Propiomazine

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); In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	Oral: 33%
Protein binding	81%
Elimination half-life	9 hours
Identifiers
	IUPAC name 1-[10-(2-dimethylaminopropyl)-10H-phenothiazin-2-yl]propan-1-one;
CAS Number	362-29-8 ;
PubChem CID	4940;
IUPHAR/BPS	7284;
DrugBank	DB00777 ;
ChemSpider	4771 ;
UNII	242Z0PM79Y;
KEGG	D02361 ;
ChEBI	CHEBI:8491 ;
ChEMBL	ChEMBL1201210 ;
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 ; Key:UVOIBTBFPOZKGP-UHFFFAOYSA-N ;
	(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]}

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-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 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]

References

^ 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.
^ ^a ^b 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.
^ "Propiomazine".
^ ^a ^b ^c ^d 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.
^ "NCI Thesaurus". ncit.nci.nih.gov. Retrieved 29 February 2020.
^ ^a ^b ^c Swiss Pharmaceutical Society (2000). Index Nominum 2000: International Drug Directory. Taylor & Francis. pp. 887–. ISBN 978-3-88763-075-1.
^ ^a ^b 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 ...

[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.

[pmid9327191-2] 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.

[DrugBank-3] "Propiomazine".

[MortonHall2012-4] 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.

[SwissPharmaceuticalSociety2000-6] Swiss Pharmaceutical Society (2000). Index Nominum 2000: International Drug Directory. Taylor & Francis. pp. 887–. ISBN 978-3-88763-075-1.

[Negwer2001-7] 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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