ChemicalBook > CAS DataBase List > Tolmetin

Tolmetin

Product Name
Tolmetin
CAS No.
26171-23-3
Chemical Name
Tolmetin
Synonyms
C07149;olmetin;McN 2559;Tolmetin;Methyiin;Tolmetine;TOLMETINUM;pyrolyzate;Tolmetin Solution, 100ppm;1-Methyl-5-p-toluoylpyrrole-2-acetic acid
CBNumber
CB2875183
Molecular Formula
C15H15NO3
Formula Weight
257.28
MOL File
26171-23-3.mol
More
Less

Tolmetin Property

Melting point:
156 °C
Boiling point:
400.53°C (rough estimate)
Density 
1.1391 (rough estimate)
refractive index 
1.5200 (estimate)
storage temp. 
2-8°C
solubility 
Chloroform (Slightly), Methanol (Slightly)
pka
pKa 3.5(H2O t undefined I undefined) (Uncertain)
form 
Solid
color 
Off-White to Pale Yellow
Water Solubility 
222 mg/L
NIST Chemistry Reference
Tolmetin(26171-23-3)
EPA Substance Registry System
1H-Pyrrole-2-acetic acid, 1-methyl-5-(4-methylbenzoyl)- (26171-23-3)
More
Less

Safety

Hazardous Substances Data
26171-23-3(Hazardous Substances Data)
More
Less

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P501Dispose of contents/container to..…

More
Less

N-Bromosuccinimide Price

TRC
Product number
M332943
Product name
1-Methyl-5-p-toluoylpyrrole-2-aceticAcid
Packaging
100mg
Price
$70
Updated
2021/12/16
AK Scientific
Product number
J10499
Product name
Tolmetin
Packaging
5mg
Price
$39
Updated
2021/12/16
Matrix Scientific
Product number
074159
Product name
1-Methyl-5-p-toluoylpyrrole-2-acetic acid
Purity
95+%
Packaging
1g
Price
$278
Updated
2021/12/16
ChemScene
Product number
CS-W008734
Product name
Tolmetin
Purity
≥98.0%
Packaging
25g
Price
$504
Updated
2021/12/16
Matrix Scientific
Product number
074159
Product name
1-Methyl-5-p-toluoylpyrrole-2-acetic acid
Purity
95+%
Packaging
10g
Price
$1000
Updated
2021/12/16
More
Less

Tolmetin Chemical Properties,Usage,Production

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.

Originator

Tolectin,McNeil,US,1976

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.

Uses

Tolmetine is an NSAID.

Definition

ChEBI: A monocarboxylic acid that is (1-methylpyrrol-2-yl)acetic acid substituted at position 5 on the pyrrole ring by a 4-methylbenzoyl group. Used in the form of its sodium salt dihydrate as a nonselective nonsteroidal anti-inflammatory drug.

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.

Manufacturing Process

5-(p-Toluoyl)-1-methylpyrrole-2-acetonitrile - To a cooled suspension of 26.6 g (0.2 mol) aluminum chloride in 80 ml dichloroethane is added dropwise 30.8 g (0.2 mol) p-toluoyl chloride. The resulting solution is added dropwise to a solution of 1-methylpyrrole-2-acetonitrile in 80 ml dichloroethane cooled externally with an ice bath. After the addition, the resulting solution is stirred at room temperature for 20 minutes and then refluxed for 3 minutes. The solution is poured into ice acidified with dilute hydrochloric acid. The organic and aqueous fractions are separated. The aqueous fraction is extracted once with chloroform.
The organic fractions are combined and washed successively with N,N_x0002_dimethyl-1,3-propanediamine, dilute hydrochloric acid, saturated sodium bicarbonate solution and saturated sodium chloride solution. The organic fraction is dried over anhydrous magnesium sulfate. The solvent is then evaporated off. Upon trituration of the residue with methanol, a solid crystallizes, 5-(p-toluoyl)-1-methylpyrrole-2-acetonitrile, which is removed by filtration and purified by recrystallization from benzene.
Additional product is isolated from the mother liquors which are combined, concentrated in vacuo and the resulting oily residue column chromatographed on neutral alumina using hexane, benzene and ether as successive solvents. The product is isolated by concentrating in vacuo the first few major compound-bearing fractions (10% ether in benzene). The solids are combined and recrystallized from methanol and then from benzene-hexane, melting point 102°C to 105°C.
5-(p-Toluoyl)-1-methylpyrrole-2-acetic acid - A solution of 3.67 g (0.015 mol) of 5-(p-toluoyl)-1-methylpyrrole-2-acetonitrile, 24 ml of 1 N sodium hydroxide and 50 ml of 95% ethanol is stirred and refluxed for 24 hours. The resulting solution is poured into ice acidified with dilute hydrochloric acid. A white solid precipitates which is extracted into ether. The ether phase is washed with a saturated solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent is evaporated and a white solid, 5-(p-toluoyl)- 1-methylpyrrole-2-acetic acid is obtained which is recrystallized twice from isopropanol, melting point 155°C to 157°C.

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.

General Description

Tolmetin sodium (Tolectin), is an arylacetic acid derivativewith a pyrrole as the aryl group. This drug is well absorbed and has a relatively short plasma half-life (1 hour). It is recommendedfor use in the management of acute and chronicRA. Its efficacy is similar to aspirin and indomethacin, butwith less frequency of the adverse effects and tinnitus associatedwith aspirin. It does not potentiate coumarin-likedrugs nor alter the blood levels of sulfonylureas or insulin.However, tolmetin, and especially its closely related drug,zomepirac (i.e., with a p-chlorobenzoyl group and an additionalmethyl group on the pyrrole ring), can produce a rarebut fatal anaphylactic reaction because of irreversible bindingof their unstable acyl glucuronides. Zomepirac waswithdrawn from market because it is eliminated only via theester-type, acyl glucuronide. It is possible that tolmetin isless toxic in this regard because it undergoes additional hepaticbenzylic hydroxylation via its p-methyl group and isexcreted as its stable ether glucuronide.

Trade name

Artrocaptin (Estedi, Spain), Tolectin (Cilag, Belgium; Janssen-Cilag, Austria; McNeil, USA).

Mechanism of action

Tolmetin inhibits both isoforms of cyclooxygenase with some preference for COX-1 .

Pharmacology

Tolmetin is administered orally, rectally, or topically (600–1800 mg/d). The peak plasma concentrations are reached within 30 to 60 min. Tolmetin shows a high plasma protein binding of 99% and a biphasic plasma half-life of 1 to 2 and 5h, respectively.

Clinical Use

Tolmetin is a nonsteroidal anti-inflammatory drug used for the treatment of mild to moderate pain states in musculoskeletal, soft-tissue, and joint disorders like rheumatoid arthritis, osteoarthritis, and gout as well as juvenile rheumatoid arthritis.

Synthesis

Tolmetin, 1-methyl-5-n-tolylpyrrol-2-acetic acid (3.2.61) is synthesized from 1- methylindole, which is aminomethylated using formaldehyde and dimethylamine, forming 2-dimethylaminomethyl-1-methylindol (3.2.57). The product is methylated by methyl iodide, giving the corresponding quaternary salt (3.2.58). Reaction of the product with sodium cyanide gives 1-methylpyrrole-2-acetonitrile (3.2.59), which is acylated at the free |á-position of the pyrrole ring by 4-methylbenzoylchloride in the presence of aluminum chloride. The resulting 1-methyl-5-n-toluylpyrrol-2-acetonitrile (3.2.60) undergoes further alkaline hydrolysis, giving corresponding acid, tolmetin (3.2.61) [116¨C118].

Tolmetin Preparation Products And Raw materials

Raw materials

Preparation Products

More
Less

Tolmetin Suppliers

Zhangjiagang huamao Fine chemical Co.,Ltd.
Tel
0512-58327208; 13962221965
Fax
0512-58327206
Email
sales@huamao-chem.com
Country
China
ProdList
34
Advantage
58
Shanghai Boyle Chemical Co., Ltd.
Tel
021-50182298 021-50180596
Fax
+86-21-57758967
Email
sales@boylechem.com
Country
China
ProdList
2208
Advantage
55
Capot Chemical Co., Ltd
Tel
+86 (0) 571 85 58 67 18
Fax
0086-571-85864795
Email
sales@capotchem.com
Country
China
ProdList
18207
Advantage
66
LGM Pharma
Tel
1-(800)-881-8210
Fax
615-250-9817
Email
inquiries@lgmpharma.com
Country
United States
ProdList
2123
Advantage
70
Shanghai Hanhong Scientific Co.,Ltd.
Tel
021-54306202 13764082696
Email
info@hanhongsci.com
Country
China
ProdList
42958
Advantage
64
Syntechem Co.,Ltd
Tel
Fax
E-Mail Inquiry
Email
info@syntechem.com
Country
China
ProdList
12984
Advantage
57
NovoChemy Ltd.
Tel
021-31261262/ 49 (0)17662837245
Fax
(0)21-33250524
Email
sales@novochemy.com
Country
Germany
ProdList
6328
Advantage
58
Shanghai Topbiochem Technology Co., Ltd
Tel
+86-21-60341587
Fax
+86-21-61294319
Email
sales@topbiochem.com
Country
China
ProdList
6175
Advantage
58
TargetMol Chemicals Inc.
Tel
021-021-33632979 15002134094
Fax
021-33632979
Email
marketing@targetmol.com
Country
China
ProdList
7783
Advantage
58
Shanghai Chainpharm Bio-medical Technology Co., Ltd.
Tel
021-61727342 13611721451
Fax
021-61294107
Email
sales@chainpharm.com
Country
China
ProdList
958
Advantage
58
More
Less

View Lastest Price from Tolmetin manufacturers

Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
Tolmetin 26171-23-3
Price
US $10.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20ton
Release date
2024-06-06
Hebei Weibang Biotechnology Co., Ltd
Product
Tolmetin 26171-23-3
Price
US $10.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
10 mt
Release date
2024-10-24
Henan Bao Enluo International TradeCo.,LTD
Product
Tolmetin 26171-23-3
Price
US $50.00/kg
Min. Order
1kg
Purity
99.9%
Supply Ability
10000MT
Release date
2023-08-02

26171-23-3, TolmetinRelated Search:


  • 2-[1-methyl-5-[(4-methylphenyl)-oxomethyl]-2-pyrrolyl]acetic acid
  • 1-Methyl-5-p-toluoylpyrrole-2-acetic acid
  • 5-[(p-Tolyl)carbonyl]-1-methylpyrrole-2-acetic acid
  • McN 2559
  • 1-Methyl-5-(4-methylbenzoyl)-1H-pyrrole-2-acetic acid
  • 1-Methyl-5-(p-toluoyl)-1H-pyrrole-2-acetic acid
  • C07149
  • 2-(1-Methyl-5-(4-Methylbenzoyl)-1H-pyrrol-2-yl)acetic acid
  • 2-{1-Methyl-5-[(4-Methylphenyl)carbonyl]-1H-pyrrol-2-yl}acetic acid
  • 1H-Pyrrole-2-acetic acid, 1-methyl-5-(4-methylbenzoyl)-
  • Tolmetine
  • TOLMETINUM
  • 2-[1-Methyl-5-(4-methylbenzoyl)-pyrrol-2-yl]acetic acid
  • Tolmetin Solution, 100ppm
  • Tolmetin
  • Methyiin
  • pyrolyzate
  • olmetin
  • 26171-23-3
  • Inhibitors
  • API
  • API intermediates