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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H20FNO4
Molecular Weight 357.3755
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CARABERSAT

SMILES

CC(=O)C1=CC2=C(OC(C)(C)[C@H](O)[C@H]2NC(=O)C3=CC=C(F)C=C3)C=C1

InChI

InChIKey=RCLXAPJEFHPYEG-ZWKOTPCHSA-N
InChI=1S/C20H20FNO4/c1-11(23)13-6-9-16-15(10-13)17(18(24)20(2,3)26-16)22-19(25)12-4-7-14(21)8-5-12/h4-10,17-18,24H,1-3H3,(H,22,25)/t17-,18+/m0/s1

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including: https://www.ncbi.nlm.nih.gov/pubmed/9283703 | https://www.ncbi.nlm.nih.gov/pubmed/19443931 | https://www.ncbi.nlm.nih.gov/pubmed/15115635

Carabersat is an anticonvulsant devoid of cardiovascular side effects with minimal central nervous system adverse actions. Carabersat does not bind to ion channels, purinergic, aminergic, opioid and other peptidergic receptors. It selectively interacts with its own binding site, which is not yet elucidated. Carabersat has no effect on sodium channels, GABAergic or glutamate pathways. Carabersat had been in phase II clinical trials for the treatment of epilepsy. It has a potential action in preventing migraines because it acts through an inhibition of the cortical spreading depression trigeminal nerve-induced vasodilatation in cats. Its good therapeutic index and the markedly reduced neurological impairments could make it a useful agent for migraine prophylaxis pending efficacy parameters of controlled studies, which are underway.

Approval Year

Conditions
Doses

Doses

DosePopulationAdverse events​
5000 mg single, oral
Highest studied dose
Dose: 5000 mg
Route: oral
Route: single
Dose: 5000 mg
Sources:
healthy
Health Status: healthy
Sex: unknown
Food Status: UNKNOWN
Sources:
PubMed

PubMed

TitleDatePubMed
Third-generation antiepileptic drugs: mechanisms of action, pharmacokinetics and interactions.
2008-03-02
Prophylactic migraine therapy: emerging treatment options.
2004-06
Novel anticonvulsant medications in development.
2002-10
Progress report on new antiepileptic drugs: a summary of the Sixth Eilat Conference (EILAT VI).
2002-09
SB-204269 SmithKline Beecham.
1998-09
The novel anticonvulsant SB 204269 binds to a stereospecific site in the mouse brain.
1996-10-31
Patents

Sample Use Guides

Rats: 1-30 mg/kg
Route of Administration: Oral
In Vitro Use Guide
The binding of [3H]SB 204269 (Carabersat) to mouse forebrain membranes is saturable (Bmax 217 fmol/mg protein, Kd 32 nM) and stereospecific.
Name Type Language
CARABERSAT
INN  
INN  
Official Name English
SB-204269-EO
Preferred Name English
carabersat [INN]
Common Name English
N-[(3R,4S)-6-Acetyl-3-hydroxy-2,2-dimethylchroman-4-yl]-4-fluorobenzamide
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C264
Created by admin on Mon Mar 31 18:26:14 GMT 2025 , Edited by admin on Mon Mar 31 18:26:14 GMT 2025
Code System Code Type Description
EPA CompTox
DTXSID6047319
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PRIMARY
INN
7764
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PRIMARY
FDA UNII
K9R83652CK
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PRIMARY
CAS
184653-84-7
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PRIMARY
PUBCHEM
193943
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PRIMARY
ChEMBL
CHEMBL39933
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PRIMARY
SMS_ID
300000034115
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PRIMARY
NCI_THESAURUS
C77999
Created by admin on Mon Mar 31 18:26:14 GMT 2025 , Edited by admin on Mon Mar 31 18:26:14 GMT 2025
PRIMARY