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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 of BITOPERTIN

SMILES

C[C@H](OC1=C(C=C(C=C1)S(C)(=O)=O)C(=O)N2CCN(CC2)C3=C(F)C=C(C=N3)C(F)(F)F)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

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

Hoffman-La Roche
135
Curator's Comment: # Hoffmann-La Roche Ltd

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
 25.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase III
665
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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
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
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
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

Sourcing

Vendor/AggregatorIDURL
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
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
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
mcule
MCULE-9186395721
https://mcule.com/MCULE-9186395721/
mcule
MCULE-9971149684
https://mcule.com/MCULE-9971149684/
MedChem Express
HY-10809
https://www.medchemexpress.com/search.html?q=HY-10809&ft=&fa=&fp=
Molnova
M16141
https://www.molnova.com/en/serch-list.html?keywords=M16141
MolPort
MolPort-028-749-206
https://www.molport.com/shop/molecule-link/MolPort-028-749-206
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
PubMed

PubMed

TitleDatePubMed
A phase II/III trial of bitopertin monotherapy compared with placebo in patients with an acute exacerbation of schizophrenia - results from the CandleLyte study.
2014-07
Effect of bitopertin, a glycine reuptake inhibitor, on negative symptoms of schizophrenia: a randomized, double-blind, proof-of-concept study.
2014-06
Selective GlyT1 inhibitors: discovery of [4-(3-fluoro-5-trifluoromethylpyridin-2-yl)piperazin-1-yl][5-methanesulfonyl-2-((S)-2,2,2-trifluoro-1-methylethoxy)phenyl]methanone (RG1678), a promising novel medicine to treat schizophrenia.
2010-06-24
Patents

Patents

20050209241
1
20080119486
1
20080167333
1
JP4799666B2
1

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 Mon Mar 31 19:21:30 GMT 2025
Edited
by admin
on Mon Mar 31 19:21:30 GMT 2025
Record UNII
Q8L6AN59YY
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
R-1678
Preferred Name English
BITOPERTIN
INN   USAN   WHO-DD  
INN   USAN  
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
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
Created by admin on Mon Mar 31 19:21:30 GMT 2025 , Edited by admin on Mon Mar 31 19:21:30 GMT 2025
FDA ORPHAN DRUG 596717
Created by admin on Mon Mar 31 19:21:30 GMT 2025 , Edited by admin on Mon Mar 31 19:21:30 GMT 2025
EU-Orphan Drug EU/3/17/1919
Created by admin on Mon Mar 31 19:21:30 GMT 2025 , Edited by admin on Mon Mar 31 19:21:30 GMT 2025
Code System Code Type Description
SMS_ID
100000175138
Created by admin on Mon Mar 31 19:21:30 GMT 2025 , Edited by admin on Mon Mar 31 19:21:30 GMT 2025
PRIMARY
PUBCHEM
24946690
Created by admin on Mon Mar 31 19:21:30 GMT 2025 , Edited by admin on Mon Mar 31 19:21:30 GMT 2025
PRIMARY
NCI_THESAURUS
C174879
Created by admin on Mon Mar 31 19:21:30 GMT 2025 , Edited by admin on Mon Mar 31 19:21:30 GMT 2025
PRIMARY
WIKIPEDIA
Bitopertin
Created by admin on Mon Mar 31 19:21:30 GMT 2025 , Edited by admin on Mon Mar 31 19:21:30 GMT 2025
PRIMARY
CAS
845614-11-1
Created by admin on Mon Mar 31 19:21:30 GMT 2025 , Edited by admin on Mon Mar 31 19:21:30 GMT 2025
PRIMARY
USAN
YY-14
Created by admin on Mon Mar 31 19:21:30 GMT 2025 , Edited by admin on Mon Mar 31 19:21:30 GMT 2025
PRIMARY
INN
9319
Created by admin on Mon Mar 31 19:21:30 GMT 2025 , Edited by admin on Mon Mar 31 19:21:30 GMT 2025
PRIMARY
EPA CompTox
DTXSID80233556
Created by admin on Mon Mar 31 19:21:30 GMT 2025 , Edited by admin on Mon Mar 31 19:21:30 GMT 2025
PRIMARY
DRUG BANK
DB12426
Created by admin on Mon Mar 31 19:21:30 GMT 2025 , Edited by admin on Mon Mar 31 19:21:30 GMT 2025
PRIMARY
FDA UNII
Q8L6AN59YY
Created by admin on Mon Mar 31 19:21:30 GMT 2025 , Edited by admin on Mon Mar 31 19:21:30 GMT 2025
PRIMARY
ChEMBL
CHEMBL1169880
Created by admin on Mon Mar 31 19:21:30 GMT 2025 , Edited by admin on Mon Mar 31 19:21:30 GMT 2025
PRIMARY
Related Record Type Details
GLYCINE TRANSPORTER-1
TARGET -> INHIBITOR
IC50
Related Record Type Details
Structure of BITOPERTIN
ACTIVE MOIETY
NIH
NCATS
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