Propiomazine

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.[1] Propiomazine is a phenothiazine,[1] but is not used therapeutically as a neuroleptic because it does not block dopamine receptors well.

Propiomazine
Clinical data
Trade namesPropavan, others
Other namesPropionylpromethazine; CB-1678; Wy-1359; NSC-169450
AHFS/Drugs.comMicromedex Detailed Consumer Information
Routes of
administration		IM, IV
ATC code
Identifiers
IUPAC name
  • 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 InfoCard100.006.043
Chemical and physical data
FormulaC20H24N2OS
Molar mass340.49 g·mol−1
3D model (JSmol)
SMILES
  • O=C(c2cc1N(c3c(Sc1cc2)cccc3)CC(N(C)C)C)CC
InChI
  • 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 Y
  • Key:UVOIBTBFPOZKGP-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

Medical uses

Propiomazine has been used in the treatment of insomnia, though little evidence exists to inform its use for this indication.[2]

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.

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.

The antipsychotic effect of propiomazine is thought to be due to antagonism of the dopamine D2 receptor and serotonin 5-HT2A receptor,[3] 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.

Chemistry

Propiomazine, also known as 10-(2-dimethylaminopropyl)-2-propionylphenothiazine or as propionylpromethazine, is a phenothiazine derivative[1] and is structurally related to promethazine. The compound is provided medically as the hydrochloride and maleate salts.[4][1][5]

Society and culture

Brand names

Propiomazine has been sold under the brand names Dorevan, Dorévane, Indorm, Largon, Phenoctyl, Propavan, Propial, and Serentin.[5][4]

Availability

In 2000, propiomazine continued to be marketed only in Sweden.[4]

References
  1. 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.
  2. De Crescenzo F, Foti F, Ciabattini M, Del Giovane C, Watanabe N, Schepisi MS, Quested DJ, Cipriani A, Barbui C, Amato, Efthimiou O, Cipriani A (July 2022). "Comparative effects of pharmacological interventions for the acute and long-term management of insomnia disorder in adults: a systematic review and network meta-analysis". The Lancet. 400 (10347): 170–184. doi:10.1016/S0140-6736(22)00878-9. ISSN 0140-6736. PMC 6457748.
  3. "NCI Thesaurus". ncit.nci.nih.gov. Retrieved 29 February 2020.
  4. Swiss Pharmaceutical Society (2000). Index Nominum 2000: International Drug Directory. Taylor & Francis. pp. 887–. ISBN 978-3-88763-075-1.
  5. 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 ...
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