BASMISANIL

Investigational

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 Search

SMILES

CC1=C(COC2=NC=C(C=C2)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

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28232865
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/27466376 | https://www.ncbi.nlm.nih.gov/pubmed/28236228 | http://www.roche.com/media/store/statements.htm | https://www.ncbi.nlm.nih.gov/pubmed/26635554

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 Target	Pharmacology	Condition	Potency
GABA receptor alpha-5 subunit 8 Target ID: CHEMBL5112 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27466376	Inverse Agonist 85

Conditions

Condition	Modality	Highest Phase	Product
Severe motor impairment following an ischemic stroke 1 Sources: https://clinicaltrials.gov/ct2/show/NCT02928393	Primary	Phase II 1147	Unknown Approved Use Unknown
Cognitive impairment associated with schizophrenia 2 Sources: https://clinicaltrials.gov/ct2/show/NCT02953639	Primary	Phase II 1147	Unknown Approved Use Unknown
Down syndrome 6 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26635554	Primary	Phase II 1147	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
1.98 μg/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/28236228	330 mg single, oral dose: 330 mg route of administration: Oral experiment type: SINGLE co-administered:		BASMISANIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FED
1.2 μg/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/28236228	120 mg single, oral dose: 120 mg route of administration: Oral experiment type: SINGLE co-administered:		BASMISANIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FED

AUC

Value	Dose	Co-administered	Analyte	Population
34.65 μg × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/28236228	330 mg single, oral dose: 330 mg route of administration: Oral experiment type: SINGLE co-administered:		BASMISANIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FED
17.5 μg × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/28236228	120 mg single, oral dose: 120 mg route of administration: Oral experiment type: SINGLE co-administered:		BASMISANIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FED

T_1/2

Value	Dose	Co-administered	Analyte	Population
7 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/28236228	120 mg single, oral dose: 120 mg route of administration: Oral experiment type: SINGLE co-administered:		BASMISANIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FED

F_unbound

Value	Dose	Co-administered	Analyte	Population
94.4% EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/28236228	120 mg single, oral dose: 120 mg route of administration: Oral experiment type: SINGLE co-administered:		BASMISANIL plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FED

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P008YU0	https://www.1pchem.com/search?query=1P008YU0
Ambeed	A106679	http://www.ambeed.com/search/Search.html?keyword=A106679
AstaTech	N13302	http://astatechinc.com/CPSResult.php?CRNO=N13302
BLD Pharm	BD764668	http://www.bldpharm.com/search/Search.html?keyword=BD764668
Cayman Chemical	21137	http://www.caymanchem.com/app/template/Product.vm/catalog/21137
Chem Scene	CS-6046	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-6046
ChemShuttle	141239	https://www.chemshuttle.com/catalogsearch/result/?q=141239
Combi-Blocks	QV-9712	http://www.combi-blocks.com/cgi-bin/find.cgi?QV-9712
eMolecules	110118882	https://orderbb.emolecules.com/search/#?query=110118882
Excenen	EX-A1272	http://www.excenen.com/searchresultlist.php?id=EX-A1272
KeyOrganics	AS-56175	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-56175
mcule	MCULE-7348196783	https://mcule.com/MCULE-7348196783/
MedChem Express	HY-16716	https://www.medchemexpress.com/search.html?q=HY-16716&ft=&fa=&fp=
Molnova	M10552	https://www.molnova.com/en/serch-list.html?keywords=M10552
MolPort	MolPort-044-561-818	https://www.molport.com/shop/molecule-link/MolPort-044-561-818
MuseChem	I000579	https://www.musechem.com/product/I000579.html
ShangHai Biochempartner	BCP19013	http://www.biochempartner.com/search_BCP19013
TargetMol	T7165	https://www.targetmol.com/search?keyword=T7165
Toronto Research Chemicals	B118715	https://www.trc-canada.com/product-detail/?CatNum=B118715
Toronto Research Chemicals	G780013	https://www.trc-canada.com/product-detail/?CatNum=G780013

PubMed

Title	Date	PubMed
Characterising Drug Release from Immediate-Release Formulations of a Poorly Soluble Compound, Basmisanil, Through Absorption Modelling and Dissolution Testing.	2017 May	28236228

Patents

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 Created by `admin` on `Mon Mar 31 21:31:13 GMT 2025` Edited by `admin` on `Mon Mar 31 21:31:13 GMT 2025`
Record UNII	788PET5SUA
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

basmisanil [INN]

Preferred Name

English

BASMISANIL

Official Name

English

Basmisanil [WHO-DD]

Common Name

English

RO5186582

Code

English

RG1662

Code

English

(1,1-DIOXIDOTHIOMORPHOLINO)(6-((3-(4-FLUOROPHENYL)-5-METHYLISOXAZOL-4-YL)METHOXY)PYRIDIN-3-YL)METHANONE

Systematic Name

English

METHANONE, (1,1-DIOXIDO-4-THIOMORPHOLINYL)(6-((3-(4-FLUOROPHENYL)-5-METHYL-4-ISOXAZOLYL)METHOXY)-3-PYRIDINYL)-

Systematic Name

English

RO5186582-000

Code

English

(1,1-DIOXO-4-THIOMORPHOLINYL)(6-((3-(4-FLUOROPHENYL)-5-METHYLISOXAZOL-4-YL)METHOXY)PYRIDIN-3-YL)METHANONE

Systematic Name

English

RO-5186582

Code

English

BASMISANIL [USAN]

Common Name

English

RG-1662

Code

English

Code System Code Type Description

SMS_ID

300000034034