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Propiomazine

Clinical data
Trade names	Propavan, others
Other names	Propionylpromethazine; CB-1678; Wy-1359; NSC-169450
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Routes of administration	Oral,IM,IV
ATC code	N05CM06 (WHO)
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]
Eliminationhalf-life	9 hours[2]
Identifiers
IUPAC name 1-[10-(2-dimethylaminopropyl)-10H-phenothiazin-2-yl]propan-1-one
CAS Number	362-29-8 Y
PubChemCID	4940
IUPHAR/BPS	7284
DrugBank	DB00777 Y
ChemSpider	4771 Y
UNII	242Z0PM79Y
KEGG	D02361 Y
ChEBI	CHEBI:8491 Y
ChEMBL	ChEMBL1201210 Y
CompTox Dashboard(EPA)	DTXSID1023520
ECHA InfoCard	100.006.043
Chemical and physical data
Formula	C20H24N2OS
Molar mass	340.49 g·mol−1
3D model (JSmol)	Interactive image
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
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Propiomazine, sold under the brand namePropavan among others, is anantihistamine which is used to treatinsomnia and to producesedation and relieveanxiety before or duringsurgery or other procedures and in combination withanalgesics as well as duringlabor.^{[4][additional citation(s) needed]} Propiomazine is aphenothiazine,^[4] but is not used therapeutically as aneuroleptic because it does not blockdopamine receptors well.^{[citation needed]}

Propiomazine has been used in the treatment ofinsomnia.

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]}

Propiomazine is anantagonist of thedopamineD₁,D₂, andD₄ receptors, theserotonin5-HT_2A and5-HT_2C receptors, themuscarinic acetylcholine receptorsM₁,M₂,M₃,M₄, andM₅ receptors,α₁-adrenergic receptor, andhistamineH₁ receptor.^{[citation needed]}

Theantipsychotic effect of propiomazine is thought to be due to antagonism of the dopamine D₂ receptor and serotonin 5-HT_2A receptor,^[5] with greater activity at the 5-HT_2A receptor than at the D₂ receptor. This may explain the lack ofextrapyramidal effects with propiomazine. Propiomazine does not appear to block dopamine within thetuberoinfundibular pathway, which may explain its lower incidence ofhyperprolactinemia than withtypical antipsychotics orrisperidone.^{[additional citation(s) needed]}

Propiomazine, also known as 10-(2-dimethylaminopropyl)-2-propionylphenothiazine or as propionylpromethazine, is aphenothiazinederivative^[4] and isstructurally related topromethazine. The compound is provided medically as thehydrochloride andmaleatesalts.^[6][4][7]

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

In 2000, propiomazine continued to be marketed only inSweden.^[6]

• H1 receptor antagonists
• Hypnotics
• Ketones
• M1 receptor antagonists
• M2 receptor antagonists
• M3 receptor antagonists
• M4 receptor antagonists
• M5 receptor antagonists
• Phenothiazines
• Sedatives

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