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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
Molecular Formula C16H12Cl2N2O2
Molecular Weight 335.185
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

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

CNS Active
3913
Curator's Comment: Lormetazepam acts through the central nervous system

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Binding Agent
1064
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8429
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
Determination of lormetazepam and its main metabolite in serum using micellar electrokinetic capillary chromatography with direct injection and ultraviolet absorbance detection.
2002 Jun 25
Musical hallucinations during a treatment with benzodiazepine.
2002 Oct
Trimipramine in primary insomnia: results of a polysomnographic double-blind controlled study.
2002 Sep
Effects of short-acting hypnotics on sleep latency in rats placed on grid suspended over water.
2003 Jan 24
The use of hypnosedative drugs in a university hospital setting.
2003 Jul-Aug
Residual effects of hypnotics: epidemiology and clinical implications.
2004
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
A randomized clinical trial comparing doses and efficacy of lormetazepam tablets or oral solution for insomnia in a general practice setting.
2004 Mar
[The use of anxiolytic and hypnotic drugs in Spain (1995-2002)].
2004 May-Jun
Screening method for benzodiazepines and hypnotics in hair at pg/mg level by liquid chromatography-mass spectrometry/mass spectrometry.
2005 Oct 15
A comparison of theoretical methods of calculation of partition coefficients for selected drugs.
2006 May-Jun
Eszopiclone: its use in the treatment of insomnia.
2007 Aug
How useful are prescribing indicators based on the DU90% method to distinguish the quality of prescribing between pharmacotherapy audit meetings with different levels of functioning?
2007 Dec
Sleep disturbances and depression: risk relationships for subsequent depression and therapeutic implications.
2008
Evaluation of anxiolytic-like effects of some short-acting benzodiazepine hypnotics in mice.
2008 Jul
Use of computerized dynamic posturography to assess balance in older adults after nighttime awakenings using zolpidem as a reference.
2008 Jul 15
Decrease in tobacco consumption after treatment with topiramate and aripiprazole: a case report.
2008 Jun 11
GABA(A) receptors in normal development and seizures: friends or foes?
2008 Mar
[Paroxetine-induced severe hyponatremic rhabdomyolisis].
2008 Oct
Clinical review: The impact of noise on patients' sleep and the effectiveness of noise reduction strategies in intensive care units.
2009
Psychoactive medication and traffic safety.
2009 Mar
Conversion visual loss: a differential diagnosis in infant amblyopia.
2009 Nov-Dec
Benzodiazepine prescription and length of hospital stay at a Japanese university hospital.
2009 Oct 9
Development and validation of an EI-GC-MS method for the determination of benzodiazepine drugs and their metabolites in blood: applications in clinical and forensic toxicology.
2010 Aug 1
The impact of perfectionism and anxiety traits on action monitoring in major depressive disorder.
2010 Jul
Analysis of six benzodiazepines in vitreous humor by high-performance liquid chromatography-photodiode-array detection.
2010 Nov
Patents

Patents

JP2012500248A
3

Sample Use Guides

In Vivo Use Guide
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
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:26:14 GMT 2023
Edited
by admin
on Fri Dec 15 15:26:14 GMT 2023
Record UNII
GU56C842ZA
Record Status Validated (UNII)
Record Version
  • Download
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 GMT 2023 , Edited by admin on Fri Dec 15 15:26:14 GMT 2023
WHO-ATC N05CD06
Created by admin on Fri Dec 15 15:26:14 GMT 2023 , Edited by admin on Fri Dec 15 15:26:14 GMT 2023
DEA NO. 2774
Created by admin on Fri Dec 15 15:26:14 GMT 2023 , Edited by admin on Fri Dec 15 15:26:14 GMT 2023
WHO-VATC QN05CD06
Created by admin on Fri Dec 15 15:26:14 GMT 2023 , Edited by admin on Fri Dec 15 15:26:14 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL22097
Created by admin on Fri Dec 15 15:26:14 GMT 2023 , Edited by admin on Fri Dec 15 15:26:14 GMT 2023
PRIMARY
MESH
C023842
Created by admin on Fri Dec 15 15:26:14 GMT 2023 , Edited by admin on Fri Dec 15 15:26:14 GMT 2023
PRIMARY
MERCK INDEX
m6909
Created by admin on Fri Dec 15 15:26:14 GMT 2023 , Edited by admin on Fri Dec 15 15:26:14 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID40862442
Created by admin on Fri Dec 15 15:26:14 GMT 2023 , Edited by admin on Fri Dec 15 15:26:14 GMT 2023
PRIMARY
ECHA (EC/EINECS)
212-700-5
Created by admin on Fri Dec 15 15:26:14 GMT 2023 , Edited by admin on Fri Dec 15 15:26:14 GMT 2023
PRIMARY
CAS
848-75-9
Created by admin on Fri Dec 15 15:26:14 GMT 2023 , Edited by admin on Fri Dec 15 15:26:14 GMT 2023
PRIMARY
CHEBI
52993
Created by admin on Fri Dec 15 15:26:14 GMT 2023 , Edited by admin on Fri Dec 15 15:26:14 GMT 2023
PRIMARY
WIKIPEDIA
LORMETAZEPAM
Created by admin on Fri Dec 15 15:26:14 GMT 2023 , Edited by admin on Fri Dec 15 15:26:14 GMT 2023
PRIMARY
PUBCHEM
13314
Created by admin on Fri Dec 15 15:26:14 GMT 2023 , Edited by admin on Fri Dec 15 15:26:14 GMT 2023
PRIMARY
FDA UNII
GU56C842ZA
Created by admin on Fri Dec 15 15:26:14 GMT 2023 , Edited by admin on Fri Dec 15 15:26:14 GMT 2023
PRIMARY
INN
4339
Created by admin on Fri Dec 15 15:26:14 GMT 2023 , Edited by admin on Fri Dec 15 15:26:14 GMT 2023
PRIMARY
EVMPD
SUB08588MIG
Created by admin on Fri Dec 15 15:26:14 GMT 2023 , Edited by admin on Fri Dec 15 15:26:14 GMT 2023
PRIMARY
DRUG BANK
DB13872
Created by admin on Fri Dec 15 15:26:14 GMT 2023 , Edited by admin on Fri Dec 15 15:26:14 GMT 2023
PRIMARY
LACTMED
Lormetazepam
Created by admin on Fri Dec 15 15:26:14 GMT 2023 , Edited by admin on Fri Dec 15 15:26:14 GMT 2023
PRIMARY
RXCUI
28894
Created by admin on Fri Dec 15 15:26:14 GMT 2023 , Edited by admin on Fri Dec 15 15:26:14 GMT 2023
PRIMARY RxNorm
SMS_ID
100000091985
Created by admin on Fri Dec 15 15:26:14 GMT 2023 , Edited by admin on Fri Dec 15 15:26:14 GMT 2023
PRIMARY
NCI_THESAURUS
C87673
Created by admin on Fri Dec 15 15:26:14 GMT 2023 , Edited by admin on Fri Dec 15 15:26:14 GMT 2023
PRIMARY
DRUG CENTRAL
1608
Created by admin on Fri Dec 15 15:26:14 GMT 2023 , Edited by admin on Fri Dec 15 15:26:14 GMT 2023
PRIMARY
Related Record Type Details
Structure of 2-CHLORODIAZEPAM
PARENT -> METABOLITE
URINE
Related Record Type Details
Structure of LORMETAZEPAM
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