Amtolmetin guacil

Base Information

• Chemical Name: Amtolmetin guacil
• CAS No.: 87344-06-7
• Deprecated CAS: 104076-16-6
• Molecular Formula: C₂₄H₂₄N₂O₅
• Molecular Weight: 420.465
• European Community (EC) Number: 681-921-0
• UNII: 323A00CRO9
• DSSTox Substance ID: DTXSID50236291
• Nikkaji Number: J428.389I
• Wikipedia: Amtolmetin_guacil
• Wikidata: Q4748890
• NCI Thesaurus Code: C72142
• ChEMBL ID: CHEMBL1766570
• Mol file: 87344-06-7.mol

Synonyms:2-methoxyphenyl 1-methyl-5-(4-methylbenzoylpyrrol)-2-acetamidoacetate;amtolmetin guacyl;amtolmetineguacil;Artromed;MED 15;MED-15;MED15;ST 679;ST-679

Chemical Property of Amtolmetin guacil

Chemical Property:

• Appearance/Colour: white needle-shaped crystal
• Vapor Pressure: 1.84E-17mmHg at 25°C
• Melting Point: 116-119 °C
• Refractive Index: 1.583
• Boiling Point: 663.3 °C at 760 mmHg
• Flash Point: 354.9 °C
• PSA: 86.63000
• Density: 1.19 g/cm³
• LogP: 3.22830
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 420.16852187
• Heavy Atom Count: 31
• Complexity: 632

Purity/Quality:

99% ^*data from raw suppliers

MED15 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)C(=O)C2=CC=C(N2C)CC(=O)NCC(=O)OC3=CC=CC=C3OC
• 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.
• Uses: Analgesic; anti-inflammatory used in the treatment of rheumatoid arthritis,

Technology Process of Amtolmetin guacil

There total 10 articles about Amtolmetin guacil which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 74.8%

2-methoxy-phenol (90-05-1) + Tolmetin glycine amide (87344-05-6) → amtolmetin guacil (104076-16-6,87344-06-7)

Guidance literature:

With potassium carbonate; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In dichloromethane; at 25 - 30 ℃; Large scale reaction;

DOI:10.1021/op900284w

Reference yield: 60.0%

amino acetic acid guacil ester hydrochloride (75368-99-9) + 1-methyl-5-(p-toluoyl)pyrrole-2-acetic acid (26171-23-3) → amtolmetin guacil (104076-16-6,87344-06-7)

Guidance literature:

With potassium carbonate; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In acetone; at -5 - 30 ℃; for 5h;

DOI:10.1021/op900284w

Reference yield:

N-Methylpyrrole (96-54-8) → amtolmetin guacil (104076-16-6,87344-06-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: dichloromethane / 1 h / -10 - 0 °C

1.2: 0.5 h / -10 - 0 °C / pH 10

2.1: hydrazine hydrate; potassium hydroxide / water / 5 h / 100 °C

3.1: potassium carbonate / dichloromethane / 3 h / 30 °C

4.1: o-xylene / 24 h / 145 °C

5.1: sodium hydroxide / methanol; water / 2 h / 30 °C

6.1: potassium carbonate; benzotriazol-1-ol; dicyclohexyl-carbodiimide / acetone / 5 h / -5 - 30 °C

With potassium carbonate; benzotriazol-1-ol; hydrazine hydrate; dicyclohexyl-carbodiimide; potassium hydroxide; sodium hydroxide; In methanol; dichloromethane; o-xylene; water; acetone; 2.1: Wolff-Kishner reduction;

DOI:10.1021/op900284w

upstream raw materials:

N-Methylpyrrole

1-methylpyrrole-2-acetic acid

tert-butyloxycarbonylamino acetic acid guacil ester

C₁₈H₂₀N₂O₄

Refernces