RADAFAXINE

Investigational

Details

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

SHOW SMILES / InChI

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	MOL RATIO 1 MOL RATIO (average)

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

Description

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 180	Inhibitor 8,297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Major depressive disorder 173	Primary		Phase II 1,132	Unknown

Doses

Doses

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Dose	Population	Adverse events
60 mg 1 times / day multiple, oral (unknown) Highest studied dose	unhealthy, ADULT n = 365

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Sourcing

Sourcing

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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

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PubMed

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

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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