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fluoxetine hydrochloride(CAS No. 59333-67-4)

fluoxetine hydrochloride C17H18F3NO.HCl (cas 59333-67-4) Molecular Structure

59333-67-4 Structure

Identification and Related Records

fluoxetine hydrochloride
【CAS Registry number】
Fluoxetine HCL
Fluoxetin HCL
【Molecular Formula】
C17H18F3NO.HCl (Products with the same molecular formula)
【Molecular Weight】
【Canonical SMILES】
【MOL File】

Chemical and Physical Properties

White to off-white powder
【Melting Point】
158-159 °C
【Boiling Point】
395.1 °C at 760 mmHg
【Flash Point】
192.8 °C
Sol (mg/mL): methanol, ethanol >100; acetone, acetonitrile, chloroform 33-100; dichloromethane 5-10; ethyl acetate 2-2.5; toluene, cyclohexane, hexane 0.5-0.67
Maximum sol in water: 14 mg/mL
Stable. Incompatible with strong oxidizing agents.
【Storage temp】
-20°C Freezer
【Spectral properties】
UV max (methanol): 227, 264, 268, 275 nm
【Computed Properties】
Molecular Weight:345.78707 [g/mol]
Molecular Formula:C17H19ClF3NO
H-Bond Donor:2
H-Bond Acceptor:5
Rotatable Bond Count:6
Exact Mass:345.110727
MonoIsotopic Mass:345.110727
Topological Polar Surface Area:21.3
Heavy Atom Count:23
Formal Charge:0
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:1
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:2

Safety and Handling

【Hazard Codes】
Xn: Harmful;
【Risk Statements】
【Safety Statements 】
Hazard Codes:Xn
Risk Statements:22-38-41
22:Harmful if swallowed
38:Irritating to the skin
41:Risk of serious damage to eyes
Safety Statements:26-36/37/39
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36/37/39:Wear suitable protective clothing, gloves and eye/face protection
WGK Germany:3
Oral: Capsules: 10 mg (of fluoxetine), Prozac Pulvules (Dista), Sarafem Pulvules (Lilly); 20 mg (of fluoxetine), Prozac Pulvules (Dista), Sarafem Pulvules (Lilly); 40 mg (of fluoxetine), Prozac Pulvules (Dista). Capsules, delayed-release (containing enteric-coated pellets): 90 mg (of Fluoxetine) Prozac Weekly (Dista). Solution: 20 mg (of fluoxetine) per 5 ml, Prozac (with alcohol 0.23%) (Dista). Tablets: 10 mg (of fluoxetine) Prozac (scored) (Dista); 20 mg (of fluoxetine), Fluoxetine Hydrochloride Tablets (Par).
【Exposure Standards and Regulations】
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl fluoxetine hydrochloride, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.

White to Off-White Powder
usageEng:A selectiive derotonin reuptake inhibitor. Used as an antidepressant
Safety Statements:26-36/37/39
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36/37/39:Wear suitable protective clothing, gloves and eye/face protection

Use and Manufacturing

A selectiive derotonin reuptake inhibitor. Used as an antidepressant

Biomedical Effects and Toxicity

【Pharmacological Action】
- A structurally and mechanistically diverse group of drugs that are not tricyclics or monoamine oxidase inhibitors. The most clinically important appear to act selectively on serotonergic systems, especially by inhibiting serotonin reuptake.
- Compounds that specifically inhibit the reuptake of serotonin in the brain. This increases the serotonin concentration in the synaptic cleft which then activates serotonin receptors to a greater extent. These agents have been used in treatment of depression, panic disorder, obsessive-compulsive behavior, and alcoholism, as analgesics, and to treat obesity and bulimia. Many of the ADRENERGIC UPTAKE INHIBITORS also inhibit serotonin uptake; they are not included here.
【Therapeutic Uses】
Antidepressive Agents, Second-Generation; Serotonin Uptake Inhibitors
Fluoxetine is indicated for the treatment of obsessions and compulsions in patients with obsessive-compulsive disorder. /Included in US product labeling/
Fluoxetine is used to relieve the symptoms of premenstrual dysphoric disorder (PMDD). PMDD was formerly known as late luteal phase dysphoric disorder (LLPDD) and is distinguishable from the cyclic changes in mood commonly known as premenstrual syndrome (PMS) by its greater severity of symptoms. (Evidence rating: B-1) /Included in US product labeling/
Fluoxetine is indicated for the treatment of major depressive disorder. Treatment of acute depressive episodes typically requires 6 to 12 months of antidepressant therapy. Patients with recurrent or chronic depression may require long-term treatment. Fluoxetine has shown effective maintenance of antidepressant response for up to 50 weeks of treatment in a placebo-controlled trial. /Included in US product labeling/
Fluoxetine has been used in a limited number of patients for the short term management of exogenous obesity. In a controlled study, obese (ie, more than 20% overweight), nondepressed individuals receiving fluoxetine (average dosage: 64.9 mg daily), benzphetamine hydrochloride (average: 97 mg daily), or placebo concurrently with reduced food intake and increased exercise for 8 weeks lost an average of about 4.8, 4, and 1.7 kg, respectively. Fluoxetine-treated patients who usually experienced carbohydrate cravings reportedly lost more weight during this study than those who did not experience such cravings.
Fluoxetine therapy was evaluated in a 31 yr old depressed diabetic woman with severe pain due to diabetic peripheral neuropathy. Therapy was initiated at a dose of 5 mg for 7 days, then increased by 5 mg every 3-4 days to 20 mg daily. A 20 mg/day dose was administered for 7 days then the dosage was gradually increased until the total daily dose was 40 mg. Overall, during the 5 wk course of therapy the patient's depression improved and her pain decreased. The patient remained pain free for a period of 7 months while taking the 40 mg/day dose. At the end of 7 months, the pain and depression returned. It was suggested that fluoxetine may be an alternative to the tricyclic antidepressants in the treatment of diabetic peripheral neuropathy.
A total of 120 patients who met DSM-III criteria for unipolar major depressive episode were equally randomized to fluoxetine am or fluoxetine pm treatment groups, such that 30 patients were in each group at each of two sites. Patients received 20 to 80 mg of fluoxetine every day for 5 wk; the dose was based on clinical response. Highly significant within-treatment improvement was reflected by changes in mean scores on the Hamilton Rating Scale for Depression (total score and factors), the Raskin Depression Scale, the Covi Anxiety Scale, the Clinical Global Impressions Scale for Severity, and the Clinical Global Impressions Scale for Improvement. No significant differences occurred between the am and pm groups for any efficacy variable. Evaluation of adverse events and vital signs indicated no clinically significant differences between the two treatment groups. The data indicate that fluoxetine is equally efficacious and well tolerated regardless of the time of day it is administered and suggest that fluoxetine may be administered at either time of day without affecting clinical course. [Usher RW et al; J Clin Psychiatry 52 (3): 134-6 (1991)]
【Biomedical Effects and Toxicity】
Fluoxetine hydrochloride appears to be well absorbed from the GI tract following oral administration. The oral bioavailability of fluoxetine in humans has not been fully elucidated to date, but at least 60-80% of an oral dose appears to be absorbed. However, the relative proportion of an oral dose reaching systemic circulation unchanged currently is not known. Limited data from animals suggest that the drug may undergo first-pass metabolism and extraction in the liver and/or lung following oral administration. In these animals (beagles), approximately 72% of an oral dose reached systemic circulation unchanged. Food appears to cause a slight decrease in the rate, but not the extent of absorption of fluoxetine in humans.
Distribution of fluoxetine and its metabolites into human body tissues and fluids has not been fully characterized. Limited pharmacokinetic data obtained during long term administration of fluoxetine to animals suggest that the drug and some of its metabolites, including norfluoxetine, are widely distributed in body tissues, with highest concentrations occurring in the lungs and liver. The drug crosses the blood-brain barrier in humans and animals. In animals, fluoxetine: norfluoxetine ratios reportedly were similar in the cerebral cortex, corpus striatum, hippocampus, hypothalamus, brain stem, and cerebellum 1 hr after administration of single dose of the drug.
In order to confirm embryonic/fetal exposure to fluoxetine and/or metabolites, dissection and whole-body autoradiographic techniques were utilized to determine the placental transfer and fetal distribution in 12 and 18 day pregnant Wistar rats 1, 4, 8, and 24 hr following a single oral 12.5 mg/kg dose of (14)C fluoxetine. On gestation Days 12 (organogenesis) and 18 (postorganogenesis), peak concentrations of radiocarbon occurred 4-8 hr after dose administration in the placenta, embryo/fetus, amniotic fluid, and maternal kidney, brain, and lung, and declined slightly at 24 hr postdose. Maternal lung contained the highest tissue concentration of radiocarbon at all time points. Placenta and maternal brain, kidney, and liver contained moderate levels of radioactivity, while embryonic/fetal tissue, amniotic fluid, and maternal plasma contained low levels of radioactivity. Mean fetal concentrations of radiocarbon at 4, 8, and 24 hr on gestation Day 18 were higher than mean embryonic concentrations on Day 12 of gestation. Analytical characterization of radioactivity indicated that combined fluoxetine and norfluoxetine concentrations accounted for 63-80% of the total radiocarbon concentrations in embryonic/fetal tissue. Results indicated that embryonic/fetal and maternal tissue levels of fluoxetine were greatest at early time points and declined with time, while norfluoxetine tissue levels were highest at the 24 hr time point. Whole-body autoradiographic techniques demonstrated that radioactivity associated with (14)C fluoxetine and/or its metabolites traversed the placenta and distributed throughout the 18 day fetus 4 hr following dose administration. Visual and quantitative evaluations of the autoradiograms indicated that the highest fetal concentrations of radiocarbon were associated with brain and thymus. Results from these studies indicate that fluoxetine and norfluoxetine traverse the placenta and distribute within the embryo/fetus during the periods of organogenesis and postorganogenesis and confirm embryonic/fetal exposure of parent and metabolite in previous negative rat teratology and reproductive studies. [Pohland RC et al; Toxicol Appl Pharmacol 98 (2): 198-205 (1989)] PubMed Abstract
Elimination: Renal: 80% excreted in the urine (11.6% fluoxetine, 7.4% fluoxetine glucuronide, 6.8% norfluoxetine, 8.2% norfluoxetine glucuronide, >20% hippuric acid, 46% other); Biliary: Approximately 15% in the feces; In dialysis--Not dialyzable because of high protein binding and large volume of distribution.
Fluoxetine and norfluoxetine are distributed into milk. Limited data indicate that concentrations of the drug and this metabolite in milk are about 20-30% of concurrent plasma concentrations.
To characterize milk/plasma (M/P) ratio and infant dose, for fluoxetine and norfluoxetine, in breast-feeding women taking fluoxetine for the treatment of depression, and to determine the plasma concentration of these drugs in their infants. Fourteen women (mean age 32.2 years) taking fluoxetine (mean dose 0.51 mg/kg/day) and their infants (mean age 3.4 months) were studied. Fluoxetine and norfluoxetine in plasma and milk were measured by high-performance liquid chromatography over a 24 hr dose interval in four patients, and by single point data collection in 10 patients. Infant exposure was estimated as the product of estimated milk production, and average drug concentration in milk, normalized to body weight and expressed as a percentage of the weight-adjusted maternal dose. RESULTS: Mean M/P values of 0.68 (95% CI 0.52-0.84) and 0.56 (95% CI 0.35-0.77) were calculated for fluoxetine and norfluoxetine, respectively. Mean total infant exposure (fluoxetine equivalents) was estimated to be 6.81% (range 2.15-12%) of the weight-adjusted maternal dose of fluoxetine. Contributions from fluoxetine and norfluoxetine were approximately equal. Fluoxetine (range 20-252 ug/L) was detected in five of the nine infants from whom samples were collected, and norfluoxetine (range 17-187 ug/L) was detected in seven of the nine infants. The highest of these concentrations was about 70% of the maternal plasma concentrations. The mean combined dose of fluoxetine and norfluoxetine transmitted to infants via breast milk is below the 10% notional level of concern. However, there was considerable interpatient variability in estimated infant dose and in some of the patients, the dose was >10%. ... Neonates exposed to these drugs in utero had higher concentrations of fluoxetine and norfluoxetine and are at greater risk of adverse effects. [Kristensen JH et al; Br J Clin Pharmacol 48 (4): 521-7 (1999)] PubMed Abstract

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