Contents

Propiomazine

Chemical compound

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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]
Elimination half-life	9 hours[2]
Identifiers
IUPAC name 1-[10-(2-dimethylaminopropyl)-10H-phenothiazin-2-yl]propan-1-one
CAS Number	362-29-8 Y
PubChem CID	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 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]}

Medical uses[edit]

Propiomazine has been used in the treatment of insomnia.

Side effects[edit]

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[edit]

Pharmacodynamics[edit]

Propiomazine is an antagonist of the dopamine D₁, D₂, and D₄ receptors, the serotonin 5-HT_2A and 5-HT_2C 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-HT_2A receptor,^[5] with greater activity at the 5-HT_2A 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 antipsychoticsorrisperidone.^{[additional citation(s) needed]}

Chemistry[edit]

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

Society and culture[edit]

Brand names[edit]

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

Availability[edit]

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

References[edit]