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HomeProduct name listTONABERSAT

TONABERSAT

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

TONABERSAT Structural

What is TONABERSAT?

The Uses of TONABERSAT

It is a cholinesterase inhibitor for treating and preventing migraine. An antimigraine agent

The Uses of TONABERSAT

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].

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.

Properties of TONABERSAT

Boiling point: 554.5±50.0 °C(Predicted)
Density  1.38
storage temp.  2-8°C
solubility  Soluble in DMSO
pka 11.86±0.60(Predicted)
form  powder
color  white to beige
optical activity [α]/D -100 to -110°, c = 1 in methanol

Safety information for TONABERSAT

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
ghs
Environment
GHS09
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H400:Hazardous to the aquatic environment, acute hazard
Precautionary Statement Codes P273:Avoid release to the environment.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P391:Collect spillage. Hazardous to the aquatic environment
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P337+P313:IF eye irritation persists: Get medical advice/attention.

Computed Descriptors for TONABERSAT

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