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Chemistry

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Also known as: Methyllorazepam, N-methyllorazepam, Noctamid, Loramet, 848-75-9, Lormetazepamum

Molecular Formula

C₁₆H₁₂Cl₂N₂O₂

Molecular Weight

335.2 g/mol

InChI Key

FJIKWRGCXUCUIG-UHFFFAOYSA-N

FDA UNII

GU56C842ZA

lormetazepam is a natural product found in Solanum tuberosum and Triticum aestivum with data available.

1 2D Structure

Lormetazepam

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

7-chloro-5-(2-chlorophenyl)-3-hydroxy-1-methyl-3H-1,4-benzodiazepin-2-one

2.1.2 InChI

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

2.1.3 InChI Key

FJIKWRGCXUCUIG-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CN1C2=C(C=C(C=C2)Cl)C(=NC(C1=O)O)C3=CC=CC=C3Cl

2.2 Other Identifiers

2.2.1 UNII

GU56C842ZA

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Methyllorazepam

2.3.2 Depositor-Supplied Synonyms

1. Methyllorazepam

2. N-methyllorazepam

3. Noctamid

4. Loramet

5. 848-75-9

6. Lormetazepamum

7. Chlorotemazepam

8. Ergocalm

9. Noctamide

10. Wy-4082

11. Loramet (tn)

12. 7-chloro-5-(o-chlorophenyl)-1,3-dihydro-3-hydroxy-1-methyl-2h-1,4-benzodiazepin-2-one

13. Ro 5-5516

14. Wy 4082

15. 7-chloro-5-(2-chlorophenyl)-1,3-dihydro-3-hydroxy-1-methyl-2h-1,4-benzodiazepin-2-one

16. 7-chloro-5-(2-chlorophenyl)-3-hydroxy-1-methyl-2,3-dihydro-1h-1,4-benzodiazepin-2-one

17. 2h-1,4-benzodiazepin-2-one, 7-chloro-5-(2-chlorophenyl)-1,3-dihydro-3-hydroxy-1-methyl-

18. 7-chloro-5-(2-chlorophenyl)-3-hydroxy-1-methyl-3h-1,4-benzodiazepin-2-one

19. Chembl22097

20. Gu56c842za

21. Chebi:52993

22. 2h-1,4-benzodiazepin-2-one, 1,3-dihydro-7-chloro-5-(o-chlorophenyl)-3-hydroxy-1-methyl-

23. 7-chloro-5-(2-chlorophenyl)-3-hydroxy-1-methyl-1,3-dihydro-2h-1,4-benzodiazepin-2-one

24. Lormetazepamum [inn-latin]

25. (rs)-lormetazepam

26. (+/-)-lormetazepam

27. Lormetazepam [usan:inn:ban:jan]

28. Einecs 212-700-5

29. Brn 0759821

30. Unii-gu56c842za

31. Loretam

32. Dea No. 2774

33. ()-lorazepam

34. (+-)-lorazepam

35. Lormetazepam [mi]

36. Lormetazepam [inn]

37. Lormetazepam [jan]

38. Lormetazepam [usan]

39. Schembl43267

40. Lormetazepam [mart.]

41. Lormetazepam [who-dd]

42. Gtpl7553

43. Lormetazepam (jan/usan/inn)

44. Dtxsid40862442

45. Lormetazepam 0.1 Mg/ml In Methanol

46. Lormetazepam 1.0 Mg/ml In Methanol

47. Ortho-chloro-3-hydroxydiazepam

48. Db13872

49. Zk-65997

50. D01657

51. Q186257

52. 7-chloro-1,3-dihydro-5-(o-chlorophenyl)-3-hydroxy-1-methyl-2h-1,4-benzodiazepin-2-one

53. 7-chloro-5-(2-chlorophenyl)-3-hydroxy-1-methyl-1,3-dihydro-2h-1,4-benzodiazepin-2-one #

54. Lormetazepam Solution, 1.0 Mg/ml In Methanol, Ampule Of 1 Ml, Certified Reference Material

2.4 Create Date

2005-03-27

3 Chemical and Physical Properties

Molecular Formula	C₁₆H₁₂Cl₂N₂O₂
Molecular Weight	335.2 g/mol
XLogP3	2.4
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	1
Exact Mass	334.0275830 g/mol
Monoisotopic Mass	334.0275830 g/mol
Topological Polar Surface Area	52.9 Å²
Heavy Atom Count	22
Formal Charge	0
Complexity	471
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

For the treatment of short-term insomnia

5 Pharmacology and Biochemistry

5.1 Pharmacology

Lormetazepam is a benzodiazepine which reduces central nervous system (CNS) activity. It produces anxiolytic, muscle relaxant, sedative and hypnotic effects. Because it is a short-acting benzodiapine, it does not produce significant sedation after waking.

5.2 MeSH Pharmacological Classification

Hypnotics and Sedatives

Drugs used to induce drowsiness or sleep or to reduce psychological excitement or anxiety. (See all compounds classified as Hypnotics and Sedatives.)

5.3 ATC Code

N05CD06

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

N - Nervous system

N05 - Psycholeptics

N05C - Hypnotics and sedatives

N05CD - Benzodiazepine derivatives

N05CD06 - Lormetazepam

5.4 Metabolism/Metabolites

Metabolised to an inactive metabolite via glucuronide conjugation

5.5 Biological Half-Life

The terminal phase half life is 11 h.

5.6 Mechanism of Action

Lormetazepam, as a benzodiazepine, binds to the regulatory site between the and subunits of -aminobutryic acid (GABA) A receptors with 2 and 1, 2, 3, or 5 subunits. This facilitates the opening of the chloride channel allowing chloride ions to flow into the neuron resulting in hyperpolarization. Hyperpolarized neurons require greater simulation to reach their action potential threshold. The general inhibitory effect on neuronal depolarization produces the effects of lormetazepam.

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