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Details

Stereochemistry RACEMIC
Molecular Formula C16H12Cl2N2O2
Molecular Weight 335.185
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LORMETAZEPAM

SMILES

CN1C2=C(C=C(Cl)C=C2)C(=NC(O)C1=O)C3=C(Cl)C=CC=C3

InChI

InChIKey=FJIKWRGCXUCUIG-UHFFFAOYSA-N
InChI=1S/C16H12Cl2N2O2/c1-20-13-7-6-9(17)8-11(13)14(19-15(21)16(20)22)10-4-2-3-5-12(10)18/h2-8,15,21H,1H3

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/1687574 https://www.ncbi.nlm.nih.gov/pubmed/6124982

Lormetazepam (or methyl-lorazepam), possesses hypnotic, anxiolytic, sedative and skeletal muscle relaxant properties. Lormetazepam is not approved for sale in the United States or Canada, though it is licensed in the Netherlands as 1 and 2 mg tablets, under the brand names Loramet and Noctamid and as generic, available from several different manufacturers. Lormetazepam is a short-acting benzodiazepine and is sometimes used in patients who have difficulty in maintaining sleep or falling asleep. Lormetazepam binds to the benzodiazepine receptor which in turn enhances the effect of the GABAA receptor producing its therapeutic effects as well as adverse effects. Lormetazepam appears to be more selective in the type of benzodiazepine receptor it binds to showing a higher affinity for the omega 1 receptor which is responsible for sedation. Changes in electroencephalography can therefore be used to measure the sedative sleep promoting properties of lormetazepam.

CNS Activity

Curator's Comment: Lormetazepam acts through the central nervous system

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Simultaneous determination of fifteen low-dosed benzodiazepines in human urine by solid-phase extraction and gas chromatography-mass spectrometry.
2001 Dec 25
Adsorption of xenobiotics to plastic tubing incorporated into dynamic in vitro systems used in pharmacological research--limits and progress.
2001 Jul
Fast withdrawal from benzodiazepines in geriatric inpatients: a randomised double-blind, placebo-controlled trial.
2002 Jan
Immobilized halogenophenylcarbamate derivatives of cellulose as novel stationary phases for enantioselective drug analysis.
2002 Jan 15
Lormetazepam effects on daytime vigilance, psychomotor performance and simulated driving in young adult healthy volunteers.
2002 Jul
Determination of lormetazepam and its main metabolite in serum using micellar electrokinetic capillary chromatography with direct injection and ultraviolet absorbance detection.
2002 Jun 25
Effects of short-acting hypnotics on sleep latency in rats placed on grid suspended over water.
2003 Jan 24
Effects on postural oscillation and memory functions of a single dose of zolpidem 5 mg, zopiclone 3.75 mg and lormetazepam 1 mg in elderly healthy subjects. A randomized, cross-over, double-blind study versus placebo.
2003 Jul
The use of hypnosedative drugs in a university hospital setting.
2003 Jul-Aug
Screening, library-assisted identification and validated quantification of 23 benzodiazepines, flumazenil, zaleplone, zolpidem and zopiclone in plasma by liquid chromatography/mass spectrometry with atmospheric pressure chemical ionization.
2004 Aug
Lormetazepam in depressive insomnia: new evidence of phase-response effects of benzodiazepines.
2004 Sep
Quantification of lorazepam and lormetazepam in human breast milk using GC-MS in the negative chemical ionization mode.
2007 May
Evaluation of anxiolytic-like effects of some short-acting benzodiazepine hypnotics in mice.
2008 Jul
A validated method for simultaneous screening and quantification of twenty-three benzodiazepines and metabolites plus zopiclone and zaleplone in whole blood by liquid-liquid extraction and ultra-performance liquid chromatography- tandem mass spectrometry.
2010 Jul-Aug
Experimental design for optimization of microwave-assisted extraction of benzodiazepines in human plasma.
2010 May
Analysis of six benzodiazepines in vitreous humor by high-performance liquid chromatography-photodiode-array detection.
2010 Nov
Patents

Patents

Sample Use Guides

1 tablet Noctamid (lormetazepam) (1 mg) as a single dose. Elderly and debilitated patients take half a tablet (0,5 mg).
Route of Administration: Oral
In Vitro Use Guide
Unknown
Name Type Language
LORMETAZEPAM
INN   JAN   MART.   MI   USAN   WHO-DD  
USAN   INN  
Official Name English
LORMETAZEPAM [USAN]
Common Name English
7-Chloro-5-(O-chlorophenyl)-1,3-dihydro-3-hydroxy-1-methyl-2H-1,4-benzodiazepin-2-one
Common Name English
LORMETAZEPAM [MART.]
Common Name English
2H-1,4-BENZODIAZEPIN-2-ONE, 7-CHLORO-5-(2-CHLOROPHENYL)-1,3-DIHYDRO-3-HYDROXY-1-METHYL-
Systematic Name English
Lormetazepam [WHO-DD]
Common Name English
7-CHLORO-5-(2-CHLOROPHENYL)-1,3-DIHYDRO-3-HYDROXY-1-METHYL-2H-1,4-BENZODIAZEPIN-2-ONE
Systematic Name English
LORMETAZEPAM [MI]
Common Name English
WY-4082
Code English
LORMETAZEPAM [JAN]
Common Name English
LORAMET
Brand Name English
lormetazepam [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1012
Created by admin on Fri Dec 15 15:26:14 UTC 2023 , Edited by admin on Fri Dec 15 15:26:14 UTC 2023
WHO-ATC N05CD06
Created by admin on Fri Dec 15 15:26:14 UTC 2023 , Edited by admin on Fri Dec 15 15:26:14 UTC 2023
DEA NO. 2774
Created by admin on Fri Dec 15 15:26:14 UTC 2023 , Edited by admin on Fri Dec 15 15:26:14 UTC 2023
WHO-VATC QN05CD06
Created by admin on Fri Dec 15 15:26:14 UTC 2023 , Edited by admin on Fri Dec 15 15:26:14 UTC 2023
Code System Code Type Description
ChEMBL
CHEMBL22097
Created by admin on Fri Dec 15 15:26:14 UTC 2023 , Edited by admin on Fri Dec 15 15:26:14 UTC 2023
PRIMARY
MESH
C023842
Created by admin on Fri Dec 15 15:26:14 UTC 2023 , Edited by admin on Fri Dec 15 15:26:14 UTC 2023
PRIMARY
MERCK INDEX
m6909
Created by admin on Fri Dec 15 15:26:14 UTC 2023 , Edited by admin on Fri Dec 15 15:26:14 UTC 2023
PRIMARY Merck Index
EPA CompTox
DTXSID40862442
Created by admin on Fri Dec 15 15:26:14 UTC 2023 , Edited by admin on Fri Dec 15 15:26:14 UTC 2023
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ECHA (EC/EINECS)
212-700-5
Created by admin on Fri Dec 15 15:26:14 UTC 2023 , Edited by admin on Fri Dec 15 15:26:14 UTC 2023
PRIMARY
CAS
848-75-9
Created by admin on Fri Dec 15 15:26:14 UTC 2023 , Edited by admin on Fri Dec 15 15:26:14 UTC 2023
PRIMARY
CHEBI
52993
Created by admin on Fri Dec 15 15:26:14 UTC 2023 , Edited by admin on Fri Dec 15 15:26:14 UTC 2023
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WIKIPEDIA
LORMETAZEPAM
Created by admin on Fri Dec 15 15:26:14 UTC 2023 , Edited by admin on Fri Dec 15 15:26:14 UTC 2023
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PUBCHEM
13314
Created by admin on Fri Dec 15 15:26:14 UTC 2023 , Edited by admin on Fri Dec 15 15:26:14 UTC 2023
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FDA UNII
GU56C842ZA
Created by admin on Fri Dec 15 15:26:14 UTC 2023 , Edited by admin on Fri Dec 15 15:26:14 UTC 2023
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INN
4339
Created by admin on Fri Dec 15 15:26:14 UTC 2023 , Edited by admin on Fri Dec 15 15:26:14 UTC 2023
PRIMARY
EVMPD
SUB08588MIG
Created by admin on Fri Dec 15 15:26:14 UTC 2023 , Edited by admin on Fri Dec 15 15:26:14 UTC 2023
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DRUG BANK
DB13872
Created by admin on Fri Dec 15 15:26:14 UTC 2023 , Edited by admin on Fri Dec 15 15:26:14 UTC 2023
PRIMARY
LACTMED
Lormetazepam
Created by admin on Fri Dec 15 15:26:14 UTC 2023 , Edited by admin on Fri Dec 15 15:26:14 UTC 2023
PRIMARY
RXCUI
28894
Created by admin on Fri Dec 15 15:26:14 UTC 2023 , Edited by admin on Fri Dec 15 15:26:14 UTC 2023
PRIMARY RxNorm
SMS_ID
100000091985
Created by admin on Fri Dec 15 15:26:14 UTC 2023 , Edited by admin on Fri Dec 15 15:26:14 UTC 2023
PRIMARY
NCI_THESAURUS
C87673
Created by admin on Fri Dec 15 15:26:14 UTC 2023 , Edited by admin on Fri Dec 15 15:26:14 UTC 2023
PRIMARY
DRUG CENTRAL
1608
Created by admin on Fri Dec 15 15:26:14 UTC 2023 , Edited by admin on Fri Dec 15 15:26:14 UTC 2023
PRIMARY