Levomepromazine: Difference between revisions

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Levomepromazine
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Pregnancy; category	Only if clearly needed;
Routes of; administration	Oral, seldom intramuscular
ATC code	N05AA02 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only) ; UK: POM (Prescription only) ;
Pharmacokinetic data
Bioavailability	approx. 50 to 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;
DrugBank	DB01403 ;
ChemSpider	65239 ;
UNII	9G0LAW7ATQ;
KEGG	D00403 ;
ChEBI	CHEBI:6838 ;
ChEMBL	ChEMBL1764 ;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C19H24N2OS
Molar mass	328.47 g/mol
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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VisualWikitext

Latest revision as of 18:13, 8 April 2015

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Levomepromazine (INN, BAN, USAN), also known as methotrimeprazine (common use in America; sold as Nosinan, Nozinan, Levoprome) is an phenothiazine neuroleptic drug. It is a low-potency antipsychotic (approximately half as potent as chlorpromazine) with strong analgesic, hypnotic and antiemetic properties that is primarily used in palliative care.^[1]^[2]

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.^[1]^[2]

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.^[1]^[2]

Medical uses

Levomepromazine is used for the treatment of psychosis, particular those of schizophrenia, and manic phases of bipolar disorder. It should be used only with caution in the treatment of agitated depressions, as it can cause akathisia as a side effect, which could worsen the agitation.^[1]^[2]

Levomepromazine is also used at lower doses for the treatment of nausea and insomnia.^[1]

Levomepromazine is frequently prescribed and valued worldwide in palliative care medicine for its multimodal action, to treat intractable nausea or vomiting, and for severe delirium/ agitation in the last days of life. Palliative care physicians will commonly prescribe it orally or via subcutaneous syringe drivers in combination with more potent opiate analgesics such as Hydromorphone.^[1]^[2]

Adverse effects

The most common side effect is akathisia.^[2] Levomepromazine has prominent sedative and anticholinergic/sympatholytic effects (dry mouth, hypotension, sinus tachycardia, night sweats) and may cause weight gain.^[2] These side effects normally preclude prescribing the drug in doses needed for full remission of schizophrenia, so it has to be combined with a more potent antipsychotic.^[2] In any case, blood pressure and EKG should be monitored regularly.^[2]

A rare but life-threatening side effect is neuroleptic malignant syndrome (NMS).^[2] The symptoms of NMS include muscle stiffness, convulsions and fever.^[2]

References

↑ ^1.0 ^1.1 ^1.2 ^1.3 ^1.4 ^1.5 Brayfield, A, ed. (13 December 2013). "Levomepromazine". Martindale: The Complete Drug Reference. London, UK: Pharmaceutical Press. Retrieved 12 May 2014.
↑ ^2.00 ^2.01 ^2.02 ^2.03 ^2.04 ^2.05 ^2.06 ^2.07 ^2.08 ^2.09 ^2.10 Template:Cite isbn

PubChem Substance Summary: Levomepromazine National Center for Biotechnology Information.
NOZINAN - Lévomépromazine Doctissimo Guides des Medicaments
[2]Grampians Palliative Care Team Publication May 2010 (Victoria, Australia)
[3] Palliative Care Guidelines, Scotland, UK

[MD-1] 1.0 ^1.1 ^1.2 ^1.3 ^1.4 ^1.5 Brayfield, A, ed. (13 December 2013). "Levomepromazine". Martindale: The Complete Drug Reference. London, UK: Pharmaceutical Press. Retrieved 12 May 2014.

[BNF-2] 2.00 ^2.01 ^2.02 ^2.03 ^2.04 ^2.05 ^2.06 ^2.07 ^2.08 ^2.09 ^2.10 Template:Cite isbn

[1]

[2]

@@ Line 4: / Line 4: @@
 | verifiedrevid = 408577545
 | IUPAC_name = (2''R'')-3-(2-Methoxyphenothiazine-10-yl-)-''N'',''N'',2-trimethylpropanamine
-| image = Levomepromazine2DCSD.svg
+| image = Levomepromazine2DCSD.png
 | width = 250
 | image2 = Levomepromazine3DanJ.gif

v t e Antipsychotics (neuroleptics) (N05A)
Typical	Benzamides: Levosulpiride • Nemonapride • Sulpiride • Sultopride • Tiapride • Veralipride; Butyrophenones: Azaperone • Benperidol • Bromperidol • Droperidol • Fluanisone • Haloperidol • Lenperone • Moperone • Pipamperone • Spiperone • Timiperone • Trifluperidol; Diphenylbutylpiperidines: Clopimozide • Fluspirilene • Penfluridol • Pimozide; Phenothiazines: Acepromazine • Acetophenazine • Butaperazine • Carphenazine • Chloracizine • Chlorproethazine • Chlorpromazine • Cyamemazine • Dixyrazine • Fluacizine • Fluphenazine • Levomepromazine/Methotrimeprazine • Mesoridazine • Perazine • Periciazine • Perphenazine • Piperacetazine • Pipotiazine • Prochlorperazine • Promazine • Promethazine • Propiomazine • Sulforidazine • Thiethylperazine • Thiopropazate • Thioproperazine • Thioridazine • Trifluoperazine • Triflupromazine; Thioxanthenes: Chlorprothixene • Clopenthixol • Flupentixol • Thiothixene • Zuclopenthixol; Tricyclics: Amoxapine • Butaclamol • Fluotracen • Loxapine • Metitepine/Methiothepin • Octoclothiepin • Trimipramine; Others: Prothipendyl
Atypical	Benzamides: Amisulpride • Remoxipride; Butyrophenones: Cinuperone • Setoperone; Benzo(iso)oxazole piperidines: Iloperidone • Ocaperidone • Paliperidone • Risperidone; Benzo(iso)thiazole piperazines: Lurasidone • Perospirone • Revospirone • Tiospirone • Ziprasidone; Diphenylbutylpiperazines: Amperozide; Phenylpiperazines: Aripiprazole • Bifeprunox • Elopiprazole • Umespirone; Tricyclics: Asenapine • Carpipramine • Clocapramine • Clotiapine • Clozapine • Fluperlapine • Gevotroline • Metitepine/Methiothepin • Mosapramine • NDMC • Olanzapine • Piquindone • Quetiapine • Tenilapine • Zotepine; Others: Blonanserin • Cariprazine • Molindone • Pimavanserin • Roxindole • Sarizotan • Sertindole • Spiramide
Others	Azacyclonol • Cannabidiol • D-Cycloserine • Lithium • Mifepristone • Oxypertine • Reserpine • Rimcazole • Secretin • Talnetant • Tetrabenazine • Vabicaserin
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III Template:Psychology navs

Clinical data


AHFS/Drugs.com	Micromedex Detailed Consumer Information
Pregnancy category	Only if clearly needed
Routes of administration	Oral, seldom intramuscular
ATC code	N05AA02 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) UK: POM (Prescription only)
Pharmacokinetic data
Bioavailability	approx. 50 to 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
DrugBank	DB01403^N
ChemSpider	65239^Y
UNII	9G0LAW7ATQ
KEGG	D00403^Y
ChEBI	CHEBI:6838^N
ChEMBL	ChEMBL1764^Y
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C₁₉H₂₄N₂OS
Molar mass	328.47 g/mol
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
^NY (what is this?) (verify)