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Details

Stereochemistry ABSOLUTE
Molecular Formula 2C20H20FNO4.H2O
Molecular Weight 732.7663
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CARABERSAT HEMIHYDRATE

SMILES

O.CC(=O)C1=CC=C2OC(C)(C)[C@H](O)[C@@H](NC(=O)C3=CC=C(F)C=C3)C2=C1.CC(=O)C4=CC=C5OC(C)(C)[C@H](O)[C@@H](NC(=O)C6=CC=C(F)C=C6)C5=C4

InChI

InChIKey=QVTLCQAMIIJUQD-LKKSXLMASA-N
InChI=1S/2C20H20FNO4.H2O/c2*1-11(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;/h2*4-10,17-18,24H,1-3H3,(H,22,25);1H2/t2*17-,18+;/m00./s1

HIDE SMILES / InChI

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
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.
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:57:30 GMT 2025
Edited
by admin
on Mon Mar 31 17:57:30 GMT 2025
Record UNII
G02OAY25RC
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BENZAMIDE, N-(6-ACETYL-3,4-DIHYDRO-3-HYDROXY-2,2-DIMETHYL-2H-1-BENZOPYRAN-4-YL)-4-FLUORO-, HYDRATE (2:1), (3R-TRANS)-
Preferred Name English
CARABERSAT HEMIHYDRATE
Common Name English
Code System Code Type Description
CAS
185122-82-1
Created by admin on Mon Mar 31 17:57:30 GMT 2025 , Edited by admin on Mon Mar 31 17:57:30 GMT 2025
PRIMARY
PUBCHEM
71498969
Created by admin on Mon Mar 31 17:57:30 GMT 2025 , Edited by admin on Mon Mar 31 17:57:30 GMT 2025
PRIMARY
FDA UNII
G02OAY25RC
Created by admin on Mon Mar 31 17:57:30 GMT 2025 , Edited by admin on Mon Mar 31 17:57:30 GMT 2025
PRIMARY
Related Record Type Details
ANHYDROUS->SOLVATE
PARENT -> SALT/SOLVATE