Perphenazine enanthate

Last updated
Perphenazine enanthate
Perphenazine enanthate.svg
Clinical data
Trade names Decentan Depot, Peratsin Enantaatti, Trilafon, Trilafon Enantato, Trilafon Enantat, Trilifan Retard
Other namesPerphenazine enantate
Routes of
administration
Intramuscular injection
Drug class Typical antipsychotic
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
  • 2-[4-[3-(2-chlorophenothiazin-10-yl)propyl]piperazin-1-yl]ethyl heptanoate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
ECHA InfoCard 100.037.739 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C28H38ClN3O2S
Molar mass 516.14 g·mol−1
3D model (JSmol)
  • CCCCCCC(=O)OCCN1CCN(CC1)CCCN2C3=CC=CC=C3SC4=C2C=C(C=C4)Cl
  • InChI=1S/C28H38ClN3O2S/c1-2-3-4-5-11-28(33)34-21-20-31-18-16-30(17-19-31)14-8-15-32-24-9-6-7-10-26(24)35-27-13-12-23(29)22-25(27)32/h6-7,9-10,12-13,22H,2-5,8,11,14-21H2,1H3
  • Key:PWEGQJCIAMJJHC-UHFFFAOYSA-N

Perphenazine enanthate, sold under the brand name Trilafon Enantat among others, is a typical antipsychotic and a depot antipsychotic ester which is used in the treatment of schizophrenia and has been marketed in Europe. [1] [2] [3] [4] [5] [6] It is formulated in sesame oil and administered by intramuscular injection and acts as a long-lasting prodrug of perphenazine. [2] [3] [4] [5] [6] Perphenazine enanthate is used at a dose of 25 to 200 mg once every 2 weeks by injection, with a time to peak levels of 2 to 3 days and an elimination half-life of 4 to 7 days. [2] [3] [4] [5] [6]

Pharmacokinetics of long-acting injectable antipsychotics
MedicationBrand nameClassVehicleDosageTmaxt1/2 singlet1/2 multiplelogPcRef
Aripiprazole lauroxil Aristada Atypical Water a441–1064 mg/4–8 weeks24–35 days ?54–57 days7.9–10.0
Aripiprazole monohydrate Abilify Maintena Atypical Water a300–400 mg/4 weeks7 days ?30–47 days4.9–5.2
Bromperidol decanoate Impromen Decanoas Typical Sesame oil 40–300 mg/4 weeks3–9 days ?21–25 days7.9 [7]
Clopentixol decanoate Sordinol Depot Typical Viscoleo b50–600 mg/1–4 weeks4–7 days ?19 days9.0 [8]
Flupentixol decanoate Depixol Typical Viscoleo b10–200 mg/2–4 weeks4–10 days8 days17 days7.2–9.2 [8] [9]
Fluphenazine decanoate Prolixin Decanoate Typical Sesame oil 12.5–100 mg/2–5 weeks1–2 days1–10 days14–100 days7.2–9.0 [10] [11] [12]
Fluphenazine enanthate Prolixin Enanthate Typical Sesame oil 12.5–100 mg/1–4 weeks2–3 days4 days ?6.4–7.4 [11]
Fluspirilene Imap, Redeptin Typical Water a2–12 mg/1 week1–8 days7 days ?5.2–5.8 [13]
Haloperidol decanoate Haldol Decanoate Typical Sesame oil 20–400 mg/2–4 weeks3–9 days18–21 days7.2–7.9 [14] [15]
Olanzapine pamoate Zyprexa Relprevv Atypical Water a150–405 mg/2–4 weeks7 days ?30 days
Oxyprothepin decanoate Meclopin Typical  ? ? ? ? ?8.5–8.7
Paliperidone palmitate Invega Sustenna Atypical Water a39–819 mg/4–12 weeks13–33 days25–139 days ?8.1–10.1
Perphenazine decanoate Trilafon Dekanoat Typical Sesame oil 50–200 mg/2–4 weeks ? ?27 days8.9
Perphenazine enanthateTrilafon Enanthate Typical Sesame oil 25–200 mg/2 weeks2–3 days ?4–7 days6.4–7.2 [16]
Pipotiazine palmitate Piportil Longum Typical Viscoleo b25–400 mg/4 weeks9–10 days ?14–21 days8.5–11.6 [9]
Pipotiazine undecylenate Piportil Medium Typical Sesame oil 100–200 mg/2 weeks ? ? ?8.4
Risperidone Risperdal Consta Atypical Microspheres 12.5–75 mg/2 weeks21 days ?3–6 days
Zuclopentixol acetate Clopixol Acuphase Typical Viscoleo b50–200 mg/1–3 days1–2 days1–2 days4.7–4.9
Zuclopentixol decanoate Clopixol Depot Typical Viscoleo b50–800 mg/2–4 weeks4–9 days ?11–21 days7.5–9.0
Note: All by intramuscular injection. Footnotes:a = Microcrystalline or nanocrystalline aqueous suspension. b = Low-viscosity vegetable oil (specifically fractionated coconut oil with medium-chain triglycerides). c = Predicted, from PubChem and DrugBank. Sources:Main: See template.

See also

Related Research Articles

<span class="mw-page-title-main">Haloperidol</span> Typical antipsychotic medication

Haloperidol, sold under the brand name Haldol among others, is a typical antipsychotic medication. Haloperidol is used in the treatment of schizophrenia, tics in Tourette syndrome, mania in bipolar disorder, delirium, agitation, acute psychosis, and hallucinations from alcohol withdrawal. It may be used by mouth or injection into a muscle or a vein. Haloperidol typically works within 30 to 60 minutes. A long-acting formulation may be used as an injection every four weeks by people with schizophrenia or related illnesses, who either forget or refuse to take the medication by mouth.

<span class="mw-page-title-main">Fluphenazine</span> Chemical compound

Fluphenazine, sold under the brand name Prolixin among others, is a high-potency typical antipsychotic medication. It is used in the treatment of chronic psychoses such as schizophrenia, and appears to be about equal in effectiveness to low-potency antipsychotics like chlorpromazine. It is given by mouth, injection into a muscle, or just under the skin. There is also a long acting injectable version that may last for up to four weeks. Fluphenazine decanoate, the depot injection form of fluphenazine, should not be used by people with severe depression.

<span class="mw-page-title-main">Typical antipsychotic</span> Class of drugs

Typical antipsychotics are a class of antipsychotic drugs first developed in the 1950s and used to treat psychosis. Typical antipsychotics may also be used for the treatment of acute mania, agitation, and other conditions. The first typical antipsychotics to come into medical use were the phenothiazines, namely chlorpromazine which was discovered serendipitously. Another prominent grouping of antipsychotics are the butyrophenones, an example of which is haloperidol. The newer, second-generation antipsychotics, also known as atypical antipsychotics, have largely supplanted the use of typical antipsychotics as first-line agents due to the higher risk of movement disorders in the latter.

<span class="mw-page-title-main">Risperidone</span> Antipsychotic medication

Risperidone, sold under the brand name Risperdal among others, is an atypical antipsychotic used to treat schizophrenia and bipolar disorder. It is taken either by mouth or by injection. The injectable versions are long-acting and last for 2–4 weeks.

<span class="mw-page-title-main">Perphenazine</span> Antipsychotic medication

Perphenazine is a typical antipsychotic drug. Chemically, it is classified as a piperazinyl phenothiazine. Originally marketed in the United States as Trilafon, it has been in clinical use for decades.

<span class="mw-page-title-main">Haloperidol decanoate</span> Chemical compound

Haloperidol decanoate, sold under the brand name Haldol Decanoate among others, is a typical antipsychotic which is used in the treatment of schizophrenia. It is administered by injection into muscle at a dose of 100 to 200 mg once every 4 weeks or monthly. The dorsogluteal site is recommended. A 3.75-cm (1.5-inch), 21-gauge needle is generally used, but obese individuals may require a 6.5-cm (2.5-inch) needle to ensure that the drug is indeed injected intramuscularly and not subcutaneously. Haloperidol decanoate is provided in the form of 50 or 100 mg/mL oil solution of sesame oil and benzyl alcohol in ampoules or pre-filled syringes. Its elimination half-life after multiple doses is 21 days. The medication is marketed in many countries throughout the world.

<span class="mw-page-title-main">Flupentixol</span> Typical antipsychotic drug of the thioxanthene class

Flupentixol (INN), also known as flupenthixol, marketed under brand names such as Depixol and Fluanxol is a typical antipsychotic drug of the thioxanthene class. It was introduced in 1965 by Lundbeck. In addition to single drug preparations, it is also available as flupentixol/melitracen—a combination product containing both melitracen and flupentixol . Flupentixol is not approved for use in the United States. It is, however, approved for use in the UK, Australia, Canada, Russian Federation, South Africa, New Zealand, Philippines, Iran, Germany, and various other countries.

<span class="mw-page-title-main">Paliperidone</span> Antipsychotic medication

Paliperidone, sold under the trade name Invega among others, is an atypical antipsychotic. It is mainly used to treat schizophrenia and schizoaffective disorder.

<span class="mw-page-title-main">Fluspirilene</span> Chemical compound

Fluspirilene is a diphenylbutylpiperidine typical antipsychotic drug, used for the treatment of schizophrenia. It is administered intramuscularly. It was discovered at Janssen Pharmaceutica in 1963. A 2007 systematic review investigated the efficacy of fluspirilene decanoate for people with schizophrenia:

<span class="mw-page-title-main">Bromperidol</span> Chemical compound

Bromperidol, sold under the brand names Bromidol and Impromen among others, is a typical antipsychotic of the butyrophenone group which is used in the treatment of schizophrenia. It was discovered at Janssen Pharmaceutica in 1966. An ester prodrug, bromperidol decanoate, is a long-acting form of bromperidol used as a depot injectable.

<span class="mw-page-title-main">Zuclopenthixol</span> Chemical compound

Zuclopenthixol, also known as zuclopentixol, is a medication used to treat schizophrenia and other psychoses. It is classed, pharmacologically, as a typical antipsychotic. Chemically it is a thioxanthene. It is the cis-isomer of clopenthixol. Clopenthixol was introduced in 1961, while zuclopenthixol was introduced in 1978.

<span class="mw-page-title-main">Clopenthixol</span> Antipsychotic medication

Clopenthixol (Sordinol), also known as clopentixol, is a typical antipsychotic drug of the thioxanthene class. It was introduced by Lundbeck in 1961.

<span class="mw-page-title-main">Paliperidone palmitate</span> Chemical compound

Paliperidone palmitate (PP), sold under the brand name Invega Sustenna among others, is an atypical antipsychotic which is used in the treatment of schizophrenia and schizoaffective disorder. It is an antipsychotic ester – specifically the palmitate ester of paliperidone – and acts as a long-lasting form of paliperidone. Paliperidone palmitate is formulated as an aqueous suspension, has a strong smell similar to alcohol, and is administered by intramuscular injection into deltoid or gluteal muscle once every 1, 3, or 6 months depending on the formulation. A formulation for injection once every 6 months is also pending regulatory approval as of September 2021.

<span class="mw-page-title-main">Pipotiazine</span> Chemical compound

Pipotiazine (Piportil), also known as pipothiazine, is a typical antipsychotic of the phenothiazine class used in the United Kingdom and other countries for the treatment of schizophrenia. Its properties are similar to those of chlorpromazine. A 2004 systematic review investigated its efficacy for people with schizophrenia:

<span class="mw-page-title-main">Aripiprazole lauroxil</span> Chemical compound

Aripiprazole lauroxil, sold under the brand name Aristada, is a long-acting injectable atypical antipsychotic that was developed by Alkermes. It is an N-acyloxymethyl prodrug of aripiprazole that is administered via intramuscular injection once every four to eight weeks for the treatment of schizophrenia. Aripiprazole lauroxil was approved by the U.S. Food and Drug Administration (FDA) on 5 October 2015.

Viscoleo is a thin or low-viscosity vegetable oil. It is specifically a proprietary form of fractionated coconut oil and a medium-chain triglyceride (MCT) oil. It is prepared from the dried, solid endosperm of the fruit Cocos nucifera via hydrolysis, fractionation, and purification. Viscoleo is composed of the medium-chain fatty acids caprylic acid (C8) (55–60%), capric acid (C10) (40%), lauric acid (C12) (1–5%), and caproic acid (C6) (0.5%). It is used as an oil vehicle for several depot antipsychotics including clopentixol decanoate, flupentixol decanoate, pipotiazine palmitate, zuclopentixol acetate, and zuclopentixol decanoate. Injectable antipsychotics using Viscoleo as a carrier may be absorbed more rapidly and have shorter durations than preparations using sesame oil.

<span class="mw-page-title-main">Bromperidol decanoate</span> Chemical compound

Bromperidol decanoate, sold under the brand names Bromidol Depot, Bromodol Decanoato, and Impromen Decanoas, is an antipsychotic which has been marketed in Europe and Latin America. It is an antipsychotic ester and long-acting prodrug of bromperidol which is administered by depot intramuscular injection once every 4 weeks.

<span class="mw-page-title-main">Oxyprothepin decanoate</span> Chemical compound

Oxyprothepin decanoate, sold under the brand name Meclopin, is a typical antipsychotic which was used in the treatment of schizophrenia in the Czech Republic but is no longer marketed. It is administered by depot injection into muscle. The medication has an approximate duration of 2 to 3 weeks. The history of oxyprothepin decanoate has been reviewed.

<span class="mw-page-title-main">Depot injection</span> Long-acting medication preparation

A depot injection is a term for an injection formulation of a medication which releases slowly over time to permit less frequent administration of a medication. They are designed to increase medication adherence and consistency, especially in patients who commonly forget to take their medicine. Depot injections can be created by modifying the drug molecule itself, as in the case of prodrugs, or by modifying the way it is administered, as in the case of oil/lipid suspensions. Depot injections can have a duration of action of one month or greater and are available for many types of drugs, including antipsychotics and hormones.

<span class="mw-page-title-main">Antipsychotic ester</span> Class of prodrugs

An antipsychotic ester is an ester of an antipsychotic. They are used clinically as prodrugs to increase fat solubility and thereby prolong duration when antipsychotics are used as depot injectables.

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