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Details

Stereochemistry ACHIRAL
Molecular Formula C16H13ClN2O
Molecular Weight 284.74
Optical Activity NONE
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 No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/24552479

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

Hoffman-La Roche
135
Curator's Comment: # Hoffmann-La Roche

Approval Year

1963
72
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2752
 8.6 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
VALIUM

Approved Use

Valium is indicated for the management of anxiety disorders or for the shortterm relief of the symptoms of anxiety. In acute alcohol withdrawal, Valium may be useful in the symptomatic relief of acute agitation, tremor, impending or acute delirium tremens and hallucinosis. Valium is a useful adjunct for the relief of skeletal muscle spasm due to reflex spasm to local pathology (such as inflammation of the muscles or joints, or secondary to trauma), spasticity caused by upper motor neuron disorders (such as cerebral palsy and paraplegia), athetosis, and stiff-man syndrome. Oral Valium may be used adjunctively in convulsive disorders, although it has not proved useful as the sole therapy.

Launch Date

1963
Palliative
Approved
8583
VALIUM

Approved Use

Valium is indicated for the management of anxiety disorders or for the shortterm relief of the symptoms of anxiety. In acute alcohol withdrawal, Valium may be useful in the symptomatic relief of acute agitation, tremor, impending or acute delirium tremens and hallucinosis. Valium is a useful adjunct for the relief of skeletal muscle spasm due to reflex spasm to local pathology (such as inflammation of the muscles or joints, or secondary to trauma), spasticity caused by upper motor neuron disorders (such as cerebral palsy and paraplegia), athetosis, and stiff-man syndrome. Oral Valium may be used adjunctively in convulsive disorders, although it has not proved useful as the sole therapy.

Launch Date

1963
Palliative
Approved
8583
VALIUM

Approved Use

Valium is indicated for the management of anxiety disorders or for the shortterm relief of the symptoms of anxiety. In acute alcohol withdrawal, Valium may be useful in the symptomatic relief of acute agitation, tremor, impending or acute delirium tremens and hallucinosis. Valium is a useful adjunct for the relief of skeletal muscle spasm due to reflex spasm to local pathology (such as inflammation of the muscles or joints, or secondary to trauma), spasticity caused by upper motor neuron disorders (such as cerebral palsy and paraplegia), athetosis, and stiff-man syndrome. Oral Valium may be used adjunctively in convulsive disorders, although it has not proved useful as the sole therapy.

Launch Date

1963
Palliative
Approved
8583
VALIUM

Approved Use

Valium is indicated for the management of anxiety disorders or for the shortterm relief of the symptoms of anxiety. In acute alcohol withdrawal, Valium may be useful in the symptomatic relief of acute agitation, tremor, impending or acute delirium tremens and hallucinosis. Valium is a useful adjunct for the relief of skeletal muscle spasm due to reflex spasm to local pathology (such as inflammation of the muscles or joints, or secondary to trauma), spasticity caused by upper motor neuron disorders (such as cerebral palsy and paraplegia), athetosis, and stiff-man syndrome. Oral Valium may be used adjunctively in convulsive disorders, although it has not proved useful as the sole therapy.

Launch Date

1963
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
208 ng/mL
Clinical Trial
https://clinicaltrials.gov/ct2/show/NCT01417078
20 mg single, intranasal
dose: 20 mg
route of administration: intranasal
experiment type: single
co-administered:
DIAZEPAM plasma
Homo sapiens
population: unhealthy
age:
sex:
food status:
75 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/1505149
2 mg single, oral
dose: 2 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DIAZEPAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
172 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/1505149
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DIAZEPAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
317 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/1505149
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DIAZEPAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1227 ng*h/mL
Clinical Trial
https://clinicaltrials.gov/ct2/show/NCT01417078
20 mg single, intranasal
dose: 20 mg
route of administration: intranasal
experiment type: single
co-administered:
DIAZEPAM plasma
Homo sapiens
population: unhealthy
age:
sex:
food status:
330 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/1505149
2 mg single, oral
dose: 2 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DIAZEPAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
779 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/1505149
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DIAZEPAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
1530 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/1505149
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DIAZEPAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
48 h
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/013263s094lbl.pdf
unknown, oral
 DIAZEPAM plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
2%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/013263s094lbl.pdf
unknown, oral
 DIAZEPAM plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
2000 mg single, oral
Overdose
Dose: 2000 mg
Route: oral
Route: single
Dose: 2000 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/357765
healthy, 28 years
Health Status: healthy
Age Group: 28 years
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/357765
Sources:
https://pubmed.ncbi.nlm.nih.gov/357765
500 mg single, oral
Overdose
Dose: 500 mg
Route: oral
Route: single
Dose: 500 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/357765
unhealthy, 61 years
Health Status: unhealthy
Age Group: 61 years
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/357765
Sources:
https://pubmed.ncbi.nlm.nih.gov/357765
0.2 mg/kg 2 times / day multiple, rectal
Recommended
Dose: 0.2 mg/kg, 2 times / day
Route: rectal
Route: multiple
Dose: 0.2 mg/kg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2021/020648s022lbl.pdf
unhealthy, > 12 years
Health Status: unhealthy
Age Group: > 12 years
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2021/020648s022lbl.pdf
Other AEs: Respiratory depression, Abuse...
Other AEs:
Respiratory depression (serious|grade 5)
Abuse (serious|grade 5)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2021/020648s022lbl.pdf
0.2 mg/kg 2 times / day multiple, rectal
Recommended
Dose: 0.2 mg/kg, 2 times / day
Route: rectal
Route: multiple
Dose: 0.2 mg/kg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2021/020648s022lbl.pdf
unhealthy, > 12 years
Health Status: unhealthy
Age Group: > 12 years
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2021/020648s022lbl.pdf
Disc. AE: Somnolence, Hypoventilation...
AEs leading to
discontinuation/dose reduction:
Somnolence (3 patients)
Hypoventilation (2 patients)
Rash (2 patients)
Asthenia (1 patient)
Hyperkinesia (1 patient)
Incoordination (1 patient)
Vasodilatation (1 patient)
Urticaria (1 patient)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2021/020648s022lbl.pdf
10 mg 2 times / day multiple, intranasal
Recommended
Dose: 10 mg, 2 times / day
Route: intranasal
Route: multiple
Dose: 10 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/211635s000lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/211635s000lbl.pdf
Other AEs: Respiratory depression...
Other AEs:
Respiratory depression (serious|grade 5)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/211635s000lbl.pdf
10 mg 4 times / day multiple, intramuscular
Recommended
Dose: 10 mg, 4 times / day
Route: intramuscular
Route: multiple
Dose: 10 mg, 4 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2021/020124s033lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2021/020124s033lbl.pdf
Other AEs: Respiratory depression, Abuse...
Other AEs:
Respiratory depression (serious|grade 5)
Abuse (serious|grade 5)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2021/020124s033lbl.pdf
10 mg 4 times / day multiple, oral
Recommended
Dose: 10 mg, 4 times / day
Route: oral
Route: multiple
Dose: 10 mg, 4 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/013263s094lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/013263s094lbl.pdf
Other AEs: Respiratory depression...
Other AEs:
Respiratory depression (serious|grade 5)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/013263s094lbl.pdf
AEs

AEs

AESignificanceDosePopulation
Abuse serious|grade 5
0.2 mg/kg 2 times / day multiple, rectal
Recommended
Dose: 0.2 mg/kg, 2 times / day
Route: rectal
Route: multiple
Dose: 0.2 mg/kg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2021/020648s022lbl.pdf
unhealthy, > 12 years
Health Status: unhealthy
Age Group: > 12 years
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2021/020648s022lbl.pdf
Respiratory depression serious|grade 5
0.2 mg/kg 2 times / day multiple, rectal
Recommended
Dose: 0.2 mg/kg, 2 times / day
Route: rectal
Route: multiple
Dose: 0.2 mg/kg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2021/020648s022lbl.pdf
unhealthy, > 12 years
Health Status: unhealthy
Age Group: > 12 years
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2021/020648s022lbl.pdf
Asthenia 1 patient
Disc. AE
0.2 mg/kg 2 times / day multiple, rectal
Recommended
Dose: 0.2 mg/kg, 2 times / day
Route: rectal
Route: multiple
Dose: 0.2 mg/kg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2021/020648s022lbl.pdf
unhealthy, > 12 years
Health Status: unhealthy
Age Group: > 12 years
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2021/020648s022lbl.pdf
Hyperkinesia 1 patient
Disc. AE
0.2 mg/kg 2 times / day multiple, rectal
Recommended
Dose: 0.2 mg/kg, 2 times / day
Route: rectal
Route: multiple
Dose: 0.2 mg/kg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2021/020648s022lbl.pdf
unhealthy, > 12 years
Health Status: unhealthy
Age Group: > 12 years
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2021/020648s022lbl.pdf
Incoordination 1 patient
Disc. AE
0.2 mg/kg 2 times / day multiple, rectal
Recommended
Dose: 0.2 mg/kg, 2 times / day
Route: rectal
Route: multiple
Dose: 0.2 mg/kg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2021/020648s022lbl.pdf
unhealthy, > 12 years
Health Status: unhealthy
Age Group: > 12 years
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2021/020648s022lbl.pdf
Urticaria 1 patient
Disc. AE
0.2 mg/kg 2 times / day multiple, rectal
Recommended
Dose: 0.2 mg/kg, 2 times / day
Route: rectal
Route: multiple
Dose: 0.2 mg/kg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2021/020648s022lbl.pdf
unhealthy, > 12 years
Health Status: unhealthy
Age Group: > 12 years
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2021/020648s022lbl.pdf
Vasodilatation 1 patient
Disc. AE
0.2 mg/kg 2 times / day multiple, rectal
Recommended
Dose: 0.2 mg/kg, 2 times / day
Route: rectal
Route: multiple
Dose: 0.2 mg/kg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2021/020648s022lbl.pdf
unhealthy, > 12 years
Health Status: unhealthy
Age Group: > 12 years
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2021/020648s022lbl.pdf
Hypoventilation 2 patients
Disc. AE
0.2 mg/kg 2 times / day multiple, rectal
Recommended
Dose: 0.2 mg/kg, 2 times / day
Route: rectal
Route: multiple
Dose: 0.2 mg/kg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2021/020648s022lbl.pdf
unhealthy, > 12 years
Health Status: unhealthy
Age Group: > 12 years
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2021/020648s022lbl.pdf
Rash 2 patients
Disc. AE
0.2 mg/kg 2 times / day multiple, rectal
Recommended
Dose: 0.2 mg/kg, 2 times / day
Route: rectal
Route: multiple
Dose: 0.2 mg/kg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2021/020648s022lbl.pdf
unhealthy, > 12 years
Health Status: unhealthy
Age Group: > 12 years
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2021/020648s022lbl.pdf
Somnolence 3 patients
Disc. AE
0.2 mg/kg 2 times / day multiple, rectal
Recommended
Dose: 0.2 mg/kg, 2 times / day
Route: rectal
Route: multiple
Dose: 0.2 mg/kg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2021/020648s022lbl.pdf
unhealthy, > 12 years
Health Status: unhealthy
Age Group: > 12 years
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2021/020648s022lbl.pdf
Respiratory depression serious|grade 5
10 mg 2 times / day multiple, intranasal
Recommended
Dose: 10 mg, 2 times / day
Route: intranasal
Route: multiple
Dose: 10 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/211635s000lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/211635s000lbl.pdf
Abuse serious|grade 5
10 mg 4 times / day multiple, intramuscular
Recommended
Dose: 10 mg, 4 times / day
Route: intramuscular
Route: multiple
Dose: 10 mg, 4 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2021/020124s033lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2021/020124s033lbl.pdf
Respiratory depression serious|grade 5
10 mg 4 times / day multiple, intramuscular
Recommended
Dose: 10 mg, 4 times / day
Route: intramuscular
Route: multiple
Dose: 10 mg, 4 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2021/020124s033lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2021/020124s033lbl.pdf
Respiratory depression serious|grade 5
10 mg 4 times / day multiple, oral
Recommended
Dose: 10 mg, 4 times / day
Route: oral
Route: multiple
Dose: 10 mg, 4 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/013263s094lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/013263s094lbl.pdf
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1946
inhibitor
2438

substrate
1193
inhibitor
2507

substrate
1388
inhibitor
2217

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP2A6
879

Cav1.2
58

Nav1.5
116

OCT3
159
CYP2C19
1119

CYP1A2
1197

CYP2A6
626

CYP2B6
776

CYP2C8
810

CYP2E1
729

CYP3A5
446
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP2A6
911
 no
CYP2C9
2497
 no
CYP2D6
2546
 no
OCT3
161
 strong [IC50 2 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP2B6
776
 major
CYP2C19
1119
 major
CYP3A4
1946
 major
CYP3A5
446
 major
CYP1A2
1197
 yes
CYP2A6
626
 yes
CYP2C8
810
 yes
CYP2C9
1193
 yes
CYP2D6
1388
 yes
CYP2E1
729
 yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
Cav1.2
63
Nav1.5
119
hERG
2263
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:49575
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:49575
eMolecules
536763
https://www.emolecules.com/cgi-bin/more?vid=536763
ZINC
ZINC000000006427
http://zinc15.docking.org/substances/ZINC000000006427
PubMed

PubMed

TitleDatePubMed
Letter: Clonazepam in the treatment of drug-induced dyskinesia.
1975 Feb 1
[The mechanism of the anticonvulsive action of diazepam].
1975 Mar
Tetany, tetanus or drug reaction? A case report.
1976 Jul
Favourable prognosis of prolonged coma associated with large doses of diazepam in severe tetanus.
1976 Sep
Influence of adenosine agonists and antiepileptic drugs on theophylline-induced seizures in rats.
1998 Oct
[A case of cardiac arrest after torsades de pointes due to prolonged QT interval syndrome possibly associated with subarachnoid hemorrhage].
1999 Jun
A fugue-like state associated with diazepam use.
1999 Jun
Effects of diazepam on extracellular brain neurotransmitters in pilocarpine-induced seizures in rats.
1999 Jun 4
Involvement of nitric oxide and nitric oxide synthase activity in anticonvulsive action.
1999 Mar 1
Anticonvulsants for soman-induced seizure activity.
1999 Mar-Apr
Etomidate-induced convulsion prior to electroconvulsive therapy.
2000 Oct
[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
Lack of reinforcing effect of the benzodiazepine and tricyclic antidepressant combination of diazepam and dothiepin.
2001 Feb
[Febrile convulsions, Treatment and prognosis].
2001 Feb 19
[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
[Effect of diazepam on apnea attacks in a 6-year-old girl with Rett syndrome: a polysomnographic study].
2001 Jan
Radial entrapment neuropathy due to chronic injection-induced triceps fibrosis.
2001 Jan
The octadecaneuropeptide ODN stimulates neurosteroid biosynthesis through activation of central-type benzodiazepine receptors.
2001 Jan
Thiopentone induction dose requirement in dogs is little influenced by co-administration of diazepam or prior treatment with phenobarbitone or corticosteroids, but is reduced in the presence of brain pathology.
2001 Jan
Evaluating the use of benzodiazepines following recent bereavement.
2001 Jan
The efficacy of oral clonidine premedication in the prevention of postoperative vomiting in children following strabismus surgery.
2001 Jan
Long-term reduction of benzodiazepine receptor density in the rat cerebellum by acute seizures and kindling and its recovery 6 months later by a pentylenetetrazole challenge.
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
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
Molecular targets for the myorelaxant action of diazepam.
2001 Mar
Pharmacological evidence for a role of gamma-aminobutyric acid A receptor mechanism in modulating nitric oxide synthase activity in rat brain.
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
Patents

Patents

04988628
2
05662911
3
JP2005520783A
40
JP2008513896A
12
JP2009519467A
53
JP2011507800A
49
JP2012500248A
3
JP4739217B2
51
JPH01265075A
2
JPH02235822A
2
JPH11228539A
2
JPS55143988A
2
JPS60208911A
2

Sample Use Guides

In Vivo Use Guide
Tale 2-10 mg, 2 to 4 times daily.
Route of Administration: Oral
In Vitro Use Guide
Sources: www.ncbi.nlm.nih.gov/pubmed/6722533
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 Wed Apr 02 08:44:35 GMT 2025
Edited
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on Wed Apr 02 08:44:35 GMT 2025
Record UNII
Q3JTX2Q7TU
Record Status Validated (UNII)
Record Version
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Name Type Language
Diazepam CIV
USP-RS  
Preferred Name English
Diazepam
EP   GREEN BOOK   HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP   VANDF   WHO-DD  
INN   USAN  
Official Name English
VALTOCO
Brand Name English
RO 5-2807
Code English
Diazepam [VANDF]
Common Name English
Ansiolisina
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
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-benzodiazepin-2-one
Systematic Name English
VALRELEASE
Brand Name English
Diazepam [MART.]
Common Name English
Diacepin
Common Name English
Diazepam [WHO-DD]
Common Name English
Diazepam [MI]
Common Name English
Diazepam [INN]
Common Name English
Diazepam [USP MONOGRAPH]
Common Name English
Diazepam [JAN]
Common Name English
NRL-1
Code English
LIBERVANT
Brand Name English
Diazepam [EP MONOGRAPH]
Common Name English
Diazepam CIV [USP-RS]
Common Name English
7-Chloro-1-methyl-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one
Systematic Name English
TRANQUASE
Common Name English
Classification Tree Code System Code
NDF-RT N0000007542
Created by admin on Wed Apr 02 08:44:36 GMT 2025 , Edited by admin on Wed Apr 02 08:44:36 GMT 2025
FDA ORPHAN DRUG 384112
Created by admin on Wed Apr 02 08:44:36 GMT 2025 , Edited by admin on Wed Apr 02 08:44:36 GMT 2025
EPA PESTICIDE CODE 600069
Created by admin on Wed Apr 02 08:44:36 GMT 2025 , Edited by admin on Wed Apr 02 08:44:36 GMT 2025
FDA ORPHAN DRUG 334911
Created by admin on Wed Apr 02 08:44:36 GMT 2025 , Edited by admin on Wed Apr 02 08:44:36 GMT 2025
FDA ORPHAN DRUG 518316
Created by admin on Wed Apr 02 08:44:36 GMT 2025 , Edited by admin on Wed Apr 02 08:44:36 GMT 2025
WHO-ESSENTIAL MEDICINES LIST 8.4
Created by admin on Wed Apr 02 08:44:36 GMT 2025 , Edited by admin on Wed Apr 02 08:44:36 GMT 2025
LIVERTOX NBK548352
Created by admin on Wed Apr 02 08:44:36 GMT 2025 , Edited by admin on Wed Apr 02 08:44:36 GMT 2025
WHO-VATC QN05BA01
Created by admin on Wed Apr 02 08:44:36 GMT 2025 , Edited by admin on Wed Apr 02 08:44:36 GMT 2025
FDA ORPHAN DRUG 543516
Created by admin on Wed Apr 02 08:44:36 GMT 2025 , Edited by admin on Wed Apr 02 08:44:36 GMT 2025
FDA ORPHAN DRUG 638118
Created by admin on Wed Apr 02 08:44:36 GMT 2025 , Edited by admin on Wed Apr 02 08:44:36 GMT 2025
WHO-ESSENTIAL MEDICINES LIST 24.3
Created by admin on Wed Apr 02 08:44:36 GMT 2025 , Edited by admin on Wed Apr 02 08:44:36 GMT 2025
FDA ORPHAN DRUG 382512
Created by admin on Wed Apr 02 08:44:36 GMT 2025 , Edited by admin on Wed Apr 02 08:44:36 GMT 2025
WHO-ATC N05BA01
Created by admin on Wed Apr 02 08:44:36 GMT 2025 , Edited by admin on Wed Apr 02 08:44:36 GMT 2025
WHO-ESSENTIAL MEDICINES LIST 05
Created by admin on Wed Apr 02 08:44:36 GMT 2025 , Edited by admin on Wed Apr 02 08:44:36 GMT 2025
DEA NO. 2765
Created by admin on Wed Apr 02 08:44:36 GMT 2025 , Edited by admin on Wed Apr 02 08:44:36 GMT 2025
NCI_THESAURUS C1012
Created by admin on Wed Apr 02 08:44:36 GMT 2025 , Edited by admin on Wed Apr 02 08:44:36 GMT 2025
FDA ORPHAN DRUG 61591
Created by admin on Wed Apr 02 08:44:36 GMT 2025 , Edited by admin on Wed Apr 02 08:44:36 GMT 2025
NDF-RT N0000175694
Created by admin on Wed Apr 02 08:44:36 GMT 2025 , Edited by admin on Wed Apr 02 08:44:36 GMT 2025
Code System Code Type Description
RS_ITEM_NUM
1185008
Created by admin on Wed Apr 02 08:44:36 GMT 2025 , Edited by admin on Wed Apr 02 08:44:36 GMT 2025
PRIMARY
MERCK INDEX
m4267
Created by admin on Wed Apr 02 08:44:36 GMT 2025 , Edited by admin on Wed Apr 02 08:44:36 GMT 2025
PRIMARY Merck Index
NSC
169897
Created by admin on Wed Apr 02 08:44:36 GMT 2025 , Edited by admin on Wed Apr 02 08:44:36 GMT 2025
PRIMARY
RXCUI
3322
Created by admin on Wed Apr 02 08:44:36 GMT 2025 , Edited by admin on Wed Apr 02 08:44:36 GMT 2025
PRIMARY RxNorm
MESH
D003975
Created by admin on Wed Apr 02 08:44:36 GMT 2025 , Edited by admin on Wed Apr 02 08:44:36 GMT 2025
PRIMARY
HSDB
3057
Created by admin on Wed Apr 02 08:44:36 GMT 2025 , Edited by admin on Wed Apr 02 08:44:36 GMT 2025
PRIMARY
LACTMED
Diazepam
Created by admin on Wed Apr 02 08:44:36 GMT 2025 , Edited by admin on Wed Apr 02 08:44:36 GMT 2025
PRIMARY
DRUG BANK
DB00829
Created by admin on Wed Apr 02 08:44:36 GMT 2025 , Edited by admin on Wed Apr 02 08:44:36 GMT 2025
PRIMARY
EPA CompTox
DTXSID4020406
Created by admin on Wed Apr 02 08:44:36 GMT 2025 , Edited by admin on Wed Apr 02 08:44:36 GMT 2025
PRIMARY
DRUG CENTRAL
852
Created by admin on Wed Apr 02 08:44:36 GMT 2025 , Edited by admin on Wed Apr 02 08:44:36 GMT 2025
PRIMARY
WIKIPEDIA
DIAZEPAM
Created by admin on Wed Apr 02 08:44:36 GMT 2025 , Edited by admin on Wed Apr 02 08:44:36 GMT 2025
PRIMARY
EVMPD
SUB07069MIG
Created by admin on Wed Apr 02 08:44:36 GMT 2025 , Edited by admin on Wed Apr 02 08:44:36 GMT 2025
PRIMARY
IUPHAR
3364
Created by admin on Wed Apr 02 08:44:36 GMT 2025 , Edited by admin on Wed Apr 02 08:44:36 GMT 2025
PRIMARY
FDA UNII
Q3JTX2Q7TU
Created by admin on Wed Apr 02 08:44:36 GMT 2025 , Edited by admin on Wed Apr 02 08:44:36 GMT 2025
PRIMARY
NCI_THESAURUS
C28982
Created by admin on Wed Apr 02 08:44:36 GMT 2025 , Edited by admin on Wed Apr 02 08:44:36 GMT 2025
PRIMARY
INN
1295
Created by admin on Wed Apr 02 08:44:36 GMT 2025 , Edited by admin on Wed Apr 02 08:44:36 GMT 2025
PRIMARY
CAS
439-14-5
Created by admin on Wed Apr 02 08:44:36 GMT 2025 , Edited by admin on Wed Apr 02 08:44:36 GMT 2025
PRIMARY
PUBCHEM
3016
Created by admin on Wed Apr 02 08:44:36 GMT 2025 , Edited by admin on Wed Apr 02 08:44:36 GMT 2025
PRIMARY
ChEMBL
CHEMBL12
Created by admin on Wed Apr 02 08:44:36 GMT 2025 , Edited by admin on Wed Apr 02 08:44:36 GMT 2025
PRIMARY
CHEBI
49575
Created by admin on Wed Apr 02 08:44:36 GMT 2025 , Edited by admin on Wed Apr 02 08:44:36 GMT 2025
PRIMARY
ECHA (EC/EINECS)
207-122-5
Created by admin on Wed Apr 02 08:44:36 GMT 2025 , Edited by admin on Wed Apr 02 08:44:36 GMT 2025
PRIMARY
SMS_ID
100000092362
Created by admin on Wed Apr 02 08:44:36 GMT 2025 , Edited by admin on Wed Apr 02 08:44:36 GMT 2025
PRIMARY
DAILYMED
Q3JTX2Q7TU
Created by admin on Wed Apr 02 08:44:36 GMT 2025 , Edited by admin on Wed Apr 02 08:44:36 GMT 2025
PRIMARY
NSC
77518
Created by admin on Wed Apr 02 08:44:36 GMT 2025 , Edited by admin on Wed Apr 02 08:44:36 GMT 2025
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
DIAZEPAM
Created by admin on Wed Apr 02 08:44:36 GMT 2025 , Edited by admin on Wed Apr 02 08:44:36 GMT 2025
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
CYTOCHROME P450 2C19
METABOLIC ENZYME -> SUBSTRATE
CYTOCHROME P450 3A5
METABOLIC ENZYME -> SUBSTRATE
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
CYTOCHROME P450 3A4
METABOLIC ENZYME -> SUBSTRATE
Structure of DIAZEPAM HYDROCHLORIDE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of TEMAZEPAM
METABOLITE ACTIVE -> PARENT
Structure of Nordazepam
METABOLITE ACTIVE -> PARENT
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PRODRUG -> METABOLITE ACTIVE
Structure of 5-Chloro-2-methylaminobenzophenone
METABOLITE -> PARENT
Structure of Oxazepam
METABOLITE ACTIVE -> PARENT
Structure of Nordazepam
METABOLITE TOXIC -> PARENT
Metabolite produces adverse autonomic nervous symptoms in man.
Related Record Type Details
Structure of N-(2-Benzoyl-4-chlorophenyl)-2-chloro-N-methylacetamide
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of Nordazepam
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 7-CHLORO-2-METHOXY-5-PHENYL-3H-1,4-BENZODIAZEPINE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 5-Chloro-2-methylaminobenzophenone
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 3-Amino-6-chloro-1-methyl-4-phenylcarbostyril
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 1-METHYL-4-PHENYL-6-CHLORO-2-QUINAZOLINONE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
Structure of Diazepam
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
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