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Details

Stereochemistry ACHIRAL
Molecular Formula C18H13ClFN3
Molecular Weight 325.7679
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BASIMGLURANT

SMILES

Cc1c(C#Cc2ccnc(c2)Cl)nc(C)n1-c3ccc(cc3)F

InChI

InChIKey=UPZWINBEAHDTLA-UHFFFAOYSA-N
InChI=1S/C18H13ClFN3/c1-12-17(8-3-14-9-10-21-18(19)11-14)22-13(2)23(12)16-6-4-15(20)5-7-16/h4-7,9-11H,1-2H3

HIDE SMILES / InChI

Molecular Formula C18H13ClFN3
Molecular Weight 325.7679
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment:: Description was created based on several sources, including http://adisinsight.springer.com/drugs/800024877 https://www.ncbi.nlm.nih.gov/pubmed/26219727

Basimglurant is a potent, selective, and safe mGlu5 inhibitor with good oral bioavailability and long half-life supportive of once-daily administration, good brain penetration, and high in vivo potency. It has antidepressant properties that are corroborated by its functional magnetic imaging profile as well as anxiolytic-like and antinociceptive features. In electroencephalography recordings, basimglurant shows wake-promoting effects followed by increased delta power during subsequent non-rapid eye movement sleep. Basimglurant has favorable drug-like properties, a differentiated molecular mechanism of action, and antidepressant-like features that suggest the possibility of also addressing important comorbidities of MDD including anxiety and pain as well as daytime sleepiness and apathy or lethargy. Basimglurant is being under development by Roche for the treatment of treatment-resistant depression (as an adjunct). It is in phase II clinical trials for this indication.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
16.3 ng × eq/mL
1 mg single, oral
dose: 1 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BASIMGLURANT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
296 ng × eq × h/mL
1 mg single, oral
dose: 1 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BASIMGLURANT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
178 h
1 mg single, oral
dose: 1 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BASIMGLURANT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
likely
likely
likely
major [Km 6.8 uM]
yes (co-administration study)
Comment: Fluvoxamine increased AUC by 60%.
major
major
minor
minor
minor
yes (co-administration study)
Comment: Ketoconazole increased Cmax and AUC by 3% and 24%.
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
yes [Km 4.2 uM]
yes [Km 48 uM]
yes
yes
yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Patents

Sample Use Guides

Participants will receive once-daily oral basimglurant capsules in a multiple ascending dose regimen. Basimglurant dose will be titrated over 22 days; dose escalations will be separated by at least 4 days, with the final dose administered for a minimum of 14 days. The minimum starting dose will be 1.5 mg, which can be titrated up to a maximum dose of 4.0 mg. Intrapatient dose increments will not exceed 1.0 mg every 4 days.
Route of Administration: Oral
Basimglurant bound with a nanomolar affinity (Ki 36nM) to the allosteric binding sites of the 3H-MPEP, the classical mGlu5 NAM, in the TM domains. In HEK293 cells stably expressing human mGlu5, basimglurant inhibited quisqualate-induced Ca2+ mobilization, with an IC50 7.0 nM, and [3H]inositol phosphate accumulation, with an IC50 5.9 nM
Substance Class Chemical
Created
by admin
on Sat Jun 26 02:15:08 UTC 2021
Edited
by admin
on Sat Jun 26 02:15:08 UTC 2021
Record UNII
3110E3AO8S
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BASIMGLURANT
INN   USAN  
USAN   INN  
Official Name English
RO-4917523
Code English
RO4917523
Code English
BASIMGLURANT [WHO-DD]
Common Name English
RG-7090
Code English
PYRIDINE, 2-CHLORO-4-(2-(1-(4-FLUOROPHENYL)-2,5-DIMETHYL-1H-IMIDAZOL-4-YL)ETHYNYL)-
Systematic Name English
BASIMGLURANT [INN]
Common Name English
2-CHLORO-4-(2-(1-(4-FLUOROPHENYL)-2,5-DIMETHYL-1H-IMIDAZOL-4-YL)ETHYNYL)PYRIDINE
Systematic Name English
BASIMGLURANT [USAN]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 333211
Created by admin on Sat Jun 26 02:15:08 UTC 2021 , Edited by admin on Sat Jun 26 02:15:08 UTC 2021
Code System Code Type Description
DRUG BANK
DB11833
Created by admin on Sat Jun 26 02:15:08 UTC 2021 , Edited by admin on Sat Jun 26 02:15:08 UTC 2021
PRIMARY
PUBCHEM
11438771
Created by admin on Sat Jun 26 02:15:08 UTC 2021 , Edited by admin on Sat Jun 26 02:15:08 UTC 2021
PRIMARY
INN
9756
Created by admin on Sat Jun 26 02:15:08 UTC 2021 , Edited by admin on Sat Jun 26 02:15:08 UTC 2021
PRIMARY
FDA UNII
3110E3AO8S
Created by admin on Sat Jun 26 02:15:08 UTC 2021 , Edited by admin on Sat Jun 26 02:15:08 UTC 2021
PRIMARY
ChEMBL
CHEMBL3301626
Created by admin on Sat Jun 26 02:15:08 UTC 2021 , Edited by admin on Sat Jun 26 02:15:08 UTC 2021
PRIMARY
NCI_THESAURUS
C166619
Created by admin on Sat Jun 26 02:15:08 UTC 2021 , Edited by admin on Sat Jun 26 02:15:08 UTC 2021
PRIMARY
CAS
802906-73-6
Created by admin on Sat Jun 26 02:15:08 UTC 2021 , Edited by admin on Sat Jun 26 02:15:08 UTC 2021
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
NEGATIVE ALLOSTERIC MODULATOR
Related Record Type Details
ACTIVE MOIETY