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

Details

Stereochemistry ACHIRAL
Molecular Formula C14H10BrN3O
Molecular Weight 316.153
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BROMAZEPAM

SMILES

BrC1=CC=C2NC(=O)CN=C(C3=CC=CC=N3)C2=C1

InChI

InChIKey=VMIYHDSEFNYJSL-UHFFFAOYSA-N
InChI=1S/C14H10BrN3O/c15-9-4-5-11-10(7-9)14(17-8-13(19)18-11)12-3-1-2-6-16-12/h1-7H,8H2,(H,18,19)

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including https://www.drugbank.ca/drugs/DB01558 | https://www.ncbi.nlm.nih.gov/pubmed/639854 | https://www.ncbi.nlm.nih.gov/pubmed/6124947 | https://www.ncbi.nlm.nih.gov/pubmed/2570451 | https://www.ncbi.nlm.nih.gov/pubmed/24241181

Bromazepam (marketed under several brand names, including Lectopam, Lexotan, Lexilium, Lexaurin, Brazepam, Rekotnil, and Lexotanil)[1] is a benzodiazepine derivative drug, patented by Roche in 1963 and developed clinically in the 1970s. It is mainly an anti-anxiety agent with similar side effects to diazepam (Valium). In addition to being used to treat anxiety or panic states, bromazepam may be used as a premedicant prior to minor surgery. Bromazepam typically comes in doses of 3 mg and 6 mg tablets.[5] Bromazepam is contraindicated and should be used with caution in women who are pregnant, the elderly, patients with a history of alcohol or other substance abuse disorders and children. Prolonged use of bromazepam causes tolerance and may lead to both physical and psychological dependence on the drug, and as a result, it is a medication which is controlled by international law. Bromazepam binds to the GABA receptor GABAA, causing a conformational change and increasing the inhibitory effects of GABA. Bromazepam is a long-acting benzodiazepine and is lipophilic and metabolized hepatically via oxidative pathways.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
45.0 nM [Ki]
Conditions
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
88 ng/mL
6 mg single, oral
dose: 6 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BROMAZEPAM serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
72 ng/mL
6 mg single, oral
dose: 6 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BROMAZEPAM serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
126 ng/mL
6 mg single, oral
dose: 6 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BROMAZEPAM serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
139 ng/mL
6 mg single, oral
dose: 6 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BROMAZEPAM serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
259 ng/mL
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BROMAZEPAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
169 ng/mL
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BROMAZEPAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
0.131 μg/mL
12 mg single, oral
dose: 12 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BROMAZEPAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
43.1 ng/mL
3 mg single, oral
dose: 3 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BROMAZEPAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1844 ng × h/mL
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BROMAZEPAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
1233 ng × h/mL
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BROMAZEPAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
2.99 μg × h/mL
12 mg single, oral
dose: 12 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BROMAZEPAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
1328 ng × h/mL
3 mg single, oral
dose: 3 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BROMAZEPAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
20.4 h
6 mg single, oral
dose: 6 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BROMAZEPAM serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
28.5 h
6 mg single, oral
dose: 6 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BROMAZEPAM serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
32.2 h
6 mg single, oral
dose: 6 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BROMAZEPAM serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
28.2 h
6 mg single, oral
dose: 6 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BROMAZEPAM serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
32.1 h
3 mg single, oral
dose: 3 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BROMAZEPAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
28.4%
6 mg single, oral
dose: 6 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BROMAZEPAM serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
29.4%
6 mg single, oral
dose: 6 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BROMAZEPAM serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
34.2%
6 mg single, oral
dose: 6 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BROMAZEPAM serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
35.5%
6 mg single, oral
dose: 6 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BROMAZEPAM serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
29.9%
BROMAZEPAM plasma
Homo sapiens
Doses

Doses

DosePopulationAdverse events​
180 mg single, oral
Overdose
Dose: 180 mg
Route: oral
Route: single
Dose: 180 mg
Sources:
unknown, ADULT
Health Status: unknown
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
Disc. AE: Coma...
AEs leading to
discontinuation/dose reduction:
Coma (1 pt)
Sources:
220 mg 1 times / day multiple, oral
Overdose
Dose: 220 mg, 1 times / day
Route: oral
Route: multiple
Dose: 220 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
Other AEs: cognitive impairment, falls...
Other AEs:
cognitive impairment (1 pt)
falls (1 pt)
dependence (1 pt)
tolerance (1 pt)
Sources:
9 mg 3 times / day steady-state, oral
Overdose
Dose: 9 mg, 3 times / day
Route: oral
Route: steady-state
Dose: 9 mg, 3 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Sources:
Other AEs: dystonia...
Other AEs:
dystonia (1 pt)
Sources:
1.5 mg 2 times / day steady-state, oral
Recommended
Dose: 1.5 mg, 2 times / day
Route: oral
Route: steady-state
Dose: 1.5 mg, 2 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
6 mg 1 times / day steady-state, oral
Recommended
Dose: 6 mg, 1 times / day
Route: oral
Route: steady-state
Dose: 6 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Sources:
Other AEs: Gastritis...
Other AEs:
Gastritis (1 pt)
Sources:
5 mg 3 times / day steady-state, oral
Studied dose
Dose: 5 mg, 3 times / day
Route: oral
Route: steady-state
Dose: 5 mg, 3 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
AEs

AEs

AESignificanceDosePopulation
Coma 1 pt
Disc. AE
180 mg single, oral
Overdose
Dose: 180 mg
Route: oral
Route: single
Dose: 180 mg
Sources:
unknown, ADULT
Health Status: unknown
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
cognitive impairment 1 pt
220 mg 1 times / day multiple, oral
Overdose
Dose: 220 mg, 1 times / day
Route: oral
Route: multiple
Dose: 220 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
dependence 1 pt
220 mg 1 times / day multiple, oral
Overdose
Dose: 220 mg, 1 times / day
Route: oral
Route: multiple
Dose: 220 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
falls 1 pt
220 mg 1 times / day multiple, oral
Overdose
Dose: 220 mg, 1 times / day
Route: oral
Route: multiple
Dose: 220 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
tolerance 1 pt
220 mg 1 times / day multiple, oral
Overdose
Dose: 220 mg, 1 times / day
Route: oral
Route: multiple
Dose: 220 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
dystonia 1 pt
9 mg 3 times / day steady-state, oral
Overdose
Dose: 9 mg, 3 times / day
Route: oral
Route: steady-state
Dose: 9 mg, 3 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Sources:
Gastritis 1 pt
6 mg 1 times / day steady-state, oral
Recommended
Dose: 6 mg, 1 times / day
Route: oral
Route: steady-state
Dose: 6 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Sources:
PubMed

PubMed

TitleDatePubMed
The role of liquid chromatography-tandem mass spectrometry (LC-MS/MS) to test blood and urine samples for the toxicological investigation of drug-facilitated crimes.
2008-04
Design and evaluation of a multi-detection system composed of ultraviolet, evaporative light scattering and inductively coupled plasma mass spectrometry detection for the analysis of pharmaceuticals by liquid chromatography.
2008-03-21
Thiodicarb and methomyl tissue distribution in a fatal multiple compounds poisoning.
2008-03
Radiofrequency ablation of osseous metastases for the palliation of pain.
2008-03
Prevalence and sociodemographic characteristics associated with benzodiazepines use among community dwelling older adults: the Bambuí Health and Aging Study (BHAS).
2008-03
Flurazepam inhibits the P-glycoprotein transport function: an insight to revert multidrug-resistance phenotype.
2008-02-26
Opioid receptors are involved in the sedative and antinociceptive effects of hesperidin as well as in its potentiation with benzodiazepines.
2008-02-12
Quetiapine: another drug with potential for misuse? A case report.
2008-01
Determination of benzodiazepines in oral fluid using LC-MS-MS.
2007-12-21
The effects of bromazepam on the early stage of visual information processing (P100).
2007-12
How useful are prescribing indicators based on the DU90% method to distinguish the quality of prescribing between pharmacotherapy audit meetings with different levels of functioning?
2007-12
[Drug-facilitated crime and sexual abuse: a pediatric observation].
2007-11
Modeling gene expression regulatory networks with the sparse vector autoregressive model.
2007-08-30
Development of a validated HPLC method for the determination of four 1,4-benzodiazepines in human biological fluids.
2007-03
Influence of bromazepam on cortical interhemispheric coherence.
2007-03
Drug screening of preserved oral fluid by liquid chromatography-tandem mass spectrometry.
2007-02
[Treatment of hydroxychloroquine poisoning with extracorporeal circulation].
2007-02
Development and validation of a high performance liquid chromatographic method for the determination of oxcarbazepine and its main metabolites in human plasma and cerebrospinal fluid and its application to pharmacokinetic study.
2007-01-17
Separation of 1,4-benzodiazepines by micellar elektrokinetic capillary chromatography.
2007-01-10
[Fixed drug eruption : about 13 cases].
2007-01
Sensitivity of P-glycoprotein tryptophan residues to benzodiazepines and ATP interaction.
2007-01
Interactions between iron(III)-hydroxide polymaltose complex and commonly used medications / laboratory studies in rats.
2007
Endocannabinoid system and synaptic plasticity: implications for emotional responses.
2007
Hyponatremia-induced seizure during carbamazepine treatment.
2007
[Drug-related toxic events in the state of São Paulo, Brazil].
2006-12
Quantification of benzodiazepines in whole blood and serum.
2006-11
Neuromodulatory effect of bromazepam on motor learning: an electroencephalographic approach.
2006-10-23
[Effects of bromazepam on motor learning: an electroencephalogram analysis based on the beta rhythm].
2006-10-13
[The effects of bromazepam on contingent negative variation and reaction time in a visuomotor task].
2006-09-29
[Appropriate use of benzodiazepines zolpidem and zopiclone in diseases attended in primary care].
2006-09-02
Anxiolytics, hypnotics, and antidepressants dispensed to adolescents in a French region in 2002.
2006-07
[Procedural learning and anxiolytic effects: electroencephalographic, motor and attentional measures].
2006-06
Benzodiazepines prescription in Dakar: a study about prescribing habits and knowledge in general practitioners, neurologists and psychiatrists.
2006-06
Fast gas chromatography-negative-ion chemical ionization mass spectrometry with microscale volume sample preparation for the determination of benzodiazepines and alpha-hydroxy metabolites, zaleplon and zopiclone in whole blood.
2006-06
[Neuromodulatory effects of bromazepam when individuals were exposed to a motor learning task: quantitative electroencephalography (qEEG)].
2006-03
Tension-type headache with aura.
2006-03
Anti-conflict effects of benzodiazepines in rhesus monkeys: relationship with therapeutic doses in humans and role of GABAA receptors.
2006-01
Double-blind, comparative study of cyamemazine vs. bromazepam in the benzodiazepine withdrawal syndrome.
2006-01
Pharmacotherapy of social anxiety disorder: what does the evidence tell us?
2006
Screening method for benzodiazepines and hypnotics in hair at pg/mg level by liquid chromatography-mass spectrometry/mass spectrometry.
2005-10-15
On-line solid-phase extraction coupled with high-performance liquid chromatography and tandem mass spectrometry (SPE-HPLC-MS-MS) for quantification of bromazepam in human plasma: an automated method for bioequivalence studies.
2005-10
Comparison of CZE, MEKC, MEEKC and non-aqueous capillary electrophoresis for the determination of impurities in bromazepam.
2005-09-01
[Trends in the pharmaceutical profile of intentional drug overdoses seen in the emergency room].
2005-07-02
Benzodiazepine prescribing behaviour and attitudes: a survey among general practitioners practicing in northern Thailand.
2005-06-23
Screening and confirmatory method for benzodiazepines and hypnotics in oral fluid by LC-MS/MS.
2005-06-10
The neuropsychiatry of Parkinson's disease.
2005-06
Analysis of the influence of bromazepam on cognitive performance through the visual evoked potential (P300).
2005-06
[Effects of Bromazepam in qEEG by type writing].
2005-06
[Electroencephalography measures in motor skill learning and effects of bromazepam].
2005-06
[Neuromodulatory effects of caffeine and bromazepam on visual event-related potential (P300): a comparative study].
2005-06
Patents

Sample Use Guides

Adults: Depending upon severity of symptoms- 6 mg to 18 mg, in equally divided doses. Treatment may be initiated at a lower dose. Elderly: Maximum of 3 mg in equally divided doses. Dose can be increased gradually as needed and tolerated.
Route of Administration: Oral
In Vitro Use Guide
500mkl of this P2-suspension (corresponding to 10mg original brain tissue) was preincubated for 5 min with Bromazepam. 25 mkl of 3H-diazepam working solution (to give a final concentration of 1.9 X 10^-9 M or approximately 14,000 cpm) was then added and the incubation continued for an additional 15 min at 37°C. The samples were then cooled in an ice bath for 30 min. IC50 values, i.e. values for 50% inhibition of specific 3H-diazepam binding, were assessed with at least 3 and up to 7 concentrations of the Bromazepam in duplicate or triplicate.
Name Type Language
BROMAZEPAM
EP   INN   MART.   MI   USAN   WHO-DD  
USAN   INN  
Official Name English
LECTOPAM
Preferred Name English
RO 5-3350
Code English
RO-5-3350
Code English
BROMAZEPAM [USAN]
Common Name English
LEXOTANIL
Brand Name English
BROMAZEPAM CIV [USP-RS]
Common Name English
2H-1,4-BENZODIAZEPIN-2-ONE, 7-BROMO-1,3-DIHYDRO-5-(2-PYRIDINYL)-
Systematic Name English
LEXOTAN
Brand Name English
bromazepam [INN]
Common Name English
BROMAZEPAM [MART.]
Common Name English
LEXATIN
Brand Name English
7-Bromo-1,3-dihydro-5-(2-pyridyl)-2H-1,4-benzodiazepin-2-one
Systematic Name English
BROMAZEPAM [EP MONOGRAPH]
Common Name English
BROMAZEPAM CIV
USP-RS  
Common Name English
NSC-140669
Code English
BROMAZEPAM [JAN]
Common Name English
Bromazepam [WHO-DD]
Common Name English
BROMAZEPAM [MI]
Common Name English
Classification Tree Code System Code
DEA NO. 2748
Created by admin on Mon Mar 31 17:49:55 GMT 2025 , Edited by admin on Mon Mar 31 17:49:55 GMT 2025
WHO-ATC N05BA08
Created by admin on Mon Mar 31 17:49:55 GMT 2025 , Edited by admin on Mon Mar 31 17:49:55 GMT 2025
NCI_THESAURUS C1012
Created by admin on Mon Mar 31 17:49:55 GMT 2025 , Edited by admin on Mon Mar 31 17:49:55 GMT 2025
WHO-VATC QN05BA08
Created by admin on Mon Mar 31 17:49:55 GMT 2025 , Edited by admin on Mon Mar 31 17:49:55 GMT 2025
Code System Code Type Description
FDA UNII
X015L14V0O
Created by admin on Mon Mar 31 17:49:55 GMT 2025 , Edited by admin on Mon Mar 31 17:49:55 GMT 2025
PRIMARY
MERCK INDEX
m2662
Created by admin on Mon Mar 31 17:49:55 GMT 2025 , Edited by admin on Mon Mar 31 17:49:55 GMT 2025
PRIMARY Merck Index
EVMPD
SUB05907MIG
Created by admin on Mon Mar 31 17:49:55 GMT 2025 , Edited by admin on Mon Mar 31 17:49:55 GMT 2025
PRIMARY
CAS
1812-30-2
Created by admin on Mon Mar 31 17:49:55 GMT 2025 , Edited by admin on Mon Mar 31 17:49:55 GMT 2025
PRIMARY
PUBCHEM
2441
Created by admin on Mon Mar 31 17:49:55 GMT 2025 , Edited by admin on Mon Mar 31 17:49:55 GMT 2025
PRIMARY
DRUG CENTRAL
399
Created by admin on Mon Mar 31 17:49:55 GMT 2025 , Edited by admin on Mon Mar 31 17:49:55 GMT 2025
PRIMARY
NSC
140669
Created by admin on Mon Mar 31 17:49:55 GMT 2025 , Edited by admin on Mon Mar 31 17:49:55 GMT 2025
PRIMARY
RXCUI
1749
Created by admin on Mon Mar 31 17:49:55 GMT 2025 , Edited by admin on Mon Mar 31 17:49:55 GMT 2025
PRIMARY RxNorm
ECHA (EC/EINECS)
217-322-4
Created by admin on Mon Mar 31 17:49:55 GMT 2025 , Edited by admin on Mon Mar 31 17:49:55 GMT 2025
PRIMARY
RS_ITEM_NUM
1076465
Created by admin on Mon Mar 31 17:49:55 GMT 2025 , Edited by admin on Mon Mar 31 17:49:55 GMT 2025
PRIMARY
WIKIPEDIA
BROMAZEPAM
Created by admin on Mon Mar 31 17:49:55 GMT 2025 , Edited by admin on Mon Mar 31 17:49:55 GMT 2025
PRIMARY
EPA CompTox
DTXSID40171081
Created by admin on Mon Mar 31 17:49:55 GMT 2025 , Edited by admin on Mon Mar 31 17:49:55 GMT 2025
PRIMARY
SMS_ID
100000092554
Created by admin on Mon Mar 31 17:49:55 GMT 2025 , Edited by admin on Mon Mar 31 17:49:55 GMT 2025
PRIMARY
NCI_THESAURUS
C87454
Created by admin on Mon Mar 31 17:49:55 GMT 2025 , Edited by admin on Mon Mar 31 17:49:55 GMT 2025
PRIMARY
INN
2692
Created by admin on Mon Mar 31 17:49:55 GMT 2025 , Edited by admin on Mon Mar 31 17:49:55 GMT 2025
PRIMARY
ChEMBL
CHEMBL277062
Created by admin on Mon Mar 31 17:49:55 GMT 2025 , Edited by admin on Mon Mar 31 17:49:55 GMT 2025
PRIMARY
MESH
D001960
Created by admin on Mon Mar 31 17:49:55 GMT 2025 , Edited by admin on Mon Mar 31 17:49:55 GMT 2025
PRIMARY
DRUG BANK
DB01558
Created by admin on Mon Mar 31 17:49:55 GMT 2025 , Edited by admin on Mon Mar 31 17:49:55 GMT 2025
PRIMARY