Ibudilast

Base Information

• Chemical Name: Ibudilast
• CAS No.: 50847-11-5
• Molecular Formula: C14H18N2O
• Molecular Weight: 230.31
• Hs Code.: 2933990090
• European Community (EC) Number: 637-150-7
• UNII: M0TTH61XC5
• DSSTox Substance ID: DTXSID7049007
• Nikkaji Number: J22.219D
• Wikipedia: Ibudilast
• Wikidata: Q261167
• NCI Thesaurus Code: C65876
• Pharos Ligand ID: LKDZKNG3A4N3
• Metabolomics Workbench ID: 43654
• ChEMBL ID: CHEMBL19449
• Mol file: 50847-11-5.mol

Synonyms:1-(2-isopropylpyrazolo(1,5-a)pyridin-3-yl)-2-methyl-1-propanone;1-(2-isopropylpyrazolo(1,5-alpha)pyridin-3-yl)-2-methyl-1-propanone;3-isobutyryl-2-isopropylpyrazolo(1,5-a)pyridine;AV 411;AV-411;AV411;ibudilast;KC 404;KC-404;MN-166;MN166

Chemical Property of Ibudilast

Chemical Property:

• Appearance/Colour: white solid
• Melting Point: 53-54 °C
• Refractive Index: 1.57
• Boiling Point: 175°C/7.5mmHg(lit.)
• PKA: 1.22±0.30(Predicted)
• PSA: 34.37000
• Density: 1.09 g/cm³
• LogP: 3.29640
• Storage Temp.: 2-8°C
• Solubility.: DMSO: 28 mg/mL, soluble
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 230.141913202
• Heavy Atom Count: 17
• Complexity: 288

Purity/Quality:

99%min ^*data from raw suppliers

Ibudilast ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)C1=NN2C=CC=CC2=C1C(=O)C(C)C
• Recent ClinicalTrials: RECLAIM: Recovering From COVID-19 Lingering Symptoms Adaptive Integrative Medicine
• Recent EU Clinical Trials: Regeneration in Cervical Degenerative Myelopathy - a multi-centre, double-blind, randomised, placebo controlled trial assessing the efficacy of Ibudilast as an adjuvant treatment to decompressive surgery for degenerative cervical myelopathy
• Recent NIPH Clinical Trials: Safetyness and mechanisms of action of inhibitor for microglia activation on the patients with neuroinflammation evidenced by PET.
• Description: Ibudilast is a leukomene antagonist and phosphodiesterase inhibitor useful in the treatment of bronchial asthma. It antagonizes leukotriene D4-induced contractions of guinea pig ileum and tracheal muscles in virro, and inhibits eosinophil accumulation in vivo.
• Uses: a phosphodiesterase inhibitor with anti-inflammatory activity Inhibitors of phosphodiesterase 4 (PDE4), which catalyzes the hydrolysis of cAMP, have potential applications in a variety of diseases, including asthma. Ibudilast is an inhibitor of PDE4 (IC50 = 54-239 nM) that, at higher doses, also inhibits PDE3 and PDE5 (IC50 = 1,600-3,510 nM). Through this action, it suppresses the elaboration of mediators involved in asthma and inflammation.[Cayman Chemical] A leukotriene D4 antagonist. Used as an antiallergic, antiasthmatic, and vasodilator (cerebral)

Technology Process of Ibudilast

There total 2 articles about Ibudilast 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: 51.3%

1-amino-2-methylpyridinium iodide (7583-90-6) + 2-Methylpropionic anhydride (97-72-3) → ibudilast (50847-11-5) + 2-isopropyl-pyrazolo[1,5-a]pyridine (59942-84-6)

Guidance literature:

With potassium carbonate; In water; ethyl acetate; at 20 ℃; for 9h; Product distribution / selectivity; Heating / reflux;

Reference yield:

→ ibudilast (50847-11-5)

Guidance literature:

1-Amino-2-methylpyridiniumiodid, Isobuttersaeureanhydrid, K2CO3;

Reference yield: 99.0%

ibudilast (50847-11-5) → 2-isopropyl-pyrazolo[1,5-a]pyridine (59942-84-6)

Guidance literature:

ibudilast; With sulfuric acid; In water; at 135 ℃; Inert atmosphere;

With sodium hydroxide; In water; at 25 ℃;

upstream raw materials:

1-amino-2-methylpyridinium iodide

2-Methylpropionic anhydride

Downstream raw materials:

(2-isopropyl-pyrazolo[1,5-a]pyridin-3-carboxylic acid)

3-(3-hydroxy-2-methylpropionyl)-2-isopropylpyrazolo<1,5-a>pyridine

2-(2-hydroxy-1-methylethyl)-3-isobutyrylpyrazolo<1,5-a>pyridine

2-(2-hydroxy-1-methylethyl)-3-(3-hydroxy-2-methylpropionyl)pyrazolo<1,5-a>pyridine

Refernces