Tolfenamic acid

Base Information

• Chemical Name: Tolfenamic acid
• CAS No.: 13710-19-5
• Molecular Formula: C14H12ClNO2
• Molecular Weight: 261.708
• Hs Code.: 29224919
• European Community (EC) Number: 237-264-3
• NSC Number: 757873
• UNII: 3G943U18KM
• DSSTox Substance ID: DTXSID1045409
• Nikkaji Number: J3.125I
• Wikipedia: Tolfenamic_acid
• Wikidata: Q59412
• NCI Thesaurus Code: C87328
• Pharos Ligand ID: P6UJVP28YX23
• Metabolomics Workbench ID: 49713
• ChEMBL ID: CHEMBL121626
• Mol file: 13710-19-5.mol

Synonyms:Bifenac;Clotam;GEA 6414;N-(3-chloro-2-methylphenyl)anthranilic acid;N-(3-chloro-o-tolyl)anthranilic acid;Rociclyn;tolfenamic acid

Chemical Property of Tolfenamic acid

Chemical Property:

• Vapor Pressure: 2.66E-07mmHg at 25°C
• Melting Point: 210-214 °C
• Refractive Index: 1.658
• Boiling Point: 405.4 °C at 760 mmHg
• PKA: 3.66±0.36(Predicted)
• Flash Point: 199 °C
• PSA: 49.33000
• Density: 1.333 g/cm³
• LogP: 4.16320
• Storage Temp.: Refrigerator
• Solubility.: Practically insoluble in water, soluble in dimethylformamide, sparingly soluble in ethanol and in methylene chloride. It dissolves in dilute solutions of alkali hydroxides.
• Water Solubility.: Soluble in water (slightly), acetone (~10 mg/ml), DMSO (52 mg/ml at 25°C), methanol (~10 mg/ml) and ethanol (50 mg/ml).
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 261.0556563
• Heavy Atom Count: 18
• Complexity: 298

Purity/Quality:

98%min ^*data from raw suppliers

Tolfenamic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C=CC=C1Cl)NC2=CC=CC=C2C(=O)O
• Recent ClinicalTrials: Evaluation of Tolfenamic Acid in Individuals With PSP at 12-Weeks
• Uses: antiinflammatory, analgesia Amidated GRF fragment equipotent to GRF in release of somatotropin from anterior pituitary A non steroidal anti-inflammatory agent found to inhibit COX-2 isoenzymes Tolfenamic acid is a non-steroidal anti-inflammatory agent. It interferes with synthesis of β-amyloid precursor protein, and thus Aβ peptides, by promoting degradation of an essential transcription factor. It inhibits fMLP- and A23187-induced Ca2+ influx in human PMNL with an IC50 value of approximately 20 μM. Non-steroidal anti-inflammatory drugs (NSAIDs).
• Clinical Use: NSAID: Treatment of migraine
• Drug interactions: Potentially hazardous interactions with other drugs ACE inhibitors and angiotensin-II antagonists: antagonism of hypotensive effect; increased risk of nephrotoxicity and hyperkalaemia. Analgesics: avoid concomitant use of 2 or more NSAIDs, including aspirin (increased side effects); avoid with ketorolac (increased risk of side effects and haemorrhage). Antibacterials: possibly increased risk of convulsions with quinolones. Anticoagulants: effects of coumarins and phenindione enhanced; possibly increased risk of bleeding with heparins, dabigatran and edoxaban. Antidepressants: increased risk of bleeding with SSRIs and venlafaxine. Antidiabetic agents: effects of sulphonylureas enhanced. Antiepileptics: possibly increased phenytoin concentration. Antivirals: increased risk of haematological toxicity with zidovudine; concentration possibly increased by ritonavir. Ciclosporin: may potentiate nephrotoxicity. Cytotoxics: reduced excretion of methotrexate; increased risk of bleeding with erlotinib. Diuretics: increased risk of nephrotoxicity; antagonism of diuretic effect; hyperkalaemia with potassium-sparing diuretics. Lithium: excretion decreased. Pentoxifylline: increased risk of bleeding. Tacrolimus: increased risk of nephrotoxicity

Technology Process of Tolfenamic acid

There total 9 articles about Tolfenamic acid 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: 88.6%

3-chloro-2-methylbenzenamine (87-60-5) + ortho-chlorobenzoic acid (118-91-2) → tolfenamic Acid (13710-19-5)

Guidance literature:

ortho-chlorobenzoic acid; With sodium hydroxide; for 1h; Reflux;

3-chloro-2-methylbenzenamine; With aluminum oxide; sodium hydroxide; for 3h; Reflux;

Reference yield: 87.0%

→ tolfenamic Acid (13710-19-5)

Guidance literature:

With copper; potassium carbonate; In N,N-dimethyl-formamide; at 130 ℃; for 12h;

Reference yield: 83.1%

3-chloro-2-methylbenzenamine (87-60-5) + 2-bromobenzoic-acid (88-65-3) → tolfenamic Acid (13710-19-5)

Guidance literature:

With copper(l) iodide; potassium carbonate; potassium iodide; In water; at 55 - 100 ℃; for 6h; Reagent/catalyst; Inert atmosphere;

upstream raw materials:

potassium o-bromobenzoate

3-chloro-2-methylbenzenamine

copper

2-bromobenzoic-acid

Downstream raw materials:

1,2:3,4-di-μ(2)-2-[(3-chloro-2-methylphenyl)amino]benzoato-O,O-1,3-bis-2-[(3-chloro-2-methylphenyl)amino]benzoato-O-1,2,4:2,3,4-di-μ(3)-oxo-tetrakis[di-n-butyltin(IV)]

1,2:3,4-di-μ(2)-2-[(3-chloro-2-methylphenyl)amino]benzoato-O,O-1,3-bis-2-[(3-chloro-2-methylphenyl)amino]benzoato-O-1,2,4:2,3,4-di-μ(3)-oxo-tetrakis[di-methyltin (IV)]

Refernces

• 1、 -. "2-arylamine compound and preparation method and application thereof". Paragraph 0108-0111; 0162-0165. . Retrieved 2021/05/05.
• 2、 Ma, Shumeng,Zhu, Longqing,Fan, Xiaohong,Luo, Tian,Liu, Dan,Liang, Ziyi,Hu, Xiaoling,Shi, Tao,Tan, Wen,Wang, Zhen. "Melatonin derivatives combat with inflammation-related cancer by targeting the Main Culprit STAT3". . . Retrieved 2020/12/02.