| Identification | Back Directory | [Name]
TONABERSAT | [CAS]
175013-84-0 | [Synonyms]
SB 22045
SB 220453
TONABERSAT
SB 220453;SB220453
Tonabersat [ban, inn]
Tonabersat (SB-220453)
Tonabersat >=98% (HPLC)
SB-220453;SB 220453;SB220453
N-((3S,4S)-6-Acetyl-3-hydroxy-2,2-diMethylchroMan-4-yl)-3-chloro-4-fluorobenzaMide
2H-Benzo(B)pyran-3-ol, 6-acetyl-4-(3-chloro-4-fluorobenzoylamino)-3,4-dihydro-2,2-dimethyl-
N-[(3S,4S)-6-Acetyl-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4-yl]-3- chloro-4-fluoro-benzamide
Benzamide, N-[(3S,4S)-6-acetyl-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4-yl]-3-chloro-4-fluoro- | [Molecular Formula]
C20H19ClFNO4 | [MDL Number]
MFCD00944458 | [MOL File]
175013-84-0.mol | [Molecular Weight]
391.82 |
| Chemical Properties | Back Directory | [Boiling point ]
554.5±50.0 °C(Predicted) | [density ]
1.38 | [storage temp. ]
2-8°C | [solubility ]
Soluble in DMSO | [form ]
powder | [pka]
11.86±0.60(Predicted) | [color ]
white to beige | [optical activity]
[α]/D -100 to -110°, c = 1 in methanol |
| Hazard Information | Back Directory | [Uses]
It is a cholinesterase inhibitor for treating and preventing migraine. An antimigraine agent | [Biological Activity]
migraine is a common, recurrent and primary headache disorder. optimisation of novel cis- and trans-4-(substituted-anfido)benzopyran-3-ol derivatives has led to the identification of tonabersat (sb-220453) with potential antimigraine activity. | [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. | [in vitro]
topiramate targets multiple cortical and subcortical loci, altering voltage-gated ion channels and chemical transmission to decrease abnormal brain excitability. preclinical studies have identified four properties that may account for the drug’s efficacy in epilepsy and migraine prophylaxis: (i) blockage of voltage-dependent sodium channels; (ii) augmentation of the activity of the neurotransmitter g-aminobutyric acid (gaba) at some subtypes of the gaba-a receptor; (iii) antagonism of the ampa/kainate subtype of the glutamate receptor; and (iv) inhibition of the carbonic anhydrase enzymes, particularly isozymes ii and iv [1]. | [in vivo]
tonabersat binds selectively to a unique site in the brain. moreover, tonabersat could markedly reduce cortical spreading depression (csd) and csd-associated events and inhibite gap-junction communication between neurons and satellite glial cells in the trigeminal ganglion. together, these findings indicate that tonabersat should have clinical application in preventing migraine attacks [2]. | [storage]
Store at -20°C | [References]
[1] silberstein sd. tonabersat, a novel gap-junction modulator for the prevention of migraine. cephalalgia. 2009;29 suppl 2:28-35.
[2] durham pl, garrett fg. neurological mechanisms of migraine: potential of the gap-junction modulator tonabersat in prevention of migraine. cephalalgia. 2009;29 suppl 2:1-6.
[3] hauge aw, asghar ms, schytz hw, christensen k, olesen j. effects of tonabersat on migraine with aura: a randomised, double-blind, placebo-controlled crossover study. lancet neurol. 2009;8(8):718-23. |
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SynAsst Chemical.
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Sigma-Aldrich
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SPIRO PHARMA
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