Aripiprazole

HCID 60795CAS 129722-12-9

Basic information

Standard SMILES
O=C1CCc2ccc(OCCCCN3CCN(c4cccc(Cl)c4Cl)CC3)cc2N1
InChIKey
CEUORZQYGODEFX-UHFFFAOYSA-N
Molecular formula
C23H27Cl2N3O2
Average molar mass
448.4 g/mol
Monoisotopic mass
447.14803246

Overview

Aripiprazole is an N-arylpiperazine that is piperazine substituted by a 4-[(2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)oxy]butyl group at position 1 and by a 2,3-dichlorophenyl group at position 4. It is an antipsychotic drug used for the treatment of Schizophrenia, and other mood disorders. It has a role as a serotonergic agonist, a H1-receptor antagonist, a drug metabolite and a second generation antipsychotic. It is a dichlorobenzene, a quinolone, an aromatic ether, a N-alkylpiperazine, a N-arylpiperazine and a delta-lactam.

Names & identifiers

Preferred name
Aripiprazole
IUPAC
7-[4-[4-(2,3-dichlorophenyl)piperazin-1-yl]butoxy]-3,4-dihydro-1H-quinolin-2-one
English name
Aripiprazole
Molecular formula
C23H27Cl2N3O2
Molecular weight
448.39

Names & synonyms

Aripiprazole129722-12-9AbilifyAbilitatOPC-14597Abilify DiscmeltaripiprazolDiscmeltOpc 14597AripiprexAbilify MyCiteOPC 31
Show more names
ARIPIPRAZOLE-D8AripirazoleArpiprazoleAripiprazole CRSAbilify-d8OPC 31-d8-
OPC-31Abilify Maintena7-[4-[4-(2,3-Dichlorophenyl)-1-piperazinyl]butoxy]-3,4-dihydro-2(1H)-quinolinonearipiprazolum7-(4-(4-(2,3-DICHLOROPHENYL)PIPERAZIN-1-YL)BUTOXY)-3,4-DIHYDROQUINOLIN-2(1H)-ONEAbilify Maintena KitDTXSID3046083NSC-759266

Database identifiers

CAS
129722-12-9
PubChem CID
60795
DTXSID
DTXSID3046083
ChEMBL
CHEMBL1112
ChEBI
CHEBI:31236
UNII
82VFR53I78
EC Number
603-355-5
Nikkaji
J573.417G

Properties

Computed structural properties

XLogP
4.6
Topological polar surface area
44.8 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
4
Rotatable bonds
7
Heavy atoms
30

Experimental & physicochemical properties

Drugs · 3 items

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals

Pharmaceuticals -> Antipsychotics

Color/FormColorless, flake crystals from ethanol
Solubility · 2 items

0.00001%

<0.3 [ug/mL] (The mean of the results at pH 7.4)

Human Drugs · 6 items

Breast Feeding; Lactation; Milk, Human; Antipsychotic Agents

FDA approved drugs -> Active ingredient

EMA approved medicines: Human medicine

EMA approved medicines: Human medicine

EMA approved medicines: Human medicine

EMA approved medicines: Human medicine

Boiling Point139.0-139.5 °C
Melting Point137-140

Physicochemical properties

Melting point
139 °C · 139°C
Boiling point
646.2 · 646.2±55.0 °C(Predicted)
Density
1.263 · 1.263±0.06 g/cm3(Predicted)
storage temp.
2 · 2-8°C
solubility
5 mg/mL, · DMSO: soluble5mg/mL, clear (warmed)
pka
14.42 · 14.42±0.20(Predicted)

Safety & regulation

GHS classification

GHS Classification · 6 items

Danger

H301 (62.7%): Toxic if swallowed [Danger Acute toxicity, oral]

P203, P264, P270, P273, P280, P301+P316, P301+P317, P318, P321, P330, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 51 reports by companies from 20 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H226: Flammable liquid and vapor [Warning Flammable liquids]

Hazard information

FDA Requirements · 1 item

The Approved Drug Products with Therapeutic Equivalence Evaluations identifies currently marketed prescription drug products, including aripiprazole, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.

Special ReportsSwainston Harrison T, Perry CM; Aripiprazole: A Review of its Use in Schizophrenia and Schizoaffective disorder; Drugs 64 (15): 1715-36 (2004).[]
Toxic Combustion ProductsSpecial hazards arising from the substance or mixture: Carbon oxides, Hydrogen chloride gas
Hazard Classes and CategoriesAcute Tox. 3 (62.7%)
Hazardous Reactivities and IncompatibilitiesIncompatible materials: Strong oxidizing agents

Safety & protection

Fire Fighting Procedures · 2 items

Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary. Use water spray to cool unopened containers.

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Storage Conditions · 1 item

Conditions for safe storage, including any incompatibilities: Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage. Storage class (TRGS 510): Flammable liquids

Cleanup Methods · 1 item

ACCIDENTAL RELEASE MEASURES. Personal precautions, protective equipment and emergency procedures: Wear respiratory protection. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapours accumulating to form explosive concentrations. Vapours can accumulate in low areas.; Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains.; Methods and materials for containment and cleaning up: Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and place in container for disposal according to local regulations.

Disposal Methods · 2 items

SRP: At the time of review, regulatory criteria for small quantity disposal are subject to significant revision, however, household quantities of waste pharmaceuticals may be managed as follows: Mix with wet cat litter or coffee grounds, double bag in plastic, discard in trash.

SRP: Expired or waste pharmaceuticals shall carefully take into consideration applicable DEA, EPA, and FDA regulations. It is not appropriate to dispose by flushing the pharmaceutical down the toilet or discarding to trash. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.

Preventive Measures · 3 items

Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.

Appropriate engineering controls: Avoid contact with skin, eyes and clothing. Wash hands before breaks and immediately after handling the product.

Precautions for safe handling: Avoid contact with skin and eyes. Avoid inhalation of vapour or mist. Keep away from sources of ignition - No smoking.Take measures to prevent the build up of electrostatic charge.

Personal Protective Equipment (PPE) · 4 items

Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with multipurpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).

Body Protection: Complete suit protecting against chemicals, Flame retardant antistatic protective clothing., The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.

Skin protection: Handle with gloves.

Eye/face protection: Face shield and safety glasses Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).

Toxicology

Treatment · 1 item

No specific information is available on the treatment of overdose with aripiprazole. An electrocardiogram should be obtained in case of overdosage and if QT interval prolongation is present, cardiac monitoring should be instituted. Otherwise, management of overdose should concentrate on supportive therapy, maintaining an adequate airway, oxygenation and ventilation, and management of symptoms. Close medical supervision and monitoring should continue until the patient recovers. Consider charcoal and hemodialysis. (A308)

Interactions · 5 items

Substrates of Hepatic Microsomal Enzymes: Substrates of CYP1A2, CYP2C9, CYP2C19, CYP2D6, and CYP3A4; pharmacokinetic interaction unlikely.

Hypotensive Agents: Potential pharmacologic interaction (additive hypotensive effects)

Famotidine: Coadministration of aripiprazole (given in a single dose of 15 mg) with a 40-mg single dose of the H2 antagonist famotidine, a potent gastric acid blocker, decreased the solubility of aripiprazole and, hence, its rate of absorption, reducing by 37% and 21% the Cmax of aripiprazole and dehydro-aripiprazole, respectively, and by 13% and 15%, respectively, the extent of absorption (AUC). No dosage adjustment of aripiprazole is required when administered concomitantly with famotidine.

Valproate: When valproate (500-1500 mg/day) and aripiprazole (30 mg/day) were coadministered at steady state, the C max and AUC of aripiprazole were decreased by 25%. No dosage adjustment of aripiprazole is required when administered concomitantly with valproate.

For more Interactions (Complete) data for ARIPIPRAZOLE (12 total), please visit the HSDB record page.

Health Effects · 1 item

Health effetcs include hyperpyrexia,muscle rigidity,altered mental status,and evidence of autonomic instability (irregular pulse or blood pressure, tachycardia, diaphoresis, and cardiac dysrhythmia). Other effects may include central anticholinergic toxicity, heat stroke, drug fever, and primary central nervous system pathology (RxList, A308).

Hepatotoxicity · 1 item

Liver test abnormalities have not been reported to occur in patients on long term therapy with aripiprazole, but most studies have not provided information on serum enzyme results. Despite its widescale use, aripiprazole has been implicated in only rare and isolated cases of clinically apparent liver injury in the literature. All reported cases have been hepatocellular arising after 1 to 3 months of therapy and with accelerated onset in one instance upon re-exposure. Immunoallergic and autoimmune features were not present. Most cases have been anicteric, and none were fatal or resulted in chronic injury. Aripiprazole has not been reported among agents implicated in large case series of drug induced liver injury. The product label for aripiprazole mentions that hepatitis and jaundice have been reported, but no specific details were provided. Thus, clinically apparent liver injury from aripiprazole must be very rare.

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 2.5X10+4(SRC), determined from a structure estimation method(2), indicates that aripiprazole is expected to be immobilein soil(SRC). The estimated pKa1 of aripiprazole is 7.46(3), indicating that this compound will exist partially in the cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization of the neutral species of aripiprazole from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 7.7X10-17 atm-cu m/mole(SRC), using a fragment constant estimation method(5). Aripiprazole is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.2X10-13 mm Hg at 25 °C(SRC), determined from a fragment constant method(2). Biodegradation data in soil were not available(SRC, 2015).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 2.5X10+4(SRC), determined from a structure estimation method(2), indicates that aripiprazole is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 7.7X10-17 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 1500(SRC), from an estimated log Kow of 5.30(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is very high(SRC). Biodegradation data in water were not available(SRC, 2015).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), aripiprazole, which has an estimated vapor pressure of 3.2X10-13 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase. Particulate-phase aripiprazole may be removed from the air by wet and dry deposition(SRC). Aripiprazole contains chromophores that absorb at wavelengths >290 nm(4) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

Adverse Effects · 1 item

Although the side effects of aripiprazole are similar to those found in typical and atypical antipsychotics, the degree of extrapyramidal symptoms (EPS) and metabolic syndromes is less due to receptor specificity. EPS, such as akathisia, Parkinsonian features such as resting tremor and shuffling gait, acute dystonic reactions, oculogyric crises, opisthotonos, and tardive dyskinesia, are manageable with benztropine or sodium benzoate. Aripiprazole is associated with lower incidences of weight gain, hypercholesterolemia, glucose dysregulation, cardiovascular abnormalities, and hyperprolactinemia. Hyperprolactinemia may manifest as galactorrhea, gynecomastia in men, sexual dysfunction, amenorrhea, or off-cycle bleeding. Other possible side effects of aripiprazole include somnolence, nausea, vomiting, akathisia, and lightheadedness. Antipsychotics agent use requires caution in older adults because it can cause or exacerbate the syndrome of inappropriate antidiuretic hormone secretion (SIADH) or hyponatremia; thus, it is crucial to monitor sodium during initiation and dosage adjustment. Children and adolescents are more susceptible than older patients to experience EPS, weight gain, and other metabolic side effects. The FDA also recently identified an association between aripiprazole use and compulsive or uncontrollable urges to engage in sex, gamble, binge eat, and shop.

Regulatory information

FDA Requirements · 1 item

The Approved Drug Products with Therapeutic Equivalence Evaluations identifies currently marketed prescription drug products, including aripiprazole, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.

Safety data

wgk
3
rtecs
VC8275950
ridadr
UN 1993C 3 / PGIII
hs_code
29349990
Toxicity
TDLo ivn-dog: 0.03 mg/kg/10M TXAPA9 173,120,2001
risk_code
11-20/21/22-36

Chemistry & industry

Pharmacology

ATC Code · 3 items

N05AX12

N - Nervous system

QN - Nervous system

Protein BindingAt therapeutic concentrations, aripiprazole and its major metabolite are greater than 99% bound to serum proteins, primarily to albumin.
Pharmacodynamics · 1 item

Aripiprazole exhibits high affinity for dopamine D<sub>2</sub> and D<sub>3</sub>, serotonin 5-HT<sub>1a</sub> and 5-HT<sub>2a</sub> receptors (Ki values of 0.34 nM, 0.8 nM, 1.7 nM, and 3.4 nM, respectively), moderate affinity for dopamine D<sub>4</sub>, serotonin 5-HT<sub>2c</sub> and 5-HT<sub>7</sub>, alpha<sub>1</sub>-adrenergic and histamine H<sub>1</sub> receptors (Ki values of 44 nM, 15 nM, 39 nM, 57 nM, and 61 nM, respectively), and moderate affinity for the serotonin reuptake site (Ki=98 nM). Aripiprazole has no appreciable affinity for cholinergic muscarinic receptors (IC<sub>50</sub>>1000 nM).

Mechanism of Action · 3 items

The antipsychotic action of aripiprazole is likely due to its partial agonist activity on D2 and 5-HT<sub>1A</sub> receptors as well as its antagonist activity at 5-HT<sub>2A</sub> receptors; however, the exact mechanism has not been fully elucidated. One of the mechanisms that have been proposed is that aripiprazole both stimulates and inhibits dopamine as it engages the D2 receptor. It lowers dopamine neuronal firing at high dopamine concentrations and increases dopamine firing at low concentrations. Its partial agonist activity gives aripiprazole an intermediate level of dopaminergic neuronal tone between full agonist and antagonist of the D2 receptor. In addition, some adverse effects may be due to action on other receptors. For example, orthostatic hypotension may be explained by antagonism of the adrenergic alpha-1 receptors.

The exact mechanism of antipsychotic action of aripiprazole has not been fully elucidated but, like that of other atypical antipsychotic agents (e.g.,olanzipine, risperidone, ziprasidon), may involve the drug's activity at dopamine D2 and serotonin type (5-HT1A) and type 2 (5-HT2A) receptors. However, aripiprazole appears to differ from other atypical antipsychotic agents because the drug demonstrates partial agonist activity at D2 and 5-HT1A receptors and antagonist activity at 5-HT2A receptors. Antagonism at other receptors (e.g., alpha1-adrenergic receptors, histamine H1 receptors) may contribute to other therapeutic and adverse effects (e.g., orthostatic hypotension, somnolence) observed with aripiprazole.

...Aripiprazole exhibits typical antagonism at dopamine (D2) receptors in the mesolimbic pathway, as well as having unique partial agonist activity at D2 receptors in the mesocortical pathway. As exemplified by other atypical antipsychotics, it displays strong 5-HT(2a) receptor antagonism and is similar to ziprasidone in also having agonistic activity at the 5-HT(1a) receptor. Among the atypical antipsychotics, aripiprazole displays the lowest affinity for alpha(1)adrenergic (alpha(1)), histamine (H1) and muscarinic (M1) receptors. This combination of effects may be responsible for its efficacy in positive and negative symptoms of schizophrenia and in bipolar disorder. ...Other early data suggest that aripiprazole may induce reductions in plasma prolactin, as well as in plasma glucose and lipid profiles ...

Biological Half-Life · 2 items

The mean elimination half-lives are about 75 hours and 94 hours for aripiprazole and dehydro-aripiprazole, respectively. For populations that are poor CYP2D6 metabolizers, the half-life of aripiprazole is 146 hours and these patients should be treated with half the normal dose. Other studies have reported a half-life of 61.03±19.59 hours for aripiprazole and 279±299 hours for the active metabolite.

The mean elimination half-lives are about 75 hours and 94 hours for aripiprazole and dehydro-aripiprazole, respectively.

Metabolism/Metabolites · 5 items

Aripiprazole is metabolized primarily by three biotransformation pathways: dehydrogenation, hydroxylation, and N-dealkylation. Based on in vitro studies, CYP3A4 and CYP2D6 enzymes are responsible for the dehydrogenation and hydroxylation of aripiprazole, and N-dealkylation is catalyzed by CYP3A4. Aripiprazole is the predominant drug moiety in systemic circulation. At steady-state, dehydro-aripiprazole, the active metabolite, represents about 40% of aripiprazole AUC in plasma.

Aripiprazole is extensively metabolized in the liver principally via dehydrogenation, hydroxylations, and N-dealkylation by the cytochrome P-450 (CYP) 2D6 and 3A4 isoenzymes. The major active metabolite of aripiprazole, dehydro-aripiprazole, exhibits affinity for D2 receptors similar to that of the parent compound and represents approximately 40% of the aripiprazole area under the concentration-time curve (AUC) in plasma. Steady-state plasma concentrations of both aripiprazole and dehydro-aripiprazole are achieved within 14 days.

ABILIFY activity is presumably primarily due to the parent drug, aripiprazole, and to a lesser extent, to its major metabolite, dehydro-aripiprazole, which has been shown to have affinities for D2 receptors similar to the parent drug and represents 40% of the parent drug exposure in plasma.

Aripiprazole has known human metabolites that include 2,3-dichlorophenylpiperazine, dehydro-aripiprazole, 4-Hydroxyaripiprazole, and 4-[(2-oxo-3,4-dihydro-1H-quinolin-7-yl)oxy]butanal.

Aripiprazole is metabolized primarily by three biotransformation pathways: dehydrogenation, hydroxylation,and N-dealkylation.Based on in vitro studies,CYP3A4 and CYP2D6 enzymes are responsible for dehydrogenation and hydroxylation of aripiprazole, and N-dealkylation is catalyzed by CYP3A4.Aripiprazole is the predominant drug moiety in the systemic circulation. At steady-state, dehydro-aripiprazole, the active metabolite, represents about 40% of aripiprazole AUC in plasma (RxList, A308). Route of Elimination: Less than 1% of unchanged aripiprazole was excreted in the urine and approximately 18% of the oral dose was recovered unchanged in the feces. Half Life: 75-146 hours

Uses & manufacturing

Uses · 4 items

MEDICATION

Antipsychotic Agents

Use (kg; approx.) in Germany (2009): >100

For the treatment of schizophrenia and related psychotic disorders.

Methods of Manufacturing · 2 items

7-Hydroxy-3,4-dihydro-2(1H)-quinolinone is refluxed with 1,4-dibromobutane plus K2CO3 in DMF to form the 7-(4-bromobutoxy) derivative which is condensed with 1-(3,4-dichlorophenyl)piperazine to yield the product.

Preparation: Y. Oshiro et al., European Patent Office patent 367141; eidem, United States of America patent 5006528 (1990,1991 both to Otsuka).

Formulations/PreparationsTable: Aripiprazole Preparations [Table#6911]
General Manufacturing InformationInformation available in 2005 indicated that Aripiprazole was used in the manufacture of pharmaceutical preparations in the following countries: Australia, Germany, Mexico, Switzerland, United Kingdom, United States (1,2)
Applications · 8 items

UsesAntipsychotics

DescriptionAripiprazole was launched for the treatment of psychoses including schizophrenia and offers a novel mechanism of action as a partial D2 receptor agonist. Aripiprazole can be synthesized in three steps beginning by the condensation of 7-hydroxy-1,2,3,4- tetrahydroquinolin-2-one with 1 ,Cdibromobutane followed by reaction with 1-(2,3- dichlorophenyl)piperazine. Aripiprazole is a significant D2 agonist/antagonist, 5-HT2 antagonist and 5-HT1α agonist combined with minimal affinity for a,-adrenergic, H1 and M1 receptors. It has a low D4:D2 selectivity ratio and a D2:5-HT2 affinity ratio that exceeds 15; resulting in different pharmacological characteristics compared to other atypical antipsychotics agents such as clozapine. In animal models, aripiprazole inhibits apomorphine-induced stereotypy without causing catalepsy and ptosis. Moreover, in contrast to classical antipsychotics that produce disabling movement disorders, aripiprazole does not cause an upregulation of D2 receptors or an increase in immediate early gene expression of e.g. the c-fos mRNA in the striatum. In patients with acute relapse of schizophrenia, treatment with aripiprazole provided significant improvement in both positive and negative syndrome scale (PANSS) total score in both short- and longterm evaluations. These results were comparable to those observed with haloperidol or risperidone; however, the early response rate was greater with aripiprazole. Aripiprazole was well tolerated with mild to moderate adverse events such as nausea, dizziness, somnolence and weight gain. The rates of extrapyramidal symptoms were lower than with haloperidol, prolactin levels increase has been uncommon and no significant Q-Tc interval prolongation was observed compared with placebo. Finally, studies suggested a minimal impact of aripiprazole administration on total cholesterol levels and on fasting blood sugar in contrast to other antipsychotics. Aripiprazole has a bioavailability of 87%, a tmax of 3-5 h and a half-life time of 48-68 h. Aripiprazole has been found to have linear kinetics and is mainly metabolized via the cytochrome systems CYP2D6 and CYP3A4. It has little effect on the blood levels of other medications; interaction with both lithium and divalproex sodium found minimal impact. Aripiprazole has also been studied in other psychiatric disorders, including bipolar disorders and has shown great efficacy.

UsesA deuterated version of Aripiprazole, a selective dopamine D2-receptor antagonist with dopamine autoreceptor agonist activity. Please note that users have reported separation of this compound and aripiprazole under normal-phase and reverse-phase

UsesA selective dopamine D2-receptor antagonist with dopamine autoreceptor agonist activity. Antipsychotic.

Usescerebral vasodilator, antimotion

UsesFor the treatment of schizophrenia and related psychotic disorders.

General DescriptionAripiprazole (Abilify). The newest, longactingaripiprazole (an arylpiperazine quinolinone derivative),appears to be partial agonist of D2 receptors (i.e., itstimulates certain D2 receptors while blocking others dependingon their locations in the brain and the concentrationof drug). Bioavailability of aripiprazole is around 87%, with peak plasma concentration attained at 3 to 5 hours afterdosing. It is metabolized by dehydrogenation, oxidative hydroxylation, and N-dealkylation, largelymediated by hepatic CYPs 3A4 and 2D6.The diphenylbutylpiperidine class can be considered amodification of the fluorobutyrophenone class. Because oftheir high lipophilicity, the compounds are inherently longacting. Pimozide has been approved for antipsychotic use,and penfluridol has undergone clinical trials in the UnitedStates. Overall, side effects for the two compounds resemblethose produced by the fluorobutyrophenones.

General DescriptionAripiprazole, (7-[4-[4-(2,3-dichlorophenyl)-1-piperazinyl]butoxy]-3,4-dihydro-2(1H)-quinolone,is an atypical antipsychotic that is available in tablets(Abilify), orally disintegrating tablets (Abilify Discmelt), anda 1-mg/mL oral solution. Unlike the other atypical antipsychotics,aripiprazole exhibits partial agonist activity at D2, D3,D4, and 5-HT1A receptors, and antagonist action at 5-HT2A receptors.Although aripiprazole exhibits a low incidence ofEPS, the compound occupies about 95% of striatal D2 receptorsat therapeutic doses. Additionally, aripiprazole does nothave a fast rate of dissociation from D2 receptors. Althoughthe mechanism of action of this compound remains to be elucidated,the atypical profile for aripiprazole may be related toits action at other monoamine receptors.The compoundis well absorbed with peak plasma levels occurring 3 to 5hours after oral administration. Food does not affect absorptionof aripiprazole. Aripiprazole is extensively metabolizedin the liver by the action of CYP2D6 and CYP3A4. The primarymetabolite in humans is dehydroaripiprazole. This metabolite represents about 40% of aripiprazoleat steady state.In the presence of CYP3A4 and CYP2D6 inhibitorsor inducers, dosage adjustments of aripiprazole maybe required. The mean elimination half-lives in extensive andpoor metabolizers are 75 hours and 146 hours, respectively.The major adverse effects of aripiprazole are headache, anxiety,and insomnia.Similar to other atypical antipsychotics,aripiprazole shows an increased risk in mortality in elderlypatients with dementia-related psychosis.Aripiprazoledemonstrates a different pharmacological profile from allother atypical antipsychotics.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
广州隽沐生物科技股份有限公司020-36607679; 13502246435 · [email protected]
Additional notes · 1 item

DefinitionChEBI: Aripiprazole is an N-arylpiperazine that is piperazine substituted by a 4-[(2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)oxy]butyl group at position 1 and by a 2,3-dichlorophenyl group at position 4. It is an antipsychotic drug used for the treatment of Schizophrenia, and other mood disorders. It has a role as a H1-receptor antagonist, a serotonergic agonist, a second generation antipsychotic and a drug metabolite. It is a quinolone, a N-arylpiperazine, a N-alkylpiperazine, a dichlorobenzene, an aromatic ether and a delta-lactam.

Related reactions

61 records

Linked notes

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