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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

Molecular Formula C20H20FNO4
Molecular Weight 357.3755
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 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
n = 35
Health Status: healthy
Sex: unknown
Food Status: UNKNOWN
Population Size: 35
Sources:
PubMed

PubMed

TitleDatePubMed
SB-204269 SmithKline Beecham.
1998 Sep
Third-generation antiepileptic drugs: mechanisms of action, pharmacokinetics and interactions.
2009 Mar-Apr
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:22:09 GMT 2023
Edited
by admin
on Fri Dec 15 16:22:09 GMT 2023
Record UNII
K9R83652CK
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CARABERSAT
INN  
INN  
Official Name English
carabersat [INN]
Common Name English
SB-204269-EO
Code 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 Fri Dec 15 16:22:09 GMT 2023 , Edited by admin on Fri Dec 15 16:22:09 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID6047319
Created by admin on Fri Dec 15 16:22:09 GMT 2023 , Edited by admin on Fri Dec 15 16:22:09 GMT 2023
PRIMARY
INN
7764
Created by admin on Fri Dec 15 16:22:09 GMT 2023 , Edited by admin on Fri Dec 15 16:22:09 GMT 2023
PRIMARY
FDA UNII
K9R83652CK
Created by admin on Fri Dec 15 16:22:09 GMT 2023 , Edited by admin on Fri Dec 15 16:22:09 GMT 2023
PRIMARY
CAS
184653-84-7
Created by admin on Fri Dec 15 16:22:09 GMT 2023 , Edited by admin on Fri Dec 15 16:22:09 GMT 2023
PRIMARY
PUBCHEM
193943
Created by admin on Fri Dec 15 16:22:10 GMT 2023 , Edited by admin on Fri Dec 15 16:22:10 GMT 2023
PRIMARY
ChEMBL
CHEMBL39933
Created by admin on Fri Dec 15 16:22:09 GMT 2023 , Edited by admin on Fri Dec 15 16:22:09 GMT 2023
PRIMARY
SMS_ID
300000034115
Created by admin on Fri Dec 15 16:22:10 GMT 2023 , Edited by admin on Fri Dec 15 16:22:10 GMT 2023
PRIMARY
NCI_THESAURUS
C77999
Created by admin on Fri Dec 15 16:22:10 GMT 2023 , Edited by admin on Fri Dec 15 16:22:10 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SOLVATE->ANHYDROUS
Related Record Type Details
ACTIVE MOIETY