Flupirtine maleate

Base Information

• Chemical Name: Flupirtine maleate
• CAS No.: 75507-68-5
• Deprecated CAS: 56995-21-2
• Molecular Formula: C₄H₄O₄*C₁₅H₁₇FN₄O₂
• Molecular Weight: 420.397
• Hs Code.: 29333990
• European Community (EC) Number: 278-225-0
• UNII: 0VCI53PK4A
• ChEMBL ID: CHEMBL1256752
• DSSTox Substance ID: DTXSID8045771
• NCI Thesaurus Code: C72785
• Wikidata: Q27231153
• Mol file: 75507-68-5.mol

Synonyms:D 9998;D-9998;ethyl 2-amino-6-((p-fluorobenzyl)amino)-3-pyridinecarbamate;flupirtin maleate;flupirtine;flupirtine maleate (1:1);Katadolon

Chemical Property of Flupirtine maleate

Chemical Property:

• Appearance/Colour: off-white crystalline powder
• Vapor Pressure: 9.1E-08mmHg at 25°C
• Melting Point: 186-188oC
• Boiling Point: 434.9 °C at 760 mmHg
• Flash Point: 216.8 °C
• PSA: 170.59000
• Density: 1.35 g/cm3
• LogP: 2.71190
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble >20mg/mL
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 8
• Exact Mass: 420.14451256
• Heavy Atom Count: 30
• Complexity: 469

Purity/Quality:

99%min ^*data from raw suppliers

FlupirtineMaleate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25-35-20

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)NC1=C(N=C(C=C1)NCC2=CC=C(C=C2)F)N.C(=CC(=O)O)C(=O)O
• Isomeric SMILES: CCOC(=O)NC1=C(N=C(C=C1)NCC2=CC=C(C=C2)F)N.C(=C\C(=O)O)\C(=O)O
• Recent EU Clinical Trials: A Phase IIb/III, Double-Blind, Placebo-Controlled, Randomized Study Investigating the Safety, Tolerability and Efficacy of Flupirtine as Adjunct to Opioids When Administered to Cancer Subjects Who Are Experiencing Pain With Neuropathic Features
• Description: Flupirtine is a selective neuronal potassium channel opener (SNEPCO) that also has N-methyl-D-aspartate (NMDA) receptor antagonist property which has been shown to be effective in the management of body pain. Flupirtine is used as an analgesic for acute pain, in moderate-to-severe cases. Its muscle relaxant properties make it popular for back pain and other orthopedic uses, but it is also used for migraines, in oncology, postoperative care, and gynecology. It is also effective in other painful conditions in which the primary requirement for analgesia is without sedation or anti-inflammatory effects. It first became available in Europe in 1984 under the brand name Katadolon. Flupirtine is a derivative of triaminopyridine with a chemical formula of ethyl-N-{2-amino-6-(4-fluorophenylmethylamino) pyridine-3 yl} cabamate. It is available as the maleate salt because flupirtine is itself poorly water soluble. Flupirtine is a base and is weakly lipophilic. Flupirtine maleate is a centrally-acting, non-addicting analgesic agent somewhat more potent than aspirin, paracetamol and pentazocine. It is reported to be useful in the treatment of postoperative and dental pain. Flupirtine is an activator of voltage-gated potassium channel 7 (Kv7/KCNQ). It induces relaxation of preconstricted pulmonary arteries isolated from wild-type and serotonin transporter-overexpressing (SERT+) mice. Flupirtine (30 mg/kg per day) decreases mean right ventricular pressure and right ventricular hypertrophy in hypoxia-induced and SERT+ mouse models of pulmonary arterial hypertension. It increases the paw withdrawal threshold in a rat model of streptozotocin-induced diabetic neuropathy when administered at a dose of 10 mg/kg and increases paw withdrawal latency in a rat model of carrageenan-induced paw inflammation when used in combination with morphine. Flupirtine also indirectly antagonizes NMDA receptors via its effects on potassium channels.
• Uses: Analgesic. Substituted pyridine with central analgesic properties. A potassium channel opener. Analgesic. Substituted pyridine with central analgesic properties.

Technology Process of Flupirtine maleate

There total 2 articles about Flupirtine maleate 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: 94.1%

→ flupirtine maleate (75507-68-5)

Guidance literature:

Reference yield:

2-amino-3-nitro-6-(p-fluoro-benzylamino)-pyridine (33400-49-6) → flupirtine maleate (75507-68-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydroxide / N,N-dimethyl-formamide / 40 °C

2.1: palladium dichloride; hydrogen; triethylamine / ethyl acetate / 3 h / 0 - 40 °C / 2250.23 - 2625.26 Torr

2.2: 1 h / 0 - 5 °C

3.1: water / 70 °C

3.2: 45 °C / pH 8-9 / Inert atmosphere

3.3: 1 h / 20 - 65 °C

With hydrogen; triethylamine; sodium hydroxide; palladium dichloride; In water; ethyl acetate; N,N-dimethyl-formamide;

Reference yield:

flupirtine maleate (75507-68-5) → p-fluorohippuric Acid (366-79-0) + D 13223

Guidance literature:

metabolism in the dog, with 14C-labelled compound;

upstream raw materials:

2-amino-3-nitro-6-(p-fluoro-benzylamino)-pyridine

Downstream raw materials:

p-fluorohippuric Acid

Refernces

• 1、 -. "Process for the preparation of pure flupirtine maleate and its A modification". . . Retrieved 2008/06/13.