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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyIdentification
- Name
- Bromazepam
- Accession Number
- DB01558
- Type
- Small Molecule
- Groups
- Approved, Illicit, Investigational
- Description
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.
- Structure
Structure for Bromazepam (DB01558)
- Synonyms
- Bromacepam
- Bromazepam
- Bromazepamum
- External IDs
- RO 5-3350 / RO-5-3350
- Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Unlock Additional DataBromazepam-1.5 - Tab 1.5mg Tablet Oral Pro Doc Limitee 1997-05-20 2010-07-13 Canada 
Bromazepam-3 - Tab 3mg Tablet Oral Pro Doc Limitee 1996-12-04 2019-04-10 Canada Bromazepam-6 - Tab 6mg Tablet Oral Pro Doc Limitee 1996-12-04 2019-06-27 Canada Lectopam Tab 1.5mg Tablet Oral Hoffmann La Roche 1986-12-31 2006-07-25 Canada Lectopam Tab 3mg Tablet Oral Hoffmann La Roche 1981-12-31 2018-02-28 Canada Lectopam Tab 6mg Tablet Oral Hoffmann La Roche 1981-12-31 2018-03-31 Canada Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Unlock Additional DataAlti-bromazepam 1.5mg Tablets Tablet Oral Altimed Pharma Inc. 1996-12-31 2005-05-27 Canada Alti-bromazepam 3mg Tablets Tablet Oral Altimed Pharma Inc. 1995-12-31 2005-05-27 Canada Alti-bromazepam 6mg Tablets Tablet Oral Altimed Pharma Inc. 1996-12-31 2005-05-27 Canada Apo-bromazepam - Tab 1.5mg Tablet Oral Apotex Corporation 1995-12-31 Not applicable Canada Apo-bromazepam - Tab 3mg Tablet Oral Apotex Corporation 1995-12-31 Not applicable Canada Apo-bromazepam - Tab 6mg Tablet Oral Apotex Corporation 1995-12-31 Not applicable Canada Gen-bromazepam - Tab 3mg Tablet Oral Genpharm Ulc 1995-12-31 2010-08-04 Canada Gen-bromazepam - Tab 6mg Tablet Oral Genpharm Ulc 1995-12-31 2010-08-04 Canada Mylan-bromazepam Tablet Oral Mylan Pharmaceuticals 1995-12-31 2012-10-19 Canada Nu-bromazepam - Tab 1.5mg Tablet Oral Nu Pharm Inc 1995-12-31 2012-09-04 Canada Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- International/Other Brands
- Calmepam / Creosedin / Durazanil / Lectopam / Lekotam / Lexaurin / Lexilium / Lexomil / Lexotan / Normoc / Ultramidol
- Categories
- Anti-Anxiety Agents
- Benzazepines
- Benzodiazepine hypnotics and sedatives
- Benzodiazepines and benzodiazepine derivatives
- Benzodiazepinones
- Central Nervous System Agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP1A2 Substrates
- Cytochrome P-450 CYP2C19 Substrates
- Cytochrome P-450 CYP2E1 Inhibitors
- Cytochrome P-450 CYP2E1 Inhibitors (strength unknown)
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Drugs that are Mainly Renally Excreted
- GABA Agents
- GABA Modulators
- Heterocyclic Compounds, Fused-Ring
- Hypnotics and Sedatives
- Muscle Relaxants
- Muscle Relaxants, Centrally Acting Agents
- Nervous System
- Neurotransmitter Agents
- Psycholeptics
- Psychotropic Drugs
- Tranquilizing Agents
- UNII
- X015L14V0O
- CAS number
- 1812-30-2
- Weight
- Average: 316.153
Monoisotopic: 315.000724604 - Chemical Formula
- C14H10BrN3O
- 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
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.
- Associated Conditions
- 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.
Target Actions Organism AGABA(A) Receptor positive allosteric modulatorHumans AGABA(A) Receptor Benzodiazepine Binding Site ligandHumans - 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.
- Toxicity
- Not Available
- Affected organisms
- Humans and other mammals
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Unlock Additional Data
Additional Data Available
Adverse Effects
Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.
Learn more Additional Data Available
Contraindications
Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.
Learn more Additional Data Available
Blackbox Warnings
Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.
Learn moreInteractions
- 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.
Drug Interaction Unlock Additional Data(R)-warfarin The metabolism of (R)-warfarin can be decreased when combined with Bromazepam. 2,5-Dimethoxy-4-ethylthioamphetamine The risk or severity of adverse effects can be increased when Bromazepam is combined with 2,5-Dimethoxy-4-ethylthioamphetamine. 3-isobutyl-1-methyl-7H-xanthine The therapeutic efficacy of Bromazepam can be decreased when used in combination with 3-isobutyl-1-methyl-7H-xanthine. 4-Bromo-2,5-dimethoxyamphetamine The risk or severity of adverse effects can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Bromazepam. 4-Methoxyamphetamine The risk or severity of adverse effects can be increased when 4-Methoxyamphetamine is combined with Bromazepam. 5-methoxy-N,N-dimethyltryptamine The risk or severity of adverse effects can be increased when Bromazepam is combined with 5-methoxy-N,N-dimethyltryptamine. 6-O-benzylguanine The therapeutic efficacy of Bromazepam can be decreased when used in combination with 6-O-benzylguanine. 7-Deazaguanine The therapeutic efficacy of Bromazepam can be decreased when used in combination with 7-Deazaguanine. 7-Nitroindazole The risk or severity of adverse effects can be increased when Bromazepam is combined with 7-Nitroindazole. 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline The risk or severity of adverse effects can be increased when Bromazepam is combined with 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- 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.
References
- General References
- Oelschlager H: [Chemical and pharmacologic aspects of benzodiazepines]. Schweiz Rundsch Med Prax. 1989 Jul 4;78(27-28):766-72. [PubMed:2570451]
- 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. [PubMed:14517708]
- van Harten J: Overview of the pharmacokinetics of fluvoxamine. Clin Pharmacokinet. 1995;29 Suppl 1:1-9. doi: 10.2165/00003088-199500291-00003. [PubMed:8846617]
- 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. [PubMed:2882883]
- Lacy CF, Armstrong LL, Goldman MP, Lance LL eds (2007). Lexicomp drug information handbook (15th ed.). Lexicomp.
- External Links
- 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
- ATC Codes
- N05BA08 — Bromazepam
- AHFS Codes
- 28:24.08 — Benzodiazepines
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Terminated Treatment Anxiety Disorders / Dementias / Depression / Psychosomatic Disorders / Schizophrenia 1 3 Unknown Status Prevention Nausea / Vomiting 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- United States Pharmacopeial Convention Inc.
- Dosage forms
Form Route Strength Tablet Oral - Prices
Unit description Cost Unit Lectopam 6 mg Tablet 0.25USD tablet Lectopam 3 mg Tablet 0.17USD tablet Apo-Bromazepam 6 mg Tablet 0.13USD tablet Gen-Bromazepam 6 mg Tablet 0.13USD tablet Novo-Bromazepam 6 mg Tablet 0.13USD tablet Apo-Bromazepam 3 mg Tablet 0.09USD tablet Gen-Bromazepam 3 mg Tablet 0.09USD tablet Novo-Bromazepam 3 mg Tablet 0.09USD tablet Apo-Bromazepam 1.5 mg Tablet 0.07USD tablet Gen-Bromazepam 1.5 mg Tablet 0.07USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source logP 2.05 SANGSTER (1994) - Predicted Properties
Property Value Source Water Solubility 0.0399 mg/mL ALOGPS logP 2.09 ALOGPS logP 2.54 ChemAxon logS -3.9 ALOGPS pKa (Strongest Acidic) 12.24 ChemAxon pKa (Strongest Basic) 2.68 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 3 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 54.35 Å2 ChemAxon Rotatable Bond Count 1 ChemAxon Refractivity 76.99 m3·mol-1 ChemAxon Polarizability 28.11 Å3 ChemAxon Number of Rings 3 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET features
Property Value Probability Human Intestinal Absorption + 0.9937 Blood Brain Barrier + 0.9848 Caco-2 permeable + 0.7571 P-glycoprotein substrate Substrate 0.5741 P-glycoprotein inhibitor I Non-inhibitor 0.7251 P-glycoprotein inhibitor II Non-inhibitor 0.924 Renal organic cation transporter Non-inhibitor 0.558 CYP450 2C9 substrate Non-substrate 0.8385 CYP450 2D6 substrate Non-substrate 0.9117 CYP450 3A4 substrate Substrate 0.7117 CYP450 1A2 substrate Inhibitor 0.9381 CYP450 2C9 inhibitor Non-inhibitor 0.6329 CYP450 2D6 inhibitor Non-inhibitor 0.8511 CYP450 2C19 inhibitor Non-inhibitor 0.5719 CYP450 3A4 inhibitor Non-inhibitor 0.7405 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.6441 Ames test Non AMES toxic 0.8607 Carcinogenicity Non-carcinogens 0.8704 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.2416 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9974 hERG inhibition (predictor II) Non-inhibitor 0.7977
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Taxonomy
- 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 / Aryl bromide / Aryl halide / Pyridine / Benzenoid / Heteroaromatic compound / Carboxamide group / Ketimine / Lactam show 17 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
Targets
- 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
- 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. [PubMed:23038269]
- 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. [PubMed:29950725]
- 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
- 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. [PubMed:23038269]
- 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. [PubMed:29950725]
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
- 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. [PubMed:9435993]
- 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
- 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. [PubMed:9435993]
- 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
- Lacy CF, Armstrong LL, Goldman MP, Lance LL eds (2007). Lexicomp drug information handbook (15th ed.). Lexicomp.
Drug created on July 31, 2007 07:10 / Updated on May 30, 2020 00:22
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