U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C16H11ClN2O3
Molecular Weight 314.723
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CLORAZEPIC ACID

SMILES

OC(=O)C1N=C(C2=CC=CC=C2)C3=C(NC1=O)C=CC(Cl)=C3

InChI

InChIKey=XDDJGVMJFWAHJX-UHFFFAOYSA-N
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)

HIDE SMILES / InChI
Clorazepate is a water-soluble benzodiazepine derivative effective in the treatment of anxiety. It has also muscle relaxant and anticonvulsant actions. Studies in healthy men have shown that clorazepate dipotassium has depressant effects on the central nervous system. clorazepate is a prodrug since orally administered it is rapidly decarboxylated to form nordiazepam, there is essentially no circulating parent drug. Nordiazepam positively modulates GABAA receptors to produce anxiolytic and anticonvulsant effects.

CNS Activity

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
TRANXENE

Approved Use

TRANXENE is indicated for the management of anxiety disorders or for the short-term relief of the symptoms of anxiety. Anxiety or tension associated with the stress of everyday life usually does not require treatment with an anxiolytic. TRANXENE tablets are indicated as adjunctive therapy in the management of partial seizures. The effectiveness of TRANXENE tablets in long-term management of anxiety, that is, more than 4 months, has not been assessed by systematic clinical studies. Long-term studies in epileptic patients, however, have shown continued therapeutic activity. The physician should reassess periodically the usefulness of the drug for the individual patient. TRANXENE tablets are indicated for the symptomatic relief of acute alcohol withdrawal. CONTRAINDICATIONS TRANXENE tablets are contraindicated in patients with a known hypersensitivity to the drug and in those with acute narrow angle glaucoma.

Launch Date

7.8019199E10
Palliative
TRANXENE

Approved Use

TRANXENE is indicated for the management of anxiety disorders or for the short-term relief of the symptoms of anxiety. Anxiety or tension associated with the stress of everyday life usually does not require treatment with an anxiolytic. TRANXENE tablets are indicated as adjunctive therapy in the management of partial seizures. The effectiveness of TRANXENE tablets in long-term management of anxiety, that is, more than 4 months, has not been assessed by systematic clinical studies. Long-term studies in epileptic patients, however, have shown continued therapeutic activity. The physician should reassess periodically the usefulness of the drug for the individual patient. TRANXENE tablets are indicated for the symptomatic relief of acute alcohol withdrawal. CONTRAINDICATIONS TRANXENE tablets are contraindicated in patients with a known hypersensitivity to the drug and in those with acute narrow angle glaucoma.

Launch Date

7.8019199E10
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
245 μg/L
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
NORDAZEPAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
413 μg/L
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
NORDAZEPAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
187 μM × h/mL × kg
15 mg single, oral
dose: 15 mg
route of administration: Oral
experiment type: SINGLE
co-administered: DIGOXIN
NORDAZEPAM plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
230 μM × h/mL × kg
15 mg single, oral
dose: 15 mg
route of administration: Oral
experiment type: SINGLE
co-administered: DIGOXIN
NORDAZEPAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.291 h
20 mg single, intramuscular
dose: 20 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
CLORAZEPIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
2.42 h
20 mg single, intravenous
dose: 20 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CLORAZEPIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
29.8 h
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
NORDAZEPAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
54.7 h
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
NORDAZEPAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
45.1 h
20 mg single, intramuscular
dose: 20 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
NORDAZEPAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
46 h
20 mg single, intravenous
dose: 20 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
NORDAZEPAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
60 mg 1 times / day multiple, oral
Recommended
Dose: 60 mg, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg, 1 times / day
Sources:
unhealthy, 9-12 years
Health Status: unhealthy
Age Group: 9-12 years
Sex: unknown
Sources:
90 mg 1 times / day multiple, oral
Recommended
Dose: 90 mg, 1 times / day
Route: oral
Route: multiple
Dose: 90 mg, 1 times / day
Sources:
unhealthy, adult
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
PubMed

PubMed

TitleDatePubMed
Systematic review of the benzodiazepines. Guidelines for data sheets on diazepam, chlordiazepoxide, medazepam, clorazepate, lorazepam, oxazepam, temazepam, triazolam, nitrazepam, and flurazepam. Committee on the Review of Medicines.
1980 Mar 29
Allosteric modulation by benzodiazepine receptor ligands of the GABAA receptor channel expressed in Xenopus oocytes.
1988 Jan
The effects of benzodiazepine use during pregnancy and lactation.
1994 Nov-Dec
Differences between the tolerance characteristics of two anticonvulsant benzodiazepines in the amygdaloid-kindled rat.
2001 Jul 20
[Catatonia de novo, report on a case: immediate vital prognosis and psychiatric prognosis in longer term].
2003 Jan-Feb
Clobazam as a new antiepileptic drug and clorazepate dipotassium as an alternative antiepileptic drug in Japan.
2004
[Benzodiazepine poisoning in a neonate: clinical and toxicokinetic evaluation following enterodialysis with activated charcoal].
2004 Jul
Acute and chronic administration of clorazepate modifies the cell surface regulation of mu opioid receptors induced by buprenorphine in specific regions of the rat brain.
2005 Aug 9
Anxiolytic properties of agomelatine, an antidepressant with melatoninergic and serotonergic properties: role of 5-HT2C receptor blockade.
2005 Feb
Piloerection induced by replacing fluvoxamine with milnacipran.
2007 Jun
[Abuse of alcohol and benzodiazepine during substitution therapy in heroin addicts: a review of the literature].
2009 Jun
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.
2010 Dec
Paradoxical reaction to midazolam reversed with flumazenil.
2010 Jul
Blood concentrations of clobazam and norclobazam in a lethal case involving clobazam, meprobamate and clorazepate.
2010 Nov
Patents

Patents

Sample Use Guides

For the symptomatic relief of anxiety: TRANXENE T-TAB tablets are administered orally in divided doses. The usual daily dose is 30 mg. The dose should be adjusted gradually within the range of 15 to 60 mg daily in accordance with the response of the patient. In elderly or debilitated patients it is advisable to initiate treatment at a daily dose of 7.5 to 15 mg. TRANXENE tablets may also be administered in a single dose daily at bedtime; the recommended initial dose is 15 mg. After the initial dose, the response of the patient may require adjustment of subsequent dosage. Lower doses may be indicated in the elderly patient. Drowsiness may occur at the initiation of treatment and with dosage increment. As an Adjunct to Antiepileptic Drugs: In order to minimize drowsiness, the recommended initial dosages and dosage increments should not be exceeded. Adults: The maximum recommended initial dose in patients over 12 years old is 7.5 mg three times a day. Dosage should be increased by no more than 7.5 mg every week and should not exceed 90 mg/day. Children (9-12 years): The maximum recommended initial dose is 7.5 mg two times a day. Dosage should be increased by no more than 7.5 mg every week and should not exceed 60 mg/day
Route of Administration: Oral
In Vitro Use Guide
Unknown
Name Type Language
CLORAZEPIC ACID
HSDB   MART.   MI   WHO-DD  
Common Name English
CLORAZEPIC ACID [MART.]
Common Name English
4306-CB FREE ACID
Code English
Clorazepic acid [WHO-DD]
Common Name English
CLORAZEPATE
VANDF  
Common Name English
CHLORAZEPATE
Common Name English
CLORAZEPIC ACID [HSDB]
Common Name English
CLORAZEPATE [VANDF]
Common Name English
CLORAZEPIC ACID [MI]
Common Name English
1H-1,4-BENZODIAZEPINE-3-CARBOXYLIC ACID, 7-CHLORO-2,3-DIHYDRO-2-OXO-5-PHENYL-
Systematic Name English
4311 CB
Code English
7-CHLORO-2,3-DIHYDRO-2-OXO-5-PHENYL-1H-1,4-BENZODIAZEPINE-3-CARBOXYLIC ACID
Systematic Name English
7-CHLORO-2,3-DIHYDRO-2,2-DIHYDROXY-5-PHENYL-1H-1,4-BENZODIAZEPINE-3-CARBOXYLIC ACID
Systematic Name English
ABBOTT-35616 FREE ACID
Code English
Classification Tree Code System Code
LIVERTOX NBK548330
Created by admin on Fri Dec 15 15:20:16 UTC 2023 , Edited by admin on Fri Dec 15 15:20:16 UTC 2023
DEA NO. 2768
Created by admin on Fri Dec 15 15:20:16 UTC 2023 , Edited by admin on Fri Dec 15 15:20:16 UTC 2023
NCI_THESAURUS C1012
Created by admin on Fri Dec 15 15:20:16 UTC 2023 , Edited by admin on Fri Dec 15 15:20:16 UTC 2023
NDF-RT N0000007542
Created by admin on Fri Dec 15 15:20:16 UTC 2023 , Edited by admin on Fri Dec 15 15:20:16 UTC 2023
WHO-ATC N05BA05
Created by admin on Fri Dec 15 15:20:16 UTC 2023 , Edited by admin on Fri Dec 15 15:20:16 UTC 2023
NDF-RT N0000175694
Created by admin on Fri Dec 15 15:20:16 UTC 2023 , Edited by admin on Fri Dec 15 15:20:16 UTC 2023
Code System Code Type Description
HSDB
3041
Created by admin on Fri Dec 15 15:20:16 UTC 2023 , Edited by admin on Fri Dec 15 15:20:16 UTC 2023
PRIMARY
ECHA (EC/EINECS)
245-926-8
Created by admin on Fri Dec 15 15:20:16 UTC 2023 , Edited by admin on Fri Dec 15 15:20:16 UTC 2023
PRIMARY
EVMPD
SUB01370MIG
Created by admin on Fri Dec 15 15:20:16 UTC 2023 , Edited by admin on Fri Dec 15 15:20:16 UTC 2023
PRIMARY
CAS
20432-69-3
Created by admin on Fri Dec 15 15:20:16 UTC 2023 , Edited by admin on Fri Dec 15 15:20:16 UTC 2023
SUPERSEDED
DRUG CENTRAL
711
Created by admin on Fri Dec 15 15:20:16 UTC 2023 , Edited by admin on Fri Dec 15 15:20:16 UTC 2023
PRIMARY
CHEBI
59590
Created by admin on Fri Dec 15 15:20:16 UTC 2023 , Edited by admin on Fri Dec 15 15:20:16 UTC 2023
PRIMARY
CAS
28425-34-5
Created by admin on Fri Dec 15 15:20:16 UTC 2023 , Edited by admin on Fri Dec 15 15:20:16 UTC 2023
SUPERSEDED
FDA UNII
D51WO0G0L4
Created by admin on Fri Dec 15 15:20:16 UTC 2023 , Edited by admin on Fri Dec 15 15:20:16 UTC 2023
PRIMARY
DRUG BANK
DB00628
Created by admin on Fri Dec 15 15:20:16 UTC 2023 , Edited by admin on Fri Dec 15 15:20:16 UTC 2023
PRIMARY
WIKIPEDIA
CLORAZEPATE
Created by admin on Fri Dec 15 15:20:16 UTC 2023 , Edited by admin on Fri Dec 15 15:20:16 UTC 2023
PRIMARY
SMS_ID
100000124395
Created by admin on Fri Dec 15 15:20:16 UTC 2023 , Edited by admin on Fri Dec 15 15:20:16 UTC 2023
PRIMARY
LACTMED
Clorazepate
Created by admin on Fri Dec 15 15:20:16 UTC 2023 , Edited by admin on Fri Dec 15 15:20:16 UTC 2023
PRIMARY
RXCUI
235408
Created by admin on Fri Dec 15 15:20:16 UTC 2023 , Edited by admin on Fri Dec 15 15:20:16 UTC 2023
PRIMARY
EPA CompTox
DTXSID20863674
Created by admin on Fri Dec 15 15:20:16 UTC 2023 , Edited by admin on Fri Dec 15 15:20:16 UTC 2023
PRIMARY
PUBCHEM
2809
Created by admin on Fri Dec 15 15:20:16 UTC 2023 , Edited by admin on Fri Dec 15 15:20:16 UTC 2023
PRIMARY
MERCK INDEX
m3662
Created by admin on Fri Dec 15 15:20:16 UTC 2023 , Edited by admin on Fri Dec 15 15:20:16 UTC 2023
PRIMARY Merck Index
IUPHAR
7548
Created by admin on Fri Dec 15 15:20:16 UTC 2023 , Edited by admin on Fri Dec 15 15:20:16 UTC 2023
PRIMARY
RXCUI
2353
Created by admin on Fri Dec 15 15:20:16 UTC 2023 , Edited by admin on Fri Dec 15 15:20:16 UTC 2023
ALTERNATIVE
ChEMBL
CHEMBL1213252
Created by admin on Fri Dec 15 15:20:16 UTC 2023 , Edited by admin on Fri Dec 15 15:20:16 UTC 2023
PRIMARY
NCI_THESAURUS
C61687
Created by admin on Fri Dec 15 15:20:16 UTC 2023 , Edited by admin on Fri Dec 15 15:20:16 UTC 2023
PRIMARY
DAILYMED
D51WO0G0L4
Created by admin on Fri Dec 15 15:20:16 UTC 2023 , Edited by admin on Fri Dec 15 15:20:16 UTC 2023
PRIMARY
CAS
23887-31-2
Created by admin on Fri Dec 15 15:20:16 UTC 2023 , Edited by admin on Fri Dec 15 15:20:16 UTC 2023
PRIMARY
EVMPD
SUB32039
Created by admin on Fri Dec 15 15:20:16 UTC 2023 , Edited by admin on Fri Dec 15 15:20:16 UTC 2023
PRIMARY
CAS
149128-42-7
Created by admin on Fri Dec 15 15:20:16 UTC 2023 , Edited by admin on Fri Dec 15 15:20:16 UTC 2023
SUPERSEDED
CHEBI
3761
Created by admin on Fri Dec 15 15:20:16 UTC 2023 , Edited by admin on Fri Dec 15 15:20:16 UTC 2023
PRIMARY