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Halazepam

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Also known as: Paxipam, Sch 12041, 23092-17-3, Halazepamum [inn-latin], Schering 12041, Sch-12041

Molecular Formula

C₁₇H₁₂ClF₃N₂O

Molecular Weight

352.7 g/mol

InChI Key

WYCLKVQLVUQKNZ-UHFFFAOYSA-N

FDA UNII

320YC168LF

Halazepam is a synthetic benzodiazepine derivative with anxiolytic property. Halazepam potentiates the inhibitory activities of gamma-aminobutyric acid (GABA) by binding to the benzodiazepine-GABA-A-chloride ionophore receptor complex located in the limbic, thalamic, and hypothalamic regions of the central nervous system (CNS). This increases the frequency of chloride channel opening, allowing the flow of chloride ions into the neuron and ultimately leading to membrane hyperpolarization and a decrease in neuronal excitability.

1 2D Structure

Halazepam

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

7-chloro-5-phenyl-1-(2,2,2-trifluoroethyl)-3H-1,4-benzodiazepin-2-one

2.1.2 InChI

InChI=1S/C17H12ClF3N2O/c18-12-6-7-14-13(8-12)16(11-4-2-1-3-5-11)22-9-15(24)23(14)10-17(19,20)21/h1-8H,9-10H2

2.1.3 InChI Key

WYCLKVQLVUQKNZ-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1C(=O)N(C2=C(C=C(C=C2)Cl)C(=N1)C3=CC=CC=C3)CC(F)(F)F

2.2 Other Identifiers

2.2.1 UNII

320YC168LF

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Sch 12041

2.3.2 Depositor-Supplied Synonyms

1. Paxipam

2. Sch 12041

3. 23092-17-3

4. Halazepamum [inn-latin]

5. Schering 12041

6. Sch-12041

7. Halazepam Civ

8. 7-chloro-1,3-dihydro-5-phenyl-1-(2,2,2-trifluoroethyl)-2h-1,4-benzodiazepin-2-one

9. 7-chloro-5-phenyl-1-(2,2,2-trifluoroethyl)-3h-1,4-benzodiazepin-2-one

10. 2h-1,4-benzodiazepin-2-one, 7-chloro-1,3-dihydro-5-phenyl-1-(2,2,2-trifluoroethyl)-

11. Pacinone

12. 7-chloro-5-phenyl-1-(2,2,2-trifluoroethyl)-1,3-dihydro-2h-1,4-benzodiazepin-2-one

13. 320yc168lf

14. Halazepamum

15. 2h-1,4-benzodiazepin-2-one, 1,3-dihydro-7-chloro-5-phenyl-1-(2,2,2-trifluoroethyl)-

16. 7-chloro-5-phenyl-1-(2,2,2-trifluoroethyl)-2,3-dihydro-1h-1,4-benzodiazepin-2-one

17. Paxipam (tn)

18. Halazepam (usan/inn)

19. Einecs 245-425-4

20. Brn 0898553

21. Alapryl

22. Halezepam

23. Unii-320yc168lf

24. Dea No. 2762

25. Halazepam [usan:usp:inn:ban]

26. Halazepam [inn]

27. Halazepam [mi]

28. Halazepam [usan]

29. Halazepam [vandf]

30. Chembl970

31. Halazepam [mart.]

32. Halazepam [who-dd]

33. Schembl78995

34. 5-24-04-00303 (beilstein Handbook Reference)

35. Chebi:5603

36. Gtpl7195

37. Halazepam [orange Book]

38. Dtxsid5023118

39. Zinc537811

40. Bdbm50408018

41. Db00801

42. D00338

43. Q5641126

44. 7-chloro-5-phenyl-1-(2,2,2-trifluorethyl)-1h-1,4-benzodiazepin-2(3h)-on

2.4 Create Date

2005-03-27

3 Chemical and Physical Properties

Molecular Formula	C₁₇H₁₂ClF₃N₂O
Molecular Weight	352.7 g/mol
XLogP3	4
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	2
Exact Mass	352.0590252 g/mol
Monoisotopic Mass	352.0590252 g/mol
Topological Polar Surface Area	32.7 Å²
Heavy Atom Count	24
Formal Charge	0
Complexity	503
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Used to relieve anxiety, nervousness, and tension associated with anxiety disorders.

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Anti-Anxiety Agents

Agents that alleviate ANXIETY, tension, and ANXIETY DISORDERS, promote sedation, and have a calming effect without affecting clarity of consciousness or neurologic conditions. ADRENERGIC BETA-ANTAGONISTS are commonly used in the symptomatic treatment of anxiety but are not included here. (See all compounds classified as Anti-Anxiety Agents.)

5.2 ATC Code

N - Nervous system

N05 - Psycholeptics

N05B - Anxiolytics

N05BA - Benzodiazepine derivatives

N05BA13 - Halazepam

5.3 Metabolism/Metabolites

Hepatic.

5.4 Mechanism of Action

Benzodiazepines bind nonspecifically to benzodiazepine receptors BNZ1, which mediates sleep, and BNZ2, which affects affects muscle relaxation, anticonvulsant activity, motor coordination, and memory. As benzodiazepine receptors are thought to be coupled to gamma-aminobutyric acid-A (GABAA) receptors, this enhances the effects of GABA by increasing GABA affinity for the GABA receptor. Binding of GABA to the site opens the chloride channel, resulting in a hyperpolarized cell membrane that prevents further excitation of the cell.