Levomepromazine information

Levomepromazine
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Pregnancy; category	Only if clearly needed;
Routes of; administration	Oral, seldom IM
Drug class	Typical antipsychotic
ATC code	N05AA02 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); BR: Class C1 (Other controlled substances); UK: POM (Prescription only);
Pharmacokinetic data
Bioavailability	~50–60%
Metabolism	Hepatic
Elimination half-life	~20 hours
Excretion	In feces and urine (metabolites), unchanged drug only 1%
Identifiers
	IUPAC name (2R)-3-(2-Methoxyphenothiazine-10-yl-)-N,N,2-trimethylpropanamine;
CAS Number	60-99-1 ; 7104-38-3 (maleate), ; 1236-99-3 HCl);
PubChem CID	72287;
IUPHAR/BPS	7603;
DrugBank	DB01403 ;
ChemSpider	65239 ;
UNII	9G0LAW7ATQ;
KEGG	D00403 ;
ChEBI	CHEBI:6838 ;
ChEMBL	ChEMBL1764 ;
CompTox Dashboard (EPA)	DTXSID1023289 ;
ECHA InfoCard	100.000.450
Chemical and physical data
Formula	C19H24N2OS
Molar mass	328.47 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O(c2cc1N(c3c(Sc1cc2)cccc3)C[C@H](C)CN(C)C)C;
	InChI InChI=1S/C19H24N2OS/c1-14(12-20(2)3)13-21-16-7-5-6-8-18(16)23-19-10-9-15(22-4)11-17(19)21/h5-11,14H,12-13H2,1-4H3/t14-/m1/s1 ; Key:VRQVVMDWGGWHTJ-CQSZACIVSA-N ;
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Levomepromazine, also known as methotrimeprazine, is a phenothiazine neuroleptic drug. Brand names include Nozinan, Levoprome, Detenler, Hirnamin, Levotomin and Neurocil. It is a low-potency antipsychotic (approximately half as potent as chlorpromazine) with strong analgesic, hypnotic and antiemetic properties that are primarily used in palliative care.^[2]^[3]

Serious side effects include tardive dyskinesia, akathisia, abnormalities in the electrical cycle of the heart, low blood pressure and the potentially fatal neuroleptic malignant syndrome.^[2]^[3]

As is typical of phenothiazine antipsychotics, levomepromazine is a "dirty drug", that is, it exerts its effects by blocking a variety of receptors, including adrenergic receptors, dopamine receptors, histamine receptors, muscarinic acetylcholine receptors and serotonin receptors.^[2]^[3]

^ 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 ^c Brayfield A, ed. (13 December 2013). "Levomepromazine". Martindale: The Complete Drug Reference. London, UK: Pharmaceutical Press. Retrieved 12 May 2014.
^ ^a ^b ^c Cite error: The named reference BNF was invoked but never defined (see the help page).

[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.

[MD-2] Brayfield A, ed. (13 December 2013). "Levomepromazine". Martindale: The Complete Drug Reference. London, UK: Pharmaceutical Press. Retrieved 12 May 2014.

[BNF-3] Cite error: The named reference BNF was invoked but never defined (see the help page).

Levomepromazine information

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Clinical data

AHFS/Drugs.com	Micromedex Detailed Consumer Information
Pregnancy category	Only if clearly needed
Routes of administration	Oral, seldom IM
Drug class	Typical antipsychotic
ATC code	N05AA02 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) BR: Class C1 (Other controlled substances)^[1] UK: POM (Prescription only)
Pharmacokinetic data
Bioavailability	~50–60%
Metabolism	Hepatic
Elimination half-life	~20 hours
Excretion	In feces and urine (metabolites), unchanged drug only 1%
Identifiers
IUPAC name (2R)-3-(2-Methoxyphenothiazine-10-yl-)-N,N,2-trimethylpropanamine
CAS Number	60-99-1^Y 7104-38-3 (maleate), 1236-99-3 HCl)
PubChem CID	72287
IUPHAR/BPS	7603
DrugBank	DB01403^N
ChemSpider	65239^Y
UNII	9G0LAW7ATQ
KEGG	D00403^Y
ChEBI	CHEBI:6838^N
ChEMBL	ChEMBL1764^Y
CompTox Dashboard (EPA)	DTXSID1023289
ECHA InfoCard	100.000.450
Chemical and physical data
Formula	C₁₉H₂₄N₂OS
Molar mass	328.47 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O(c2cc1N(c3c(Sc1cc2)cccc3)C[C@H](C)CN(C)C)C
InChI InChI=1S/C19H24N2OS/c1-14(12-20(2)3)13-21-16-7-5-6-8-18(16)23-19-10-9-15(22-4)11-17(19)21/h5-11,14H,12-13H2,1-4H3/t14-/m1/s1^Y Key:VRQVVMDWGGWHTJ-CQSZACIVSA-N^Y
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