NAV

Halazepam

Identification

Generic Name
Halazepam
DrugBank Accession Number
DB00801
Background

Halazepam is abenzodiazepinederivative drug exerting anxiolytic, anticonvulsant, sedative, a muscle relaxing effects.1,2It has been shown to be less toxic than chlordiazepoxide or diazepam.1This drug is no longer marketed in the United States, and was withdrawn bySchering, its manufacturer, in 2009.3,4

Type
Small Molecule
Groups
Approved, Illicit, Withdrawn
Structure
 3D
Similar Structures
Weight
Average: 352.738
Monoisotopic: 352.059025338
Chemical Formula
C17H12ClF3N2O
Synonyms
  • Halazépam
  • Halazepam
  • Halazepamum
External IDs
  • Sch 12041
  • SCH-12041

Pharmacology

Indication

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

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

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.

Target Actions Organism
AGABA(A) Receptor
positive allosteric modulator
 Humans
UGABA(A) Receptor Benzodiazepine Binding Site
ligand
 Humans
Absorption

Not Available

的体积分布

Not Available

Protein binding

Not Available

Metabolism

Hepatic.

Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRsBrowse all" title="" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug InteractionsLearn More" title="" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction
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1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Halazepam is combined with 1,2-Benzodiazepine.
Acetazolamide The risk or severity of CNS depression can be increased when Halazepam is combined with Acetazolamide.
Acetophenazine The risk or severity of CNS depression can be increased when Halazepam is combined with Acetophenazine.
Agomelatine The risk or severity of CNS depression can be increased when Halazepam is combined with Agomelatine.
Alfentanil The risk or severity of adverse effects can be increased when Alfentanil is combined with Halazepam.
Alimemazine The risk or severity of CNS depression can be increased when Halazepam is combined with Alimemazine.
Almotriptan The risk or severity of CNS depression can be increased when Halazepam is combined with Almotriptan.
Alosetron The risk or severity of CNS depression can be increased when Halazepam is combined with Alosetron.
Alprazolam The risk or severity of CNS depression can be increased when Alprazolam is combined with Halazepam.
Alverine The risk or severity of CNS depression can be increased when Halazepam is combined with Alverine.
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Food Interactions
Not Available

Products

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International/Other Brands
Alapryl (Menarini)/Pacinone (Schering-Plough)/Paxipam (Schering-Plough)

Categories

ATC Codes
N05BA13 — Halazepam
Drug Categories
Chemical TaxonomyProvided byClassyfire
Description
This compound belongs to the class of organic compounds known as 1,4-benzodiazepines. These are organic compounds containing a benzene ring fused to a 1,4-azepine.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzodiazepines
Sub Class
1,4-benzodiazepines
Direct Parent
1,4-benzodiazepines
Alternative Parents
Alpha amino acids and derivatives/Benzene and substituted derivatives/Aryl chlorides/Tertiary carboxylic acid amides/Lactams/Ketimines/Propargyl-type 1,3-dipolar organic compounds/Azacyclic compounds/Organopnictogen compounds/Organofluorides
show 5 more
Substituents
1,4-benzodiazepine/Alkyl fluoride/Alkyl halide/Alpha-amino acid or derivatives/Aromatic heteropolycyclic compound/Aryl chloride/Aryl halide/Azacycle/Benzenoid/Carbonyl group
show 19 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
320YC168LF
CAS number
23092-17-3
InChI Key
WYCLKVQLVUQKNZ-UHFFFAOYSA-N
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
IUPAC Name
7-chloro-5-phenyl-1-(2,2,2-trifluoroethyl)-2,3-dihydro-1H-1,4-benzodiazepin-2-one
SMILES
FC(F)(F)CN1C2=C(C=C(Cl)C=C2)C(=NCC1=O)C1=CC=CC=C1

References

Synthesis Reference

U.S. Patents 3,429,874 and 3,641,147.
一般引用
  1. Fann WE, Pitts WM, Wheless JC: Pharmacology, efficacy, and adverse effects of halazepam, a new benzodiazepine. Pharmacotherapy. 1982 Mar-Apr;2(2):72-9. [Article]
  2. Richards BL, Whittle SL, Buchbinder R: Muscle relaxants for pain management in rheumatoid arthritis. Cochrane Database Syst Rev. 2012 Jan 18;1:CD008922. doi: 10.1002/14651858.CD008922.pub2. [Article]
  3. Paxipam approval, FDA [Link]
  4. Federal drug register, FDA [Link]
Human Metabolome Database
HMDB0014939
KEGG Drug
D00338
PubChem Compound
31640
PubChem Substance
46508415
ChemSpider
29343
BindingDB
50408018
RxNav
26412
ChEBI
5603
ChEMBL
CHEMBL970
ZINC
ZINC000000537811
Therapeutic Targets Database
DAP000679
PharmGKB
PA164746526
Drugs.com
Drugs.com Drug Page
Wikipedia
Halazepam

Clinical Trials

Clinical TrialsLearn More" title="" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count

Pharmacoeconomics

Manufacturers
  • Schering corp sub schering plough corp
Packagers
Not Available
Dosage Forms
Form Route Strength
Tablet
价格
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Property Value Source
melting point (°C) 165 °C PhysProp
logP 3.97 SANGSTER (1994)
Predicted Properties
Property Value Source
Water Solubility 0.0017 mg/mL ALOGPS
logP 3.52 ALOGPS
logP 4.03 Chemaxon
logS -5.3 ALOGPS
pKa (Strongest Acidic) 18.88 Chemaxon
pKa (Strongest Basic) 2.33 Chemaxon
Physiological Charge 0 Chemaxon
沪元drogen Acceptor Count 2 Chemaxon
沪元drogen Donor Count 0 Chemaxon
Polar Surface Area 32.67 Å2 Chemaxon
Rotatable Bond Count 3 Chemaxon
Refractivity 85.26米3·mol-1 Chemaxon
Polarizability 31.8 Å3 Chemaxon
Number of Rings 3 Chemaxon
Bioavailability 1 Chemaxon
Rule of Five Yes Chemaxon
Ghose Filter Yes Chemaxon
Veber's Rule Yes Chemaxon
MDDR-like规则 No Chemaxon
Predicted ADMET Features
Property Value Probability
Human Intestinal Absorption + 0.9952
Blood Brain Barrier + 0.9966
Caco-2 permeable + 0.6558
P-glycoprotein substrate Substrate 0.6489
P-glycoprotein inhibitor I Inhibitor 0.739
P-glycoprotein inhibitor II Inhibitor 0.6548
Renal organic cation transporter Inhibitor 0.5819
CYP450 2C9 substrate Non-substrate 0.7819
CYP450 2D6 substrate Non-substrate 0.8422
CYP450 3A4 substrate Substrate 0.7404
CYP450 1A2 substrate Inhibitor 0.776
CYP450 2C9 inhibitor Inhibitor 0.5458
CYP450 2D6 inhibitor Non-inhibitor 0.809
CYP450 2C19 inhibitor Inhibitor 0.7949
CYP450 3A4 inhibitor Inhibitor 0.5085
CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.7781
Ames test Non AMES toxic 0.8369
Carcinogenicity Non-carcinogens 0.7657
Biodegradation 没有准备好可生物降解 1.0
Rat acute toxicity 1.7143 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9836
hERG inhibition (predictor II) Inhibitor 0.5729
ADMET data is predicted usingadmetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
Spectrum Spectrum Type Splash Key
Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available
Mass Spectrum (Electron Ionization) MS splash10-0fmi-3539000000-76854e3f82279b906a7f
Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available

Targets

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Details 1.GABA(A) Receptor (Protein Group)
Kind
Protein group
Organism
Humans
Pharmacological action
Yes
Actions
Positive allosteric modulator
Curator comments
The GABA(A) receptor is pentameric (i.e. comprising 5 subunit proteins) and therefore has a multitude of potential isoforms. The above target is a collection of all possible GABA(A) subunits that may participate in the formation of the pentameric receptor and is not meant to imply direct a drug-protein interaction for each individual subunit.
General Function
Inhibitory extracellular ligand-gated ion channel activity
Specific Function
Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...
Components:
名字 UniProt ID
Gamma-aminobutyric acid receptor subunit alpha-1 P14867
Gamma-aminobutyric acid receptor subunit alpha-2 P47869
Gamma-aminobutyric acid receptor subunit alpha-3 P34903
Gamma-aminobutyric acid receptor subunit alpha-4 P48169
Gamma-aminobutyric acid receptor subunit alpha-5 P31644
Gamma-aminobutyric acid receptor subunit alpha-6 Q16445
Gamma-aminobutyric acid receptor subunit beta-1 P18505
Gamma-aminobutyric acid receptor subunit beta-2 P47870
Gamma-aminobutyric acid receptor subunit beta-3 P28472
Gamma-aminobutyric acid receptor subunit delta O14764
Gamma-aminobutyric acid receptor subunit epsilon P78334
Gamma-aminobutyric acid receptor subunit gamma-1 Q8N1C3
Gamma-aminobutyric acid receptor subunit gamma-2 P18507
Gamma-aminobutyric acid receptor subunit gamma-3 Q99928
Gamma-aminobutyric acid receptor subunit pi O00591
Gamma-aminobutyric acid receptor subunit theta Q9UN88
References
  1. Sigel E, Steinmann ME: Structure, function, and modulation of GABA(A) receptors. J Biol Chem. 2012 Nov 23;287(48):40224-31. doi: 10.1074/jbc.R112.386664. Epub 2012 Oct 4. [Article]
  2. Zhu S, Noviello CM, Teng J, Walsh RM Jr, Kim JJ, Hibbs RE: Structure of a human synaptic GABAA receptor. Nature. 2018 Jul;559(7712):67-72. doi: 10.1038/s41586-018-0255-3. Epub 2018 Jun 27. [Article]
Details 2.GABA(A) Receptor Benzodiazepine Binding Site (Protein Group)
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Ligand
Curator comments
Benzodiazepines modulate GABA(A) function by binding at the interface between alpha (α) and gamma (γ) subunits. Of the 6 α-subunits, only 4 (α-1, -2, -3, and -5) participate in the formation of this binding site. The above target is a collection of all α- and γ-subunits that are known to participate in the formation of the benzodiazepine binding site.
General Function
Inhibitory extracellular ligand-gated ion channel activity
Specific Function
Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...
Components:
名字 UniProt ID
Gamma-aminobutyric acid receptor subunit alpha-1 P14867
Gamma-aminobutyric acid receptor subunit alpha-2 P47869
Gamma-aminobutyric acid receptor subunit alpha-3 P34903
Gamma-aminobutyric acid receptor subunit alpha-5 P31644
Gamma-aminobutyric acid receptor subunit gamma-1 Q8N1C3
Gamma-aminobutyric acid receptor subunit gamma-2 P18507
Gamma-aminobutyric acid receptor subunit gamma-3 Q99928
References
  1. Zhu S, Noviello CM, Teng J, Walsh RM Jr, Kim JJ, Hibbs RE: Structure of a human synaptic GABAA receptor. Nature. 2018 Jul;559(7712):67-72. doi: 10.1038/s41586-018-0255-3. Epub 2018 Jun 27. [Article]
  2. Sigel E, Steinmann ME: Structure, function, and modulation of GABA(A) receptors. J Biol Chem. 2012 Nov 23;287(48):40224-31. doi: 10.1074/jbc.R112.386664. Epub 2012 Oct 4. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 03, 2023 17:39