Bromazepam

Identification

Summary

Bromazepam is a short-acting benzodiazepine with intermediate onset commonly used to treat panic disorders and severe anxiety.

Generic Name
Bromazepam
DrugBank Accession Number
DB01558
Background

One of the benzodiazepines that is used in the treatment of anxiety disorders. It is a Schedule IV drug in the U.S. and Canada and under the Convention on Psychotropic Substances. It is a intermediate-acting benzodiazepine.

Type
Small Molecule
Groups
Approved, Illicit, Investigational
Structure
Weight
Average: 316.153
Monoisotopic: 315.000724604
Chemical Formula
C14H10BrN3O
Synonyms
  • Bromacepam
  • Bromazepam
  • Bromazepamum
External IDs
  • RO 5-3350
  • RO-5-3350

Pharmacology

Indication

For the short-term treatment of insomnia, short-term treatment of anxiety or panic attacks, if a benzodiazepine is required, and the alleviation of the symptoms of alcohol- and opiate-withdrawal.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Symptomatic treatment ofAcute anxiety••••••••••••
Symptomatic treatment ofSevere anxiety••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Bromazepam is a lipophilic, long-acting benzodiazepine and with sedative, hypnotic, anxiolytic and skeletal muscle relaxant properties. It does not possess any antidepressant qualities. Bromazepam, like other benzodiazepines, presents a risk of abuse, misuse, and dependence. According to many psychiatric experts, Bromazepam has a greater abuse potential than other benzodiazepines because of fast resorption and rapid onset of action.

Mechanism of action

Bromazepam binds to the GABA-A receptor producing a conformational change and potentiating its inhibitory effects. Other neurotransmitters are not influenced.

TargetActionsOrganism
AGABA(A) Receptor
positive allosteric modulator
Humans
AGABA(A) Receptor Benzodiazepine Binding Site
ligand
Humans
Absorption

Bioavailability is 84% following oral administration. The time to peak plasma level is 1 - 4 hours. Bromazepam is generally well absorbed after oral administration.

Volume of distribution

1.56 L/kg

Protein binding

70%

Metabolism

Hepatically, via oxidative pathways (via an enzyme belonging to the Cytochrome P450 family of enzymes). One of the main metabolites is 3-hydroxybromazepam. It is pharmacologically active and the half life is similar to that of the parent compound.

Route of elimination

Urine (69%), as metabolites

Half-life

10-20 hours

Clearance

0.82 mL/min/kg.

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when Bromazepam is combined with 1,2-Benzodiazepine.
AbacavirAbacavir may decrease the excretion rate of Bromazepam which could result in a higher serum level.
AbametapirThe serum concentration of Bromazepam can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Bromazepam can be increased when combined with Abatacept.
AbirateroneThe serum concentration of Bromazepam can be increased when it is combined with Abiraterone.
Food Interactions
  • Avoid alcohol. Ingesting alcohol may increase the sedative and CNS depressant effects of bromazepam.
  • Take with or without food. Taking bromazepam with food may reduce its Cmax and AUC.

Products

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International/Other Brands
Calmepam / Creosedin / Durazanil / Lectopam / Lekotam / Lexaurin / Lexilium / Lexomil / Lexotan / Normoc / Ultramidol
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
BromazepamTablet1.5 mgOralApotex Corporation1995-12-31Not applicableCanada flag
BromazepamTablet6 mgOralApotex Corporation1995-12-31Not applicableCanada flag
BromazepamTablet3 mgOralApotex Corporation1995-12-31Not applicableCanada flag
Bromazepam-1.5 - Tab 1.5mgTablet1.5 mgOralPro Doc Limitee1997-05-202010-07-13Canada flag
Bromazepam-3 - Tab 3mgTablet3 mgOralPro Doc Limitee1996-12-042019-04-10Canada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Alti-bromazepam 1.5mg TabletsTablet1.5 mgOralAltimed Pharma Inc.1996-12-312005-05-27Canada flag
Alti-bromazepam 3mg TabletsTablet3 mgOralAltimed Pharma Inc.1995-12-312005-05-27Canada flag
Alti-bromazepam 6mg TabletsTablet6 mgOralAltimed Pharma Inc.1996-12-312005-05-27Canada flag
Apo-bromazepamTablet1.5 mgOralApotex Corporation1995-12-31Not applicableCanada flag
Apo-bromazepamTablet3 mgOralApotex Corporation1995-12-31Not applicableCanada flag

Categories

ATC Codes
N05BA08 — Bromazepam
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as 1,4-benzodiazepines. These are organic compounds containing a benzene ring fused to a 1,4-azepine.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzodiazepines
Sub Class
1,4-benzodiazepines
Direct Parent
1,4-benzodiazepines
Alternative Parents
Alpha amino acids and derivatives / Pyridines and derivatives / Benzenoids / Aryl bromides / Heteroaromatic compounds / Secondary carboxylic acid amides / Lactams / Ketimines / Propargyl-type 1,3-dipolar organic compounds / Azacyclic compounds
show 5 more
Substituents
1,4-benzodiazepine / Alpha-amino acid or derivatives / Aromatic heteropolycyclic compound / Aryl bromide / Aryl halide / Azacycle / Benzenoid / Carbonyl group / Carboxamide group / Carboxylic acid derivative
show 17 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
X015L14V0O
CAS number
1812-30-2
InChI Key
VMIYHDSEFNYJSL-UHFFFAOYSA-N
InChI
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)
IUPAC Name
7-bromo-5-(pyridin-2-yl)-2,3-dihydro-1H-1,4-benzodiazepin-2-one
SMILES
BrC1=CC2=C(NC(=O)CN=C2C2=CC=CC=N2)C=C1

References

General References
  1. Oelschlager H: [Chemical and pharmacologic aspects of benzodiazepines]. Schweiz Rundsch Med Prax. 1989 Jul 4;78(27-28):766-72. [Article]
  2. Oda M, Kotegawa T, Tsutsumi K, Ohtani Y, Kuwatani K, Nakano S: The effect of itraconazole on the pharmacokinetics and pharmacodynamics of bromazepam in healthy volunteers. Eur J Clin Pharmacol. 2003 Nov;59(8-9):615-9. Epub 2003 Sep 27. [Article]
  3. van Harten J: Overview of the pharmacokinetics of fluvoxamine. Clin Pharmacokinet. 1995;29 Suppl 1:1-9. doi: 10.2165/00003088-199500291-00003. [Article]
  4. Ochs HR, Greenblatt DJ, Friedman H, Burstein ES, Locniskar A, Harmatz JS, Shader RI: Bromazepam pharmacokinetics: influence of age, gender, oral contraceptives, cimetidine, and propranolol. Clin Pharmacol Ther. 1987 May;41(5):562-70. [Article]
  5. Lacy CF, Armstrong LL, Goldman MP, Lance LL eds (2007). Lexicomp drug information handbook (15th ed.). Lexicomp.
Human Metabolome Database
HMDB0015511
KEGG Drug
D01245
PubChem Compound
2441
PubChem Substance
46505694
ChemSpider
2347
RxNav
1749
ChEBI
31302
ChEMBL
CHEMBL277062
ZINC
ZINC000000001051
Therapeutic Targets Database
DAP001035
PharmGKB
PA10035
Drugs.com
Drugs.com Drug Page
Wikipedia
Bromazepam

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3TerminatedTreatmentAnxiety Disorders / Dementia / Depression / Psychosomatic Disorders / Schizophrenia1
3Unknown StatusPreventionNausea / Vomiting1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • United States Pharmacopeial Convention Inc.
Dosage Forms
FormRouteStrength
TabletOral3.000 mg
TabletOral3 mg/1
TabletOral6 mg/1
TabletOral6 mg
SuspensionOral6 mg
Solution / dropsOral2.5 MG/ML
TabletOral1.5 MG
TabletOral3 MG
Tablet, film coatedOral
CapsuleOral
Solution / dropsOral
CapsuleOral
CapsuleOral1.5 MG
CapsuleOral12 MG
CapsuleOral3 MG
CapsuleOral6 MG
TabletOral300000 mg
TabletOral
TabletOral3 mg / tab
TabletOral6.000 mg
TabletOral6 mg / tab
Prices
Unit descriptionCostUnit
Lectopam 6 mg Tablet0.25USD tablet
Lectopam 3 mg Tablet0.17USD tablet
Apo-Bromazepam 6 mg Tablet0.13USD tablet
Gen-Bromazepam 6 mg Tablet0.13USD tablet
Novo-Bromazepam 6 mg Tablet0.13USD tablet
Apo-Bromazepam 3 mg Tablet0.09USD tablet
Gen-Bromazepam 3 mg Tablet0.09USD tablet
Novo-Bromazepam 3 mg Tablet0.09USD tablet
Apo-Bromazepam 1.5 mg Tablet0.07USD tablet
Gen-Bromazepam 1.5 mg Tablet0.07USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
logP2.05SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.0399 mg/mLALOGPS
logP2.09ALOGPS
logP2.54Chemaxon
logS-3.9ALOGPS
pKa (Strongest Acidic)12.24Chemaxon
pKa (Strongest Basic)2.65Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area54.35 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity76.99 m3·mol-1Chemaxon
Polarizability28.11 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9937
Blood Brain Barrier+0.9848
Caco-2 permeable+0.7571
P-glycoprotein substrateSubstrate0.5741
P-glycoprotein inhibitor INon-inhibitor0.7251
P-glycoprotein inhibitor IINon-inhibitor0.924
Renal organic cation transporterNon-inhibitor0.558
CYP450 2C9 substrateNon-substrate0.8385
CYP450 2D6 substrateNon-substrate0.9117
CYP450 3A4 substrateSubstrate0.7117
CYP450 1A2 substrateInhibitor0.9381
CYP450 2C9 inhibitorNon-inhibitor0.6329
CYP450 2D6 inhibitorNon-inhibitor0.8511
CYP450 2C19 inhibitorNon-inhibitor0.5719
CYP450 3A4 inhibitorNon-inhibitor0.7405
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6441
Ames testNon AMES toxic0.8607
CarcinogenicityNon-carcinogens0.8704
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.2416 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9974
hERG inhibition (predictor II)Non-inhibitor0.7977
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-000i-0091000000-cf3c3fba2d2e801551b1
Mass Spectrum (Electron Ionization)MSsplash10-00n0-9463000000-abe7fdab778f08fe18c4
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-03di-0049000000-67c4bd48b889caf68ca3
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-000i-0090000000-8d6819f4db99e73f4dbe
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-002r-6090000000-f5e0ef1096bea72d5c89
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-004i-9010000000-19864d6c0a50c513bb18
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-004i-9000000000-59557fda51a0ea2c63d7
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-004i-9000000000-6b0acd4d149e1fb20f9a
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-004i-9000000000-6b0acd4d149e1fb20f9a
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-004i-9000000000-6b0acd4d149e1fb20f9a
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-004i-9000000000-6b0acd4d149e1fb20f9a
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-014i-0379000000-14ceeb34a706f6a12f41
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-014i-0009000000-09662342e908d558048e
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-014i-0029000000-4b93291583996cb3cbda
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-05o0-0492000000-035f589c482b481c5152
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-053r-1890000000-1997ad0374625359f483
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-053r-1960000000-4f105348e7e7804313ce
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-053r-1930000000-b0f688a41f88a133b74b
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0f89-1910000000-c0dd1d47a44a292c87b6
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0fb9-2900000000-706d4c35cde468a8387d
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-004i-6900000000-85795e315602b7e61a6b
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0009000000-99f4dfe5439d3dd8c80f
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0009000000-b2c47603b92e2e6a3ba0
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-4009000000-5a053eaa9e6f8096bc0c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0009000000-145bc9aa0c21e6a0e341
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9020000000-448369b122422b784871
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-052p-0490000000-ed76996c5885f708c7e0
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-163.6724324
predicted
DarkChem Lite v0.1.0
[M-H]-157.40865
predicted
DeepCCS 1.0 (2019)
[M+H]+164.2958324
predicted
DarkChem Lite v0.1.0
[M+H]+159.80421
predicted
DeepCCS 1.0 (2019)
[M+Na]+163.8897324
predicted
DarkChem Lite v0.1.0
[M+Na]+165.81105
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein group
Organism
Humans
Pharmacological action
Yes
Actions
Positive allosteric modulator
Curator comments
The GABA(A) receptor is pentameric (i.e. comprising 5 subunit proteins) and therefore has a multitude of potential isoforms. The above target is a collection of all possible GABA(A) subunits that may participate in the formation of the pentameric receptor and is not meant to imply direct a drug-protein interaction for each individual subunit.
General Function
Inhibitory extracellular ligand-gated ion channel activity
Specific Function
Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...

Components:
References
  1. Sigel E, Steinmann ME: Structure, function, and modulation of GABA(A) receptors. J Biol Chem. 2012 Nov 23;287(48):40224-31. doi: 10.1074/jbc.R112.386664. Epub 2012 Oct 4. [Article]
  2. Zhu S, Noviello CM, Teng J, Walsh RM Jr, Kim JJ, Hibbs RE: Structure of a human synaptic GABAA receptor. Nature. 2018 Jul;559(7712):67-72. doi: 10.1038/s41586-018-0255-3. Epub 2018 Jun 27. [Article]
Kind
Protein group
Organism
Humans
Pharmacological action
Yes
Actions
Ligand
Curator comments
Benzodiazepines modulate GABA(A) function by binding at the interface between alpha (α) and gamma (γ) subunits. Of the 6 α-subunits, only 4 (α-1, -2, -3, and -5) participate in the formation of this binding site. The above target is a collection of all α- and γ-subunits that are known to participate in the formation of the benzodiazepine binding site.
General Function
Inhibitory extracellular ligand-gated ion channel activity
Specific Function
Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...

Components:
References
  1. Sigel E, Steinmann ME: Structure, function, and modulation of GABA(A) receptors. J Biol Chem. 2012 Nov 23;287(48):40224-31. doi: 10.1074/jbc.R112.386664. Epub 2012 Oct 4. [Article]
  2. Zhu S, Noviello CM, Teng J, Walsh RM Jr, Kim JJ, Hibbs RE: Structure of a human synaptic GABAA receptor. Nature. 2018 Jul;559(7712):67-72. doi: 10.1038/s41586-018-0255-3. Epub 2018 Jun 27. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Sproule BA, Naranjo CA, Brenmer KE, Hassan PC: Selective serotonin reuptake inhibitors and CNS drug interactions. A critical review of the evidence. Clin Pharmacokinet. 1997 Dec;33(6):454-71. doi: 10.2165/00003088-199733060-00004. [Article]
  2. Lectopam monograph [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Sproule BA, Naranjo CA, Brenmer KE, Hassan PC: Selective serotonin reuptake inhibitors and CNS drug interactions. A critical review of the evidence. Clin Pharmacokinet. 1997 Dec;33(6):454-71. doi: 10.2165/00003088-199733060-00004. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Curator comments
Information regarding this enzyme action is limited in the literature at this time.
General Function
Steroid hydroxylase activity
Specific Function
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
Gene Name
CYP2E1
Uniprot ID
P05181
Uniprot Name
Cytochrome P450 2E1
Molecular Weight
56848.42 Da
References
  1. Tassaneeyakul W, Birkett DJ, Miners JO: Inhibition of human hepatic cytochrome P4502E1 by azole antifungals, CNS-active drugs and non-steroidal anti-inflammatory agents. Xenobiotica. 1998 Mar;28(3):293-301. doi: 10.1080/004982598239579 . [Article]
  2. Lacy CF, Armstrong LL, Goldman MP, Lance LL eds (2007). Lexicomp drug information handbook (15th ed.). Lexicomp.

Drug created at July 31, 2007 13:10 / Updated at March 18, 2024 16:48