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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2D Structure
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Physico-chemical Properties
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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
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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
1. Bancke LL, Dworak HA, Rodvold KA, Halvorsen MB, Gidal BE. (2015)
Pharmacokinetics, pharmacodynamics, and safety of USL261, a midazolam formulation optimized for intranasal delivery, in a randomized study with healthy volunteers.
Epilepsia, 56 (11): 1723-31. [PMID:26332539]
2. Detyniecki K, Van Ess PJ, Sequeira DJ, Wheless JW, Meng TC, Pullman WE. (2019)
Safety and efficacy of midazolam nasal spray in the outpatient treatment of patients with seizure clusters-a randomized, double-blind, placebo-controlled trial.
Epilepsia, 60 (9): 1797-1808. [PMID:31140596]
3. Drummond AH, Hughes PJ, Ruiz-Larrea F, Joels LA. (1989)
Use of receptor antagonist in elucidating the mechanism of action of TRH in GH3 cells.
Ann N Y Acad Sci, 553: 197-204. [PMID:2566295]
4. Waugh DJ, Gaivin RJ, Damron DS, Murray PA, Perez DM. (1999)
Binding, partial agonism, and potentiation of alpha(1)-adrenergic receptor function by benzodiazepines: A potential site of allosteric modulation.
J Pharmacol Exp Ther, 291 (3): 1164-71. [PMID:10565838]
5. Williams JA, Ring BJ, Cantrell VE, Jones DR, Eckstein J, Ruterbories K, Hamman MA, Hall SD, Wrighton SA. (2002)
Comparative metabolic capabilities of CYP3A4, CYP3A5, and CYP3A7.
Drug Metab Dispos, 30 (8): 883-91. [PMID:12124305]