Synonym: (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
CAS Number: 175013-84-0
Empirical Formula (Hill Notation): C20H19ClFNO4
Molecular Weight: 391.82
MDL Number: MFCD00944458
Linear Formula: C20H19ClFNO4
Product Type: Chemical
| assay |
≥98% (HPLC) |
| color |
white to beige |
| form |
powder |
| 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 |
| optical activity |
[α]/D -100 to -110°, c = 1 in methanol |
| Quality Level |
100  |
| 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 |
| solubility |
DMSO: 20 mg/mL, clear |
| storage temp. |
2-8°C |
| 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. |
| Biochem/physiol Actions: |
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. |
| Biochem/physiol Actions: |
Tonabersat is a potent inhibitor of neuronal-glial gap junctions. |
| Packaging: |
5, 25 mg in glass bottle |
| Purity |
≥98% (HPLC) |
| Storage Temp. |
2-8°C |
| UNSPSC |
12352202 |
GHS07,GHS09