Radafaxine

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C13H18ClNO2
Molecular Weight	255.741
Optical Activity	( + )
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@@H]1NC(C)(C)CO[C@@]1(O)C2=CC=CC(Cl)=C2

InChI

InChIKey=RCOBKSKAZMVBHT-TVQRCGJNSA-N

InChI=1S/C13H18ClNO2/c1-9-13(16,17-8-12(2,3)15-9)10-5-4-6-11(14)7-10/h4-7,9,15-16H,8H2,1-3H3/t9-,13+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C13H18ClNO2
Molecular Weight	255.741
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15780851 | https://www.ncbi.nlm.nih.gov/pubmed/21522056 | https://www.ncbi.nlm.nih.gov/pubmed/12909199 | http://adisinsight.springer.com/drugs/800017221

Radafaxine (GW353162, ( )-(2S,3S)-2-(3-chlorophenyl-3,5,5-trimethyl-2-morphinol) or S,S-hydroxybupropion) is an active metabolite of bupropion. It acts as an inhibitor of the dopamine transporter. Radafaxine was investigated for the treatment of depression however, development was discontinued.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Dopamine transporter 183 Target ID: CHEMBL2799 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15780851 \| https://www.ncbi.nlm.nih.gov/pubmed/12909199	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Major depressive disorder 179 Sources: http://adisinsight.springer.com/drugs/800017221	Primary		Phase II 1147	Unknown Approved Use Unknown

Doses

Dose	Population	Adverse events
60 mg 1 times / day multiple, oral Highest studied dose Dose: 60 mg, 1 times / day Route: oral Route: multiple Dose: 60 mg, 1 times / day Sources: https://web.archive.org/web/20070928035216/http://213.219.8.102/pdfs/gsk/cns_seminar/353162.pdf	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: unknown Food Status: UNKNOWN Sources: https://web.archive.org/web/20070928035216/http://213.219.8.102/pdfs/gsk/cns_seminar/353162.pdf	Sources: https://web.archive.org/web/20070928035216/http://213.219.8.102/pdfs/gsk/cns_seminar/353162.pdf

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P008U3N	https://www.1pchem.com/search?query=1P008U3N
1PlusChem LLC	1P00BY4R	https://www.1pchem.com/search?query=1P00BY4R
AK Scientific	3998AH	https://aksci.com/item_detail.php?cat=3998AH
Angene	AGN-PC-04XRSH	http://www.angenechemical.com/productshow/AGN-PC-04XRSH.html
Angene	AGN-PC-0WH21J	http://www.angenechemical.com/productshow/AGN-PC-0WH21J.html
ApexBio Technology	B8305	https://www.apexbt.com/catalogsearch/result/?q=B8305
AstaTech	43004	http://astatechinc.com/CPSResult.php?CRNO=43004
Axon MedChem	1123	https://www.axonmedchem.com/product/1123
BOC Sciences	106083-71-0	http://www.bocsci.com/description.asp?cas=106083-71-0
BOC Sciences	192374-14-4	http://www.bocsci.com/description.asp?cas=192374-14-4
BOC Sciences	357399-43-0	http://www.bocsci.com/description.asp?cas=357399-43-0
Cayman Chemical	9000522	http://www.caymanchem.com/app/template/Product.vm/catalog/9000522
Chem Scene	CS-3815	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-3815
Debye Scientific	DB-024969	https://www.debyesci.com/index.php?id=product&ext[cno]=DB-024969
eMolecules	16573966	https://orderbb.emolecules.com/search/#?query=16573966
eMolecules	168767612	https://orderbb.emolecules.com/search/#?query=168767612
eMolecules	225774432	https://orderbb.emolecules.com/search/#?query=225774432
eMolecules	31228869	https://orderbb.emolecules.com/search/#?query=31228869
eMolecules	36366928	https://orderbb.emolecules.com/search/#?query=36366928
Lab Network	LN01309187	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01309187
Lab Network	LN01341606	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01341606
mcule	MCULE-6487414387	https://mcule.com/MCULE-6487414387/
mcule	MCULE-7436745384	https://mcule.com/MCULE-7436745384/
mcule	MCULE-9642855522	https://mcule.com/MCULE-9642855522/
MedChem Express	HY-17590	https://www.medchemexpress.com/search.html?q=HY-17590&ft=&fa=&fp=
Molnova	M10270	https://www.molnova.com/en/serch-list.html?keywords=M10270
MolPort	MolPort-019-990-036	https://www.molport.com/shop/molecule-link/MolPort-019-990-036
MuseChem	I008500	https://www.musechem.com/product/I008500.html
MuseChem	R001764	https://www.musechem.com/product/R001764.html
Tetrahedron	TS28841	http://www.thsci.com/search.do?q=TS28841
Toronto Research Chemicals	H830670	https://www.trc-canada.com/product-detail/?CatNum=H830670
Toronto Research Chemicals	H830675	https://www.trc-canada.com/product-detail/?CatNum=H830675
Wonderchem	WD05I4S	http://www.wonder-chem.com/search.html?text=WD05I4S
Wonderchem	WD05I4T	http://www.wonder-chem.com/search.html?text=WD05I4T
Wonderchem	WD05Z92	http://www.wonder-chem.com/search.html?text=WD05Z92

PubMed

Title	Date	PubMed
In vitro assessment of P450 induction potential of novel chemopreventive agents SR13668, 9-cis-UAB30, and pentamethychromanol in primary cultures of human hepatocytes.	2009-05-15	19135037
[Obesity: a review of currently used antiobesity drugs and new compounds in clinical development].	2007-10-19	17971763
Obesity drugs in clinical development.	2006-04	16625817
The slow and long-lasting blockade of dopamine transporters in human brain induced by the new antidepressant drug radafaxine predict poor reinforcing effects.	2005-03-15	15780851
Validated assays for human cytochrome P450 activities.	2004-06	15155557

Patents

Sample Use Guides

In Vivo Use Guide

Once-daily oral radafaxine (GW353162) (20-40-60mg) was investigated over an eight-week treatment period in phase 2 study in subjects with major depressive disorder

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:16:22 GMT 2025` Edited by `admin` on `Mon Mar 31 18:16:22 GMT 2025`
Record UNII	Q47741214K
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

GW-353,162

Preferred Name

English

Radafaxine

Official Name

English

radafaxine [INN]

Common Name

English

(+)-(2S,3S)-2-(3-chlorophenyl)-3,5,5-trimethyl-2-morpholinol

Systematic Name

English

GW-353162

Code

English

(2S,3S)-Hydroxybupropion

Common Name

English

2-Morpholinol, 2-(3-chlorophenyl)-3,5,5-trimethyl-, (2S,3S)-

Systematic Name

English

(2S,3S)-2-(3-Chlorophenyl)-3,5,5-trimethyl-2-morpholinol

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C66884