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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H19ClFNO4
Molecular Weight 391.821
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TONABERSAT

SMILES

CC(=O)C1=CC=C2OC(C)(C)[C@@H](O)[C@@H](NC(=O)C3=CC=C(F)C(Cl)=C3)C2=C1

InChI

InChIKey=XLIIRNOPGJTBJD-ROUUACIJSA-N
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

HIDE SMILES / InChI
Molecular Formula C20H19ClFNO4
Molecular Weight 391.821
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created on several sources, including https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3142555/

Tonabersat is a unique compound with demonstrated activity as a gap-junction inhibitor in animal studies. In preclinical and clinical trials, tonabersat was well tolerated, with no cardiovascular effects; the pharmacokinetic profile suggested its usefulness in the prophylaxis of migraine. The basis of its high efficacy is inhibiting neuronal hyperexcitability and trigeminal nerve stimulated neurogenic inflammation in rodent models. Tonabersat inhibits the CSD (cortical spreading depression) that is believed to underlie the aura of migraine.

CNS Activity

Originator

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Gap junction
4
Target ID: map04540
Sources: www.ncbi.nlm.nih.gov/pubmed/24611055
Inhibitor
8504
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Phase II
1147
Unknown

Approved Use

Unknown
Preventing
Phase II
1147
Unknown

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse events​
80 mg single, oral
Highest studied dose
Dose: 80 mg
Route: oral
Route: single
Dose: 80 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/19723122
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/19723122
Other AEs: Dizziness, Nausea...
Other AEs:
Dizziness (5.5%)
Nausea (4.6%)
Vertigo (4.6%)
Somnolence (0.9%)
Abdominal pain (0.9%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/19723122
40 mg 1 times / day multiple, oral
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/19222510
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/19222510
Disc. AE: Drowsiness, nausea...
AEs leading to
discontinuation/dose reduction:
Drowsiness (severe, 1 pt)
nausea (1 pt)
dizziness (1 pt)
nausea (2 patients)
headache (1 pt)
Sources:
https://pubmed.ncbi.nlm.nih.gov/19222510
AEs

AEs

AESignificanceDosePopulation
Abdominal pain 0.9%
80 mg single, oral
Highest studied dose
Dose: 80 mg
Route: oral
Route: single
Dose: 80 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/19723122
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/19723122
Somnolence 0.9%
80 mg single, oral
Highest studied dose
Dose: 80 mg
Route: oral
Route: single
Dose: 80 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/19723122
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/19723122
Nausea 4.6%
80 mg single, oral
Highest studied dose
Dose: 80 mg
Route: oral
Route: single
Dose: 80 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/19723122
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/19723122
Vertigo 4.6%
80 mg single, oral
Highest studied dose
Dose: 80 mg
Route: oral
Route: single
Dose: 80 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/19723122
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/19723122
Dizziness 5.5%
80 mg single, oral
Highest studied dose
Dose: 80 mg
Route: oral
Route: single
Dose: 80 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/19723122
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/19723122
dizziness 1 pt
Disc. AE
40 mg 1 times / day multiple, oral
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/19222510
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/19222510
headache 1 pt
Disc. AE
40 mg 1 times / day multiple, oral
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/19222510
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/19222510
nausea 1 pt
Disc. AE
40 mg 1 times / day multiple, oral
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/19222510
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/19222510
nausea 2 patients
Disc. AE
40 mg 1 times / day multiple, oral
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/19222510
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/19222510
Drowsiness severe, 1 pt
Disc. AE
40 mg 1 times / day multiple, oral
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/19222510
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/19222510
Sourcing

Sourcing

Vendor/AggregatorIDURL
1PlusChem LLC
1P0020KT
https://www.1pchem.com/search?query=1P0020KT
AK Scientific
X6315
https://aksci.com/item_detail.php?cat=X6315
Alfa Chemistry
ACM175013840
http://www.alfa-chemistry.com/search.aspx?q=ACM175013840
BLD Pharm
BD154391
http://www.bldpharm.com/search/Search.html?keyword=BD154391
BOC Sciences
175013-84-0
http://www.bocsci.com/description.asp?cas=175013-84-0
Cayman Chemical
19796
http://www.caymanchem.com/app/template/Product.vm/catalog/19796
Chem Scene
CS-0676
http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0676
eMolecules
11312708
https://orderbb.emolecules.com/search/#?query=11312708
eMolecules
275105177
https://orderbb.emolecules.com/search/#?query=275105177
eMolecules
300125756
https://orderbb.emolecules.com/search/#?query=300125756
KeyOrganics
ES-0039
http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=ES-0039
Lab Network
LN01312354
https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01312354
mcule
MCULE-1253821635
https://mcule.com/MCULE-1253821635/
mcule
MCULE-6929365328
https://mcule.com/MCULE-6929365328/
mcule
MCULE-8632127641
https://mcule.com/MCULE-8632127641/
MedChem Express
HY-15204
https://www.medchemexpress.com/search.html?q=HY-15204&ft=&fa=&fp=
MolPort
MolPort-003-850-578
https://www.molport.com/shop/molecule-link/MolPort-003-850-578
MuseChem
I002283
https://www.musechem.com/product/I002283.html
Tetrahedron
TS80773
http://www.thsci.com/search.do?q=TS80773
Toronto Research Chemicals
T539500
https://www.trc-canada.com/product-detail/?CatNum=T539500
PubMed

PubMed

TitleDatePubMed
Tonabersat inhibits trigeminal ganglion neuronal-satellite glial cell signaling.
2009-01
A double-blind study of SB-220453 (Tonerbasat) in the glyceryltrinitrate (GTN) model of migraine.
2004-10
Tonabersat (SB-220453) a novel benzopyran with anticonvulsant properties attenuates trigeminal nerve-induced neurovascular reflexes.
2001-04
The potential anti-migraine compound SB-220453 does not contract human isolated blood vessels or myocardium; a comparison with sumatriptan.
2000-07
Repetitive cortical spreading depression in a gyrencephalic feline brain: inhibition by the novel benzoylamino-benzopyran SB-220453.
2000-07
SB-220453, a potential novel antimigraine agent, inhibits nitric oxide release following induction of cortical spreading depression in the anaesthetized cat.
2000-03
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.
1999-01-18
Patents

Patents

WO9618650
1
WO9811890
1

Sample Use Guides

In Vivo Use Guide
Take 40 mg daily for 12 weeks.
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Wed Apr 02 08:28:15 GMT 2025
Edited
by admin
on Wed Apr 02 08:28:15 GMT 2025
Record UNII
2XD9773ZMN
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SB-220453
Preferred Name English
TONABERSAT
INN   WHO-DD  
INN  
Official Name English
tonabersat [INN]
Common Name English
Tonabersat [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C264
Created by admin on Wed Apr 02 08:28:15 GMT 2025 , Edited by admin on Wed Apr 02 08:28:15 GMT 2025
Code System Code Type Description
DRUG BANK
DB06578
Created by admin on Wed Apr 02 08:28:15 GMT 2025 , Edited by admin on Wed Apr 02 08:28:15 GMT 2025
PRIMARY
FDA UNII
2XD9773ZMN
Created by admin on Wed Apr 02 08:28:15 GMT 2025 , Edited by admin on Wed Apr 02 08:28:15 GMT 2025
PRIMARY
EPA CompTox
DTXSID40169923
Created by admin on Wed Apr 02 08:28:15 GMT 2025 , Edited by admin on Wed Apr 02 08:28:15 GMT 2025
PRIMARY
NCI_THESAURUS
C97277
Created by admin on Wed Apr 02 08:28:15 GMT 2025 , Edited by admin on Wed Apr 02 08:28:15 GMT 2025
PRIMARY
INN
7765
Created by admin on Wed Apr 02 08:28:15 GMT 2025 , Edited by admin on Wed Apr 02 08:28:15 GMT 2025
PRIMARY
CAS
175013-84-0
Created by admin on Wed Apr 02 08:28:15 GMT 2025 , Edited by admin on Wed Apr 02 08:28:15 GMT 2025
PRIMARY
EVMPD
SUB79261
Created by admin on Wed Apr 02 08:28:15 GMT 2025 , Edited by admin on Wed Apr 02 08:28:15 GMT 2025
PRIMARY
PUBCHEM
6918324
Created by admin on Wed Apr 02 08:28:15 GMT 2025 , Edited by admin on Wed Apr 02 08:28:15 GMT 2025
PRIMARY
MESH
C118706
Created by admin on Wed Apr 02 08:28:15 GMT 2025 , Edited by admin on Wed Apr 02 08:28:15 GMT 2025
PRIMARY
ChEMBL
CHEMBL318191
Created by admin on Wed Apr 02 08:28:15 GMT 2025 , Edited by admin on Wed Apr 02 08:28:15 GMT 2025
PRIMARY
SMS_ID
100000138878
Created by admin on Wed Apr 02 08:28:15 GMT 2025 , Edited by admin on Wed Apr 02 08:28:15 GMT 2025
PRIMARY
Related Record Type Details
Structure of TONABERSAT
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