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26171-23-3 molecular structure
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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 and InChIs

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

Cite this record

CBID:383 http://www.chembase.cn/molecule-383.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
Tolmetine [INN-French]
Tolmetino [INN-Spanish]
Tolmetinum [INN-Latin]
Tolmetina [DCIT]
Tolmetin Sodium
Tolmetin
1-Methyl-5-p-toluoylpyrrole-2-acetic acid
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
2-(1-Methyl-5-(4-Methylbenzoyl)-1H-pyrrol-2-yl)acetic acid
Tolmetin Sodium Salt Dihydrate
CAS Number
26171-23-3
64490-92-2
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

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 3.9581683  H Acceptors
H Donor LogD (pH = 5.5) 1.1776481 
LogD (pH = 7.4) -0.4552389  Log P 2.727331 
Molar Refractivity 72.3928 cm3 Polarizability 27.405663 Å3
Polar Surface Area 59.3 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 2.81  LOG S -3.29 
Solubility (Water) 1.31e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
222 mg/L expand Show data source
Water expand Show data source
Apperance
White Solid expand Show data source
Melting Point
>288°C (dec.) expand Show data source
Hydrophobicity(logP)
2.6 expand Show data source
Storage Condition
-20°C Freezer expand Show data source
Storage Warning
IRRITANT expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
TSCA Listed
false expand Show data source
Admin Routes
oral expand Show data source
Half Life
1-2 hours, next phase up to 5 hours expand Show data source
Purity
95+% expand Show data source
97% expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia TRC TRC
DrugBank - DB00500 external link
Item Information
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

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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)
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PATENTS

PATENTS

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INTERNET

INTERNET

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