ContaminantDB: Clorazepate

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (21)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:27:17 UTC

Update Date

2026-05-14 16:44:31 UTC

Accession Number

CHEM002234

Identification

Common Name

Clorazepate

Class

Small Molecule

Description

Clorazepate is only found in individuals that have used or taken this drug. It is a water-soluble benzodiazepine derivative effective in the treatment of anxiety. It has also muscle relaxant and anticonvulsant actions. [PubChem]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 (GABA_A) receptors, this enhances the effects of GABA by increasing GABA affinity for the GABA receptor. Binding of the inhibitory neurotransmitter GABA to the site opens the chloride channel, resulting in a hyperpolarized cell membrane that prevents further excitation of the cell.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins

Contaminant Type

Amide
Amine
Anti-Anxiety Agent
Anticonvulsant
Drug
GABA Modulator
Metabolite
Organic Compound
Organochloride
Synthetic Compound

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
7-Chloro-2,3-dihydro-2,2-dihydroxy-5-phenyl-1H-1,4-benzodiazepine-3-carboxylic acid	ChEBI
Clorazepate	ChEBI
7-Chloro-2,3-dihydro-2,2-dihydroxy-5-phenyl-1H-1,4-benzodiazepine-3-carboxylate	Generator
Chlorazepate	MeSH
Clorazepate dipotassium	MeSH
Clorazepate monopotassium	MeSH
Dipotassium chlorazepate	MeSH
Tranxene	MeSH
Tranxilium	MeSH
Clorazepic acid	Generator, KEGG
Dipotassium, clorazepate	MeSH, HMDB
Monopotassium, clorazepate	MeSH, HMDB
Chlorazepate, dipotassium	MeSH, HMDB

Chemical Formula

C₁₆H₁₁ClN₂O₃

Average Molecular Mass

314.723 g/mol

Monoisotopic Mass

314.046 g/mol

CAS Registry Number

23887-31-2

IUPAC Name

7-chloro-2-oxo-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepine-3-carboxylic acid

Traditional Name

clorazepate

SMILES

OC(=O)C1N=C(C2=CC=CC=C2)C2=C(NC1=O)C=CC(Cl)=C2

InChI Identifier

InChI=1S/C16H11ClN2O3/c17-10-6-7-12-11(8-10)13(9-4-2-1-3-5-9)19-14(16(21)22)15(20)18-12/h1-8,14H,(H,18,20)(H,21,22)

InChI Key

XDDJGVMJFWAHJX-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Substituents

1,4-benzodiazepine
Alpha-amino acid or derivatives
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Benzenoid
1,3-dicarbonyl compound
Carboxamide group
Ketimine
Lactam
Secondary carboxylic acid amide
Carboxylic acid derivative
Carboxylic acid
Azacycle
Organic 1,3-dipolar compound
Monocarboxylic acid or derivatives
Propargyl-type 1,3-dipolar organic compound
Organopnictogen compound
Organic oxygen compound
Imine
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organohalogen compound
Organochloride
Organonitrogen compound
Organooxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

1,4-benzodiazepinone (CHEBI:3761 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

GABA modulator

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Very soluble

Predicted Properties

Property	Value	Source
Water Solubility	0.025 g/L	ALOGPS
logP	2.68	ALOGPS
logP	3.21	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	3.32	ChemAxon
pKa (Strongest Basic)	-0.64	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	78.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	82.68 m³·mol⁻¹	ChemAxon
Polarizability	30.63 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-2090000000-36dc0db4681a42cb62d1	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00xr-9153000000-20955633c43ee4b5fcf3	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0039000000-04f8ade5dbb98231f6d5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0194000000-77f2c863a9b5ed450724	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0w4r-3390000000-08793ab9fa2d5c97ebe8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03xr-0089000000-f7743c0f914c2fc65685	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-1092000000-a7f9ddb60f21ad0d8c34	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9010000000-4ba3a72ff61da2cab011	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0009000000-3b6dc9550f10c7fb899e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kb-0095000000-26882b3fd53c73fd3908	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-0090000000-4b8c3ab746b6ade0d1f6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0009000000-4c893c51087ae5eb95c9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-2090000000-16b08349edcd85152d86	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001l-9000000000-071a2b32b700b46350ad	Spectrum

Toxicity Profile

Route of Exposure

Rapidly absorbed following oral administration (bioavailability is 91%).

Mechanism of Toxicity

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 (GABA_A) receptors, this enhances the effects of GABA by increasing GABA affinity for the GABA receptor. Binding of the inhibitory neurotransmitter GABA to the site opens the chloride channel, resulting in a hyperpolarized cell membrane that prevents further excitation of the cell.

Metabolism

The drug is metabolized in the liver and excreted primarily in the urine. The primary metabolite, nordiazepam, is further metabolized by hydroxylation. The major urinary metabolite is conjugated oxazepam (3-hydroxynordiazepam), and smaller amounts of conjugated p-hydroxynordiazepam and nordiazepam are also found in the urine. Route of Elimination: The drug is metabolized in the liver and excreted primarily in the urine. Half Life: The serum half-life is about 2 days. Nordiazepam, the primary metabolite, quickly appears in the blood and is eliminated from the plasma with an apparent half-life of about 40 to 50 hours.

Toxicity Values

LD50: 1320 mg/kg (Oral, Rat) (1) LD50: >1600 mg/kg (Oral, Rat)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For the management of anxiety disorders or for the short-term relief of the symptoms of anxiety. Also used as adjunctive therapy in the management of partial seizures and for the symptomatic relief of acute alcohol withdrawal.

Minimum Risk Level

Not Available

Health Effects

May cause a potentially dangerous rash that may develop into Stevens Johnson syndrome, an extremely rare but potentially fatal skin disease.

Symptoms

Not Available

Treatment

The treatment of overdosage should consist of the general measures employed in the management of overdosage of any CNS depressant. Gastric evacuation either by the induction of emesis, lavage, or both, should be performed immediately. General supportive care, including frequent monitoring of the vital signs and close observation of the patient, is indicated. Hypotension, though rarely reported, may occur with large overdoses. In such cases the use of agents such as norepinephrine bitartrate injection, USP or metaraminol bitartrate injection, USP should be considered. Flumazenil, a specific benzodiazepine receptor antagonist, is indicated for the complete or partial reversal of the sedative effects of benzodiazepines and may be used in situations when an overdose with a benzodiazepine is known or suspected. (4)

Concentrations

Not Available

External Links

DrugBank ID

DB00628

HMDB ID

HMDB0244826

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID