U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C18H13ClFN3
Molecular Weight 325.767
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MIDAZOLAM

SMILES

CC1=NC=C2CN=C(C3=CC=CC=C3F)C4=CC(Cl)=CC=C4N12

InChI

InChIKey=DDLIGBOFAVUZHB-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C18H13ClFN3
Molecular Weight 325.767
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Midazolam, previously marketed under the trade name Versed, is a medication used for anesthesia, procedural sedation, trouble sleeping, and severe agitation. Midazolam is a short-acting benzodiazepine central nervous system (CNS) depressant. Pharmacodynamic properties of midazolam and its metabolites, which are similar to those of other benzodiazepines, include sedative, anxiolytic, amnesic and hypnotic activities. Benzodiazepine pharmacologic effects appear to result from reversible interactions with the γ-amino butyric acid (GABA) benzodiazepine receptor in the CNS, the major inhibitory neurotransmitter in the central nervous system. The action of midazolam is readily reversed by the benzodiazepine receptor antagonist, flumazenil. Data from published reports of studies in pediatric patients clearly demonstrate that oral midazolam provides safe and effective sedation and anxiolysis prior to surgical procedures that require anesthesia as well as before other procedures that require sedation but may not require anesthesia. The most commonly reported effective doses range from 0.25 to 1 mg/kg in children (6 months to <16 years). The single most commonly reported effective dose is 0.5 mg/kg. Time to onset of effect is most frequently reported as 10 to 20 minutes. The effects of midazolam on the CNS are dependent on the dose administered, the route of administration, and the presence or absence of other medications.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Computerised advice on drug dosage to improve prescribing practice.
2001
Propofol vs midazolam for ICU sedation : a Canadian multicenter randomized trial.
2001 Apr
A lack of evidence of superiority of propofol versus midazolam for sedation in mechanically ventilated critically ill patients: a qualitative and quantitative systematic review.
2001 Apr
The preemptive analgesic effect of intraarticular bupivacaine and morphine after ambulatory arthroscopic knee surgery.
2001 Apr
Stress response in infants undergoing cardiac surgery: a randomized study of fentanyl bolus, fentanyl infusion, and fentanyl-midazolam infusion.
2001 Apr
Using intranasal midazolam spray to prevent claustrophobia induced by MR imaging.
2001 Apr
Distinct functional and pharmacological properties of tonic and quantal inhibitory postsynaptic currents mediated by gamma-aminobutyric acid(A) receptors in hippocampal neurons.
2001 Apr
Metabolism of levo-alpha-Acetylmethadol (LAAM) by human liver cytochrome P450: involvement of CYP3A4 characterized by atypical kinetics with two binding sites.
2001 Apr
Prediction of midazolam-CYP3A inhibitors interaction in the human liver from in vivo/in vitro absorption, distribution, and metabolism data.
2001 Apr
Triazolam discrimination in squirrel monkeys distinguishes high-efficacy agonists from other benzodiazepines and non-benzodiazepine drugs.
2001 Feb
Sedation for cataract surgery.
2001 Feb
Preparation, premedication, and surveillance.
2001 Feb
[Epileptogenic drugs in anesthesia].
2001 Feb
Propofol as a continuous infusion during cardiopulmonary bypass does not affect changes in serum free fatty acids.
2001 Feb
Small doses of remifentanil or sufentanil for blunting cardiovascular changes induced by tracheal intubation: a double-blind comparison.
2001 Feb
Bilateral frontal haemorrhages associated with continuous spinal analgesia.
2001 Feb
The use of thiopentone/propofol admixture for laryngeal mask airway insertion.
2001 Feb
Transdermal delivery of antisense oligonucleotides can induce changes in gene expression in vivo.
2001 Feb
[Fastrach laryngeal mask, sevoflurane and remifentanil: an anesthetic alternative for the myasthenic patient].
2001 Feb
Pharmacoeconomic assessment of propofol 2% used for prolonged sedation.
2001 Feb
[Anesthetic management for the correction of pectus excavatum using pectus bar under video-assistance].
2001 Feb
[Anesthetic management for left ventricular assist device implantation in patients waiting for heart transplantation].
2001 Feb
Inhibitory effects of CYP3A4 substrates and their metabolites on P-glycoprotein-mediated transport.
2001 Feb
A randomized prospective comparative study of general versus epidural anesthesia for transcervical hysteroscopic endometrial resection.
2001 Feb
Oral transmucosal midazolam premedication for preschool children.
2001 Feb
[Premedication in ambulatory surgery].
2001 Feb 12
[Premedication for endoscopy].
2001 Feb 2
Sedation for children requiring wound repair: a randomised controlled double blind comparison of oral midazolam and oral ketamine.
2001 Jan
Intra-nasal midazolam in conscious sedation of young paediatric dental patients.
2001 Jan
Ketamine-midazolam total intravenous anaesthesia for prolonged abdominal surgery.
2001 Jan
Pulse oximetry saturation levels during routine unsedated diagnostic upper gastrointestinal endoscopy.
2001 Jan
[Anesthetic experience of emergency coronary artery bypass graft operation in a patient with cardioamyloidosis].
2001 Jan
[Anesthetic management for mitral valve replacement in a patient with idiopathic hypereosinophilic syndrome].
2001 Jan
A retrospective study on the effectiveness of intranasal midazolam in pediatric burn patients.
2001 Jan-Feb
Synergistic analgesic effects of intrathecal midazolam and NMDA or AMPA receptor antagonists in rats.
2001 Mar
Selective spinal anesthesia for outpatient laparoscopy. II: epinephrine and spinal cord function.
2001 Mar
Drugs and syringe drivers: a survey of adult specialist palliative care practice in the United Kingdom and Eire.
2001 Mar
Midazolam reduces the dose of propofol required for induction of anaesthesia and laryngeal mask airway insertion.
2001 Mar
Re: Koshy et al.--The use of propofol versus midazolam.
2001 Mar
Lack of correlation between in vitro inhibition of CYP3A-mediated metabolism by a PPAR-gamma agonist and its effect on the clinical pharmacokinetics of midazolam, an in vivo probe of CYP3A activity.
2001 Mar
Comparison of midazolam with or without fentanyl for conscious sedation and hemodynamics in coronary angiography.
2001 Mar
Anaesthetic technique for transoesophageal echocardiography in children.
2001 Mar
The comparison of midazolam and topical lidocaine spray versus the combination of midazolam, meperidine, and topical lidocaine spray to sedate patients for upper endoscopy.
2001 Mar
Propofol is not effective for hyperventilation syndrome.
2001 Mar
The effect of anxiety and personality on the pharmacokinetics of oral midazolam.
2001 Mar
Management of background pain and anxiety in critically burned children requiring protracted mechanical ventilation.
2001 Mar-Apr
Burn patients' pain and anxiety experiences.
2001 Mar-Apr
Onset and duration of action of rocuronium--from tracheal intubation, through intense block to complete recovery.
2001 May
Characterization of discriminative stimulus effects of the neuroactive steroid pregnanolone.
2001 May
Inhibition of CYP3A4 in a rapid microtiter plate assay using recombinant enzyme and in human liver microsomes using conventional substrates.
2001 May
Patents

Sample Use Guides

In Vivo Use Guide
Midazolam hydrochloride syrup is indicated for use as a single dose (0.25 to 1 mg/kg with a maximum dose of 20 mg) for preprocedural sedation and anxiolysis in pediatric patients. Midazolam hydrochloride syrup is not intended for chronic administration.
Route of Administration: Oral
In Vitro Use Guide
Midazolam (1 uM) decreased GABA-activated currents in acutely dissociated neurons, isolated from the medial septum/nucleus of the diagonal band (MS/nDB) of the adult rat brains.
Substance Class Chemical
Created
by admin
on Mon Oct 21 22:31:03 UTC 2019
Edited
by admin
on Mon Oct 21 22:31:03 UTC 2019
Record UNII
R60L0SM5BC
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MIDAZOLAM
EP   INN   JAN   MART.   MI   USP   VANDF   WHO-DD  
INN  
Official Name English
MIDAZOLAM [WHO-DD]
Common Name English
MIDAZOLAM [MI]
Common Name English
USL-261
Code English
MIDAZOLAM [MART.]
Common Name English
MIDAZOLAM [INN]
Common Name English
MIDAZOLAM CIV [USP-RS]
Common Name English
4H-IMIDAZO(1,5-A)(1,4)BENZODIAZEPINE, 8-CHLORO-6-(2-FLUOROPHENYL)-1-METHYL
Common Name English
MIDAZOLAM CIV
USP-RS  
Common Name English
NAYZILAM
Brand Name English
MIDAZOLAM [JAN]
Common Name English
MIDAZOLAM [VANDF]
Common Name English
DORMICUM
Brand Name English
MIDAZOLAM [EP]
Common Name English
USL261
Code English
8-CHLORO-6-(2-FLUOROPHENYL)-1-METHYL-4H-IMIDAZO(1,5-A)(1,4)BENZODIAZEPINE
Systematic Name English
MIDAZOLAM [USP]
Common Name English
Classification Tree Code System Code
DEA NO. 2884
Created by admin on Mon Oct 21 22:31:03 UTC 2019 , Edited by admin on Mon Oct 21 22:31:03 UTC 2019
WHO-VATC QN05CD08
Created by admin on Mon Oct 21 22:31:03 UTC 2019 , Edited by admin on Mon Oct 21 22:31:03 UTC 2019
FDA ORPHAN DRUG 514115
Created by admin on Mon Oct 21 22:31:03 UTC 2019 , Edited by admin on Mon Oct 21 22:31:03 UTC 2019
FDA ORPHAN DRUG 508215
Created by admin on Mon Oct 21 22:31:03 UTC 2019 , Edited by admin on Mon Oct 21 22:31:03 UTC 2019
LIVERTOX 635
Created by admin on Mon Oct 21 22:31:03 UTC 2019 , Edited by admin on Mon Oct 21 22:31:03 UTC 2019
FDA ORPHAN DRUG 373912
Created by admin on Mon Oct 21 22:31:03 UTC 2019 , Edited by admin on Mon Oct 21 22:31:03 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 1.3
Created by admin on Mon Oct 21 22:31:03 UTC 2019 , Edited by admin on Mon Oct 21 22:31:03 UTC 2019
FDA ORPHAN DRUG 622817
Created by admin on Mon Oct 21 22:31:03 UTC 2019 , Edited by admin on Mon Oct 21 22:31:03 UTC 2019
FDA ORPHAN DRUG 507615
Created by admin on Mon Oct 21 22:31:03 UTC 2019 , Edited by admin on Mon Oct 21 22:31:03 UTC 2019
NCI_THESAURUS C1012
Created by admin on Mon Oct 21 22:31:03 UTC 2019 , Edited by admin on Mon Oct 21 22:31:03 UTC 2019
FDA ORPHAN DRUG 277809
Created by admin on Mon Oct 21 22:31:03 UTC 2019 , Edited by admin on Mon Oct 21 22:31:03 UTC 2019
FDA ORPHAN DRUG 217405
Created by admin on Mon Oct 21 22:31:03 UTC 2019 , Edited by admin on Mon Oct 21 22:31:03 UTC 2019
WHO-ATC N05CD08
Created by admin on Mon Oct 21 22:31:03 UTC 2019 , Edited by admin on Mon Oct 21 22:31:03 UTC 2019
NDF-RT N0000175694
Created by admin on Mon Oct 21 22:31:03 UTC 2019 , Edited by admin on Mon Oct 21 22:31:03 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 8.4
Created by admin on Mon Oct 21 22:31:03 UTC 2019 , Edited by admin on Mon Oct 21 22:31:03 UTC 2019
Code System Code Type Description
EPA CompTox
59467-70-8
Created by admin on Mon Oct 21 22:31:03 UTC 2019 , Edited by admin on Mon Oct 21 22:31:03 UTC 2019
PRIMARY
RXCUI
6960
Created by admin on Mon Oct 21 22:31:03 UTC 2019 , Edited by admin on Mon Oct 21 22:31:03 UTC 2019
PRIMARY RxNorm
INN
4497
Created by admin on Mon Oct 21 22:31:03 UTC 2019 , Edited by admin on Mon Oct 21 22:31:03 UTC 2019
PRIMARY
WIKIPEDIA
MIDAZOLAM
Created by admin on Mon Oct 21 22:31:03 UTC 2019 , Edited by admin on Mon Oct 21 22:31:03 UTC 2019
PRIMARY
NCI_THESAURUS
C62049
Created by admin on Mon Oct 21 22:31:03 UTC 2019 , Edited by admin on Mon Oct 21 22:31:03 UTC 2019
PRIMARY
MESH
D008874
Created by admin on Mon Oct 21 22:31:03 UTC 2019 , Edited by admin on Mon Oct 21 22:31:03 UTC 2019
PRIMARY
EVMPD
SUB08950MIG
Created by admin on Mon Oct 21 22:31:03 UTC 2019 , Edited by admin on Mon Oct 21 22:31:03 UTC 2019
PRIMARY
CAS
59467-70-8
Created by admin on Mon Oct 21 22:31:03 UTC 2019 , Edited by admin on Mon Oct 21 22:31:03 UTC 2019
PRIMARY
ECHA (EC/EINECS)
261-774-5
Created by admin on Mon Oct 21 22:31:03 UTC 2019 , Edited by admin on Mon Oct 21 22:31:03 UTC 2019
PRIMARY
DRUG BANK
DB00683
Created by admin on Mon Oct 21 22:31:03 UTC 2019 , Edited by admin on Mon Oct 21 22:31:03 UTC 2019
PRIMARY
LactMed
59467-70-8
Created by admin on Mon Oct 21 22:31:03 UTC 2019 , Edited by admin on Mon Oct 21 22:31:03 UTC 2019
PRIMARY
MERCK INDEX
M7531
Created by admin on Mon Oct 21 22:31:03 UTC 2019 , Edited by admin on Mon Oct 21 22:31:03 UTC 2019
PRIMARY Merck Index
IUPHAR
3342
Created by admin on Mon Oct 21 22:31:03 UTC 2019 , Edited by admin on Mon Oct 21 22:31:03 UTC 2019
PRIMARY
PUBCHEM
4192
Created by admin on Mon Oct 21 22:31:03 UTC 2019 , Edited by admin on Mon Oct 21 22:31:03 UTC 2019
PRIMARY
ChEMBL
CHEMBL655
Created by admin on Mon Oct 21 22:31:03 UTC 2019 , Edited by admin on Mon Oct 21 22:31:03 UTC 2019
PRIMARY
HSDB
59467-70-8
Created by admin on Mon Oct 21 22:31:03 UTC 2019 , Edited by admin on Mon Oct 21 22:31:03 UTC 2019
PRIMARY
Related Record Type Details
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
BINDER->LIGAND
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> INHIBITOR
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
METABOLIC ENZYME -> INHIBITOR
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
Related Record Type Details
METABOLITE ACTIVE -> PARENT
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC