BITOPERTIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H20F7N3O4S
Molecular Weight	543.455
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@H](OC1=CC=C(C=C1C(=O)N2CCN(CC2)C3=NC=C(C=C3F)C(F)(F)F)S(C)(=O)=O)C(F)(F)F

InChI

InChIKey=YUUGYIUSCYNSQR-LBPRGKRZSA-N

InChI=1S/C21H20F7N3O4S/c1-12(20(23,24)25)35-17-4-3-14(36(2,33)34)10-15(17)19(32)31-7-5-30(6-8-31)18-16(22)9-13(11-29-18)21(26,27)28/h3-4,9-12H,5-8H2,1-2H3/t12-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C21H20F7N3O4S
Molecular Weight	543.455
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20491477 | http://www.mind-and-brain-blog.de/en/1707/bad-news-not-only-for-roche-but-for-psychiatry/ | https://www.ecnp.eu/~/media/Files/ecnp/Projects%20and%20initiatives/Medicines%20Chest/Bitopertin.pdf?la=en

Bitopertin is a Glycine transporter type 1 inhibitor which was developed by Hoffmann-La Roche for the treatment of patients with schizophrenia. The drug was shown to be potent in vitro, however it failed to meet primary endpoints in phase III. Bitopertin was also tested for the treatment of obsessive-compulsive disorder, but the development stopped in phase II.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Glycine transporter 1 7 Target ID: CHEMBL2337 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20491477	Inhibitor 8297		25.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Schizophrenia 298 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24735806	Primary		Phase III 656	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
76.5 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26341813	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:		BITOPERTIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
214 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26341813	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:		BITOPERTIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

AUC

Value	Dose	Co-administered	Analyte	Population
2300 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26341813	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:		BITOPERTIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
6570 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26341813	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:		BITOPERTIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

T_1/2

Value	Dose	Co-administered	Analyte	Population
52.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26341813	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:		BITOPERTIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
44.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26341813	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:		BITOPERTIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

F_unbound

Value	Dose	Co-administered	Analyte	Population
2% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20491477	unknown, unknown		BITOPERTIN plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00G44J	https://www.1pchem.com/search?query=1P00G44J
1PlusChem LLC	1P00G44K	https://www.1pchem.com/search?query=1P00G44K
AK Scientific	X5392	https://aksci.com/item_detail.php?cat=X5392
Angene	AGN-PC-0OJ74V	http://www.angenechemical.com/productshow/AGN-PC-0OJ74V.html
ApexBio Technology	A3242	https://www.apexbt.com/catalogsearch/result/?q=A3242
AstaTech	41226	http://astatechinc.com/CPSResult.php?CRNO=41226
BOC Sciences	845614-11-1	http://www.bocsci.com/description.asp?cas=845614-11-1
Cayman Chemical	19896	http://www.caymanchem.com/app/template/Product.vm/catalog/19896
Chem Scene	CS-0939	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0939
ChemShuttle	140128	https://www.chemshuttle.com/catalogsearch/result/?q=140128
Combi-Blocks	QJ-3755	http://www.combi-blocks.com/cgi-bin/find.cgi?QJ-3755
KeyOrganics	AS-75194	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-75194
Lab Seeker	SC-93536	http://www.labseeker.com/search.php?keywords=SC-93536&category=0
LabSeeker	SC-93536	http://www.labseeker.com/search.php?keywords=SC-93536&category=0
MedChem Express	HY-10809	https://www.medchemexpress.com/search.html?q=HY-10809&ft=&fa=&fp=
MolPort	MolPort-028-749-206	https://www.molport.com/shop/molecule-link/MolPort-028-749-206
Molnova	M16141	https://www.molnova.com/en/serch-list.html?keywords=M16141
Selleck Chemicals	S8219	http://www.selleckchem.com/search.html?searchDTO.searchParam=S8219
ShangHai Biochempartner	BCP000624	http://www.biochempartner.com/search_BCP000624
TargetMol	T6788	https://www.targetmol.com/search?keyword=T6788
Toronto Research Chemicals	B591450	https://www.trc-canada.com/product-detail/?CatNum=B591450
Vesino Industrial Co Ltd	VA11991	http://www.vsnchem.com/search.do?a=s&psize=20&q=VA11991
Wonderchem	WD06SBM	http://www.wonder-chem.com/search.html?text=WD06SBM
eMolecules	300763673	https://orderbb.emolecules.com/search/#?query=300763673
eMolecules	44811552	https://orderbb.emolecules.com/search/#?query=44811552
eMolecules	46013844	https://orderbb.emolecules.com/search/#?query=46013844
eNovation Chemicals	D489197	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D489197&searchbtn.x=0&searchbtn.y=0
mcule	MCULE-9186395721	https://mcule.com/MCULE-9186395721/
mcule	MCULE-9971149684	https://mcule.com/MCULE-9971149684/

PubMed

Title	Date	PubMed

Patents

Sample Use Guides

In Vivo Use Guide

Patients receive bitopertin at dose of 10 or 30 mg, once a day for 52 weeks.

Route of Administration: Oral

In Vitro Use Guide

In hippocampal CA1 pyramidal cells, RG1678 enhanced NMDA-dependent long-term potentiation (LTP) at 30 nM, 100 nM but not at 300 nM.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:48:21 UTC 2023` Edited by `admin` on `Fri Dec 15 18:48:21 UTC 2023`
Record UNII	Q8L6AN59YY
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

BITOPERTIN

Official Name

English

RG-1678

Code

English

Bitopertin [WHO-DD]

Common Name

English

DISC-1459

Code

English

(4-(3-FLUORO-5-(TRIFLUOROMETHYL)PYRIDIN-2-YL)PIPERAZIN-1-YL)(5-(METHANESULFONYL)-2-(((2S)-1,1,1-TRIFLUOROPROPAN-2-YL)OXY)PHENYL)METHANONE

Systematic Name

English

R-1678

Code

English

METHANONE, (4-(3-FLUORO-5-(TRIFLUOROMETHYL)-2-PYRIDINYL)-1-PIPERAZINYL)(5-(METHYLSULFONYL)-2-((1S)-2,2,2-TRIFLUORO-1-METHYLETHOXY)PHENYL)-

Systematic Name

English

RO-4917838

Code

English

PIPERAZINE, 1-(3-FLUORO-5-(TRIFLUOROMETHYL)-2-PYRIDINYL)-4-(5-(METHYLSULFONYL)-2-((1S)-2,2,2-TRIFLUORO-1-METHYLETHOXY)BENZOYL)-

Systematic Name

English

bitopertin [INN]

Common Name

English

RO-4917939

Code

English

(4-(3-FLUORO-5-TRIFLUOROMETHYLPYRIDIN-2-YL)PIPERAZIN-1-YL)(5-METHYLSULFONYL-2-(((S)-2,2,2-TRIFLUORO-1-METHYLETHYL)OXY)PHENYL)METHANONE

Systematic Name

English

RO4917838

Code

English

BITOPERTIN [USAN]

Common Name

English

PALIFLUTINE

Common Name

English

BITOPERTIN [JAN]

Common Name

English

(S)-(4-(3-FLUORO-5-TRIFLUOROMETHYLPYRIDIN-2-YL)PIPERAZIN-1-YL)(5-(METHANESULFONYL)-2-(2,2,2-TRIFLUORO-1-METHYLETHOXY)PHENYL)METHANONE

Systematic Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

916222