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Additional information about the drug Quetiapine


Quetiapine, marketed as Seroquel among other names, is an atypical antipsychotic used for the treatment of schizophrenia, bipolar disorder, and major depressive disorder.
Common side effects include sleepiness, constipation, weight gain, and dry mouth.
Quetiapine was developed in 1985 and approved for medical use in the United States in 1997.
Contents
1 Medical uses
1.1 Schizophrenia
1.2 Bipolar disorder
1.3 Major depressive disorder
1.4 Alzheimer’s disease
1.5 Others
2 Adverse effects
2.1 Discontinuation and withdrawal
2.2 Pregnancy and lactation
3 Overdose
4 Pharmacology
4.1 Pharmacodynamics
4.2 Pharmacokinetics
5 Chemistry
5.1 Synthesis
6 History
6.1 Sustained-release
7 Society and culture
7.1 Regulatory status
7.2 Cost
7.3 Lawsuits
7.4 Controversy
7.5 Nurofen Plus tampering case
8 References
9 External links
Medical uses
Quetiapine (Seroquel) 25 mg tablets, next to US one-cent coin for comparison.
Seroquel XR 150 mg tablet box
Quetiapine is primarily used to treat schizophrenia or bipolar disorder.
Schizophrenia
A 2013 Cochrane review compared quetiapine to typical antipsychotics:
Quetiapine compared to typical antipsychotics for schizophrenia
Summary
Quetiapine may not differ from typical antipsychotics in the treatment of positive symptoms, general psychopathology, and negative symptoms. However, it causes fewer adverse effects in terms of abnormal ECG, extrapyramidal effects, abnormal prolactin levels and weight gain.
Outcome
Findings in words
Findings in numbers
Quality of evidence
Global state
No clinical significant response
There is no clear difference between people given quetiapine and those receiving typical antipsychotic drugs. These findings are based on data of moderate quality.
RR 0.96 (0.75 to 1.23)
Moderate
Mental state
Average positive symptom score ( PANSS )
On average, people receiving quetiapine scored higher (worse) than people treated with typical antipsychotic drugs. There was, however, no clear difference between the groups. This finding is based on data of moderate quality.
MD 0.02 higher (0.39 lower to 0.43 higher)*
Moderate
Average negative symptom score ( PANSS )
On average, people receiving quetiapine scored lower (better) than people treated with typical antipsychotic drugs. This finding is based on data of moderate quality.
MD 0.82 lower (1.59 to 0.04 lower)*
Moderate
Cognitive function
Average score
On average, people receiving quetiapine scored higher (better) than people treated with typical antipsychotic drugs. There was no clear difference between the groups. This finding is based on data of very limited quality.
MD 1.55 higher (0.62 lower to 3.72 higher)*
Very low
Leaving the study early
For any reason
Quetiapine is not clearly more acceptable than typical antipsychotic drugs. These findings are based on data of moderate quality.
RR 0.91 (0.81 to 1.01)
Moderate
Adverse effects
Extrapyramidal effects
Quetiapine may reduce the chance of experiencing these movement disorders. This finding is based on data of moderate quality.
RR 0.17 (0.09 to 0.32)
Moderate
Prolactin level Average level (ng/mL)
On average, people receiving quetiapine scored lower (better) than people treated with typical antipsychotic drugs. There was a clear difference between the groups. This finding is based on data of moderate quality.
MD 16.20 lower (23.34 to 9.07 lower)*
Moderate
*The meaning of these findings for day-to-day care is not clear
In a 2013 comparison of 15 antipsychotics in effectiveness in treating schizophrenia, quetiapine demonstrated standard effectiveness. It was 13-16% more effective than ziprasidone, chlorpromazine, and asenapine and approximately as effective as haloperidol and aripiprazole.
There is tentative evidence of the benefit of quetiapine versus placebo in schizophrenia; however, definitive conclusions are not possible due to the high rate of attrition in trials (greater than 50%) and the lack of data on economic outcomes, social functioning, or quality of life.
It is debatable whether, as a class, typical or atypical antipsychotics are more effective.
A Cochrane review comparing quetiapine to other atypical antipsychotic agents tentatively concluded that it may be less efficacious than olanzapine and risperidone ; produce fewer movement related side effects than paliperidone, aripiprazole, ziprasidone, risperidone and olanzapine; and produce weight gain similar to risperidone, clozapine and aripiprazole. They concluded that it produces suicide attempt, suicide; death; QTc prolongation, low blood pressure ; tachycardia ; sedation; gynaecomastia ; galactorrhoea, menstrual irregularity and white blood cell count at a rate similar to first generation antipsychotics.
Bipolar disorder
In those with bipolar disorder, quetiapine is used to treat depressive episodes; acute manic episodes associated with bipolar I disorder (as either monotherapy or adjunct therapy to lithium ; valproate or lamotrigine ); and maintenance treatment of bipolar I disorder (as adjunct therapy to lithium or divalproex).
Major depressive disorder
Quetiapine is effective when used by itself
In the United States,
Alzheimer’s disease
Quetiapine does not decrease agitation among people with Alzheimer’s. Quetiapine worsens intellectual functioning in the elderly with dementia and therefore is not recommended.
Others
The use of low doses of quetiapine for insomnia, while common, is not recommended; there is little evidence of benefit and concerns regarding adverse effects.
It is sometimes used off-label, often as an augmentation agent, to treat conditions such as Tourette syndrome,
Quetiapine and clozapine are the most widely used medications for the treatment of Parkinson’s disease psychosis due to their very low extrapyramidal side-effect liability. Owing to the risks associated with clozapine (e.g. agranulocytosis, diabetes mellitus, etc.), clinicians often attempt treatment with quetiapine first, although the evidence to support quetiapine’s use for this indication is significantly weaker than that of clozapine.
Adverse effects
Sources for incidence lists:
Very common (>10% incidence) adverse effects
Dry mouth
Dizziness
Headache
Somnolence (drowsiness; of 15 antipsychotics quetiapine causes the 5th most sedation. Extended release (XR) formulations tend to produce less sedation, dose-by-dose than the immediate release formulations)
Common (1–10% incidence) adverse effects
High blood pressure
Orthostatic hypotension
High pulse rate
High blood cholesterol
Elevated serum triglycerides
Abdominal pain
Constipation
Increased appetite
Vomiting
Increased liver enzymes
Backache
Asthenia
Insomnia
Lethargy
Tremor
Agitation
Nasal congestion
Pharyngitis
Fatigue
Pain
Dyspepsia (Indigestion)
Peripheral oedema
Dysphagia
Extrapyramidal disease : quetiapine and clozapine are noted for their relative lack of extrapyramidal side effects
Weight gain: SMD 0.43 kg when compared to placebo. Produces roughly as much weight gain as risperidone, less weight gain than clozapine, olanzapine and zotepine and more weight gain than ziprasidone, lurasidone, aripiprazole and asenapine.
Rare (<1% incidence) adverse effects Prolonged QT interval (had an odds ratio for prolonging the QT interval over placebo of 0.17) Sudden cardiac death Syncope Diabetic ketoacidosis Restless legs syndrome Hyponatraemia, low blood sodium. Jaundice, yellowing of the eyes, skin and mucous membranes due to an impaired ability of the body to clear bilirubin, a by product of haem breakdown. Pancreatitis, pancreas swelling. Agranulocytosis, a potentially fatal drop in white blood cell count. Leukopenia, a drop in white blood cell count, not as severe as agranulocytosis. Neutropenia, a drop in neutrophils, the cell of the immune cells that defends the body against bacterial infections. Eosinophilia Anaphylaxis, a potentially fatal allergic reaction. Seizure Hypothyroidism, underactive thyroid gland. Myocarditis, swelling of the myocardium. Cardiomyopathy Hepatitis, swelling of the liver. Suicidal ideation Priapism. A prolonged and painful erection. Stevens-Johnson syndrome. A potentially fatal skin reaction. Neuroleptic malignant syndrome a rare and potentially fatal complication of antipsychotic drug treatment. It is characterised by the following symptoms: tremor, rigidity, hyperthermia, tachycardia, mental status changes (e.g. confusion), etc. Tardive Dyskinesia. A rare and often irreversible neurological condition characterised by involuntary movements of the face, tongue, lips and rest of the body. Most commonly occurs after prolonged treatment with antipsychotics. It is believed to be particularly uncommon with atypical antipsychotics, especially quetiapine and clozapine Both typical and atypical antipsychotics can cause tardive dyskinesia. Weight gain can be a problem for some, with quetiapine causing more weight gain than fluphenazine, haloperidol, loxapine, molindone, olanzapine, pimozide, risperidone, thioridazine, thiothixene, trifluoperazine, and ziprasidone, but less than chlorpromazine, clozapine, perphenazine, and sertindole. Studies conducted on beagles have resulted in the formation of cataracts. While there are reports of cataracts occurring in humans, controlled studies including thousands of patients have not demonstrated a clear causal association between quetiapine therapy and this side-effect. still recommends users have eye examinations every six months. As with some other anti-psychotics, quetiapine may lower the seizure threshold, and should be taken with caution in combination with drugs such as bupropion. Discontinuation and withdrawal Quetiapine should be discontinued gradually, with careful consideration from the prescribing doctor, to avoid withdrawal symptoms or relapse. The British National Formulary recommends a gradual withdrawal when discontinuing anti-psychotic treatment to avoid acute withdrawal syndrome or rapid relapse. Due to compensatory changes at dopamine, serotonin, adrenergic and histamine receptor sites in the central nervous system, withdrawal symptoms can occur during abrupt or over-rapid reduction in dosage. However, despite increasing demand for safe and effective antipsychotic withdrawal protocols or dose-reduction schedules, no specific guidelines with proven safety and efficacy are currently available. Withdrawal symptoms reported to occur after discontinuation of antipsychotics include nausea; emesis ; lightheadedness; diaphoresis ; dyskinesia ; orthostatic hypotension ; tachycardia ; insomnia ; nervousness; dizziness; headache; non-stop crying; and anxiety. Pregnancy and lactation Placental exposure is least for quetiapine compared to other atypical antipsychotics. Overdose Most instances of acute overdosage result in only sedation, hypotension and tachycardia, but cardiac arrhythmia, coma and death have occurred in adults. Serum or plasma quetiapine concentrations are usually in the 1–10 mg/L range in overdose survivors, while postmortem blood levels of 10–25 mg/L are generally observed in fatal cases. Pharmacology Pharmacodynamics See also: Atypical antipsychotic § Pharmacodynamics, and Antipsychotic § Comparison of medications Quetiapine (and metabolite) Site QTP NQTP Action Ref SERT >10,000
927
Blocker
NET
>10,000
58
Blocker
DAT
>10,000
>10,000
ND
5-HT 1A
320–432
45
Partial agonist
5-HT 1B
1,109–2,050
1,117
ND
5-HT 1D
>10,000
249
ND
5-HT 1E
1,250–2,402
97
ND
5-HT 1F
2,240
ND
ND
5-HT 2A
96–101
48
Antagonist
5-HT 2B
ND
14
Antagonist
5-HT 2C
2,502
107
Antagonist
5-HT 3
>10,000
394
Antagonist
5-HT 4
ND
ND
ND
ND
5-HT 5A
3,120
768
ND
5-HT 6
1,865
503
Antagonist
5-HT 7
307
76
Antagonist
α 1A
22
144
Antagonist
α 1B
39
95
Antagonist
α 2A
2,230–3,630
237
Antagonist
α 2B
90–747
378
Antagonist
α 2C
28.7–350
736
Antagonist
β 1
>10,000
>10,000
ND
β 2
>10,000
>10,000
ND
D 1
712
214
Antagonist
D 2
245
196
Antagonist
D 2L
700
ND
Antagonist
D 2S
390
ND
Antagonist
D 3
340–483
567
Antagonist
D 4
1,202
1,297
Antagonist
D 4.2
1,600
ND
Antagonist
D 5
1,738
1,419
Antagonist
H 1
2.2–11
3.5
Antagonist
H 2
>10,000
298
Antagonist
H 3
>10,000
>10,000
ND
H 4
>10,000
1,660
ND
M 1
858
39
Antagonist
M 2
1,339
453
ND
M 3
>10,000
23
Antagonist
M 4
542
110
ND
M 5
1,942
23
Antagonist
σ 1
220–3,651
>10,000
ND
σ 2
1,344
1,050
ND
NMDA ( PCP )
>10,000
ND
Antagonist
VDCC
>10,000
ND
ND
hERG
ND
>10,000 ( IC 50 )
ND
Values are K i (nM), unless otherwise noted. The smaller the value, the more strongly the drug binds to the site. All data are for human cloned proteins, except σ 1 (guinea pig), σ 2 (rat), and VDCC (rat).
Quetiapine has the following pharmacological actions:
Dopamine D 1, D 2, D 3, D 4, and D 5 receptor antagonist
Serotonin 5-HT 1A receptor partial agonist, 5-HT 2A, 5-HT 2B, 5-HT 2C, 5-HT 3, 5-HT 6, and 5-HT 7 receptor antagonist, and 5-HT 1B, 5-HT 1D, 5-HT 1E, and 5-HT 1F receptor ligand
α 1 – and α 2 -adrenergic receptor antagonist
Histamine H 1 receptor antagonist
Muscarinic acetylcholine receptor antagonist
This means quetiapine is a dopamine, serotonin, and adrenergic antagonist, and a potent antihistamine with some anticholinergic properties. Some of the antagonized receptors (serotonin, norepinephrine) are actually autoreceptors whose blockade tends to increase the release of neurotransmitters.
At very low doses, quetiapine acts primarily as a histamine receptor blocker (antihistamine) and α 1 -adrenergic blocker. When the dose is increased, quetiapine activates the adrenergic system and binds strongly to serotonin receptors and autoreceptors. At high doses, quetiapine starts blocking significant amounts of dopamine receptors.
Pharmacokinetics
The major active metabolite of quetiapine is norquetiapine ( N -desalkylquetiapine).
Skeletal formula of norquetiapine
Chemistry
Quetiapine is a tetracyclic compound and is closely related structurally to clozapine, olanzapine, loxapine, and other tetracyclic antipsychotics.
Synthesis
The synthesis of quetiapine begins with a dibenzothiazepinone. The lactam is first treated with phosphoryl chloride to produce a dibenzothiazepine. A nucleophilic substitution is used to introduce the sidechain.
History
Sustained-release
AstraZeneca submitted a new drug application for a sustained-release version of quetiapine in the United States, Canada, and the European Union in the second half of 2006 for treatment of schizophrenia. AstraZeneca was to retain the exclusive right to market sustained-release quetiapine until 2017. The sustained-release quetiapine is marketed mainly as Seroquel XR. Other marketing names are Seroquel Prolong, Seroquel Depot and Seroquel XL
On May 18, 2007, AstraZeneca announced that the U.S. FDA approved Seroquel XR for acute treatment of schizophrenia. The company has not provided a reason for the delay of Seroquel XR’s launch.
Health Canada approved sale of Seroquel XR on September 27, 2007.
In early October 2008, the FDA approved Seroquel XR for the treatment of bipolar depression and bipolar mania. According to AstraZeneca, Seroquel XR is “the first medication approved by the FDA for the once-daily acute treatment of both depressive and manic episodes associated with bipolar.”
On July 31, 2008, Handa Pharmaceuticals, based in Fremont, California, announced that its abbreviated new drug application (“ANDA”) for quetiapine fumarate extended-release tablets, the generic version of AstraZeneca’s SEROQUEL XR, has been accepted by the FDA.
On December 1, 2008, Biovail announced that the FDA had accepted the company’s ANDA to market its own version of sustained-release quetiapine. Biovail’s sustained-release tablets will compete with AstraZeneca’s Seroquel XR.
On December 24, 2008, AstraZeneca notified shareholders that the FDA had asked for additional information on the company’s application to expand the use of sustained-release quetiapine for treatment of depression.
Society and culture
Regulatory status
In the United States, the Food and Drug Administration (FDA) has approved quetiapine for the treatment of schizophrenia and of acute manic episodes associated with bipolar disorder ( bipolar mania ) and for treatment of bipolar depression.
Quetiapine received its initial indication from U.S. FDA for treatment of schizophrenia in 1997. In 2007 and 2008, studies were conducted on quetiapine’s efficacy in treating generalized anxiety disorder and major depression.
Cost
In the United States as of 2015, the branded extended-release 400 mg pills cost between US$ 9.68 and US$ 23.16 each.
In the United Kingdom, a month’s supply, as of 2017, costs the NHS approximately £107.45.
Lawsuits
In April 2010, the U. S. Department of Justice fined Astra-Zeneca $520 million for the company’s aggressive marketing of Seroquel for off-label uses.
Multiple lawsuits have been filed in relation to quetiapine’s side-effects, in particular, diabetes.
Approximately 10,000 have been filed against AstraZeneca, alleging that quetiapine caused problems ranging from slurred speech and chronic insomnia to deaths.
Controversy
In 2004, a young man named Dan Markingson committed suicide in a controversial Seroquel clinical trial at the University of Minnesota while under an involuntary commitment order.
Nurofen Plus tampering case
In August 2011, the UK’s Medicines and Healthcare products Regulatory Agency (MHRA) issued a class-4 drug alert following reports that some batches of Nurofen plus contained Seroquel XL instead.
Following the issue of the Class-4 Drug Alert, Reckitt Benckiser (UK) Ltd received further reports of rogue blister strips in cartons of two additional batches of Nurofen Plus tablets. One of the new batches contained Seroquel XL 50 mg tablets and one contained the Pfizer product Neurontin 100 mg capsules.
Following discussions with the MHRA’s Defective Medicines Report Centre (DMRC), Reckitt Benckiser (UK) Ltd decided to recall all remaining unexpired stock of Nurofen Plus tablets in any pack size, leading to a Class-1 Drug Alert.
The contamination was later traced to in-store tampering by a customer.

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