2-[1-methyl-5-(4-methylbenzoyl)-1H-pyrrol-2-yl]acetic acid

• ChemBase ID: 383
• Molecular Formular: C15H15NO3
• Molecular Mass: 257.2845
• Monoisotopic Mass: 257.10519335
• SMILES: O=C(c1n(c(cc1)CC(=O)O)C)c1ccc(cc1)C
• Canonical SMILES: OC(=O)Cc1ccc(n1C)C(=O)c1ccc(cc1)C
• InChI: InChI=1S/C15H15NO3/c1-10-3-5-11(6-4-10)15(19)13-8-7-12(16(13)2)9-14(17)18/h3-8H,9H2,1-2H3,(H,17,18)
• InChIKey: UPSPUYADGBWSHF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[1-methyl-5-(4-methylbenzoyl)-1H-pyrrol-2-yl]acetic acid
• IUPAC Traditional name: [1-methyl-5-(4-methylbenzoyl)pyrrol-2-yl]acetic acid; tolmetin
• Brand Name: Tolectin; Tolectin DS
• Synonyms: 1-Methyl-5-(4-methylbenzoyl)-1H-pyrrole-2-acetic Acid Sodium Dihydrate; 1-Methyl-5-p-toluoylpyrrole-2-acetic Acid Sodium Dihydrate; 5-[(p-Tolyl)carbonyl]-1-methylpyrrole-2-acetic Acid Sodium Dihydrate; McN 2559-21-98; Tolectin; Tolmene; Tolmetin Sodium Salt Dihydrate; Tolmetine [INN-French]; Tolmetino [INN-Spanish]; Tolmetinum [INN-Latin]; Tolmetina [DCIT]; Tolmetin Sodium; Tolmetin; 1-Methyl-5-p-toluoylpyrrole-2-acetic acid; 2-(1-Methyl-5-(4-Methylbenzoyl)-1H-pyrrol-2-yl)acetic acid

Database IDs

• CAS Number: 64490-92-2; 26171-23-3
• MDL Number: MFCD00599595
• PubChem SID: 46507060; 160963846
• PubChem CID: 5509
• ATC CODE: M02AA21; M01AB03
• CHEMBL: 1020
• Chemspider ID: 5308
• DrugBank ID: DB00500
• KEGG ID: D02355
• Unique Ingredient Identifier: D8K2JPN18B
• Wikipedia Title: Tolmetin
• Medline Plus: a681033

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.9581683
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.1776481
• LogD (pH = 7.4): -0.4552389
• Log P: 2.727331
• Molar Refractivity: 72.3928 cm^3
• Polarizability: 27.405663 Å^3
• Polar Surface Area: 59.3 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.81
• LOG S: -3.29
• Solubility (Water): 1.31e-01 g/l

PROPERTIES

Physical Property

• Solubility: 222 mg/L; Water
• Apperance: White Solid
• Melting Point: >288°C (dec.)
• Hydrophobicity(logP): 2.6

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: IRRITANT
• TSCA Listed: false

Pharmacology Properties

• Admin Routes: oral
• Half Life: 1-2 hours, next phase up to 5 hours

Product Information

• Purity: 95+%; 97%

DETAILS

DrugBank - DB00500

• Drug Groups: approved
• Description: A non-steroidal anti-inflammatory agent (anti-inflammatory agents, NON-steroidal) similar in mode of action to indomethacin. [PubChem]
• Indication: For the relief of signs and symptoms of rheumatoid arthritis and osteoarthritis, including the treatment of acute flares long-term management. Also for treatment of juvenile rheumatoid arthritis.
• Pharmacology: Tolmetin is a nonsteroidal anti-inflammatory agent. Studies in animals have shown tolmetin to possess anti-inflammatory, analgesic and antipyretic activity. In the rat, tolmetin prevents the development of experimentally induced polyarthritis and also decreases established inflammation. In patients with either rheumatoid arthritis or osteaoarthritis, tolmetin is as effective as aspirin and indomethacin in controlling disease activity, but the frequency of the milder gastrointestinal adverse effects and tinnitus was less than in aspirin-treated patients, and the incidence of central nervous system adverse effects was less than in indomethacin-treated patients. In patients with juvenile rheumatoid arthritis, tolmetin is as effective as aspirin in controlling disease activity, with a similar incidence of adverse reactions. tolmetin has produced additional therapeutic benefit when added to a regimen of gold salts and, to a lesser extent, with corticosteroids. Tolmetin should not be used in conjunction with salicylates since greater benefit from the combination is not likely, but the potential for adverse reactions is increased.
• Toxicity: Symptoms of overdose include lethargy, drowsiness, nausea, vomiting, and epigastric pain.
• Affected Organisms: Humans and other mammals
• Biotransformation: Essentially all of the administered dose is recovered in the urine in 24 hours either as an inactive oxidative metabolite or as conjugates of tolmetin.
• Absorption: Rapidly and almost completely absorbed with peak plasma levels being reached within 30-60 minutes after an oral therapeutic dose.
• Half Life: Biphasic elimination from the plasma consisting of a rapid phase with a half-life of one to 2 hours followed by a slower phase with a half-life of about 5 hours.
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Toronto Research Chemicals - T535350

Anti-inflammatory.

REFERENCES

• Carson, et al.: J. Med. Chem., 14, 646 (1971)
• Wong, S., et al.: J. Pharmacol. Exp. Ther., 185, 127 (1971)
• Brogden, R.N., et al.: Drugs, 15, 429 (1971)