Tranilast

Base Information

• Chemical Name: Tranilast
• CAS No.: 53902-12-8
• Molecular Formula: C₁₈H₁₇NO₅
• Molecular Weight: 327.337
• European Community (EC) Number: 621-256-5
• UNII: HVF50SMY6E
• ChEMBL ID: CHEMBL415324
• Metabolomics Workbench ID: 150783
• NCI Thesaurus Code: C152712
• Nikkaji Number: J1.065K,J68.174A
• NSC Number: 758970
• Pharos Ligand ID: 55MN3LU3PTY1
• Wikidata: Q2325594,Q27164069
• Wikipedia: Tranilast
• Mol file: 53902-12-8.mol

Synonyms:1 N-(3'-4'-dimethoxycinnamoyl) anthranilic acid (N-5'), N(3',4'-dimethoxycinnamoyl) anthranilic acid (N-5');2-((3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl)amino)benzoic acid;MK-341;MK341;N (3', 4'-dimethoxycinnamoyl) anthranilic acid (N-5');N-(3',4'-dimethoxycinnamoyl)anthranilic acid;Rizaben;tranilast;tranilast hydrate;tranilast sodium salt

Chemical Property of Tranilast

Chemical Property:

• Appearance/Colour: white with light yellow crystalline powder
• Vapor Pressure: 1.49E-14mmHg at 25°C
• Melting Point: 166-168 °C
• Refractive Index: 1.647
• Boiling Point: 585.6 °C at 760 mmHg
• PKA: 3.47±0.36(Predicted)
• Flash Point: 307.9 °C
• PSA: 84.86000
• Density: 1.299 g/cm³
• LogP: 3.12690
• Storage Temp.: 2-8°C
• Solubility.: DMSO: 18 mg/mL
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 327.11067264
• Heavy Atom Count: 24
• Complexity: 464

Purity/Quality:

99%, ^*data from raw suppliers

N5- ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)C=CC(=O)NC2=CC=CC=C2C(=O)O)OC
• Isomeric SMILES: COC1=C(C=C(C=C1)/C=C/C(=O)NC2=CC=CC=C2C(=O)O)OC
• Recent ClinicalTrials: Tranilast as a Radiosensitizer in Reradiation of Nasopharyngeal Carcinoma
• Recent EU Clinical Trials: A Phase II, Randomized Multi-Center, Double-Blind Study of Tranilast with Concomitant Methotrexate (MTX) Compared to MTX Alone in Patients with Active Rheumatoid Arthritis (RA).
• Recent NIPH Clinical Trials: Effect of tranilast on facial neuralgia
• Description: Tranilast (53902-12-8) is an anti-allergy agent (inhibitor of mast cell degranulation) that has been shown to have potent immunomodulatory effects via inhibition of endotoxin induced: PGE2, IC50 = 1-20 μM; TXB2, IC50 = 10-50 μM; TGFβ1, IC50 = 100-200 μM; IL-8, IC50 = 100 μM .1-3 Tranilast also displays anti-angiogenic properties.4,5
• Uses: Antiallergic drug, used to treat bronchial asthma, allergic rhinitis and atopic dermatitis. coronary vasodilator Tranilast is a compound that exhibits anti-inflammatory and immunomodulatory effects by inhibiting lipid mediator and cytokine release from inflammatory cells and interfering with PDGF- and TGF-β1-induced proliferation and migration of vascular medial smooth muscle cells. Tranilast suppresses production of prostaglandin D2 (IC50 = 0.1 mM), prostaglandin E2 (IC50 = ~1-20 μM), thromboxane B2 (IC50 = ~10-50 μM), TGF-β1 (IC50 = ~100-200 μM), and interleukin-8 (IC50 = ~100 μM) in in vitro models as well as attenuates of the proinflammatory activity of human monocytes. While originally marketed as an antiallergenic drug, the efficacy of tranilast in preventing restenosis after percutaneous coronary intervention has been tested in a large-scale clinical trial. Additionally, tranilast inhibits VEGF-induced angiogenetic activities (i.e., proliferation, migration and tube formation of vascular endothelial cells) with IC50 values of 22, 18 and 193 μM, which may prove therapeutic for various retinal diseases.[Cayman Chemical]

Technology Process of Tranilast

There total 4 articles about Tranilast 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: 62.0%

2-[(2-carboxyacetyl)amino]benzoic acid (53947-84-5) + 3,4-dimethoxy-benzaldehyde (120-14-9) → N-(3,4-dimethoxycinnamoyl)anthranilic acid (53902-12-8,70806-55-2,91920-58-0)

Guidance literature:

2-[(2-carboxyacetyl)amino]benzoic acid; 3,4-dimethoxy-benzaldehyde; With piperidine; In toluene; for 3h; Reflux; Dean-Stark;

With methanol; In water; at 40 ℃;

With hydrogenchloride; In water;

DOI:10.1016/j.ejmech.2019.02.074

Reference yield: 48.0%

→ N-(3,4-dimethoxycinnamoyl)anthranilic acid (53902-12-8,70806-55-2,91920-58-0)

Guidance literature:

Reference yield:

3,4-dimethoxy-trans-cinnamic acid (14737-89-4) + 2-carbomethoxyaniline (134-20-3) → N-(3,4-dimethoxycinnamoyl)anthranilic acid (53902-12-8,70806-55-2,91920-58-0)

Guidance literature:

With pyridine; trichlorophosphate; In 1,4-dioxane; ethanol;

upstream raw materials:

3,4-dimethoxy-trans-cinnamic acid

2-carbomethoxyaniline

anthranilic acid

2-[(2-carboxyacetyl)amino]benzoic acid

Refernces

• 1、 -. "Aromatic carboxylic amide derivatives". . . Retrieved 2008/06/13.