Propiomazine

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Propiomazine
Propiomazine.svg
Clinical data
Trade names Propavan, others
Other namesPropionylpromethazine; CB-1678; Wy-1359; NSC-169450
AHFS/Drugs.com Micromedex Detailed Consumer Information
Routes of
administration
Oral, IM, IV
ATC code
Legal status
Legal status
  • BR: Class C1 (Other controlled substances) [1]
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability Oral: 33% [2]
Protein binding 81% [3]
Elimination half-life 9 hours [2]
Identifiers
  • 1-[10-(2-dimethylaminopropyl)-10H-phenothiazin-2-yl]propan-1-one
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.006.043 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C20H24N2OS
Molar mass 340.49 g·mol−1
3D model (JSmol)
  • O=C(c2cc1N(c3c(Sc1cc2)cccc3)CC(N(C)C)C)CC
  • InChI=1S/C20H24N2OS/c1-5-18(23)15-10-11-20-17(12-15)22(13-14(2)21(3)4)16-8-6-7-9-19(16)24-20/h6-12,14H,5,13H2,1-4H3 Yes check.svgY
  • Key:UVOIBTBFPOZKGP-UHFFFAOYSA-N Yes check.svgY
   (verify)

Propiomazine, sold under the brand name Propavan among others, is an antihistamine which is used to treat insomnia and to produce sedation and relieve anxiety before or during surgery or other procedures and in combination with analgesics as well as during labor. [4] [ additional citation(s) needed ] Propiomazine is a phenothiazine, [4] but is not used therapeutically as a neuroleptic because it does not block dopamine receptors well.[ citation needed ]

Contents

Medical uses

Propiomazine has been used in the treatment of insomnia.

Side effects

Drowsiness is a usual side effect. Rare, serious side effects include convulsions (seizures); difficult or unusually fast breathing; fast or irregular heartbeat or pulse; fever (high); high or low blood pressure; loss of bladder control; muscle stiffness (severe); unusual increase in sweating; unusually pale skin; and unusual tiredness or weakness.[ citation needed ]

Pharmacology

Pharmacodynamics

Propiomazine is an antagonist of the dopamine D1, D2, and D4 receptors, the serotonin 5-HT2A and 5-HT2C receptors, the muscarinic acetylcholine receptors M1, M2, M3, M4, and M5 receptors, α1-adrenergic receptor, and histamine H1 receptor.[ citation needed ]

The antipsychotic effect of propiomazine is thought to be due to antagonism of the dopamine D2 receptor and serotonin 5-HT2A receptor, [5] with greater activity at the 5-HT2A receptor than at the D2 receptor. This may explain the lack of extrapyramidal effects with propiomazine. Propiomazine does not appear to block dopamine within the tuberoinfundibular pathway, which may explain its lower incidence of hyperprolactinemia than with typical antipsychotics or risperidone.[ additional citation(s) needed ]

Chemistry

Propiomazine, also known as 10-(2-dimethylaminopropyl)-2-propionylphenothiazine or as propionylpromethazine, is a phenothiazine derivative [4] and is structurally related to promethazine. The compound is provided medically as the hydrochloride and maleate salts. [6] [4] [7]

Society and culture

Brand names

Propiomazine has been sold under the brand names Dorevan, Dorévane, Indorm, Largon, Phenoctyl, Propavan, Propial, and Serentin. [7] [6]

Availability

In 2000, propiomazine continued to be marketed only in Sweden. [6]

Related Research Articles

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<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">Atypical antipsychotic</span> Class of pharmaceutical drugs

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

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<span class="mw-page-title-main">Aripiprazole</span> Atypical antipsychotic

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

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

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

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

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

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<span class="mw-page-title-main">Pipamperone</span> Antipsychotic drug

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

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

Pimavanserin, sold under the brand name Nuplazid, is an atypical antipsychotic which is approved for the treatment of Parkinson's disease psychosis and is also being studied for the treatment of Alzheimer’s disease psychosis, schizophrenia, agitation, and major depressive disorder. Unlike other antipsychotics, pimavanserin is not a dopamine receptor antagonist.

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

Clocapramine, also known as 3-chlorocarpipramine, is an atypical antipsychotic of the iminostilbene class which was introduced in Japan in 1974 by Yoshitomi for the treatment of schizophrenia. In addition to psychosis, clocapramine has also been used to augment antidepressants in the treatment of anxiety and panic.

<span class="mw-page-title-main">Cariprazine</span> Atypical antipsychotic medicine

Cariprazine, sold under the brand names Vraylar and Reagila among others, is an atypical antipsychotic originated by Gedeon Richter, which is used in the treatment of schizophrenia, bipolar mania, bipolar depression, and major depressive disorder. It acts primarily as a D3 and D2 receptor partial agonist, with a preference for the D3 receptor. Cariprazine is also a partial agonist at the serotonin 5-HT1A receptor and acts as an antagonist at 5-HT2B and 5-HT2A receptors, with high selectivity for the D3 receptor. It is taken by mouth.

<span class="mw-page-title-main">Brexpiprazole</span> Atypical antipsychotic

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

Perlapine, sold under the brand names Hypnodine and Pipnodine, is a hypnotic and sedative of the tricyclic group which is marketed in Japan. It acts primarily as a potent antihistamine, and also has anticholinergic, antiserotonergic, antiadrenergic, and some antidopaminergic activity. The drug has relatively weak affinity for the dopamine D2 receptor (IC50Tooltip Half-maximal inhibitory concentration = 1,803 nM) and, in accordance, is said to be ineffective as an antipsychotic. However, it retains higher affinity for the dopamine D1 receptor (IC50 = 198 nM). Its IC50 values are 19 nM for the α1-adrenergic receptor, 4,945 nM for the α2-adrenergic receptor, and 70 nM for the serotonin 5-HT2A receptor. Perlapine is closely related to clotiapine, clozapine, fluperlapine, loxapine, and tilozepine.

References

  1. Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  2. 1 2 Dehlin O, Bengtsson C, Rubin B (1997). "A comparison of zopiclone and propiomazine as hypnotics in outpatients: a multicentre, double-blind, randomized, parallel-group comparison of zopiclone and propiomazine in insomniacs". Curr Med Res Opin. 13 (10): 565–72. doi:10.1185/03007999709113330. PMID   9327191.
  3. "Propiomazine".
  4. 1 2 3 4 Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 234–. ISBN   9789401144391. OCLC   1243535030.
  5. "NCI Thesaurus". ncit.nci.nih.gov. Retrieved 29 February 2020.
  6. 1 2 3 Swiss Pharmaceutical Society (2000). Index Nominum 2000: International Drug Directory. Taylor & Francis. pp. 887–. ISBN   978-3-88763-075-1.
  7. 1 2 Negwer M (2001). Organic-chemical Drugs and Their Synonyms: An International Survey, Volume 3 (8 ed.). Wiley-VCH. p. 1946. ISBN   978-3-527-30247-5. OCLC   50441207. Propiomazine**, Propionylpromethazine ... 9600-02 (7787-02) R Maleate (1:1) S 1678 C.B., Dorevan, Dorévane, Indorm, Phenoctyl, Propavan, Propial, Serentin, Wy-1359 U Sedative (pre-anesthetic), hypnotic ...