Quetiapine - Wikipedia, The Free Encyclopedia

6/16/2014 Quetiapine - Wikipedia, the free encyclopedia
http://en.wikipedia.org/wiki/Seroquel 1/20
Quetiapine
Systematic (IUPAC) name
2-(2-(4-dibenzo[b,f][1,4]t hiazepine- 11-yl- 1-
piperazinyl)et hoxy)et hanol
Clinical data
Trade names Seroquel
AHFS/Drugs.com monograph
MedlinePlus a698019
Licence data US FDA:link
Pregnancy cat. B3 (AU) C (US)
Legal status Prescription Only (S4) (AU)
POM (UK) -only (US)
Routes Oral
Pharmacokinetic data
Bioavailability
Quetiapine
From Wikipedia, the free encyclopedia
(Redirected from Seroquel)
Quetiapine (/kwta.pin/ kwi-TY--peen) (branded as
Seroquel, Xeroquel, Ketipinor) is a short-acting atypical
antipsychotic approved for the treatment of schizophrenia,
bipolar disorder, and along with an antidepressant to treat
major depressive disorder.
Annual sales are approximately $5.7 billion worldwide, with
$2.9 billion in the United States.
[6]
The U.S. patent,
[7]
which
was set to expire in 2011, received a pediatric exclusivity
extension which pushed its expiration to March 26,
2012.
[6][8]
The patent has already expired in Canada.
Quetiapine was developed by AstraZeneca from 1992-1996
as an improvement from first generation antipsychotics. It
was first approved by the FDA in 1997. There are now
several generic versions of quetiapine, such as Quepin,
Syquel and Ketipinor.
[9]
Contents
1 Medical uses
1.1 Schizophrenia
1.2 Bipolar disorder
1.3 Major depressive disorder
1.4 Alzheimer's disease
1.5 Other
2 Adverse effects
2.1 Discontinuation
2.2 Overdosage
2.3 Pregnancy and lactation
3 Pharmacology
4 Synthesis
5 Dosage
5.1 Sustained-release
6 Society and culture
6.1 Regulatory status
100%[1]
Protein binding 83%[2]
Metabolism Hepatic via CYP3A4-catalysed
sulfoxidation to its active
metabolite norquetiapine (N-
desalkylquetiapine)[3]
Half-life 7 hours (parent compound); 9-
12 hours (active metabolite,
norquetiapine)[2][4]
Excretion Renal (73%), faeces
(20%)[1][2][4][5]
Identifiers
CAS number
111974-69-7

ATC code N05AH04
PubChem CID 5002
IUPHAR ligand 50
DrugBank DB01224
ChemSpider
4827

UNII
BGL0JSY5SI

KEGG
D08456

ChEBI
CHEBI:8707

ChEMBL
CHEMBL716

Chemical data
Formula
C
21
H
25
N
3
O
2
S

Mol. mass 383.5099 g/mol
Physical data
Solubility in
water
3.29 mg/mL (20 C)
(what is this?) (verify)
6.2 Lawsuits
6.3 Controversy
6.4 Recreational use
6.5 Nurofen Plus tampering case
7 References
8 External links
Medical uses
Quetiapine fumarate is primarily used to treat schizophrenia
or bipolar disorder.
[10]
Schizophrenia
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.
[11]
It is debatable whether, as a class, typical or atypical
antipsychotics are more effective.
[12]
Both have equal drop-
out and symptom relapse rates when typicals are used at low
to moderate dosages.
[13]
While quetiapine has lower rates of
extrapyramidal side effects, there is greater sleepiness and
rates of dry mouth.
[11]
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).
[14][15]
Major depressive disorder
Quetiapine is effective when used by itself
[16]
and when used
along with other medications in major depressive disorder (MDD).
[16][17]
However, sedation is often an
undesirable side effect.
[16]
SMILES
InChI
Quetiapine (Seroquel) 25 mg tablets,
next to US one-cent coin for
comparison.
Seroquel XR 150 mg tablet box
In the US,
[4]
the UK
[18]
and Australia (in this indication it isn't covered by the Pharmaceutical Benefits Scheme),
quetiapine is licensed for use as an adjunct in the treatment of MDD.
[19]
Alzheimer's disease
Quetiapine does not decrease agitation among people with Alzheimer's,
whose usage of the drug once constituted 29% of sales. Quetiapine
worsens intellectual functioning in the elderly with dementia and therefore
is not recommended.
[20]
Other
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.
[21][22]
It is sometimes used off-label, often as an augmentation agent, to treat
conditions such as Tourette syndrome,
[23]
musical hallucinations
[24]
and
anxiety disorders.
[25]
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.
[26][27]
Adverse effects
Sources for incidence lists:
[1][4][18][19][27][28]
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)
[29]
Common (1-10% incidence) adverse effects
High blood pressure
Extrapyramidal disease quetiapine and clozapine are noted for their relative lack of extrapyramidal side
effects
[18][27][29]
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.
[29]
As with many other atypical antipsychotics this action
is likely due to its actions at the H
1
histamine receptor and 5-HT2C receptor.
[3]
Rare (<1% incidence) adverse effects
Prolonged QT interval (had an odds ratio for prolonging the QT interval over placebo of 0.17)
[29]
Sudden cardiac death
Syncope
Diabetic ketoacidosis
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
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
[19][30]
There is an emerging controversy regarding quetiapine fatalities. The deaths of at least six U.S. military veterans
who were given drug cocktails including quetiapine
[31]
have been attributed to its inclusion by military doctors to
treat PTSD. Approximately 10,000
[32]
lawsuits
[33][34][35][36][37]
against AstraZeneca for problems ranging from
slurred speech and chronic insomnia to death have been filed by individuals from civilian populations.
It is marketed as one of the most sedating of all anti-psychotics, although those claims are contested.
[38]
Beginning
users may feel extremely tired and 'out of it' for the first few days, and sometimes longer. Quetiapine's newest
indication, for bipolar depression, usually specifically calls for the entire dose to be taken before bedtime due to its
sedative effects. The sedative effects may disappear after some time on the drug, or with a change of dosage, and
with possibly different, non-sedative side-effects emerging.
Both typical and atypical antipsychotics can cause tardive dyskinesia.
[39]
According to one study, rates are lower
with the atypicals at 3.9% as opposed to the typicals at 5.5%.
[39]
Although Quetiapine and Clozapine are atypical
antipsychotics, switching to these atypicals is an option to minimize symptoms of tardive dyskinesia caused by other
atypicals.
[40]
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.
[41]
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. However, the Seroquel website
[42]
still recommends
users have eye examinations every six months.
As with some other anti-psychotics, quetiapine may lower the seizure threshold,
[43]
and should be taken with
caution in combination with drugs such as bupropion.
A recent comparative study of anti-psychotics drugs has found that quetiapine mono treatment was associated with
increased risk of death relative to the other analyzed treatments (but still better than no anti-psychotics drug
treatment at all).
[44]
Discontinuation
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.
[45]
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, excessive non-stop crying, and anxiety.
[46][47]
According to Eli Lilly internal documents, discontinuation
of atypical neuroleptics similar to seroquel can also cause psoriasis, gingivitis and other inflammatory conditions,
dyspepsia, headache, high blood sugar and other health conditions unrelated to psychiatric condition.[1]
(http://nonpsychiatry.files.wordpress.com/2012/12/7-zy397116.pdf)[2]
(http://nonpsychiatry.files.wordpress.com/2012/12/8-zy621218.pdf) Some have argued that additional somatic and
psychiatric symptoms associated with dopaminergic super-sensitivity, including dyskinesia and acute psychosis, are
common features of withdrawal in individuals treated with neuroleptics.
[48][49][50][51]
This has led some to suggest
that the withdrawal process might itself be psychosis-mimetic, producing psychotic-like symptoms even in
previously healthy patients, indicating a possible pharmacological origin of mental illness in a yet unknown
percentage of patients currently and previously treated with antipsychotics. This question is unresolved, and remains
a highly controversial issue among professionals in the medical and mental health communities, as well the public.
[52]
Overdosage
Most instances of acute overdosage result only in sedation, hypotension and tachycardia, but cardiac arrythmia,
coma and death have occurred in adults. Serum or plasma quetiapine concentrations are usually in the 110 mg/L
range in overdose survivors, while postmortem blood levels of 1025 mg/L are generally observed in fatal
cases.
[53]
Pregnancy and lactation
Placental exposure is least for quetiapine compared to other atypical antipsychotics.
[27]
The evidence is insufficient
to rule out any risk to the foetus but available data suggests it is unlikely to result in any major foetal
malformations.
[2][5][28]
It is secreted in breast milk and hence quetiapine-treated mothers are advised not to
breastfeed.
[2][5][28]
Pharmacology
Quetiapine has the following pharmacological actions:
[58][59][60][61]
D
1
(IC
50
= 1268nM), D
2
(IC
50
= 329nM), D
3
, and D
4
receptor antagonist
5-HT
1A
(IC
50
= 717nM) partial agonist, 5-HT
2A
(IC
50
= 148nM), 5-HT
2C
, and 5-HT
7
receptor antagonist
1
-adrenergic (IC
50
= 94nM) and
2
-adrenergic receptor (IC
50
= 271nM) antagonist
H
1
receptor (IC
50
= 30nM) antagonist
mACh receptor (IC
50
= >5000nM) antagonist
This means Quetiapine is a dopamine, serotonin, and adrenergic antagonist, and a potent antihistamine with clinically
negligible anticholinergic properties. Quetiapine binds strongly to serotonin receptors; the drug acts as partial
agonist at 5-HT
1A
receptors.
[62]
Serial PET scans evaluating the D
2
receptor occupancy of quetiapine have
demonstrated that quetiapine very rapidly disassociates from the D
2
receptor.
[63]
Theoretically, this allows for
normal physiological surges of dopamine to elicit normal effects in areas such as the nigrostriatal and
tuberoinfundibular pathways, thus minimizing the risk of side-effects such as pseudo-parkinsonism as well as
elevations in prolactin.
[64]
Some of the antagonized receptors (serotonin, norepinephrine) are actually autoreceptors
whose blockade tends to increase the release of neurotransmitters.
Comparison of affinities (Ki, nM)
[54][55][56][57]
Receptor Quetiapine (Cloned human receptors) Norquetiapine (Cloned human receptors)
D
1
994.5 99.8 (Rat receptor)
D
2
379 196
D
3
340 -
D
4
2019 -
5-HT
1A
394.2 45
5-HT
2A
118 48
5-HT
2C
1843 107
5-HT
6
948.75 -
5-HT
7
307 76
1A
22 144
1B
14.6 46.4 (Rat receptor)
2A
3630 237
2C
28.85 -
H
1
6.9 3.5
H
2
41.24 -
M
1
489 38.3 (Rat receptor)
M
3
1631.5 -
NET >10000 12
Norquetiapine's 3D molecular
structure in ball and stick format
Norquetiapine's 2D molecular
structure
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.
[65]
Dosage
At very low doses, quetiapine acts primarily as a histamine receptor blocker (antihistamine) and
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.
[66][67]
Use of low-dose quetiapine is not recommended except temporarily during drug titration period
(less than 30 days).
[68]
Due to compensatory changes at dopamine, serotonin, adrenergic and histamine receptor sites in the central
nervous system, a gradual reduction in dosage is recommended to minimise or avoid withdrawal symptoms.
Withdrawal symptoms reported to occur after discontinuation of quetiapine include insomnia, nausea, emesis,
lightheadedness, diaphoresis, orthostatic hypotension, tachycardia, as well as nervousness, dizziness, headache, and
anxiety. The present evidence suggests that these symptoms affect a small number of susceptible individuals treated
with quetiapine.
[46]
The British National Formulary recommends a gradual withdrawal when discontinuing antipsychotic treatment to
avoid acute withdrawal syndrome or rapid relapse.
[45]
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.
[69][70]
AstraZeneca will
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.
[71]
During its 2007 Q2 earnings conference, AstraZeneca announced plans to launch Seroquel XR in
the U.S. during August 2007.
[72]
However, Seroquel XR has become available in U.S. pharmacies only after the
FDA approved Seroquel XR for use as maintenance treatment for schizophrenia, in addition to acute treatment of
the illness, on November 16, 2007.
[73]
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.
[74]
The FDA approved Seroquel XR for the treatment of bipolar depression and bipolar mania in early October 2008.
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 AstraZenecas
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.
[75]
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.
[76]
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.
[77]
In 2009, quetiapine XR was approved as adjunctive treatment of major depressive
disorder.
[78]
Quetiapine received its initial indication from U.S. FDA for treatment of schizophrenia in 1997.
[79]
In 2004, it
received its second indication for the treatment of mania-associated bipolar disorder.
[80]
In 2007 and 2008, studies
were conducted on quetiapines efficacy in treating generalized anxiety disorder and major depression. In April
2009, the Psychopharmacologic Drugs Advisory Committee of the FDA held a public meeting to discuss whether
study results supported the FDA's approval for anxiety and depression, with risks of metabolic side-effects and of
tardive dyskinesia and sudden cardiac death.
[81]
Lawsuits
In April 2010, AstraZeneca settled a longstanding U. S. Department of Justice investigation into its aggressive
marketing of Seroquel for such off-label uses with a $520-million fine.
[77]
According to the Department of Justice,
"the company recruited doctors to serve as authors of articles that were ghostwritten by medical literature
companies and about studies the doctors in question did not conduct. AstraZeneca then used those studies and
articles as the basis for promotional messages about unapproved uses of Seroquel."
[77]
Multiple lawsuits have been filed in relation to quetiapine's side-effects, in particular, diabetes.
[82][83][84][85]
In
2009, documents unsealed in litigation against AstraZeneca indicated that Dr. Charles Schulz, Chair of the
Department of Psychiatry at the University of Minnesota and a consultant for AstraZeneca, had misrepresented the
benefits of Seroquel in research presentations and press releases.
[86]
Controversy
AstraZeneca has been sued by the U.S. government (resulting from a qui tam lawsuit filed by Stefan P.
Kruszewski) over the marketing of quetiapine. A $520-million settlement was reached on October 29, 2009.
[87]
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.
[88]
A group of University of Minnesota
bioethicists charged that the trial involved an alarming number of ethical violations, but the university declined to
investigate.
[89]
Quetiapine may have been a factor in the deaths of several US veterans who were taking large
doses as part of a cocktail of drugs for PTSD.
[90]
In Australia, Professor Patrick McGorry, a key mental-health advisor, proposed a trial in Melbourne in 2011. Its
purpose was to investigate whether Seroquel would decrease or delay the risk that people aged between 15 and
40 with early signs of mental illness, might develop a later psychotic disorder. However in July 2011, psychiatrists,
psychologists and researchers from Australia, New Zealand, Canada, Britain and the US lodged a complaint with
the ethics committee of Melbourne Health. They opposed the trial
[91]
as "unethical" and "dangerous".
Recreational use
Quetiapine is not classified as a controlled substance; "abusive self-administration seems to be driven by
quetiapines sedative and anxiolytic effects (to help with sleep or to 'calm down') rather than by its antipsychotic
properties."
[92]
Reports of quetiapine abuse have emerged in medical literature. In addition to oral administration,
the drug is also taken intranasally by snorting pulverized tablets (insufflation). There have been reports of
intravenous abuse and intravenous co-administration with cocaine as well.
[93]
This is commonly referred to as a "Q-
Ball".
[93]
A 2004 letter to the editor of the American Journal of Psychiatry provided an anecdotal estimate that up
to 30% of inmates who were seen for psychiatric services in the Los Angeles County Jail were faking psychotic
symptoms in an attempt to obtain quetiapine.
[94]
Also known as "quell", "Snoozeberries", or "Susie-Q", the drug
may be more commonly abused in prisons due to its capacity to be regularly prescribed as a sedative and the
unavailability in prison of more commonly abused substances. A letter to the editor that appeared in the January
2007 American Journal of Psychiatry has proposed a need for additional studies to explore the addiction-
potential of quetiapine. The letter reports that its authors are physicians who work in the Ohio correctional system.
They report that prisoners ... have threatened legal action and even suicide when presented with discontinuation of
quetiapine and that they have not seen similar drug-seeking behavior with other second-generation antipsychotics
of comparable efficacy. It has also been reported that when Seroquel is used with methadone, it causes the user to
experience a buzz, or opioid euphoria.
[95]
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.
[96]
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.
[97]
The contamination was later traced to in-store tampering by a customer.
[98]
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b

c
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