SML1354

Tonabersat

≥98% (HPLC)

• Synonym(s): (3S-cis)-N-(6-Acetyl-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4-yl)-3-chloro-4-fluoro-benzamide, N-[(3S,4S)-6-Acetyl-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4-yl]-3-chloro-4-fluoro-benzamide, SB 220453, SB-220453
• Empirical Formula (Hill Notation): C₂₀H₁₉ClFNO₄
• CAS Number: 175013-84-0
• Molecular Weight: 391.82
• MDL number: MFCD00944458
• UNSPSC Code: 12352202
• PubChem Substance ID: 329825809
• NACRES: NA.77

Properties

• Quality Level: 100
• assay: ≥98% (HPLC)
• form: powder
• optical activity: [α]/D -100 to -110°, c = 1 in methanol
• color: white to beige
• solubility: DMSO: 20 mg/mL, clear
• storage temp.: 2-8°C
• SMILES string: CC(C1=CC=C2C([C@H](NC(C3=CC=C(F)C(Cl)=C3)=O)[C@H](O)C(C)(C)O2)=C1)=O
• InChI: 1S/C20H19ClFNO4/c1-10(24)11-5-7-16-13(8-11)17(18(25)20(2,3)27-16)23-19(26)12-4-6-15(22)14(21)9-12/h4-9,17-18,25H,1-3H3,(H,23,26)/t17-,18-/m0/s1
• InChI key: XLIIRNOPGJTBJD-ROUUACIJSA-N

Description

Biochem/physiol Actions

Tonabersat (SB-220453) exhibits anticonvulsant property. It is a member of the family of novel benzoylamino-benzopyran compounds. Tonabersat is used as a therapeutic for trigeminal nerve-induced neurovascular reflexes. In addition, it acts as a putative migraine prophylactic agent containing an unique stereospecific binding site in the brain.

Tonabersat is a potent inhibitor of neuronal-glial gap junctions in trigeminal ganglion that inhibits cortical spreading depression (CSD) and neurogenic inflammation in animal models of migraine.

Safety Information

• pictograms: GHS07,GHS09
• signalword: Warning
• hcodes: H315,H319,H400
• pcodes: P264 - P273 - P280 - P302 + P352 - P305 + P351 + P338 - P332 + P313
• Hazard Classifications: Aquatic Acute 1 - Eye Irrit. 2 - Skin Irrit. 2
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable