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SML1354

Sigma-Aldrich

Tonabersat

≥98% (HPLC)

Sinónimos:

(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

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About This Item

Fórmula empírica (notación de Hill):
C20H19ClFNO4
Número de CAS:
175013-84-0
Peso molecular:
391.82
MDL number:
MFCD00944458
UNSPSC Code:
12352202
PubChem Substance ID:
329825809
NACRES:
NA.77

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

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.

pictograms

Exclamation markEnvironment
GHS07,GHS09

signalword

Warning

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

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Tonabersat (SB?220453) a novel benzopyran with anticonvulsant properties attenuates trigeminal nerve?induced neurovascular reflexes.
Parsons A A, et al.
British Journal of Pharmacology, 132(7), 1549-1557 (2001)
Randomized, double-blind, placebo-controlled, proof-of-concept study of the cortical spreading depression inhibiting agent tonabersat in migraine prophylaxis.
Goadsby P J, et al.
Cephalalgia, 29(7), 742-750 (2009)
Esther N Arwert et al.
Nature cell biology, 22(7), 758-766 (2020-06-03)
Cancer-associated fibroblasts (CAFs) perform diverse roles and can modulate therapy responses1. The inflammatory environment within tumours also influences responses to many therapies, including the efficacy of oncolytic viruses2; however, the role of CAFs in this context remains unclear. Furthermore, little

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