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

Details

Stereochemistry RACEMIC
Molecular Formula C16H10ClN2O3.2K.HO
Molecular Weight 408.919
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CLORAZEPATE DIPOTASSIUM

SMILES

[OH-].[K+].[K+].[O-]C(=O)C1N=C(C2=CC=CC=C2)C3=C(NC1=O)C=CC(Cl)=C3

InChI

InChIKey=QCHSEDTUUKDTIG-UHFFFAOYSA-L
InChI=1S/C16H11ClN2O3.2K.H2O/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);;;1H2/q;2*+1;/p-2

HIDE SMILES / InChI

Molecular Formula C16H10ClN2O3
Molecular Weight 313.715
Charge -1
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Molecular Formula K
Molecular Weight 39.0983
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula HO
Molecular Weight 17.0073
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
The effects of benzodiazepine use during pregnancy and lactation.
1994 Nov-Dec
[Acute intermittent porphyria revealed by a paradoxical reaction to a benzodiazepine].
2001 Aug-Sep
Comparison of patient questionnaires, medical records, and plasma assays in assessing exposure to benzodiazepines in elderly subjects.
2001 Jun
Settlement plan approved for lorazepam, clorazepate overcharges.
2001 Jun 15
[Voluntary poisoning by ingestion of Datura stramonium. Another cause of hospitalization in youth seeking strong sensations].
2003 Jun
[Can treatment associated with ticlopidine and nifedipine increase serum levels of phenobarbital?].
2003 Mar 1-15
Clorazepate dipotassium versus midazolam for premedication in clear corneal cataract surgery.
2003 Oct
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
Hypersensitivity to chlorazepate dipotassium.
2005 Feb
Anxiolytic properties of agomelatine, an antidepressant with melatoninergic and serotonergic properties: role of 5-HT2C receptor blockade.
2005 Feb
Interactions of buprenorphine and dipotassium clorazepate on anxiety and memory functions in the mouse.
2006 Nov 8
[Psoriasis and anxiety: marked improvement after anxiolytic therapy].
2006 Sep
Piloerection induced by replacing fluvoxamine with milnacipran.
2007 Jun
A rapid fluorimetric screening method for the 1,4-benzodiazepines: determination of their metabolite oxazepam in urine.
2007 May 15
The beta-lactam antibiotic ceftriaxone inhibits physical dependence and abstinence-induced withdrawal from cocaine, amphetamine, methamphetamine, and clorazepate in planarians.
2008 Apr 28
[Tolerance of prostate biopsy with use of local anesthesia and benzodiazepines: a randomized, prospective study].
2010 Jan
Paradoxical reaction to midazolam reversed with flumazenil.
2010 Jul
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
Substance Class Chemical
Created
by admin
on Sat Dec 16 16:44:24 UTC 2023
Edited
by admin
on Sat Dec 16 16:44:24 UTC 2023
Record UNII
63FN7G03XY
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CLORAZEPATE DIPOTASSIUM
JAN   ORANGE BOOK   USAN   USP   VANDF   WHO-DD  
USAN  
Official Name English
Clorazepate dipotassium [WHO-DD]
Common Name English
GEN-XENE
Brand Name English
CLORAZEPIC ACID DIPOTASSIUM SALT
MI  
Common Name English
1H-1,4-BENZODIAZEPINE-3-CARBOXYLIC ACID, 7-CHLORO-2,3-DIHYDRO-2-OXO-5-PHENYL-, POTASSIUM SALT COMPOUND WITH POTASSIUM HYDROXIDE (1:1)
Systematic Name English
DIPOTASSIUM CLORAZEPATE
EP   INN   MART.  
INN  
Official Name English
CLORAZEPIC ACID DIPOTASSIUM SALT [MI]
Common Name English
CLORAZEPATE DIPOTASSIUM CIV [USP-RS]
Common Name English
CLORAZEPATE DIPOTASSIUM CIV
USP-RS  
Common Name English
4306CB
Code English
CM 4306
Code English
CLORAZEPATE DIPOTASSIUM [ORANGE BOOK]
Common Name English
AB 35616
Code English
TRANXENE
Brand Name English
Potassium 7-chloro-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepine-3-carboxylate compound with potassium hydroxide (1:1)
Systematic Name English
DIPOTASSIUM CLORAZEPATE [MART.]
Common Name English
TR 19119
Code English
ABBOTT-35616
Code English
4306 CB
Code English
CLORAZEPATE DIPOTASSIUM [USAN]
Common Name English
CLORAZEPATE DIPOTASSIUM [JAN]
Common Name English
CLORAZEPATE DIPOTASSIUM [VANDF]
Common Name English
4306-CB
Code English
CLORAZEPATE DIPOTASSIUM [USP MONOGRAPH]
Common Name English
dipotassium clorazepate [INN]
Common Name English
DIPOTASSIUM CLORAZEPATE [EP IMPURITY]
Common Name English
CB 4306
Code English
Classification Tree Code System Code
WHO-VATC QN05BA05
Created by admin on Sat Dec 16 16:44:25 UTC 2023 , Edited by admin on Sat Dec 16 16:44:25 UTC 2023
NCI_THESAURUS C1012
Created by admin on Sat Dec 16 16:44:25 UTC 2023 , Edited by admin on Sat Dec 16 16:44:25 UTC 2023
Code System Code Type Description
CHEBI
3762
Created by admin on Sat Dec 16 16:44:25 UTC 2023 , Edited by admin on Sat Dec 16 16:44:25 UTC 2023
PRIMARY
CAS
57109-90-7
Created by admin on Sat Dec 16 16:44:25 UTC 2023 , Edited by admin on Sat Dec 16 16:44:25 UTC 2023
PRIMARY
INN
2224
Created by admin on Sat Dec 16 16:44:25 UTC 2023 , Edited by admin on Sat Dec 16 16:44:25 UTC 2023
PRIMARY
RS_ITEM_NUM
1140509
Created by admin on Sat Dec 16 16:44:25 UTC 2023 , Edited by admin on Sat Dec 16 16:44:25 UTC 2023
PRIMARY
MERCK INDEX
m3662
Created by admin on Sat Dec 16 16:44:25 UTC 2023 , Edited by admin on Sat Dec 16 16:44:25 UTC 2023
PRIMARY Merck Index
FDA UNII
63FN7G03XY
Created by admin on Sat Dec 16 16:44:25 UTC 2023 , Edited by admin on Sat Dec 16 16:44:25 UTC 2023
PRIMARY
DAILYMED
63FN7G03XY
Created by admin on Sat Dec 16 16:44:25 UTC 2023 , Edited by admin on Sat Dec 16 16:44:25 UTC 2023
PRIMARY
EPA CompTox
DTXSID20972578
Created by admin on Sat Dec 16 16:44:25 UTC 2023 , Edited by admin on Sat Dec 16 16:44:25 UTC 2023
PRIMARY
MESH
D003009
Created by admin on Sat Dec 16 16:44:25 UTC 2023 , Edited by admin on Sat Dec 16 16:44:25 UTC 2023
PRIMARY
SMS_ID
100000090126
Created by admin on Sat Dec 16 16:44:25 UTC 2023 , Edited by admin on Sat Dec 16 16:44:25 UTC 2023
PRIMARY
NCI_THESAURUS
C47459
Created by admin on Sat Dec 16 16:44:25 UTC 2023 , Edited by admin on Sat Dec 16 16:44:25 UTC 2023
PRIMARY
RXCUI
2607
Created by admin on Sat Dec 16 16:44:25 UTC 2023 , Edited by admin on Sat Dec 16 16:44:25 UTC 2023
PRIMARY RxNorm
PUBCHEM
167305
Created by admin on Sat Dec 16 16:44:25 UTC 2023 , Edited by admin on Sat Dec 16 16:44:25 UTC 2023
PRIMARY
ECHA (EC/EINECS)
260-565-6
Created by admin on Sat Dec 16 16:44:25 UTC 2023 , Edited by admin on Sat Dec 16 16:44:25 UTC 2023
PRIMARY
DRUG BANK
DBSALT000953
Created by admin on Sat Dec 16 16:44:25 UTC 2023 , Edited by admin on Sat Dec 16 16:44:25 UTC 2023
PRIMARY
EVMPD
SUB11919MIG
Created by admin on Sat Dec 16 16:44:25 UTC 2023 , Edited by admin on Sat Dec 16 16:44:25 UTC 2023
PRIMARY
ChEMBL
CHEMBL1213252
Created by admin on Sat Dec 16 16:44:25 UTC 2023 , Edited by admin on Sat Dec 16 16:44:25 UTC 2023
PRIMARY
CAS
23895-00-3
Created by admin on Sat Dec 16 16:44:25 UTC 2023 , Edited by admin on Sat Dec 16 16:44:25 UTC 2023
ALTERNATIVE
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY