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

Details

Stereochemistry ACHIRAL
Molecular Formula C16H13ClN2O
Molecular Weight 284.74
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIAZEPAM

SMILES

CN1C2=CC=C(Cl)C=C2C(=NCC1=O)C3=CC=CC=C3

InChI

InChIKey=AAOVKJBEBIDNHE-UHFFFAOYSA-N
InChI=1S/C16H13ClN2O/c1-19-14-8-7-12(17)9-13(14)16(18-10-15(19)20)11-5-3-2-4-6-11/h2-9H,10H2,1H3

HIDE SMILES / InChI

Molecular Formula C16H13ClN2O
Molecular Weight 284.74
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Diazepam is a benzodiazepine first discovered at Hoffman-La Roche in the late 1950s. Diazepam was approved by FDA for the treatment of anxiety disorders as well as for such conditions as skeletal muscle spasm, alcohol withdrawal syndrom and convulsions (under the most known brand Valium). The drug acts by binding to GABA-A receptors and potentiating GABA evoked current. Chronic diazepam use is associated with tolerance, dependence, and withdrawal.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
[The mechanism of the anticonvulsive action of diazepam].
1975 Mar
The effect of cold and diazepam on the toxicity of fenfluramine in mice.
1975 Mar 15
[Potentiation of local anesthesia in endonasal surgery].
2001
Negative inotropic effect of diazepam in isolated guinea pig heart.
2001 Feb
[Prevention of postoperative nausea and vomiting in gynecologic surgery with 3 fixed doses of metoclopramide, droperidol or placebo].
2001 Feb
Extracellular serotonin is enhanced in the striatum, but not in the dorsal hippocampus or prefrontal cortex, in rats subjected to an operant conflict procedure.
2001 Feb
Molecular modeling and QSAR analysis of the interaction of flavone derivatives with the benzodiazepine binding site of the GABA(A) receptor complex.
2001 Feb
Prenatal stress and postnatal development of neonatal rats--sex-dependent effects on emotional behavior and learning ability of neonatal rats.
2001 Feb
Acyl-CoA binding protein is essential in bloodstream form Trypanosoma brucei.
2001 Feb
Lack of reinforcing effect of the benzodiazepine and tricyclic antidepressant combination of diazepam and dothiepin.
2001 Feb
Effects of different preparations of propofol, diazepam, and etomidate on human neutrophils in vitro.
2001 Feb
Regional and subunit-specific downregulation of acid-sensing ion channels in the pilocarpine model of epilepsy.
2001 Feb
Diazepam in the treatment of GHB dependence.
2001 Feb
[Premedication in ambulatory surgery].
2001 Feb 12
[Febrile convulsions, Treatment and prognosis].
2001 Feb 19
Alterations in cerebral diazepam binding inhibitor expression in drug dependence: a possible biochemical alteration common to drug dependence.
2001 Feb 2
[Premedication for endoscopy].
2001 Feb 2
Inhibition of shock-induced foot tapping behaviour in the gerbil by a tachykinin NK1 receptor antagonist.
2001 Feb 2
Effects of a novel uncompetitive NMDA receptor antagonist, MRZ 2/579 on ethanol self-administration and ethanol withdrawal seizures in the rat.
2001 Feb 9
Evaluation of native GABA(A) receptors containing an alpha 5 subunit.
2001 Feb 9
Chronic benzodiazepine administration facilitates the subsequent development of ethanol dependence.
2001 Feb 9
The role of nitrergic system in lidocaine-induced convulsion in the mouse.
2001 Jan
[Anesthesia for a patient with cardiac sarcoidosis].
2001 Jan
Development of differential tolerance to the sedative and anti-stress effects of benzodiazepines.
2001 Jan
Effect of diazepam and midazolam on the antinociceptive effect of morphine, metamizol and indomethacin in mice.
2001 Jan
Neuropharmacological actions of some binuclear lanthanide(III) complexes.
2001 Jan
Sedative properties of the decoction of the rhizome of Cyperus articulatus.
2001 Jan
Treatment of nonfebrile status epilepticus in Rochester, Minn, from 1965 through 1984.
2001 Jan
Radial entrapment neuropathy due to chronic injection-induced triceps fibrosis.
2001 Jan
The effects of diazepam on sleep spindles: a qualitative and quantitative analysis.
2001 Jan
Effects of melatonin, morphine and diazepam on formalin-induced nociception in mice.
2001 Jan 12
Intranasal midazolam for treating febrile seizures in children. Buccal midazolam for childhood seizures at home preferred to rectal diazepam.
2001 Jan 13
Detection of aneuploidy in rodent and human sperm by multicolor FISH after chronic exposure to diazepam.
2001 Jan 25
In vivo, the direct and seizure-induced neuronal cytotoxicity of kainate and AMPA is modified by the non-competitive antagonist, GYKI 52466.
2001 Jan 26
Simple and sensitive high-performance liquid chromatographic method for the determination of 1,5-benzodiazepine clobazam and its active metabolite N-desmethylclobazam in human serum and urine with application to 1,4-benzodiazepines analysis.
2001 Jan 5
Brain-derived neurotrophic factor superinduction parallels anti-epileptic--neuroprotective treatment in the pilocarpine epilepsy model.
2001 Mar
[3H]Ro 15-1788 binding sites to brain membrane of the saltwater Mugil cephalus.
2001 Mar
Topical anesthesia for cataract surgery: a population-based perspective.
2001 Mar
Effect of leaf essential oil from Piper solmsianum C.DC. in mice behaviour.
2001 Mar
Molecular targets for the myorelaxant action of diazepam.
2001 Mar
Anxiogenic-like effects limit rewarding effects of cocaine in balb/cbyj mice.
2001 Mar
Modulation of GABA(A) receptors by benzodiazepines and barbiturates is autonomous of PKC activation.
2001 Mar
Trimethylolpropane phosphate induces epileptiform discharges in the CA1 region of the rat hippocampus.
2001 Mar 1
A behavioral economic analysis of polydrug abuse in alcoholics: asymmetrical substitution of alcohol and cocaine.
2001 Mar 1
Evidence for a common binding cavity for three general anesthetics within the GABAA receptor.
2001 Mar 15
Female gastrin-releasing peptide receptor (GRP-R)-deficient mice exhibit altered social preference for male conspecifics: implications for GRP/GRP-R modulation of GABAergic function.
2001 Mar 16
Dual effects of melatonin on barbiturate-induced narcosis in rats.
2001 Mar 16
Systemic EMD 68843 injections reduce anxiety in the shock-probe, but not the plus-maze test.
2001 Mar 2
The octadecaneuropeptide [diazepam-binding inhibitor (33-50)] exerts potent anorexigenic effects in rodents.
2001 Mar 2
The R100Q mutation of the GABA(A) alpha(6) receptor subunit may contribute to voluntary aversion to ethanol in the sNP rat line.
2001 Mar 5
Patents

Sample Use Guides

In Vivo Use Guide
Tale 2-10 mg, 2 to 4 times daily.
Route of Administration: Oral
In Vitro Use Guide
Rat brain membranes were treated with diazepam (1-1000 nM) and the drug was shown to enhance the effects of iontophoretically applied GABA.
Substance Class Chemical
Created
by admin
on Mon Oct 21 21:21:56 UTC 2019
Edited
by admin
on Mon Oct 21 21:21:56 UTC 2019
Record UNII
Q3JTX2Q7TU
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIAZEPAM
EP   GREEN BOOK   HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP   VANDF   WHO-DD  
INN   USAN  
Official Name English
DIAZEPAM [EP]
Common Name English
RO 5-2807
Code English
DIAZEPAM [VANDF]
Common Name English
ANSIOLISINA
Common Name English
DIAZEPAM CIV
USP-RS  
Common Name English
VALIUM
Brand Name English
LA-III
Code English
DIAZEPAM [GREEN BOOK]
Common Name English
DIZAC
Brand Name English
SERVIZEPAM
Common Name English
DIAZEPAM [IARC]
Common Name English
RO-5-2807
Code English
DIAZEPAM [USAN]
Common Name English
DIASTAT
Brand Name English
NSC-77518
Code English
LA III
Code English
2H-1,4-BENZODIAZEPIN-2-ONE, 7-CHLORO-1,3-DIHYDRO-1-METHYL-5-PHENYL-
Systematic Name English
NSC-169897
Code English
DIAZEPAM [ORANGE BOOK]
Common Name English
RO-52807
Code English
7-CHLORO-1-METHYL-5-PHENYL-3H-1,4-BENZODIAZEPIN-2(1H)-ONE
Systematic Name English
DIAZEPAM [HSDB]
Common Name English
DIAZEPAM [WHO-DD]
Common Name English
WY-3467
Code English
METHYL DIAZEPINONE
Systematic Name English
CENTRAZEPAM
Common Name English
Q-PAM
Brand Name English
7-CHLORO-1,3-DIHYDRO-1-METHYL-5-PHENYL-2H-1,4-BENZODIAZEPINE-2-ONE
Systematic Name English
VALRELEASE
Brand Name English
DIAZEPAM [MART.]
Common Name English
DIACEPIN
Common Name English
DIAZEPAM [MI]
Common Name English
DIAZEPAM [INN]
Common Name English
DIAZEPAM [USP]
Common Name English
DIAZEPAM [JAN]
Common Name English
NRL-1
Code English
DIAZEPAM CIV [USP-RS]
Common Name English
7-CHLORO-1,3-DIHYDRO-1-METHYL-5-PHENYL-2H-1,4-BENZODIAZEPIN-2-ONE
Systematic Name English
TRANQUASE
Common Name English
Classification Tree Code System Code
NDF-RT N0000007542
Created by admin on Mon Oct 21 21:21:56 UTC 2019 , Edited by admin on Mon Oct 21 21:21:56 UTC 2019
FDA ORPHAN DRUG 384112
Created by admin on Mon Oct 21 21:21:56 UTC 2019 , Edited by admin on Mon Oct 21 21:21:56 UTC 2019
EPA PESTICIDE CODE 600069
Created by admin on Mon Oct 21 21:21:56 UTC 2019 , Edited by admin on Mon Oct 21 21:21:56 UTC 2019
FDA ORPHAN DRUG 334911
Created by admin on Mon Oct 21 21:21:56 UTC 2019 , Edited by admin on Mon Oct 21 21:21:56 UTC 2019
FDA ORPHAN DRUG 518316
Created by admin on Mon Oct 21 21:21:56 UTC 2019 , Edited by admin on Mon Oct 21 21:21:56 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 8.4
Created by admin on Mon Oct 21 21:21:56 UTC 2019 , Edited by admin on Mon Oct 21 21:21:56 UTC 2019
LIVERTOX 295
Created by admin on Mon Oct 21 21:21:56 UTC 2019 , Edited by admin on Mon Oct 21 21:21:56 UTC 2019
WHO-VATC QN05BA01
Created by admin on Mon Oct 21 21:21:56 UTC 2019 , Edited by admin on Mon Oct 21 21:21:56 UTC 2019
FDA ORPHAN DRUG 543516
Created by admin on Mon Oct 21 21:21:56 UTC 2019 , Edited by admin on Mon Oct 21 21:21:56 UTC 2019
FDA ORPHAN DRUG 638118
Created by admin on Mon Oct 21 21:21:56 UTC 2019 , Edited by admin on Mon Oct 21 21:21:56 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 24.3
Created by admin on Mon Oct 21 21:21:56 UTC 2019 , Edited by admin on Mon Oct 21 21:21:56 UTC 2019
WHO-ATC N05BA01
Created by admin on Mon Oct 21 21:21:56 UTC 2019 , Edited by admin on Mon Oct 21 21:21:56 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 05
Created by admin on Mon Oct 21 21:21:56 UTC 2019 , Edited by admin on Mon Oct 21 21:21:56 UTC 2019
FDA ORPHAN DRUG 382512
Created by admin on Mon Oct 21 21:21:56 UTC 2019 , Edited by admin on Mon Oct 21 21:21:56 UTC 2019
DEA NO. 2765
Created by admin on Mon Oct 21 21:21:56 UTC 2019 , Edited by admin on Mon Oct 21 21:21:56 UTC 2019
NCI_THESAURUS C1012
Created by admin on Mon Oct 21 21:21:56 UTC 2019 , Edited by admin on Mon Oct 21 21:21:56 UTC 2019
FDA ORPHAN DRUG 61591
Created by admin on Mon Oct 21 21:21:56 UTC 2019 , Edited by admin on Mon Oct 21 21:21:56 UTC 2019
NDF-RT N0000175694
Created by admin on Mon Oct 21 21:21:56 UTC 2019 , Edited by admin on Mon Oct 21 21:21:56 UTC 2019
Code System Code Type Description
MERCK INDEX
M4267
Created by admin on Mon Oct 21 21:21:56 UTC 2019 , Edited by admin on Mon Oct 21 21:21:56 UTC 2019
PRIMARY Merck Index
RXCUI
3322
Created by admin on Mon Oct 21 21:21:56 UTC 2019 , Edited by admin on Mon Oct 21 21:21:56 UTC 2019
PRIMARY RxNorm
MESH
D003975
Created by admin on Mon Oct 21 21:21:56 UTC 2019 , Edited by admin on Mon Oct 21 21:21:56 UTC 2019
PRIMARY
HSDB
439-14-5
Created by admin on Mon Oct 21 21:21:56 UTC 2019 , Edited by admin on Mon Oct 21 21:21:56 UTC 2019
PRIMARY
DRUG BANK
DB00829
Created by admin on Mon Oct 21 21:21:56 UTC 2019 , Edited by admin on Mon Oct 21 21:21:56 UTC 2019
PRIMARY
EPA CompTox
439-14-5
Created by admin on Mon Oct 21 21:21:56 UTC 2019 , Edited by admin on Mon Oct 21 21:21:56 UTC 2019
PRIMARY
WIKIPEDIA
DIAZEPAM
Created by admin on Mon Oct 21 21:21:56 UTC 2019 , Edited by admin on Mon Oct 21 21:21:56 UTC 2019
PRIMARY
EVMPD
SUB07069MIG
Created by admin on Mon Oct 21 21:21:56 UTC 2019 , Edited by admin on Mon Oct 21 21:21:56 UTC 2019
PRIMARY
IUPHAR
3364
Created by admin on Mon Oct 21 21:21:56 UTC 2019 , Edited by admin on Mon Oct 21 21:21:56 UTC 2019
PRIMARY
LactMed
439-14-5
Created by admin on Mon Oct 21 21:21:56 UTC 2019 , Edited by admin on Mon Oct 21 21:21:56 UTC 2019
PRIMARY
NCI_THESAURUS
C28982
Created by admin on Mon Oct 21 21:21:56 UTC 2019 , Edited by admin on Mon Oct 21 21:21:56 UTC 2019
PRIMARY
INN
1295
Created by admin on Mon Oct 21 21:21:56 UTC 2019 , Edited by admin on Mon Oct 21 21:21:56 UTC 2019
PRIMARY
CAS
439-14-5
Created by admin on Mon Oct 21 21:21:56 UTC 2019 , Edited by admin on Mon Oct 21 21:21:56 UTC 2019
PRIMARY
PUBCHEM
3016
Created by admin on Mon Oct 21 21:21:56 UTC 2019 , Edited by admin on Mon Oct 21 21:21:56 UTC 2019
PRIMARY
ChEMBL
CHEMBL12
Created by admin on Mon Oct 21 21:21:56 UTC 2019 , Edited by admin on Mon Oct 21 21:21:56 UTC 2019
PRIMARY
ECHA (EC/EINECS)
207-122-5
Created by admin on Mon Oct 21 21:21:56 UTC 2019 , Edited by admin on Mon Oct 21 21:21:56 UTC 2019
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
DIAZEPAM
Created by admin on Mon Oct 21 21:21:56 UTC 2019 , Edited by admin on Mon Oct 21 21:21:56 UTC 2019
PRIMARY Description: A white or almost white, crystalline powder; odourless or almost odourless. Solubility: Very slightly soluble in water; soluble in ethanol (~750 g/l) TS. Category: Tranquillizer. Storage: Diazepam should be kept in a well-closed container, protected from light. Definition: Diazepam contains not less than 99.0% and not more than 101.0% of C16H13ClN2O, calculated with reference to the dried substance.
Related Record Type Details
METABOLIC ENZYME -> SUBSTRATE
BINDER->LIGAND
BINDING
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
SALT/SOLVATE -> PARENT
Related Record Type Details
PRODRUG -> METABOLITE ACTIVE
METABOLITE ACTIVE -> PARENT
METABOLITE ACTIVE -> PARENT
METABOLITE ACTIVE -> PARENT
METABOLITE TOXIC -> PARENT
Metabolite produces adverse autonomic nervous symptoms in man.
Related Record Type Details
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
pKa CHEMICAL
Volume of Distribution PHARMACOKINETIC
Tmax PHARMACOKINETIC IV: 8 minutes

IM: 1.31 hours (SYRINGE)

IM: 1.47 hours (AUTOINJECTOR)

EFFECT OF FOOD: DELAYED Tmax

RECTAL GEL: 1.5 hours

PROTEIN BINDING PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC IV: 15-21 HOURS (CHILD 2-12 YEARS)

IV: 40-50 HOURS (INFANT AND TODDLER 1 MONTH TO 2 YEARS)

IV: 18-20 HOURS (ADOLESCENT 12-16 YEARS)

IV: 50-95 HOURS (NEONATE, BIRTH UP TO 1 MONTH)

IV: ABOUT 100 HOURS (ELDERLY 95 YEARS)

IV: ABOUT 15 HOURS (YOUNG ADULT 18 YEARS)

PREMATURE INFANTS, 28-34 WEEKS GESTATIONAL AGE AND 8-81 DAYS POSTPARTUM: 54 HOURS

DESMETHYLDIAZEPAM: UP TO 100 HOURS

GERIATRICS: INCREASES BY ABOUT 1 HOUR FOR EACH YEAR OF AGE BEGINNING WITH A HALF-LIFE OF 20 HOURS AT 20 YEARS OF AGE

CHILDREN 3-8 YEARS: 18 HOURS

FULL TERM INFANTS: 30 HOURS

MAXIMUM TOLERATED DOSE TOXICITY SEDATION, ENDOSCOPIC PROCEDURE: 20 mg IV IMMEDIATELY PRIOR TO PROCEDURE

SEVERE, RECURRENT SEIZURE: 30 mg/dose IV

ORAL BIOAVAILABILITY PHARMACOKINETIC
BIOAVAILABILTY PHARMACOKINETIC