Duloxetine hydrochloride

Description

Duloxetine is a selective serotonin (5-HT) and norepinephrine reuptake inhibitor (SSNRI) for oral administration, and it is currently approved in the US and in Europe for the treatment of major depressive disorder (MDD) and diabetic peripheral neuropathic pain (DPN). Additionally, it is indicated for the treatment of stress urinary incontinence (SUI) in Europe. 

Chemical properties

White Crystalline Solid

Originator

Lilly (US)

The Uses of Duloxetine hydrochloride

Duloxetine Hydrochloride is an antidepressant that functions as a dual serotonin and norepinephrine reuptake inhibitor (SNRI). It exhibits linear pharmacokinetics in mice and is not associated with any drastic changes in blood pressure or heart rate.

The Uses of Duloxetine hydrochloride

Labelled Duloxetine, which is used as an antidepressant. A dual serotonin and norepinephrine reuptake inhibitor (SNRI). Current lot is 97% d7 with no d0, d1 or d2

The Uses of Duloxetine hydrochloride

An antidepressant. A dual serotonin and norepinephrine reuptake inhibitor (SNRI). Used in treatment of stress urinary incontinence.

The Uses of Duloxetine hydrochloride

leucotriene antagonist, antiasthmatic

The Uses of Duloxetine hydrochloride

anti-depressant, analgesic for osteoarthiritis and musculoskeletal pain

The Uses of Duloxetine hydrochloride

solubility H2O: soluble5 mg/mL (clear solution, warmed)

What are the applications of Application

Duloxetine Hydrochloride is a dual serotonin and norepinephrine reuptake inhibitor.

Definition

ChEBI: A duloxetine hydrochloride in which the duloxetine moiety has S configuration.

brand name

Cymbalta (Lilly).

Biochem/physiol Actions

Duloxetine hydrochloride is a dual serotonin/norepinephrine reuptake inhibitor (SNRI), widely used clinically as an antidepressant and anxiolytic.

Synthesis

The synthesis from Lilly?ˉs group is depicted in Scheme 4. Friedel-Crafts acylation of thiophene (24) by 3- chloropropanoyl chloride (25) with SnCl4 as Lewis acid gave ketone 26 which was then enantioselectively reduced with (R )-1-methyl-3,3-diphenyl-tetrahydropyrrolo[1,2- c][1,3,2]oxazaborole (27) in the presence of borane in THF to give (S)-3-chloro-1-(2-thienyl)-1-propanol (28). Compound 28 was subjected to Finkelstein reaction to give (S)-3-iodio-1-(2-thienyl)-1-propanol which was reacted with methylamine in THF to give compound 29. The alcohol 29 was then used in a nucleophilic displacement reaction with 1-fluoronaphthalene (30) in the presence of sodium hydride in DMA to give duloxetine free base in 88% yield. Finally, the free base was treated with HCl to yield duloxetine hydrochloride (IV).

storage

Room temperature