An anti-migraine agent
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Product Type

Biochemicals

Research Area

Neuroscience
Pain Research

Tonabersat

Item No. 19796

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(3S,4S)-6-acetyl-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4-yl]-3-chloro-4-fluoro-benzamide
CAS Number
175013-84-0
Synonyms
  • SB-220453
Molecular Formula
C20H19ClFNO4
Formula Weight
391.8
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS (pH 7.2)(1:9): 0.1 mg/mlEthanol: 20 mg/ml
λmax
228, 276 nm
SMILES
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 Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    1 mg

    $41

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    5 mg

    $178

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    10 mg

    $312

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    25 mg

    $680

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    Product Description

    Tonabersat is an anti-migraine agent.1,2 It binds to connexin43 hemichannels and inhibits ATP release in vitro during injury and reperfusion in a dose-dependent manner.3 This inhibition blocks trigeminal ganglion neuronal-satellite glial cell signaling and cortical spreading depression, a trigger of migraine pain.3,2,4 In vivo, tonabersat (10 mg/kg) increases the seizure threshold in maximal electroshock seizure threshold (MEST) mice and rats (143 and 1192%, respectively) and completely blocks neurogenic plasma extravasation, a marker of migraine pain, in a rat trigeminal nerve migraine model.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Dahlöf , C.G.H., Hauge, A.W., and Olesen, J. Efficacy and safety of tonabersat, a gap-junction modulator, in the acute treatment of migraine: A double-blind, parallel-group, randomized study. Cephalalgia 29 (Suppl 2), 7-16 (2009).

    2. Damodaram, S., Thalakoti, S., Freeman, S.E., et al. Tonabersat inhibits trigeminal ganglion neuronal-satellite glial cell signaling. Headache 49(1), 5-20 (2009).

    3. Kim, Y., Griffin, J.M., Nor, M.N.M., et al. Tonabersat prevents inflammatory damage in the central nervous system by blocking connexin43 hemichannels. Neurotherapeutics (2017).

    4. Durham, P.L., and Garrett, F.G. Neurological mechanisms of migraine: potential of the gap-junction modulator tonabersat in prevention of migraine. Cephlalalgia 29(Suppl 2), (2009).

    5. Chan, W.N., Evans, J.M., Hadley, M.S., et al. Identification of (−)-cis-6-acetyl-4S-(3-chloro-4-fluoro-benzoylamino)-3,4-dihydro-2,2-dimethyl-2H-benzo[b]pyran-3S-ol as a potential antimigraine agent. Bioorg. Med. Chem. Lett. 9(2), 285-290 (1999).