The Structure of Aripiprazole

Aripiprazole is one possible part of a regimen of mental health care drugs that doctors may prescribe.

Doctors prescribe aripiprazole, also called Abilify, for the treatment of schizophrenia and other mental health problems. An aripiprazole molecule has a complex chemical structure including carbon, hydrogen, nitrogen, oxygen and chlorine atoms. Aripiprazole, classified as an atypical antipsychotic, has effects which are not well understood on receptors for the neurotransmitters dopamine and serotonin in the brain.

Function

Aripiprazole, also known as Abilify, functions as an antipsychotic and sometimes as an antidepressant. Clinicians often prescribe it for schizophrenia, sometimes for bipolar disorder and sometimes for irritability in autistic children, according to Drugs.com.

Nobody knows its exact mechanism of action, according to FDA Access Data, but it does have an affinity for dopamine and serotonin receptors, meaning that it probably affects the ways these neurotransmitters function in the brain. This probably accounts for its ability to lessen the symptoms of some mental illnesses.

Formula

Aripiprazole has the chemical formula C23H27Cl2N3O2. This means that an aripiprazole molecule contains 23 carbon, 27 hydrogen, two chlorine, three nitrogen and two oxygen atoms. Because many possible kinds of molecules can contain these atoms, the configuration of the molecule becomes important.

Organic chemistry nomenclature as put forth by IUPAC (the International Union of Pure and Applied Chemistry) names the molecule 7-[4-[4-(2,3-dichlorophenyl)-1- piperazinyl]butoxy] -3,4- dihydrocarbostyril, according to FDA Access Data. Organic chemists can use this name to understand what the molecule's structure looks like.

Structure

The structure of aripiprazole, visually described, consists of the following: a benzene ring substituted with two chlorines ortho (adjacent) and meta (two carbons away) from a connected piperazine ring. The opposite nitrogen on the piperazine ring connects to a chain of four carbons, each bonded to two hydrogens. The fourth carbon in this chain connects to an oxygen atom, which in turn is bonded to a benzene ring that is fused with a heterocyclic six-membered ring. A nitrogen atom occupies a place in this ring next to the shared bond in the fused structure; a carbonyl group appears in the next position. (The nitrogen and the carbonyl together constitute an amide group.)

Effects

In addition to its desired effects on mental health problems, Drugs.com reports that common side effects of aripiprazole can include high blood sugar, drowsiness, dizziness, difficulty swallowing, minor stomach and gastrointestinal trouble, insomnia and weight gain.

Warning

Less common and more serious side effects, to which patients should respond by calling a physician or going to a hospital, include allergic reactions (hives, swelling and trouble breathing), fever and chills and other flu-like symptoms, severe stomach upset, faintness, sudden headache or numbness, seizures, mouth sores, jaundice and difficulty urinating.

Aripiprazole can interact with other medications, so users must make sure to inform their prescribing doctors if taking antifungals, antibiotics, other mental health medications or heart medications, according to Drugs.com.

The Mayo Clinic advises avoiding this drug during pregnancy.

References

• Drugs.com: Abilify
• FDA Access Data: Aripiprazole (Abilify)
• Mayo Clinic: Aripiprazole