PRAZEPAM

Details

Stereochemistry	ACHIRAL
Molecular Formula	C19H17ClN2O
Molecular Weight	324.804
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

ClC1=CC2=C(C=C1)N(CC3CC3)C(=O)CN=C2C4=CC=CC=C4

InChI

InChIKey=MWQCHHACWWAQLJ-UHFFFAOYSA-N

InChI=1S/C19H17ClN2O/c20-15-8-9-17-16(10-15)19(14-4-2-1-3-5-14)21-11-18(23)22(17)12-13-6-7-13/h1-5,8-10,13H,6-7,11-12H2

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1959497
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/6106488

Prazepam is a benzodiazepine derivative and is indicated to treat symptoms of anxiety. Benzodiazepines are used to treat severe incapacitating symptoms or symptoms leading to an extreme suffering for the patient. Prazepam is believed to stimulate GABA receptors in the ascending reticular activating system. Since GABA is inhibitory, receptor stimulation increases inhibition and blocks both cortical and limbic arousal following stimulation of the brain stem reticular formation. Prazepam is a prodrug for N-desmethyl-diazepam, which is responsible for the therapeutic effects of prazepam. Prazepam was discontinued in USA.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
GABA-A receptor; anion channel 202 Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/?term=6114911	Activator 1430

Conditions

Condition	Modality	Targets	Highest Phase	Product
Anxiety 267 Sources: http://mri.medagencies.org/download/BE_H_0143_002_FinalPL.pdf	Primary		Approved 8429	PRAZEPAM Approved Use Unknown Launch Date 1987

C_max

Value	Dose	Co-administered	Analyte	Population
20 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/387419/	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:		PRAZEPAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
36 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/387419/	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:		PRAZEPAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.31 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/387419/	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:		PRAZEPAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
20 mg 4 times / day multiple, oral Highest studied dose Dose: 20 mg, 4 times / day Route: oral Route: multiple Dose: 20 mg, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/4883786	unhealthy, 44 years (range: 29 - 65 years) n = 23 Health Status: unhealthy Condition: alcoholics Age Group: 44 years (range: 29 - 65 years) Sex: M Population Size: 23 Sources: https://pubmed.ncbi.nlm.nih.gov/4883786	Sources: https://pubmed.ncbi.nlm.nih.gov/4883786

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A4 1737	substrate 3367 Sources: https://link.springer.com/article/10.1007/s40262-015-0317-8;https://pubmed.ncbi.nlm.nih.gov/28903606/ Page: 7.0	yes

Sourcing

Vendor/Aggregator	ID	URL
AHH Chemical co.,ltd	MT-58139	http://www.ahhchemical.com/product/MT-58139.html
Alsachim	1620	http://www.alsachim.com/product-C4171-glo.bal-view.html
Ambinter	Amb13889655	http://www.ambinter.com/reference/13889655
Aurora Fine Chemicals LLC	A17.913.329	http://online.aurorafinechemicals.com/info?ID=A17.913.329
Avantor Inc	75835-922	https://us.vwr.com/store/product/21998648/exempted-drug-of-abuse-reference-standards-restek
Clearsynth	CS-EB-01761	https://www.clearsynth.com/en/CSEB01761.html
Clearsynth	CS-ER-01753	https://www.clearsynth.com/en/CSER01753.html
Clearsynth	CS-T-60715	https://www.clearsynth.com/en/CST60715.html
Debye Scientific	DB-047601	http://www.debyesci.com/cas_2955-38-6.html
LGC Standards	DRE-A16286280ME-1000	https://www.lgcstandards.com/US/en/p/DRE-A16286280ME-1000
LGC Standards	LGCAMP1258.00-01	https://www.lgcstandards.com/US/en/p/LGCAMP1258.00-01
LGC Standards	LGCAMP1258.00-02	https://www.lgcstandards.com/US/en/p/LGCAMP1258.00-02
LGC Standards	LGCFOR1258.00	https://www.lgcstandards.com/US/en/p/LGCFOR1258.00
LGC Standards	MM1258.00	https://www.lgcstandards.com/US/en/p/MM1258.00
MuseChem	R032414	https://www.musechem.com/product/R032414.html
Sigma-Aldrich	P-906_CERILLIAN	https://www.sigmaaldrich.com/catalog/product/cerillian/p906?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	P2669000_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/p2669000?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	P3654_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/p3654?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	1554501_USP	https://www.sigmaaldrich.com/catalog/product/usp/1554501?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S540132	http://www.smolecule.com/products/s540132
THE BioTek	bt-279666	https://www.thebiotek.com/product/inhibitors/bt-279666

PubMed

Title	Date	PubMed
Anti-spasticity agents for multiple sclerosis.	2001	11687107
Determination of midazolam and 1'-hydroxymidazolam by liquid chromatography-mass spectrometry in plasma of patients undergoing methadone maintenance treatment.	2003 Jan 5	12450551
Colchicine poisoning: case report of two suicides.	2004 Jul 16	15240048
Polyuria after olanzapine overdose.	2004 Jun	15169711
Development and validation of a liquid chromatographic/electrospray ionization mass spectrometric method for the quantitation of prazepam and its main metabolites in human plasma.	2005 Apr	15712230
Benzodiazepines prescription in Dakar: a study about prescribing habits and knowledge in general practitioners, neurologists and psychiatrists.	2006 Jun	16671957
Using molecular similarity to highlight the challenges of routine immunoassay-based drug of abuse/toxicology screening in emergency medicine.	2009 Apr 28	19400959
Drugs associated with more suicidal ideations are also associated with more suicide attempts.	2009 Oct 2	19798416
Eight self-administered 24-hour dietary recalls using the Internet are feasible in African Americans and Whites: the energetics study.	2010 Jun	20497774

Patents

Sample Use Guides

In Vivo Use Guide

The usual dose is between 10 and 60 mg prazepam. If you are less than 18 years old your dose will be adjusted according to your age and body weight. The maximum dose is 1 mg per kg of body weight per day.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Name

Type

Language

PRAZEPAM

Official Name

English

PRAZEPAM [JAN]

Common Name

English

PRAZEPAM [EP MONOGRAPH]

Common Name

English

NSC-277179

Code

English

PRAZEPAM CIV [USP-RS]

Common Name

English

PRAZEPAM [ORANGE BOOK]

Common Name

English

PRAZEPAM [MI]

Common Name

English

PRAZEPAM [VANDF]

Common Name

English

2H-1,4-BENZODIAZEPIN-2-ONE, 7-CHLORO-1-(CYCLOPROPYLMETHYL)-1,3-DIHYDRO-5-PHENYL-

Systematic Name

English

PRAZEPAM [USAN]

Common Name

English

W 4020

Code

English

PRAZEPAM [IARC]

Common Name

English

PRAZEPAM CIV

Common Name

English

CENTRAX

Brand Name

English

W-4020

Code

English

PRAZEPAM [MART.]

Common Name

English

prazepam [INN]

Common Name

English

7-Chloro-1-(cyclopropylmethyl)-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one

Systematic Name

English

Prazepam [WHO-DD]

Common Name

English

Classification Tree Code System Code

WHO-ATC

N05BA11