| Identification | More | [Name]
Amtolmetin guacil | [CAS]
87344-06-7 | [Synonyms]
AMTOLMETIN GUACIL
2-methoxyphenyl1-methyl-5-p-methylbenzoylpyrrole-2-acetoamidoacetate
med15
n-((1-methyl-5-(4-methylbenzoyl)-1h-pyrrol-2-yl)acetyl)-glycin2-methoxyphe
Amtolmetin
AMTOLMETIO GUACIL
2-Methoxyphenyl 2-(1-methyl-5-(4-methylbenzoyl)-1H-pyrrole-2-acetylamino)acetate
N-[[5-(4-Methylbenzoyl)-1-methyl-1H-pyrrol-2-yl]acetyl]glycine 2-methoxyphenyl ester | [Molecular Formula]
C24H24N2O5 | [MDL Number]
MFCD00866153 | [Molecular Weight]
420.46 | [MOL File]
87344-06-7.mol |
| Chemical Properties | Back Directory | [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) |
| Hazard Information | Back Directory | [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 .
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