Tolmetin

Base Information

• Chemical Name: Tolmetin
• CAS No.: 26171-23-3
• Deprecated CAS: 87344-04-5
• Molecular Formula: C15H15NO3
• Molecular Weight: 257.289
• Hs Code.: 2933990090
• European Community (EC) Number: 247-497-2
• UNII: D8K2JPN18B
• DSSTox Substance ID: DTXSID2043951
• Nikkaji Number: J20.519B
• Wikipedia: Tolmetin
• Wikidata: Q3992411
• NCI Thesaurus Code: C29503
• RXCUI: 10636
• Pharos Ligand ID: VUJQ1ZN9PFPT
• Metabolomics Workbench ID: 42844
• ChEMBL ID: CHEMBL1020
• Mol file: 26171-23-3.mol

Synonyms:Anhydrous Tolmetin Sodium;Anhydrous, Tolmetin Sodium;Dihydrate Tolmetin Sodium;McN 2559;McN-2559;McN2559;Sodium Anhydrous, Tolmetin;Sodium, Tolmetin;Tolectin;Tolmetin;Tolmetin Sodium;Tolmetin Sodium Anhydrous;Tolmetin Sodium, Anhydrous;Tolmetin Sodium, Dihydrate

Chemical Property of Tolmetin

Chemical Property:

• Appearance/Colour: Off-white crystalline power
• Vapor Pressure: 7.77E-10mmHg at 25°C
• Melting Point: 156 °C
• Refractive Index: 1.589
• Boiling Point: 483.19 °C at 760 mmHg
• PKA: pKa 3.5(H2O t undefined I undefined) (Uncertain)
• Flash Point: 246.025 °C
• PSA: 59.30000
• Density: 1.18 g/cm³
• LogP: 2.19160
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: 222 mg/L
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 257.10519334
• Heavy Atom Count: 19
• Complexity: 347

Purity/Quality:

99% ^*data from raw suppliers

1-Methyl-5-p-toluoylpyrrole-2-aceticAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Nonsteroidal Antiinflammatory Drugs
• Canonical SMILES: CC1=CC=C(C=C1)C(=O)C2=CC=C(N2C)CC(=O)O
• Description: An antiinflammatory, analgesic, and antipyretic that is as efficacious as moderate doses of aspirin and better tolerated. Tolmetin produces a number of adverse effects including epigastric pain, dyspepsia, nausea, and vomiting. Tolmetin is approximately 99% plasma protein bound, yet does not interfere with concurrent treatment with oral hypoglycemics. Tolmetin has been found to be effective in the treatment of osteoarthritis and rheumatoid arthritis.
• Uses: inhibits synthesis of prostaglandins and exhibits expressed analgesic, anti-inflammatory, and fever-reducing properties. It is used for relieving weak to moderate pain in rheumatoid arthritis and osteoarthritis. Tolmetine is an NSAID.
• Indications: Tolmetin (Tolectin) is indicated for the relief of osteoarthritis, rheumatoid arthritis, ankylosing spondylitis, and moderate pain. It is ineffective in gouty arthritis for unknown reasons.Tolmetin can inhibit both COX-1 and COX-2 but has a moderate selectivity for COX-1. The most frequently reported side effects are GI disturbance and CNS reactions (e.g., headache, asthenia, and dizziness). These effects are less frequently observed than after aspirin or indomethacin use. Blood pressure elevation, edema, and weight gain or loss have been associated with tolmetin administration. Tolmetin metabolites in urine have been found to produce pseudoproteinuria in some laboratory tests.
• Therapeutic Function: Antiinflammatory
• Biological Functions: Tolmetin (Tolectin) is an antiinflammatory, analgesic, and antipyretic agent that produces the usual gastric distress and ulceration observed with NSAIDs. However, tolmetin is better tolerated than aspirin and produces less tinnitus and vertigo. Tolmetin is a substitute for indomethacin in indomethacin-sensitive patients and is unique among such drugs in that it can be used to treat juvenile arthritis.

Technology Process of Tolmetin

There total 30 articles about Tolmetin 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: 100.0%

ethyl 2-(1-methyl-5-(4-methylbenzoyl)-1H-pyrrol-2-yl)acetate (52074-58-5) → 1-methyl-5-(p-toluoyl)pyrrole-2-acetic acid (26171-23-3)

Guidance literature:

With sodium hydroxide; In methanol; water; for 2h; Reflux;

DOI:10.1016/j.tetlet.2010.09.025

Reference yield: 98.0%

1-Methyl-5-(4-methylbenzoyl)pyrrole-2-acetonitrile (26171-22-2) → 1-methyl-5-(p-toluoyl)pyrrole-2-acetic acid (26171-23-3)

Guidance literature:

1-Methyl-5-(4-methylbenzoyl)pyrrole-2-acetonitrile; With water; sodium hydroxide; In ethanol; for 6h; Reflux;

With hydrogenchloride; at 20 ℃;

DOI:10.1039/c6cc08213k

Reference yield: 98.0%

methyl 1-Methyl-5-(4-methylbenzoyl)-1H-pyrrole-2-acetate (33369-52-7) → 1-methyl-5-(p-toluoyl)pyrrole-2-acetic acid (26171-23-3)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; at 20 ℃;

DOI:10.1021/jacs.5b07098

upstream raw materials:

ethyl 2-(1-methyl-5-(4-methylbenzoyl)-1H-pyrrol-2-yl)acetate

1-Methyl-5-(4-methylbenzoyl)pyrrole-2-acetonitrile

N-Methylpyrrole

1-metil-5-p-metilbenzoil-1H-pirrolo-2-carbossialdeide

Downstream raw materials:

3-Bromo-1-methyl-5-(p-toluoyl)pyrrole-2-acetic acid

Refernces

• 1、 Kü?ükgüzel, ?. Güniz,Ko?, Derya,?ikla-Süzgün, Pelin,?zsavci, Derya,Bing?l-?zakpinar, ?zlem,Mega-Tiber,Orun, Oya,Erzincan,Sa?-Erdem, Safiye,?ahin, Fikrettin. "Synthesis of Tolmetin Hydrazide-Hydrazones and Discovery of a Potent Apoptosis Inducer in Colon Cancer Cells". . p. 730 - 742. Retrieved 2015.
• 2、 Santiago, Carlos,Rubio, Ibon,Sotomayor, Nuria,Lete, Esther. "Selective PdII-Catalyzed Acylation of Pyrrole with Aldehydes. Application to the Synthesis of Celastramycin Analogues and Tolmetin". . p. 4284 - 4295. Retrieved 2020/05/25.