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==Research==
==Research==
Perhaps owing to its mechanism of action relating to dopamine receptors, there is some evidence to suggest that aripiprazole blocks cocaine-seeking behavior in animal models without significantly affecting other rewarding behaviors (such as food self-administration).<ref>'Aripiprazole Blocks Reinstatement of Cocaine Seeking in an Animal Model of Relapse' Biological Psychiatry. Volume 61, Issue 5, Pages 582-590 (1 March 2007)http://www.journals.elsevierhealth.com/periodicals/bps/article/S0006-3223%2806%2900484-7/abstract</ref> The book ''Addiction Medicine'' mentions studies that suggest aripiprazole would be counter-therapeutic as treatment for methamphetamine dependency because it increased methamphetamine's stimulant and euphoric effects, and increased the baseline level of desire for methamphetamine.<ref>'Addiction Medicine:Science and Practice. Author: Bankole A. Johnson. url=http://books.google.com.br/books?id=zvbr4Zn9S9MC&pg=PA145&lpg=PA145&dq=dissulfiram+stop+craving+for+amphetamines&source=bl&ots=PkBZ_o4vXK&sig=J22yh5pVYFggqKMRaiJE0Ejmmgg&hl=pt-BR&ei=7v-xToz9LsLFgAeM3r2kAQ&sa=X&oi=book_result&ct=result&resnum=2&ved=0CC0Q6AEwAQ#v=onepage&q&f=false</ref>
Perhaps owing to its mechanism of action relating to dopamine receptors, there is some evidence to suggest that aripiprazole blocks cocaine-seeking behavior in animal models without significantly affecting other rewarding behaviors (such as food self-administration).<ref>'Aripiprazole Blocks Reinstatement of Cocaine Seeking in an Animal Model of Relapse' Biological Psychiatry. Volume 61, Issue 5, Pages 582-590 (1 March 2007)http://www.journals.elsevierhealth.com/periodicals/bps/article/S0006-3223%2806%2900484-7/abstract</ref> The book ''Addiction Medicine'' mentions studies that suggest aripiprazole would be counter-therapeutic as treatment for methamphetamine dependency because it increased methamphetamine's stimulant and euphoric effects, and increased the baseline level of desire for methamphetamine.<ref>'Addiction Medicine:Science and Practice. Author: Bankole A. Johnson. url=http://books.google.com.br/books?id=zvbr4Zn9S9MC&pg=PA145&lpg=PA145&dq=dissulfiram+stop+craving+for+amphetamines&source=bl&ots=PkBZ_o4vXK&sig=J22yh5pVYFggqKMRaiJE0Ejmmgg&hl=pt-BR&ei=7v-xToz9LsLFgAeM3r2kAQ&sa=X&oi=book_result&ct=result&resnum=2&ved=0CC0Q6AEwAQ#v=onepage&q&f=false</ref>

Also, 7-{4-[4-(2,3-Dichlorophenyl)piperazin-1-yl]butoxy}-3,4-dihydroquinolin-2(1H)-one, as well as 4-[2-[4-(6-fluorobenzo[d]isoxazol-3-yl)-
1-piperidyl]ethyl]-3-methyl-
2,6-diazabicyclo[4.4.0]deca-1,3-dien-5-one, and 4-[4-(4-Chlorophenyl)-4-hydroxy-1-piperidyl]-1-(4-fluorophenyl)-butan-1-one, and
5-(2-chlorophenyl)-7-nitro-2,3-dihydro-1,4-benzodiazepin-2-one,
which may or may not be quite identical to abilify, Risperdal, haloperidol, and clonapin,
are definitely tools of an attempted series of war crimes [punishable under the Geneva conventions,]. anybody who knows anything about chemistry will be able to tell you this.


== References ==
== References ==

Revision as of 05:27, 7 April 2014

Aripiprazole
Clinical data
Trade namesAbilify
AHFS/Drugs.comMonograph
MedlinePlusa603012
License data
Pregnancy
category
  • AU: B3
Routes of
administration		Oral (via tablets, orodispersable tablets, and oral solution); intramuscular (including as a depot)
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability87%[2][3][4][5]
Protein binding>99%[2][3][4][5]
MetabolismHepatic (liver; mostly via CYP3A4 and CYP2D6[2][3][4][5])
Elimination half-life75 hours (active metabolite is 94 hours)[2][3][4][5]
ExcretionRenal (27%; <1% unchanged), Faecal (60%; 18% unchanged)[2][3][4][5]
Identifiers
  • 7-{4-[4-(2,3-Dichlorophenyl)piperazin-1-yl]butoxy}-3,4-dihydroquinolin-2(1H)-one
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.112.532 Edit this at Wikidata
Chemical and physical data
FormulaC23H27Cl2N3O2
Molar mass448.385 g·mol−1
3D model (JSmol)
  • Clc4cccc(N3CCN(CCCCOc2ccc1c(NC(=O)CC1)c2)CC3)c4Cl
  • InChI=1S/C23H27Cl2N3O2/c24-19-4-3-5-21(23(19)25)28-13-11-27(12-14-28)10-1-2-15-30-18-8-6-17-7-9-22(29)26-20(17)16-18/h3-6,8,16H,1-2,7,9-15H2,(H,26,29) checkY
  • Key:CEUORZQYGODEFX-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Aripiprazole (/ˌɛər[invalid input: 'ɨ']ˈpɪprəzoʊl/ AIR-i-PIP-rə-zohl; brand names: Abilify, Aripiprex) is a partial dopamine agonist of the second generation (or atypical) class of antipsychotics that is primarily used in the treatment of schizophrenia, bipolar disorder, major depressive disorder (as an adjunct), tic disorders, and irritability associated with autism.[6] It was approved by the U.S. Food and Drug Administration (FDA) for schizophrenia on November 15, 2002 and the European Medicines Agency on 4 June 2004; for acute manic and mixed episodes associated with bipolar disorder on October 1, 2004; as an adjunct for major depressive disorder on November 20, 2007;[7] and to treat irritability in children with autism on 20 November 2009.[8] Likewise it was approved for use as a treatment for schizophrenia by the TGA of Australia in May 2003.[2] Aripiprazole was developed by Otsuka in Japan, and in the United States, Otsuka America markets it jointly with Bristol-Myers Squibb. Some doctors say that, because of promotion by the pharmaceutical industry, second-generation drugs like aripiprazole, which are appropriate for a few serious psychiatric disorders, are prescribed inappropriately for conditions it may not treat effectively, such as anxiety.[9]

Medical uses

Aripiprazole is primarily used for the treatment of schizophrenia or bipolar disorder.[10]

Schizophrenia

There is tentative evidence aripiprazole may be useful in schizophrenia; however, definitive conclusions are difficult to draw as there was a high rate of attrition during trials and there is a lack of outcome data regarding general functioning, behavior, mortality, economic outcomes, or cognitive functioning.[11][12] It is similar to other typical and atypical antipsychotics with respect to benefit.[11] Compared to typical antipsychotics, there is less extrapyramidal side effects, but higher rates of dizziness.[13] With respect to other atypicals, it is difficult to determine differences in adverse effects as data quality is poor.[14] The efficacy and tolerability of aripiprazole was in the middle range of 15 antipsychotics for efficacy, but had superior tolerability when compared to the other antipsychotic drugs (4th lowest SMD for weight gain, 5th lowest OR for extrapyramidal symptoms, lowest SMD for prolactin elevation, 2nd lowest OR for QTc prolongation, 5th lowest OR for sedation).[15] In a large (N=361) 12-week open-label (hence, no definitive conclusions can be drawn from this study alone) clinical trial, significant improvements in verbal memory and fluency were seen in patients with schizophrenia treated with aripiprazole.[16]

Bipolar disorder

When used by itself for bipolar disorder, aripiprazole does not appear to improve symptoms of depression,[17] although it may be useful in preventing mania.[18] Thus, it is often used in combination with an additional mood stabilizer; however, co-administration with a mood stabilizer increases the risk of extrapyramidal side effects.[19]

Major depression

Aripiprazole is an effective adjunct treatment for major depressive disorder. However, there is a greater rate of side effects as an adjunctive therapy (such as weight gain and akathisia).[20][21] Aripiprazole is the most efficacious antipsychotic to alleviate symptoms of treatment-resistant major depressive disorder (although not significantly).[22] Likewise, in a few earlier meta-analyses, similar results were obtained.[23][24] Aripiprazole may pharmacokinetically interact with some antidepressants, especially SSRIs. There are significant interactions with fluoxetine and paroxetine and lesser interactions with sertraline, escitalopram, citalopram and fluvoxamine, which inhibit CYP2D6, for which aripiprazole is a substrate.[2]

Autism

Short-term data (8 weeks) shows reduced irritability, hyperactivity, and stereotypy.[25] Adverse effects included weight gain, sleepiness, drooling and tremors.[25] Long-term outcomes are not clear.[25]

Regulatory Approval Status

Regulatory Administration (Country)[26][27][28] Schizophrenia Acute Mania Bipolar Maintenance Major Depressive Disorder (as an adjunct) Autism
Food and Drug Administration (US) Yes Yes Yes (as an adjunct to lithium/valproate) Yes Yes
Therapeutic Goods Administration (AU) Yes Yes (as an adjunct to lithium/valproate) Yes No No
Medicines and Healthcare products Regulatory Agency (UK) Yes No Yes (to prevent mania) No No

Side effects

Adverse effect incidences
In Adults[2][3][4][5][29]

Very Common (>10% incidence) adverse effects
  • Weight gain
  • Headache
  • Agitation
  • Insomnia
  • Anxiety
  • Nausea & vomiting
  • Akathisia — a sense of inner restlessness that presents itself with the inability to stay still
  • Lightheadedness
  • Constipation
Common (1-10% incidence) adverse effects
  • Dizziness
  • Dyspepsia — indigestion
  • Somnolence — which is usually mild and transient and less severe than that seen with most antipsychotics.[15]
  • Fatigue
  • Restlessness
  • Dry mouth
  • Extrapyramidal side effects (e.g. dystonia, parkinsonism, tremor, etc.)
  • Orthostatic hypotension
  • Musculoskeletal stiffness
  • Abdominal discomfort
  • Blurred vision
  • Cough
  • Pain
  • Myalgia
  • Rash
  • Rhinitis
Uncommon (0.1-1% incidence) adverse effects
  • Leukopenia
  • Neutropenia
  • Thrombocytopenia
  • Bradycardia (low heart rate)
  • Palpitations
  • Orthostatic hypotension
  • Dry eye
  • Photophobia
  • Diplopia
  • Eyelid oedema
  • Photopsia
  • Diarrhoea
  • Gastritis
  • Dysphagia
  • Gastroesophageal reflux disease
  • Swollen tongue
  • Oesophagitis
  • Hypoaesthesia oral
  • Face oedema
  • Gait disturbance
  • Chills
  • Discomfort
  • Feeling abnormal
  • Mobility decreased
  • Self-mutilation
  • Heart rate increased
  • Blood glucose increased
  • Pyrexia
  • Blood prolactin increased
  • Blood urea increased
  • Electrocardiogram QT prolonged
  • Blood bilirubin increased
  • Hepatic enzyme increased
  • Increased appetite
  • Nocturia
  • Polyuria
  • Pollakiuria
  • Incontinence
  • Urinary retention
  • Sexual dysfunction
  • Amenorrhoea
  • Pruritus (itchiness)
  • Photosensitivity reaction
  • Urticaria
Rare (<0.1%) adverse effects include

Sudden unexplained death has been reported, however the frequency is unknown.[33]

Common in children
  • Feeling sleepy
  • Headache
  • Vomiting
  • Fatigue
  • Increased appetite
  • Insomnia
  • Nausea
  • Stuffy nose
  • Weight gain
  • Uncontrolled movement such as restlessness, tremor muscle stiffness [34]

Discontinuation

Aripiprazole 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.[35] 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. Withdrawal symptoms reported to occur after discontinuation of antipsychotics include nausea, emesis, lightheadedness, diaphoresis, dyskinesia, orthostatic hypotension, tachycardia, rhabdomyolysis, nervousness, dizziness, headache, excessive non-stop crying, and anxiety.[36][37] 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.[38][39][40][41] This has led some to suggest that the withdrawal process might itself be schizo-mimetic, producing schizophrenia-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.[42]

Overdosage

Children or adults who ingested acute overdoses have usually manifested central nervous system depression ranging from mild sedation to coma; serum concentrations of aripiprazole and dehydroaripiprazole in these patients were elevated by up to 3-4 fold over normal therapeutic levels, yet to date no deaths have been recorded.[43]

Drug interactions

Aripiprazole is a substrate of CYP2D6 and CYP3A4. Coadministration with medications that inhibit (e.g. paroxetine, fluoxetine) or induce (e.g. carbamazepine) these metabolic enzymes are known to increase and decrease, respectively, plasma levels of aripiprazole.[44] As such, anyone taking aripiprazole should be aware that their dosage of aripiprazole may need to be decreased.

Aripiprazole may change the subjective effects of alcohol. One study[45] found that aripiprazole increased the sedative effect and reduced the sense of euphoria normally associated with alcohol consumption. However, another alcohol study[46] found that there was no difference in subjective effect between a placebo group and a group taking aripiprazole.

For the purpose of D2 blockage, aripiprazole, a partial agonist on D2 receptor site, should not be used with a full antagonist.[medical citation needed]

Pharmacology

Binding profile

Aripiprazole acts as an antagonist/inverse agonist (unless otherwise noted) of the following receptors and transporters:[47][48][49][50][51][52][53][54]

Aripiprazole's mechanism of action is different from those of the other FDA-approved atypical antipsychotics (e.g., clozapine, olanzapine, quetiapine, ziprasidone, and risperidone). Rather than antagonizing the D2 receptor, aripiprazole acts as a D2 partial agonist.[55][56] Aripiprazole is also a partial agonist at the 5-HT1A receptor, and like the other atypical antipsychotics displays an antagonist profile at the 5-HT2A receptor.[57][58] It also antagonizes the 5-HT7 receptor and acts as a partial agonist at the 5-HT2C receptor, both with high affinity. The latter action may underlie the minimal weight gain seen in the course of therapy.[59] Aripiprazole has moderate affinity for histamine, α-adrenergic, and D4 receptors as well as the serotonin transporter, while it has no appreciable affinity for cholinergic muscarinic receptors.[48]

D2 and D3 receptor occupancy levels are high, with average levels ranging between ~71% at 2 mg/day to ~96% at 40 mg/day.[60][61] Most atypical antipsychotics bind preferentially to extrastriatal receptors, but aripiprazole appears to be less preferential in this regard, as binding rates are high throughout the brain.[62]

Recently, it has been demonstrated that in 5-HT7 receptor knockout mice, aripiprazole does not reduce immobility time in the forced swim test (FST), and actually increases it.[63][64] This implicates 5-HT7 antagonism as playing a major role in aripiprazole's antidepressant effects, similarly to amisulpride.[63][64][65] Note, however, humans possess a splice variant not found in other mammals (the "d" isoform), while mice possess one not found in humans (the "c"). The significantly altered c-terminus observed in 5-HT7(d) results in a similar binding affinity to the other forms of this receptor, however, the "c" variant found in other mammals differs in affinity. This difference in expression means the receptor's function in modulating thalamic and hypothalamic output, and corresponding effect on fatigue perception and alertness may not be homologous in mice and humans.

Aripiprazole produces 2,3-dichlorophenylpiperazine (DCPP) as a metabolite in a similar fashion to the reactions of trazodone and nefazodone to give 3-chlorophenylpiperazine (mCPP) and the conversion of niaprazine to 4-fluorophenylpiperazine (pFPP).[66] It is unknown whether DCPP contributes to aripiprazole's pharmacology.[citation needed]

Pharmacokinetics

Aripiprazole displays linear kinetics and has an elimination half-life of approximately 75 hours. Steady-state plasma concentrations are achieved in about 14 days. Cmax (maximum plasma concentration) is achieved 3–5 hours after oral dosing. Bioavailability of the oral tablets is about 90% and the drug undergoes extensive hepatic metabolization (dehydrogenation, hydroxylation, and N-dealkylation), principally by the enzymes CYP2D6 and CYP3A4. Its only known active metabolite is dehydro-aripiprazole, which typically accumulates to approximately 40% of the aripiprazole concentration. The parenteral drug is excreted only in traces, and its metabolites, active or not, are excreted via feces and urine.[48] When dosed daily, brain concentrations of aripiprazole will increase for a period of 10–14 days, before reaching stable constant levels.[citation needed]

Society and culture

Regulator status

In the United States, the FDA has approved aripiprazole for the treatment of schizophrenia in adults and adolescents (aged 13–17), of manic and mixed episodes associated with Bipolar I (One) Disorder with or without psychotic features in adults, children and adolescents (aged 10–17),[67] of irritability associated with autism in pediatric patients (aged 6–17),[68] and of depression when used along with antidepressants in adults.[69]

Aripiprazole is also used off-label for schizophrenia in children (aged 10–12), and to treat dementia-related psychosis in geriatric patients, though Bristol-Myers Squibb was penalized for promoting such uses in the United States.[70]

Aripiprazole has been approved by the FDA for the treatment of acute manic and mixed episodes, in both pediatric patients aged 10–17 and in adults.[71]

In 2007, aripiprazole was approved by the FDA for the treatment of unipolar depression when used adjunctively with an antidepressant medication.[72] It has not been FDA-approved for use as monotherapy in unipolar depression.

Patent status

Otsuka's US patent on aripiprazole expires on October 20, 2014;[73] however, due to a pediatric extension, a generic will not become available until at least April 20, 2015.[71] Barr Laboratories (now Teva Pharmaceuticals) initiated a patent challenge under the Hatch-Waxman Act in March 2007.[74] On November 15, 2010, this challenge was rejected by a United States district court in New Jersey.[1][2]

Dosage forms

File:Abilify bottle.jpg
Abilify 2mg tablets (US)
  • Intramuscular injection, solution: 9.75 mg/mL (1.3 mL)
  • Solution, oral: 1 mg/mL (150 mL) [contains propylene glycol, sucrose 400 mg/mL, and fructose 200 mg/mL; orange cream flavor]
  • Tablet: 2 mg, 5 mg, 10 mg, 15 mg, 20 mg, 30 mg
  • Tablet, orally disintegrating: 10 mg [contains phenylalanine 1.12 mg; creme de vanilla flavor]; 15 mg [contains phenylalanine 1.68 mg; creme de vanilla flavor]

Synthesis

Aripiprazole can be synthesized beginning with a dichloroaniline and bis(2-chloroethyl)amine:[75]

Research

Perhaps owing to its mechanism of action relating to dopamine receptors, there is some evidence to suggest that aripiprazole blocks cocaine-seeking behavior in animal models without significantly affecting other rewarding behaviors (such as food self-administration).[76] The book Addiction Medicine mentions studies that suggest aripiprazole would be counter-therapeutic as treatment for methamphetamine dependency because it increased methamphetamine's stimulant and euphoric effects, and increased the baseline level of desire for methamphetamine.[77]

Also, 7-{4-[4-(2,3-Dichlorophenyl)piperazin-1-yl]butoxy}-3,4-dihydroquinolin-2(1H)-one, as well as 4-[2-[4-(6-fluorobenzo[d]isoxazol-3-yl)- 

1-piperidyl]ethyl]-3-methyl-
2,6-diazabicyclo[4.4.0]deca-1,3-dien-5-one, and 4-[4-(4-Chlorophenyl)-4-hydroxy-1-piperidyl]-1-(4-fluorophenyl)-butan-1-one, and

5-(2-chlorophenyl)-7-nitro-2,3-dihydro-1,4-benzodiazepin-2-one, which may or may not be quite identical to abilify, Risperdal, haloperidol, and clonapin, are definitely tools of an attempted series of war crimes [punishable under the Geneva conventions,]. anybody who knows anything about chemistry will be able to tell you this.

References

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  3. ^ a b c d e f "ABILIFY (aripiprazole) tablet ABILIFY (aripiprazole) solution ABILIFY DISCMELT (aripiprazole) tablet, orally disintegrating ABILIFY (aripiprazole) injection, solution [Otsuka America Pharmaceutical, Inc.]". DailyMed. Otsuka America Pharmaceutical, Inc. April 2013. Retrieved 22 October 2013.
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Aripiprazole-induced oculogyric crisis (acute dystonia).Jyotik T Bhachech.Journal of Pharmacology and Pharmacotherapeutics. Jul-Sept 2012,3:279-81.http://www.jpharmacol.com/article.asp?issn=0976-500X;year=2012;volume=3;issue=3;spage=279;epage=281;aulast=Bhachech;type=0

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