 1974, 2 337 340; CA, 80, 108366q, (synth, pharmacol)
• Randall, L.O. et al., Arch. Int. Pharmacodyn. Ther., 1976, 220, 94, (pharmacol)
• Hodshon, B.J. et al., Biomed. Mass Spectrom., 1979, 6, 325, (ms)
• Kemmerer, J.M. et al., J. Pharm. Sci., 1979, 68, 1274, (isomers)
• Strub, K. et al., Eur. J. Rheumatol. Inflammation, 1982, 5, 478; 492, (pharmacol, rev)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 10
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, CCK800