Fluoxetine hydrochloride

Fluoxetine hydrochloride (Prozac) is a widely prescribed antidepressant drug introduced by Eh Lilly Co in 1986 It differs from Compound A in having an —NHCH3 group in place of —N(CH3)2 What IS the structure of Prozac" ... 

An extensive study was undertaken to optimize the carbonyl-ene reaction between benzaldehyde (143, Scheme 30) and 3-methylene-2,3-dihydrofuran 144, which was utilized in the enantioselective synthesis of fluoxetine hydrochloride, a selective seratonin reuptake inhibitor.89 The degree of hydration of the molecular sieves proved important in the stereoselectivity of the reaction, with lower enantioselectivities reported both with highly active... 

Understandably, the impurity profiles of the same drug substance produced by different S3mthetic routes will differ qualitatively and quantitatively. This is commonly observed when a drug substance is provided by different suppliers. For example, the HPLC chromatograms from samples of fluoxetine hydrochloride obtained from four different suppliers show the differences in the impurities produced by the presumably different synthetic routes (Figure 1.1) [7]. Supplier A is the innovator company. Supplier B is in Italy, and Suppliers C and D are in India. 

Figure 1.1 HPLC chromatograms of samples of fluoxetine hydrochloride from four different suppliers (A-D). Reproduced from [7], Reproduced by permission from the publisher and authors. (Column 250 X 4.6 mm i.d. 5 pm Zorbax SB-C8 mobile-phase gradient acetonitrile water triflu-oroacetic 20 80 0.07 for 5 min, to 85 15 0.07 over 25 min, maintain at 85 15 0.07 for 5 min, return to initial conditions over 5 min, re-equilibrate for 10 min flow rate 1 mEmin injection 10 pi of 10 mg/ml solution in the initial mobile phase detector UV 260 nm.)...

Depending on the nature of the drug substance and impurities, GC may sometimes be an appropriate technique. For example, the USP method for amantadine involves GC. Figure 1.7 [7] illustrates the impurities found in two samples of fluoxetine hydrochloride as determined by GC. Compounds monitored by GC are normally low molecular weight compounds that are not heat sensitive. 

Renal impairment - Use with caution in patients with severe renal impairment. FLUOXETINE HYDROCHLORIDE ... 

Selective serotonin reuptake inhibitors (SSRIs) citalopram hydrobromide fluoxetine hydrochloride fluvoxamine maleate... 

Selective serotonin reuptake inhibitors fluoxetine hydrochloride fluvoxamine maleate paroxetine hydrochloride sertraline hydrochloride... 

Fluoxetine hydrochloride is most recognized as an antidepressant, but it is also used to relieve symptoms of premenstrual dysphoric disorder (PMDD) (premenstrual syndrome). These symptoms include mood swings, tension, bloating, irritability, and breast tenderness. Eh Lilly began marketing fluoxetine hydrochloride as Sarafem in 2000 for treating PMDD. 

Wirth DD, Baertschi SW, Johnson RA, et al. Maillard reaction of lactose and fluoxetine hydrochloride, a secondary amine. J Pharm Sci 1998 87(1) 31 39. 

USAN Fluoxetine Hydrochloride Trade Name- Prozac ... 

The most widely known SSRIs are fluoxetine hydrochloride (4, Prozac , Lilly), sertraline hydrochloride (5, Zoloft , Pfizer) and paroxetine hydrochloride (6, Paxil , GSK). Fluoxetine (4, Prozac ) was the first SSRl approved and effected a revolutionary change in the treatment of depression. In 2000, it was the most widely prescribed antidepressant drug in the United States with worldwide sales of 2.58B. Sertraline (5, Zoloft ) has been available in the United States since 1992 and had worldwide sales of 2.14B in 2000. Compared to fluoxetine (4), it has a shorter duration of action and fewer CNS activating side-effects such as nervousness and anxiety. Paroxetine (6, Paxil ) generated worldwide sales of 2.35B in 2000 and has a relatively benign side-effect profile, which favors its use with elderly patients. 

Synthesis of fluoxetine hydrochloride 10.3 Synthesis of sertraline hydrochloride 10.4 Synthesis of paroxetine hydrochloride 10.5 References... 

Prozac (Fluoxetine hydrochloride) differs from compound A in having an —NHCH3 group in place of —N(CH3)2. 

The older generation of drags are less desirable than the new selective serotonin reuptake inhibitors, because they have many actions in the body other than their antidepressant effect. Prozac (fluoxetine hydrochloride) is among this group. Other trade names in this group are Celexa, Paxil, and Zoloft. 

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