BASIMGLURANT SULFATE

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C18H13ClFN3.H2O4S
Molecular Weight	423.846
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OS(O)(=O)=O.CC1=NC(C#CC2=CC(Cl)=NC=C2)=C(C)N1C3=CC=C(F)C=C3

InChI

InChIKey=RPRPXJNEEIIWAL-UHFFFAOYSA-N

InChI=1S/C18H13ClFN3.H2O4S/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;1-5(2,3)4/h4-7,9-11H,1-2H3;(H2,1,2,3,4)

HIDE SMILES / InChI

Molecular Formula	H2O4S
Molecular Weight	98.078
Charge	0
Count

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

Molecular Formula	C18H13ClFN3
Molecular Weight	325.767
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/25665805
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Metabotropic glutamate receptor 5 40 Target ID: CHEMBL3227 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25565255 https://www.ncbi.nlm.nih.gov/pubmed/25665805	Negative Allosteric Modulator 43		7.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Major depressive disorder 179 Sources: https://clinicaltrials.gov/ct2/show/NCT01437657	Primary		Phase II 1147	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
16.3 ng × eq/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27123695	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

Value	Dose	Co-administered	Analyte	Population
296 ng × eq × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27123695	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
178 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27123695	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

CYP3A4	CYP2C9	CYP2D6	hERG
	substrate 1193	substrate 1388	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP2B6 776 CYP2E1 729 CYP2C8 810 UGT1A1 479 CYP4A11 137 UGT1A6 343 UGT1A4 399 CYP1A2 1197 CYP3A4/5 91 CYP2C19 1119 UGT1A9 423 UGT2B7 456 UGT1A3 470 CYP1A1 389 UGT1A7 249 CYP2A6 626 UGT1A8 323 UGT2B10 131 UGT1A10 331 P-gp 2052 UGT2B4 278 UGT2B15 236 UGT2B17 237

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
UGT2B17 237	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27821711/	likely	M1 18
UGT2B17 237	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27821711/	likely	M2 12
UGT2B7 456	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27821711/	likely	M2 12
CYP1A2 1197	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27821711/	major [Km 6.8 uM]		yes (co-administration study) Comment: Fluvoxamine increased AUC by 60%. Sources: https://pubmed.ncbi.nlm.nih.gov/27821711/
UGT1A9 423	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27821711/	major	M1 18
UGT1A9 423	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27821711/	major	M2 12
UGT1A10 331	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27821711/	minor	M2 12
UGT1A7 249	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27821711/	minor	M2 12
CYP3A4/5 91	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27821711/	minor		yes (co-administration study) Comment: Ketoconazole increased Cmax and AUC by 3% and 24%. Sources: https://pubmed.ncbi.nlm.nih.gov/27821711/
CYP2A6 626	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27821711/	no
CYP2B6 776	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27821711/	no
CYP2C8 810	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27821711/	no
CYP2C9 1193	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27821711/	no
CYP2D6 1388	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27821711/	no
CYP2E1 729	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27821711/	no
CYP4A11 137	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27821711/	no
P-gp 2052	substrate 4014 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1346987#sid=363680975	no
UGT1A1 479	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27821711/	no	M1 18
UGT1A1 479	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27821711/	no	M2 12
UGT1A10 331	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27821711/	no	M1 18
UGT1A3 470	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27821711/	no	M2 12
UGT1A4 399	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27821711/	no	M1 18
UGT1A4 399	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27821711/	no	M2 12
UGT1A6 343	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27821711/	no	M1 18
UGT1A6 343	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27821711/	no	M2 12
UGT1A8 323	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27821711/	no	M1 18
UGT1A8 323	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27821711/	no	M2 12
UGT2B10 131	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27821711/	no	M1 18
UGT2B10 131	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27821711/	no	M2 12
UGT2B15 236	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27821711/	no	M1 18
UGT2B15 236	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27821711/	no	M2 12
UGT2B4 278	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27821711/	no	M1 18
UGT2B4 278	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27821711/	no	M2 12
CYP1A1 389	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27821711/	yes [Km 4.2 uM]
CYP2C19 1119	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27821711/	yes [Km 48 uM]
UGT1A3 470	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27821711/	yes	M1 18
UGT1A7 249	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27821711/	yes	M1 18
UGT2B7 456	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27821711/	yes	M1 18

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubmed.ncbi.nlm.nih.gov/25565255/

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00G44Q	https://www.1pchem.com/search?query=1P00G44Q
A2B Chem	AH51050	http://a2bchem.com/prod/AH51050
AChemBlock	L13487	http://www.achemblock.com/catalogsearch/result/?q=L13487
ApexBio Technology	B4808	https://www.apexbt.com/catalogsearch/result/?q=B4808
AstaTech	P14045	http://astatechinc.com/CPSResult.php?CRNO=P14045
BLD Pharm	BD301060	http://www.bldpharm.com/search/Search.html?keyword=BD301060
Chem Scene	CS-3388	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-3388
Combi-Blocks	QM-8773	http://www.combi-blocks.com/cgi-bin/find.cgi?QM-8773
eMolecules	50281307	https://orderbb.emolecules.com/search/#?query=50281307
KeyOrganics	AS-51978	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-51978
Lab Network	LN01341873	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01341873
mcule	MCULE-4074341289	https://mcule.com/MCULE-4074341289/
MedChem Express	HY-15446	https://www.medchemexpress.com/search.html?q=HY-15446&ft=&fa=&fp=
MolPort	MolPort-039-063-482	https://www.molport.com/shop/molecule-link/MolPort-039-063-482
MuseChem	I003950	https://www.musechem.com/product/I003950.html
ShangHai Biochempartner	BCP15864	http://www.biochempartner.com/search_BCP15864

PubMed

Title	Date	PubMed
Low Potential of Basimglurant to Be Involved in Drug-Drug Interactions: Influence of Non-Michaelis-Menten P450 Kinetics on Fraction Metabolized.	2017-01	27821711
Pharmacology of basimglurant (RO4917523, RG7090), a unique metabotropic glutamate receptor 5 negative allosteric modulator in clinical development for depression.	2015-04	25665805
Metabotropic glutamate receptor 5 negative allosteric modulators: discovery of 2-chloro-4-[1-(4-fluorophenyl)-2,5-dimethyl-1H-imidazol-4-ylethynyl]pyridine (basimglurant, RO4917523), a promising novel medicine for psychiatric diseases.	2015-02-12	25565255

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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 `Mon Mar 31 18:48:15 GMT 2025` Edited by `admin` on `Mon Mar 31 18:48:15 GMT 2025`
Record UNII	MQ04IL403Q
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PYRIDINE, 2-CHLORO-4-(2-(1-(4-FLUOROPHENYL)-2,5-DIMETHYL-1H-IMIDAZOL-4-YL)ETHYNYL)-, SULFATE (1:1)

Preferred Name

English

BASIMGLURANT SULFATE

Common Name

English

RO-4917523 SULPHATE

Common Name

English

NOE-101 SULFATE

Code

English

RO4917523 SULPHATE

Common Name

English

Code System Code Type Description

PUBCHEM

131634700

Created by admin on Mon Mar 31 18:48:15 GMT 2025 , Edited by admin on Mon Mar 31 18:48:15 GMT 2025

PRIMARY

FDA UNII

MQ04IL403Q

Created by admin on Mon Mar 31 18:48:15 GMT 2025 , Edited by admin on Mon Mar 31 18:48:15 GMT 2025

PRIMARY

CAS

1034442-21-1

Created by admin on Mon Mar 31 18:48:15 GMT 2025 , Edited by admin on Mon Mar 31 18:48:15 GMT 2025

PRIMARY

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PARENT -> SALT/SOLVATE

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					3110E3AO8S

BASIMGLURANT

ACTIVE MOIETY

Details

SMILES

InChI

DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/25665805Curator's Comment: Description was created based on several sources, including http://adisinsight.springer.com/drugs/800024877 https://www.ncbi.nlm.nih.gov/pubmed/26219727

CNS Activity

Originator

Approval Year

Targets

Conditions

Approved Use

Cmax

AUC

T1/2

Overview

OverviewOther

Drug as victim

Tox targets

Sourcing

PubMed

Patents

Sample Use Guides

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25665805
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

C_max

T_1/2