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Details

Stereochemistry ACHIRAL
Molecular Formula C21H20FN3O5S
Molecular Weight 445.464
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BASMISANIL

SMILES

CC1=C(COC2=CC=C(C=N2)C(=O)N3CCS(=O)(=O)CC3)C(=NO1)C4=CC=C(F)C=C4

InChI

InChIKey=VCGRFBXVSFAGGA-UHFFFAOYSA-N
InChI=1S/C21H20FN3O5S/c1-14-18(20(24-30-14)15-2-5-17(22)6-3-15)13-29-19-7-4-16(12-23-19)21(26)25-8-10-31(27,28)11-9-25/h2-7,12H,8-11,13H2,1H3

HIDE SMILES / InChI

Molecular Formula C21H20FN3O5S
Molecular Weight 445.464
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Basmisanil (INN) (developmental code names RG-1662, RO5186582) is a highly selective inverse agonist/negative allosteric modulator of α5 subunit-containing GABAA receptors which is under development by Roche for the treatment of cognitive impairment associated with Down syndrome. The phase II trials were recently terminated due to lack of efficacy. This outcome suggests either that the α5-NAM was insufficiently effective to restore neuronal plasticity or alternatively that the hypothesis of excessive GABAergic inhibition obstructing neuronal plasticity does not extend to individuals with DS.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
1.98 μg/mL
330 mg single, oral
BASMISANIL plasma
Homo sapiens
1.2 μg/mL
120 mg single, oral
BASMISANIL plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
34.65 μg × h/mL
330 mg single, oral
BASMISANIL plasma
Homo sapiens
17.5 μg × h/mL
120 mg single, oral
BASMISANIL plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
7 h
120 mg single, oral
BASMISANIL plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
94.4%
120 mg single, oral
BASMISANIL plasma
Homo sapiens

PubMed

Sample Use Guides

In Vivo Use Guide
120 or 240 mg (80 or 160 mg for subjects 12 and 13 years of age) orally twice daily, 26 weeks
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Record UNII
788PET5SUA
Record Status Validated (UNII)
Record Version