Basic information Safety Supplier Related

Amtolmetin guacil

Basic information Safety Supplier Related

Amtolmetin guacil Basic information

Product Name:
Amtolmetin guacil
Synonyms:
  • 2-(2-Methoxyphenyl)-2-(N-{1-Methyl-5-[(4-Methylphenyl)carbonyl]-1H-pyrrol-2-yl}acetaMido)acetate
  • ArtroMed
  • Eufans
  • AMtolMethin Guacil
  • AMtolMetin Guacyl
  • N-[2-[1-Methyl-5-(4-Methylbenzoyl)-1H-pyrrol-2-yl]acetyl]glycine 2-Methoxyphenyl Ester
  • 2-Methoxyphenyl 2-(2-(1-Methyl-5-(4-Methylbenzoyl)-1H-pyrrol-2-yl)acetaMido)acetate
  • 2-methoxyphenyl1-methyl-5-p-methylbenzoylpyrrole-2-acetoamidoacetate
CAS:
87344-06-7
MF:
C24H24N2O5
MW:
420.46
Product Categories:
  • Aromatics
  • Heterocycles
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
Mol File:
87344-06-7.mol
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Amtolmetin guacil Chemical Properties

Melting point:
117-120°
Boiling point:
663.3±55.0 °C(Predicted)
Density 
1.19±0.1 g/cm3(Predicted)
storage temp. 
Sealed in dry,Room Temperature
solubility 
DMSO (Slightly), Methanol (Slightly)
form 
Solid
pka
13.90±0.46(Predicted)
color 
Pale Brown to Light Brown
CAS DataBase Reference
87344-06-7(CAS DataBase Reference)
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Safety Information

Toxicity
LD50 in male mice, rats (mg/kg): 1370, 1100 i.p.; >1500, 1450 orally (Baglioni)
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Amtolmetin guacil Usage And Synthesis

Description

Amtolmetin guacil is an orally active non-steroidal antiinflammatory drug (NSAID) introduced for the treatment of osteoarthritis, rheumatoid arthritis and post-operative pain. Amtolmetin guacil is reported to elicit a more rapid and improved analgesic action than other agents such as paracetamol. In models of adjuvant arthritis and rheumatic diseases, amtolmetin guacil is more efficacious than existing drugs such as naproxen, indomethacin and piroxicam. As a non-acidic prodrug of tolmetin, it has similar in vivo activity to the parent but with minor ulcerogenic action, lower acute toxicity, and excellent biological and gastric tolerability.

Originator

Sigma Tau (Italy)

Uses

Analgesic; anti-inflammatory used in the treatment of rheumatoid arthritis,

Definition

ChEBI: Amtolmetin guacil is a N-acyl-amino acid.

brand name

Artromed

Clinical Use

Amtolmetin guacil (AMG) is a non-steroidal anti-inflammatory drug developed by Sigma-Tau for the treatment of pain and inflammation. It acts similarly to tolmetin, and in preclinical trials displayed long-lasting anti-inflammatory and analgesic activity. Amtolmetin has a good gastrointestinal tolerability in humans and does not induce gastric ulcers in the rat . The good gastrointestinal tolerability and even a gastroprotective effect was related to an increase of endogenous NO via stimulation of inducible NO synthase in the gastric mucosa .

Synthesis

The condensation of 1-methyl- 5-(4-methylbenzoyl)pyrrole-2-acetic acid with glycine ethyl ester in the presence of carbonyldiimidazole and triethylamine in tetrahydrofuran gives the corresponding ethyl 2-acetate, which is hydrolyzed with NaOH in tetrahydrofuran – water yielding 2- - acetamido]acetic acid. Finally, this compound is esterified with 2-methoxyphenol (guaiacol) in hot tetrahydrofuran with carbonyldiimidazole as catalyst .

Amtolmetin guacilSupplier

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