LORMETAZEPAM

Possibly Marketed Outside US

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 Search

SMILES

CN1C2=CC=C(Cl)C=C2C(=NC(O)C1=O)C3=CC=CC=C3Cl

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
Sources: http://home.intekom.com/pharm/schering/noctamid.html
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
GABA-A receptor; benzodiazepine site 38 Target ID: CHEMBL2109243 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1687574	Binding Agent 1076

Conditions

Condition	Modality	Targets	Highest Phase	Product
Insomnia 111 Sources: http://home.intekom.com/pharm/schering/noctamid.html	Curative		Approved 8583	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
27.2 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1974495/	0.03 mg/kg single, oral dose: 0.03 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		LORMETAZEPAM plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
13.9 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1974495/	0.03 mg/kg single, oral dose: 0.03 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		LORMETAZEPAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Analyte	Population
167 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1974495/	0.03 mg/kg single, oral dose: 0.03 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	LORMETAZEPAM plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
64 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1974495/	0.015 mg/kg single, intravenous dose: 0.015 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	LORMETAZEPAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
85 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1974495/	0.015 mg/kg single, intravenous dose: 0.015 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	LORMETAZEPAM plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
84 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1974495/	0.03 mg/kg single, oral dose: 0.03 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	LORMETAZEPAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
13.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/43806/	2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered:		LORMETAZEPAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
13.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/43806/	0.2 mg single, intravenous dose: 0.2 mg route of administration: Intravenous experiment type: SINGLE co-administered:		LORMETAZEPAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
0.2 mg single, intravenous Studied dose Dose: 0.2 mg Route: intravenous Route: single Dose: 0.2 mg Sources: https://pubmed.ncbi.nlm.nih.gov/43806/	healthy Health Status: healthy Sex: M Food Status: FED Sources: https://pubmed.ncbi.nlm.nih.gov/43806/	Sources: https://pubmed.ncbi.nlm.nih.gov/43806/
2 mg single, oral Studied dose Dose: 2 mg Route: oral Route: single Dose: 2 mg Sources: https://pubmed.ncbi.nlm.nih.gov/43806/	healthy Health Status: healthy Sex: M Food Status: FED Sources: https://pubmed.ncbi.nlm.nih.gov/43806/	Sources: https://pubmed.ncbi.nlm.nih.gov/43806/

PubMed

Title	Date	PubMed
Simultaneous determination of fifteen low-dosed benzodiazepines in human urine by solid-phase extraction and gas chromatography-mass spectrometry.	2001 Dec 25	11767312
Effects of short-acting hypnotics on sleep latency in rats placed on grid suspended over water.	2003 Jan 24	12559374
A randomized clinical trial comparing doses and efficacy of lormetazepam tablets or oral solution for insomnia in a general practice setting.	2004 Mar	14994324
Eszopiclone: its use in the treatment of insomnia.	2007 Aug	19300573
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	17909774
Sleep disturbances and depression: risk relationships for subsequent depression and therapeutic implications.	2008	19170404
GABA(A) receptors in normal development and seizures: friends or foes?	2008 Mar	19305785
[Paroxetine-induced severe hyponatremic rhabdomyolisis].	2008 Oct	18842231
The impact of perfectionism and anxiety traits on action monitoring in major depressive disorder.	2010 Jul	20473695
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	20663286
Analysis of six benzodiazepines in vitreous humor by high-performance liquid chromatography-photodiode-array detection.	2010 Nov	21073805

Patents

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

Name

Type

Language

LORMETAZEPAM

Official Name

English

LORAMET

Preferred 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

lormetazepam [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1012