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
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)
| Molecular Formula | C14H10BrN3O |
| Molecular Weight | 316.153 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator'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
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
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL1907607 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24241181 |
45.0 nM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | LECTOPAM Approved UseUnknown |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2882883/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2882883/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2882883/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14517708/ |
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14517708/ |
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2882883/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2882883/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2882883/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14517708/ |
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2882883/ |
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% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2882883/ |
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% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2882883/ |
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
| Dose | Population | Adverse events |
|---|---|---|
180 mg single, oral Overdose |
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) Sources: falls (1 pt) dependence (1 pt) tolerance (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: |
Other AEs: dystonia... |
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... |
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
| AE | Significance | Dose | Population |
|---|---|---|---|
| Coma | 1 pt Disc. AE |
180 mg single, oral Overdose |
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
| Title | Date | PubMed |
|---|---|---|
| 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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/639854
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.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 17:49:55 GMT 2025
by
admin
on
Mon Mar 31 17:49:55 GMT 2025
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| Record UNII |
X015L14V0O
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| Record Status |
Validated (UNII)
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| Record Version |
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| Classification Tree | Code System | Code | ||
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DEA NO. |
2748
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WHO-ATC |
N05BA08
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NCI_THESAURUS |
C1012
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WHO-VATC |
QN05BA08
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X015L14V0O
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m2662
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SUB05907MIG
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1812-30-2
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2441
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399
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140669
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1749
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217-322-4
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1076465
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BROMAZEPAM
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DTXSID40171081
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100000092554
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C87454
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2692
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CHEMBL277062
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D001960
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DB01558
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