U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C19H24N2OS.C4H4O4
Molecular Weight 444.544
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of LEVOMEPROMAZINE MALEATE

SMILES

OC(=O)\C=C/C(O)=O.COC1=CC=C2SC3=CC=CC=C3N(C[C@H](C)CN(C)C)C2=C1

InChI

InChIKey=IFLZPECPTYCEBR-VIEYUMQNSA-N
InChI=1S/C19H24N2OS.C4H4O4/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;5-3(6)1-2-4(7)8/h5-11,14H,12-13H2,1-4H3;1-2H,(H,5,6)(H,7,8)/b;2-1-/t14-;/m1./s1

HIDE SMILES / InChI

Molecular Formula C19H24N2OS
Molecular Weight 328.472
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

Levomepromazine (also known as methotrimeprazine) is a phenothiazine neuroleptic drug. It is sold in many countries under the generic name (levomepromazine) or under brand names such as Nozinan, Detenler and many more. Levomepromazine is an antipsychotic drug is commonly used as an antiemetic to alleviate nausea and vomiting in palliative care settings particularly in terminal illness. Levomepromazine is a phenothiazine with pharmacological activity similar to that of both chlorpromazine and promethazine. It has the histamine-antagonist properties of the antihistamines together with central nervous system effects resembling those of chlorpromazine. Levomepromazine's antipsychotic effect is largely due to its antagonism of dopamine receptors in the brain. In addition, it can block 5HT2 receptors and some others, like histamine, serotonin.

CNS Activity

Approval Year

PubMed

PubMed

TitleDatePubMed
[Reversible cardiomyopathy induced by psychotropic drugs: case report and literature overview].
2002 Dec
[Continuous subcutaneous infusion in palliative care, an undervalued method].
2002 Nov 23
Effect of some psychotropic drugs on luminol-dependent chemiluminescence induced by O2-, *OH, HOCl.
2002 Nov-Dec
[Neutropenia in a patient treated with clozapine in combination with other psychotropic drugs].
2002 Nov-Dec
In vitro chloroquine resistance modulation study on fresh isolates of Brazilian Plasmodium falciparum: intrinsic antimalarial activity of phenothiazine drugs.
2002 Oct
Neuroleptic malignant syndrome complicated by massive intestinal bleeding in a patient with chronic renal failure.
2002 Oct
Delayed-onset nocturnal akathisia due to risperidone and levomepromazine: a case report.
2002 Sep
Olanzapine for intractable nausea in palliative care patients.
2003 Apr
[Prolonged hyperthermia after isocarboxazid poisoning].
2003 Apr 28
Effect of phenothiazines on protein kinase C- and calcium-dependent activation of peritoneal macrophages.
2003 Feb
In vitro human plasma leucine(5)-enkephalin degradation is inhibited by a select number of drugs with the phenothiazine molecule in their chemical structure.
2003 Jan
Determination of risperidone and 9-hydroxyrisperidone in human plasma by liquid chromatography: application to the evaluation of CYP2D6 drug interactions.
2003 Jan 5
Simultaneous determination of levomepromazine, midazolam and their major metabolites in human plasma by reversed-phase liquid chromatography.
2003 Jul 5
Fatal acute topiramate toxicity.
2003 Jul-Aug
[Antipsychotic medication as a cause of deep hypothermia].
2003 Jun 21
Photochemistry and in vitro phototoxicity studies of levomepromazine (methotrimeprazine), a phototoxic neuroleptic drug.
2003 May
Interaction of alcohol and drugs in fatal poisonings.
2003 May
A CYP2D6 phenotype-genotype mismatch in Japanese psychiatric patients.
2003 Sep
Focus on levomepromazine.
2004 Dec
[Effect of a levopromazine-thymalin combination on the development of toxic edema and swelling in the brain].
2004 Jan-Feb
A case of transient myopia in a patient with multiple myeloma secondary to levomepromazine.
2005 Apr
Neuroleptic malignant syndrome associated with risperidone in a male with early-onset schizophrenia.
2005 Dec
Determination of several psychiatric drugs in whole blood using capillary gas-liquid chromatography with nitrogen phosphorus detection: comparison of two solid phase extraction procedures.
2005 Dec 20
[Palliative sedation].
2005 Feb 26
[Levomepromazine-induced peripheral edema].
2005 Jan
Low-dose levomepromazine in refractory emesis in advanced cancer patients: an open-label study.
2005 Jan
Inhibition of rat liver CYP2D in vitro and after 1-day and long-term exposure to neuroleptics in vivo-possible involvement of different mechanisms.
2005 Jan
[The algimetry evaluation by thermic and pressoric nociceptive stimulus in dogs pre treated with methotrimeprazine, midazolam and ketamine with or without butorphanol or buprenorphine].
2005 Jan-Feb
[Methadone and sleep apnea syndrome].
2005 Mar
Little effects of low dosage of levomepromazine on plasma risperidone levels.
2005 Mar
Validity of Simpson-Angus Scale (SAS) in a naturalistic schizophrenia population.
2005 Mar 17
False-positive results in the detection of methadone in urines of patients treated with psychotropic substances.
2005 Nov
The use of levomepromazine in Hyperemesis Gravidarum resistant to drug therapy--a case series.
2005 Nov-Dec
Enantioseparation of phenothiazines in cyclodextrin-modified capillary zone electrophoresis using sulfated cyclodextrins as chiral selectors.
2005 Oct
Determination of oxcarbazepine and its metabolites in postmortem blood and hair by means of liquid chromatography with mass detection (HPLC/APCI/MS).
2005 Oct 15
An open study of methotrimeprazine in the management of nausea and vomiting in patients with advanced cancer.
2005 Sep
Region specific distribution of levomepromazine in the human brain.
2006 Mar
Optimization of the separation of some psychotropic drugs and their respective metabolites by liquid chromatography.
2006 May 3
Systematic review of antipsychotics for the treatment of hospital-associated delirium in medically or surgically ill patients.
2006 Nov
Simple and simultaneous determination for 12 phenothiazines in human serum by reversed-phase high-performance liquid chromatography.
2007 Jul 1
Continuous infusion in adult females dogs submitted to ovariohysterectomy with midazolam-xylazine and/or medetomidine pre-treated with methotrimeprazine and buprenorphine.
2007 Jul-Aug
Hypothermia following antipsychotic drug use.
2007 Jun
Simultaneous prescribing of atypical antipsychotics, conventional antipsychotics and anticholinergics-a European study.
2007 Jun
A fatal case of amoxapine poisoning under the influence of chronic use of psychotropic drugs.
2007 Mar
Possible levomepromazine-clozapine interaction: two case reports.
2007 Mar 30
Association between 5-HT2A, TPH1 and GNB3 genotypes and response to typical neuroleptics: a serotonergic approach.
2007 May 23
Enantioseparation of phenothiazines in CD-modified CZE using single isomer sulfated CD as a chiral selector.
2007 Nov
Quetiapine and drug interactions: evidence from a routine therapeutic drug monitoring service.
2007 Oct
[Recurrent dysregulation of body temperature during antipsychotic pharmacotherapy].
2008 Mar
Role of selenium in heart lesions produced by neuroleptics in the rabbit.
2008 Mar
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Levomepromazine Injection may be administered by intramuscular injection or intravenous injection after dilution with an equal volume of normal saline. The usual dose for adults and the elderly is 12.5 mg to 25 mg (0.5 ml to 1 ml) by intramuscular injection, or by the intravenous route after dilution with an equal volume of normal saline immediately before use. In cases of severe agitation, up to 50 mg (2ml) may be used, repeated every 6 to 8 hours. Continuous subcutaneous infusion: Levomepromazine Injection may be administered over a 24 hour period via a syringe driver. The required dose of Levomepromazine Injection (25 mg to 200 mg per day) should be diluted with the calculated volume of normal saline. Levomepromazine tablets 25 mg may be substituted for the injection if oral therapy is more convenient.
Route of Administration: Intramuscular; intravenous; subcutaneous; oral
Substance Class Chemical
Created
by admin
on Tue Oct 22 00:44:09 UTC 2019
Edited
by admin
on Tue Oct 22 00:44:09 UTC 2019
Record UNII
5KN5Y9V01K
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LEVOMEPROMAZINE MALEATE
EP   MART.   MI   USAN   WHO-DD  
USAN  
Official Name English
TISERCIN
Brand Name English
LEVOMEPROMAZINUM
HPUS  
Common Name English
LEVOMEPROMAZINE MALEATE [JAN]
Common Name English
MINOZINAN
Brand Name English
(2R)-3-(2-METHOXY-10H-PHENOTHIAZIN-10-YL)-N,N,2-TRIMETHYLPROPAN-1-AMINE (2Z)-BUT-2-ENEDIOATE
Systematic Name English
NEURACTIL
Brand Name English
SOFMIN
Brand Name English
10H-PHENOTHIAZINE-10-PROPANAMINE, 2-METHOXY-N,N,.BETA.-TRIMETHYL-, (.BETA.R)-, (2Z)-2-BUTENEDIOATE (1:1)
Common Name English
LEVOMEPROMAZINE MALEATE [WHO-DD]
Common Name English
LEVOMEPROMAZINE MALEATE [EP]
Common Name English
LEVOMEPROMAZINE MALEATE [MART.]
Common Name English
VERACTIL
Brand Name English
NEUROCIL
Brand Name English
LEVOMEPROMAZINUM [HPUS]
Common Name English
LEVOMEPROMAZINE MALEATE [MI]
Common Name English
LEVOMEPROMAZINE HYDROGEN MALEATE
Common Name English
MILEZIN
Brand Name English
HIRNAMIN
Brand Name English
NOZINAN
Brand Name English
LEVOMEPROMAZINE MALEATE [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C740
Created by admin on Tue Oct 22 00:44:10 UTC 2019 , Edited by admin on Tue Oct 22 00:44:10 UTC 2019
Code System Code Type Description
CAS
7104-38-3
Created by admin on Tue Oct 22 00:44:10 UTC 2019 , Edited by admin on Tue Oct 22 00:44:10 UTC 2019
PRIMARY
EVMPD
SUB02909MIG
Created by admin on Tue Oct 22 00:44:10 UTC 2019 , Edited by admin on Tue Oct 22 00:44:10 UTC 2019
PRIMARY
MESH
C017901
Created by admin on Tue Oct 22 00:44:10 UTC 2019 , Edited by admin on Tue Oct 22 00:44:10 UTC 2019
PRIMARY
ChEMBL
CHEMBL1764
Created by admin on Tue Oct 22 00:44:10 UTC 2019 , Edited by admin on Tue Oct 22 00:44:10 UTC 2019
PRIMARY
EVMPD
SUB28708
Created by admin on Tue Oct 22 00:44:10 UTC 2019 , Edited by admin on Tue Oct 22 00:44:10 UTC 2019
PRIMARY
EPA CompTox
7104-38-3
Created by admin on Tue Oct 22 00:44:10 UTC 2019 , Edited by admin on Tue Oct 22 00:44:10 UTC 2019
PRIMARY
RXCUI
160372
Created by admin on Tue Oct 22 00:44:10 UTC 2019 , Edited by admin on Tue Oct 22 00:44:10 UTC 2019
PRIMARY RxNorm
PUBCHEM
5282484
Created by admin on Tue Oct 22 00:44:10 UTC 2019 , Edited by admin on Tue Oct 22 00:44:10 UTC 2019
PRIMARY
MERCK INDEX
M6788
Created by admin on Tue Oct 22 00:44:10 UTC 2019 , Edited by admin on Tue Oct 22 00:44:10 UTC 2019
PRIMARY Merck Index
ECHA (EC/EINECS)
230-412-8
Created by admin on Tue Oct 22 00:44:10 UTC 2019 , Edited by admin on Tue Oct 22 00:44:10 UTC 2019
PRIMARY
NCI_THESAURUS
C66009
Created by admin on Tue Oct 22 00:44:10 UTC 2019 , Edited by admin on Tue Oct 22 00:44:10 UTC 2019
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY