midazolam   Click here for help

GtoPdb Ligand ID: 3342

Synonyms: Buccolam® | Dormicum® | Nayzilam® | USL261 (nasal spray formulation) [1] | Versed®
Approved drug PDB Ligand
midazolam is an approved drug (FDA (2000), EMA (2011))
Compound class: Synthetic organic
Comment: Midazolam is a benzodiazepine class sedative drug.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 2
Hydrogen bond donors 0
Rotatable bonds 1
Topological polar surface area 29.66
Molecular weight 325.08
XLogP 4.57
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES Clc1ccc2c(c1)C(=NCc1n2c(C)nc1)c1ccccc1F
Isomeric SMILES Clc1ccc2c(c1)C(=NCc1n2c(C)nc1)c1ccccc1F
InChI InChI=1S/C18H13ClFN3/c1-11-21-9-13-10-22-18(14-4-2-3-5-16(14)20)15-8-12(19)6-7-17(15)23(11)13/h2-9H,10H2,1H3
InChI Key DDLIGBOFAVUZHB-UHFFFAOYSA-N
No information available.
Summary of Clinical Use Click here for help
Used as an agent for sedation, anziolysis or amnesia prior to surgical, diagnostic or endoscopic procedures. Also used in the induction of general anaesthesia.
In May 2019, the FDA approved the use of a nasal spray formulation of midazolam (Nayzilam®) as an anti-epileptic therapy, based on results from clinical trial NCT01390220 [2]. Nayzilam® is indicated as a short-term treatment for seizure clusters in patients (≥12 years old) with epilepsy.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Midazolam is a benzodiazepine (BZ) drug binds to the allosteric BZ site on the GABAA channel. This potentiates the inhibitory activity of GABA by increasing the period for which the chloride channel remains open.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT01390220 Study to Evaluate the Safety and Efficacy of USL261 (Intranasal Midazolam) in Patients With Seizure Clusters Phase 3 Interventional UCB Pharma
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)
Drugs.com
European Medicines Agency (EMA)