Promazine

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Promazine
Promazine.svg
Promazine3d.png
Clinical data
AHFS/Drugs.com Micromedex Detailed Consumer Information
MedlinePlus a600010
Drug class Typical antipsychotic
ATC code
Pharmacokinetic data
Protein binding 94%
Elimination half-life 20-40 hr
Identifiers
  • N,N-dimethyl-3-(10H-phenothiazin-10-yl)-propan-1-amine
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.000.347 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C17H20N2S
Molar mass 284.42 g·mol−1
3D model (JSmol)
  • CN(C)CCCN1c2ccccc2Sc3c1cccc3
  • InChI=1S/C17H20N2S/c1-18(2)12-7-13-19-14-8-3-5-10-16(14)20-17-11-6-4-9-15(17)19/h3-6,8-11H,7,12-13H2,1-2H3 Yes check.svgY
  • Key:ZGUGWUXLJSTTMA-UHFFFAOYSA-N Yes check.svgY
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Promazine (brand name Sparine among others), [1] is used as a short-term add-on treatment for psychomotor agitation. [2] [3] Its approved uses in people is limited, but is used as a tranquilizer in veterinary medicine. [2] It has weak antipsychotic effects but is generally not used to treat psychoses. [2]

Contents

It acts similar to chlorpromazine and causes sedation. [2] It has predominantly anticholinergic side effects, though extrapyramidal side effects are not uncommon. It belongs to the typical antipsychotic and phenothiazine class of drugs. [4]

Promazine was approved for medical use in the United States in the 1950s, although it is no longer commercially available there. [1] [5]

Uses

Promazine is a short-term add-on treatment for psychomotor agitation. [3]

Adverse effects

Common side effects include agitation, absent menstruation, arrhythmias, constipation, drowsiness and dizziness, dry mouth, problems with erection, tiredness, milky nipple discharge, large breasts, high sugars, difficulty sleeping, low blood pressure, prolonged QT, fits, shaking, vomiting and weight gain, among others. [3]

Overdose

In overdose, it may cause blood pressure to drop, lowering of body temperature, increased heart rate, and an irregular heart beat. [3]

Sudden death may occur, although rare. [3]

Other animals

Promazine, given as promazine hydrochloride, is one of the primary tranquilizers used by veterinarians as a pre-anaesthesia injection in horses. [6] [7] It does not provide analgesia and is not a very strong sedative, hence it is used combined with opioids or α2 adrenoreceptor agonists, such as clonidine, or both. [7] [8] It can be used alone when performing a non-painful procedure such as the fitting a horseshoe. [8] Low blood pressure, fast heart rate and paralysis of the penis are side effects. [6] It is also an antiemetic, antispasmodic and hypothermic agent. [7] Additionally it is used to lower blood pressure in animals with laminitis and kidney failure. [7] It is available in the US for veterinary use under the names Promazine and Tranquazine.[ citation needed ]

Synthesis

Synthesis: Patents: ~75%: Promazine synthesis.svg
Synthesis: Patents: ~75%:

Related Research Articles

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

Antipsychotics, also known as neuroleptics, are a class of psychotropic medication primarily used to manage psychosis, principally in schizophrenia but also in a range of other psychotic disorders. They are also the mainstay together with mood stabilizers in the treatment of bipolar disorder.

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

Trifluoperazine, marketed under the brand name Stelazine among others, is a typical antipsychotic primarily used to treat schizophrenia. It may also be used short term in those with generalized anxiety disorder but is less preferred to benzodiazepines. It is of the phenothiazine chemical class.

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

Chlorpromazine (CPZ), marketed under the brand names Thorazine and Largactil among others, is an antipsychotic medication. It is primarily used to treat psychotic disorders such as schizophrenia. Other uses include the treatment of bipolar disorder, severe behavioral problems in children including those with attention deficit hyperactivity disorder, nausea and vomiting, anxiety before surgery, and hiccups that do not improve following other measures. It can be given orally, by intramuscular injection, or intravenously.

<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">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">Quetiapine</span> Atypical antipsychotic medication

Quetiapine, sold under the brand name Seroquel among others, is an atypical antipsychotic medication used for the treatment of schizophrenia, bipolar disorder, borderline personality disorder, and major depressive disorder. Despite being widely used as a sleep aid due to its sedating effect, the benefits of such use do not appear to generally outweigh the side effects. It is taken orally.

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

Ziprasidone, sold under the brand name Geodon among others, is an atypical antipsychotic used to treat schizophrenia and bipolar disorder. It may be used by mouth and by injection into a muscle (IM). The IM form may be used for acute agitation in people with schizophrenia.

<span class="mw-page-title-main">Maprotiline</span> Antidepressant

Maprotiline, sold under the brand name Ludiomil among others, is a tetracyclic antidepressant (TeCA) that is used in the treatment of depression. It may alternatively be classified as a tricyclic antidepressant (TCA), specifically a secondary amine. In terms of its chemistry and pharmacology, maprotiline is closely related to other secondary amine TCAs like nortriptyline and protriptyline, and has similar effects to them.

<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">Amoxapine</span> Chemical compound

Amoxapine, sold under the brand name Asendin among others, is a tricyclic antidepressant (TCA). It is the N-demethylated metabolite of loxapine. Amoxapine first received marketing approval in the United States in 1992, approximately 30 to 40 years after most of the other TCAs were introduced in the United States.

<span class="mw-page-title-main">Promethazine</span> Pharmaceutical drug

Promethazine, sold under the brand name Phenergan among others, is a first-generation antihistamine, antipsychotic, sedative, and antiemetic used to treat allergies, insomnia, and nausea. It may also help with some symptoms associated with the common cold and may also be used for sedating people who are agitated or anxious, an effect that has led to some recreational use. Promethazine is taken by mouth (Oral), as a rectal suppository, or by injection into a muscle (IM).

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

Acepromazine, acetopromazine, or acetylpromazine is a phenothiazine derivative antipsychotic drug. It was used in humans during the 1950s as an antipsychotic, but is now almost exclusively used on animals as a sedative and antiemetic. Its closely related analogue, chlorpromazine, is still used as an antipsychotic in humans. Acepromazine is used primarily as a chemical restraint in hyperactive or fractious animals.

<span class="mw-page-title-main">Reserpine</span> Drug used to treat high blood pressure

Reserpine is a drug that is used for the treatment of high blood pressure, usually in combination with a thiazide diuretic or vasodilator. Large clinical trials have shown that combined treatment with reserpine plus a thiazide diuretic reduces mortality of people with hypertension. Although the use of reserpine as a solo drug has declined since it was first approved by the FDA in 1955, the combined use of reserpine and a thiazide diuretic or vasodilator is still recommended in patients who do not achieve adequate lowering of blood pressure with first-line drug treatment alone. The reserpine-hydrochlorothiazide combo pill was the 17th most commonly prescribed of the 43 combination antihypertensive pills available In 2012.

<span class="mw-page-title-main">Prochlorperazine</span> Medication for nausea, psychosis, and anxiety

Prochlorperazine, formerly sold under the brand name Compazine among others, is a medication used to treat nausea, migraines, schizophrenia, psychosis and anxiety. It is a less preferred medication for anxiety. It may be taken by mouth, rectally, injection into a vein, or injection into a muscle.

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

Levomepromazine, also known as methotrimeprazine, is a phenothiazine neuroleptic drug. Brand names include Nozinan, Levoprome, Detenler, Hirnamin, Levotomin and Neurocil. It is a low-potency antipsychotic with strong analgesic, hypnotic and antiemetic properties that are primarily used in palliative care.

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

Tiotixene, or thiothixene, sold under the brand name Navane among others, is a typical antipsychotic of the thioxanthene class which is related to chlorprothixene and is used in the treatment of psychoses like schizophrenia and bipolar mania. It was introduced in the United States in 1967 by Pfizer.

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

Chlorprothixene, sold under the brand name Truxal among others, is a typical antipsychotic of the thioxanthene group.

<span class="mw-page-title-main">Tricyclic</span> Organic compound having 3 fused rings

Tricyclics are cyclic chemical compounds that contain three fused rings of atoms.

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

Alfaxalone, also known as alphaxalone or alphaxolone and sold under the brand name Alfaxan, is a neuroactive steroid and general anesthetic which is used currently in veterinary practice as an induction agent for anesthesia and as an injectable anesthetic. Though it is more expensive than other induction agents, it often preferred due to the lack of depressive effects on the cardiovascular system. The most common side effect seen in current veterinary practice is respiratory depression when Alfaxan is administered concurrently with other sedative and anesthetic drugs; when premedications aren't given, veterinary patients also become agitated and hypersensitive when waking up.

<span class="mw-page-title-main">Maropitant</span> Veterinary medication

Maropitant (INN; trade name: Cereniasə-REE-nee-ə), used as maropitant citrate (USAN), is a neurokinin-1 (NK1) receptor antagonist developed by Zoetis specifically for the treatment of motion sickness and vomiting in dogs. It was approved by the FDA in 2007 for use in dogs and in 2012 for cats.

References

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  3. 1 2 3 4 5 "BNF". NICE. Retrieved 4 August 2021.
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  5. "Drugs@FDA: FDA-Approved Drugs". New Drug Application (NDA): 010942 Sparine. U.S. Food and Drug Administration.
  6. 1 2 Hendrickson DA (2007). "2. Anaesthesia and fluid therapy". Techniques in Large Animal Surgery (3rd ed.). Blackwell Publishing. p. 16. ISBN   978-0-7817-8255-5.
  7. 1 2 3 4 "Promazine". Equimed - Horse Health Matters. 20 January 2014. Archived from the original on 4 August 2021. Retrieved 4 August 2021.
  8. 1 2 Ringer SK, Mama KR (2019). "23. Chemical restraint for standing procedures". In Auer JA, Stick JA (eds.). Equine Surgery (5th ed.). St Louis, Missouri: Elsevier. pp. 351–352. ISBN   978-0-323-48420-6.
  9. Wirth W (August 1958). "[The pharmacological action of promazine]". Arzneimittel-Forschung. 8 (8): 507–511. PMID   13584240.
  10. Szabo WA, Chung RH, Tam CC, Tishler M (February 1980). "Synthetic applications and mechanism of the pyrolysis of phenothiazine carbamates". The Journal of Organic Chemistry. 45 (4): 744–746. doi:10.1021/jo01292a048.
  11. Schmolka SJ, Zimmer H (1984). "N -Dimethylaminopropylation in a Solid-Liquid Two Phase System: Synthesis of Chlorpromazine, its Analogs, and Related Compounds". Synthesis. 1984 (1): 29–31. doi:10.1055/s-1984-30719.
  12. US 2519886,Charpentier P,issued 1950, assigned to Rhône-Poulenc.
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  14. Dahl T, Tornøe CW, Bang-Andersen B, Nielsen P, Jørgensen M (15 February 2008). "Palladium-Catalyzed Three-Component Approach to Promazine with Formation of One Carbon–Sulfur and Two Carbon–Nitrogen Bonds". Angewandte Chemie International Edition. 47 (9): 1726–1728. doi:10.1002/anie.200705209.