Details
Stereochemistry | ACHIRAL |
Molecular Formula | C18H13ClFN3.C4H4O4 |
Molecular Weight | 441.839 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)\C=C/C(O)=O.CC1=NC=C2CN=C(C3=C(F)C=CC=C3)C4=C(C=CC(Cl)=C4)N12
InChI
InChIKey=XYGVIBXOJOOCFR-BTJKTKAUSA-N
InChI=1S/C18H13ClFN3.C4H4O4/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;5-3(6)1-2-4(7)8/h2-9H,10H2,1H3;1-2H,(H,5,6)(H,7,8)/b;2-1-
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.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
2.0 nM [Ki] | |||
Target ID: CHEMBL1810 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2566295 |
3.2 µM [Ki] | ||
Target ID: CHEMBL232 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10565838 |
183.0 µM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Midazolam Approved UseMidazolam hydrochloride syrup is indicated for use in pediatric patients for sedation, anxiolysis and amnesia prior to diagnostic, therapeutic or endoscopic procedures or before induction of anesthesia.
Midazolam hydrochloride syrup is intended for use in monitored settings only and not for chronic or home use (see WARNINGS). MIDAZOLAM HYDROCHLORIDE SYRUP MUST BE USED AS SPECIFIED IN THE LABEL.
Midazolam is associated with a high incidence of partial or complete impairment of recall for the next several hours Launch Date1985 |
|||
Primary | Midazolam Approved UseMidazolam HCl syrup is indicated for use in pediatric patients for sedation, anxiolysis and amnesia prior to diagnostic, therapeutic or endoscopic procedures or before induction of anesthesia. Midazolam HCl syrup is intended for use in monitored settings only and not for chronic or home use (see WARNINGS). MIDAZOLAM HCl SYRUP MUST BE USED AS SPECIFIED IN THE LABEL. Midazolam is associated with a high incidence of partial or complete impairment of recall for the next several hours Launch Date1985 |
|||
Primary | Midafresa Approved UseEpilepsy Launch Date2014 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
54.7 ng/mL |
5 mg single, nasal dose: 5 mg route of administration: Nasal experiment type: SINGLE co-administered: |
MIDAZOLAM unknown | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
113.9 ng/mL |
10 mg single, intramuscular dose: 10 mg route of administration: Intramuscular experiment type: SINGLE co-administered: |
MIDAZOLAM unknown | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
35.124 ng/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01989169 |
6 mg single, oral dose: 6 mg route of administration: oral experiment type: single co-administered: |
MIDAZOLAM plasma | Homo sapiens population: healthy age: Adults sex: food status: |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
126.2 ng × h/mL |
5 mg single, nasal dose: 5 mg route of administration: Nasal experiment type: SINGLE co-administered: |
MIDAZOLAM unknown | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
402.7 ng × h/mL |
10 mg single, intramuscular dose: 10 mg route of administration: Intramuscular experiment type: SINGLE co-administered: |
MIDAZOLAM unknown | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
100.935 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01989169 |
6 mg single, oral dose: 6 mg route of administration: oral experiment type: single co-administered: |
MIDAZOLAM plasma | Homo sapiens population: healthy age: Adults sex: food status: |
|
103.348 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01989169 |
6 mg single, oral dose: 6 mg route of administration: oral experiment type: single co-administered: |
MIDAZOLAM plasma | Homo sapiens population: healthy age: Adults sex: food status: |
|
30 nM*h Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01361217 |
2 mg single, oral dose: 2 mg route of administration: oral experiment type: single co-administered: |
MIDAZOLAM plasma | Homo sapiens population: healthy age: adults sex: food status: |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3% |
5 mg single, nasal dose: 5 mg route of administration: Nasal experiment type: SINGLE co-administered: |
MIDAZOLAM unknown | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
3% |
10 mg single, intramuscular dose: 10 mg route of administration: Intramuscular experiment type: SINGLE co-administered: |
MIDAZOLAM unknown | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
5 mg single, intranasal MTD Dose: 5 mg Route: intranasal Route: single Dose: 5 mg Co-administed with:: sufentanil(0.4 mg/kg) Sources: |
unknown, 18 - 65 years n = 30 Health Status: unknown Condition: gastroscopy Age Group: 18 - 65 years Sex: unknown Population Size: 30 Sources: |
Other AEs: Nausea, Hypotension... |
5 mg 1 times / month multiple, intranasal (mean) Recommended Dose: 5 mg, 1 times / month Route: intranasal Route: multiple Dose: 5 mg, 1 times / month Sources: |
unhealthy, > 12 years n = 161 Health Status: unhealthy Condition: seizure clusters Age Group: > 12 years Sex: unknown Population Size: 161 Sources: |
Disc. AE: Nasal discomfort, Somnolence... Other AEs: Nasal discomfort, Somnolence... AEs leading to discontinuation/dose reduction: Nasal discomfort (1 patient) Other AEs:Somnolence (1 patient) Nasal discomfort (12.4%) Sources: Somnolence (9.3%) |
5 mg single, intranasal (mean) Recommended Dose: 5 mg Route: intranasal Route: single Dose: 5 mg Sources: |
unknown, adult and children n = 87740 Health Status: unknown Condition: gastroscopy Age Group: adult and children Sex: M+F Population Size: 87740 Sources: |
Other AEs: Hypoxemia, Hypotension... Other AEs: Hypoxemia (90 patients) Sources: Hypotension (5 patients) |
5 mg single, intranasal Recommended Dose: 5 mg Route: intranasal Route: single Dose: 5 mg Sources: |
unhealthy, adult n = 91 Health Status: unhealthy Condition: intermittent, stereotypic episodes of frequent seizure activity Age Group: adult Sex: unknown Population Size: 91 Sources: |
Other AEs: Somnolence, Headache... Other AEs: Somnolence (10%) Sources: Headache (7%) Dysarthria (2%) Nasal discomfort (5%) Throat irritation (2%) Rhinorrhea (3%) Lacrimation increased (1%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Hypotension | 5 mg single, intranasal MTD Dose: 5 mg Route: intranasal Route: single Dose: 5 mg Co-administed with:: sufentanil(0.4 mg/kg) Sources: |
unknown, 18 - 65 years n = 30 Health Status: unknown Condition: gastroscopy Age Group: 18 - 65 years Sex: unknown Population Size: 30 Sources: |
|
Nausea | 5 mg single, intranasal MTD Dose: 5 mg Route: intranasal Route: single Dose: 5 mg Co-administed with:: sufentanil(0.4 mg/kg) Sources: |
unknown, 18 - 65 years n = 30 Health Status: unknown Condition: gastroscopy Age Group: 18 - 65 years Sex: unknown Population Size: 30 Sources: |
|
Nasal discomfort | 1 patient Disc. AE |
5 mg 1 times / month multiple, intranasal (mean) Recommended Dose: 5 mg, 1 times / month Route: intranasal Route: multiple Dose: 5 mg, 1 times / month Sources: |
unhealthy, > 12 years n = 161 Health Status: unhealthy Condition: seizure clusters Age Group: > 12 years Sex: unknown Population Size: 161 Sources: |
Somnolence | 1 patient Disc. AE |
5 mg 1 times / month multiple, intranasal (mean) Recommended Dose: 5 mg, 1 times / month Route: intranasal Route: multiple Dose: 5 mg, 1 times / month Sources: |
unhealthy, > 12 years n = 161 Health Status: unhealthy Condition: seizure clusters Age Group: > 12 years Sex: unknown Population Size: 161 Sources: |
Nasal discomfort | 12.4% | 5 mg 1 times / month multiple, intranasal (mean) Recommended Dose: 5 mg, 1 times / month Route: intranasal Route: multiple Dose: 5 mg, 1 times / month Sources: |
unhealthy, > 12 years n = 161 Health Status: unhealthy Condition: seizure clusters Age Group: > 12 years Sex: unknown Population Size: 161 Sources: |
Somnolence | 9.3% | 5 mg 1 times / month multiple, intranasal (mean) Recommended Dose: 5 mg, 1 times / month Route: intranasal Route: multiple Dose: 5 mg, 1 times / month Sources: |
unhealthy, > 12 years n = 161 Health Status: unhealthy Condition: seizure clusters Age Group: > 12 years Sex: unknown Population Size: 161 Sources: |
Hypotension | 5 patients | 5 mg single, intranasal (mean) Recommended Dose: 5 mg Route: intranasal Route: single Dose: 5 mg Sources: |
unknown, adult and children n = 87740 Health Status: unknown Condition: gastroscopy Age Group: adult and children Sex: M+F Population Size: 87740 Sources: |
Hypoxemia | 90 patients | 5 mg single, intranasal (mean) Recommended Dose: 5 mg Route: intranasal Route: single Dose: 5 mg Sources: |
unknown, adult and children n = 87740 Health Status: unknown Condition: gastroscopy Age Group: adult and children Sex: M+F Population Size: 87740 Sources: |
Lacrimation increased | 1% | 5 mg single, intranasal Recommended Dose: 5 mg Route: intranasal Route: single Dose: 5 mg Sources: |
unhealthy, adult n = 91 Health Status: unhealthy Condition: intermittent, stereotypic episodes of frequent seizure activity Age Group: adult Sex: unknown Population Size: 91 Sources: |
Somnolence | 10% | 5 mg single, intranasal Recommended Dose: 5 mg Route: intranasal Route: single Dose: 5 mg Sources: |
unhealthy, adult n = 91 Health Status: unhealthy Condition: intermittent, stereotypic episodes of frequent seizure activity Age Group: adult Sex: unknown Population Size: 91 Sources: |
Dysarthria | 2% | 5 mg single, intranasal Recommended Dose: 5 mg Route: intranasal Route: single Dose: 5 mg Sources: |
unhealthy, adult n = 91 Health Status: unhealthy Condition: intermittent, stereotypic episodes of frequent seizure activity Age Group: adult Sex: unknown Population Size: 91 Sources: |
Throat irritation | 2% | 5 mg single, intranasal Recommended Dose: 5 mg Route: intranasal Route: single Dose: 5 mg Sources: |
unhealthy, adult n = 91 Health Status: unhealthy Condition: intermittent, stereotypic episodes of frequent seizure activity Age Group: adult Sex: unknown Population Size: 91 Sources: |
Rhinorrhea | 3% | 5 mg single, intranasal Recommended Dose: 5 mg Route: intranasal Route: single Dose: 5 mg Sources: |
unhealthy, adult n = 91 Health Status: unhealthy Condition: intermittent, stereotypic episodes of frequent seizure activity Age Group: adult Sex: unknown Population Size: 91 Sources: |
Nasal discomfort | 5% | 5 mg single, intranasal Recommended Dose: 5 mg Route: intranasal Route: single Dose: 5 mg Sources: |
unhealthy, adult n = 91 Health Status: unhealthy Condition: intermittent, stereotypic episodes of frequent seizure activity Age Group: adult Sex: unknown Population Size: 91 Sources: |
Headache | 7% | 5 mg single, intranasal Recommended Dose: 5 mg Route: intranasal Route: single Dose: 5 mg Sources: |
unhealthy, adult n = 91 Health Status: unhealthy Condition: intermittent, stereotypic episodes of frequent seizure activity Age Group: adult Sex: unknown Population Size: 91 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes [Ki 3.7 uM] | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/15544435/ Page: 9.0 |
yes [Ki 5.8 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/211321Orig1s000ClinPharmR.pdf#page=11 Page: 11,12 |
major | yes (co-administration study) Comment: INHIBITORS: Coadministration with cimetidine: AUC increase of MDZ=10-102%; diltiazem: AUC increase of MDZ=275%; erythromycin: AUC increase of MDZ=281-341; fluconazole: AUC increase of MDZ=250%; grapefruit juice: AUC increase of 52%; itraconazole: AUC increase of MDZ=240-980%; ketoconazole: AUC increase of MDZ=1490%; ranitidine: AUC increase of MDZ=9-66%. INDUCERS: coadministration with carbamazepine: AUC decrease of MDZ=94%; phenytoin: AUC decrease of MDZ=94%; rifampin: AUC decrease of MDZ=96%; Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/211321Orig1s000ClinPharmR.pdf#page=11 Page: 11,12 |
||
minor | ||||
minor | ||||
minor | ||||
no | ||||
no | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/18256203/ Page: 8.0 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/18256203/ Page: 8.0 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/18256203/ Page: 8.0 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/18256203/ Page: 8.0 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/18256203/ Page: 8.0 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/18256203/ Page: 8.0 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/18256203/ Page: 8.0 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/18256203/ Page: 8.0 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/18256203/ Page: 8.0 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/18256203/ Page: 8.0 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/18256203/ Page: 8.0 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/18256203/ Page: 8.0 |
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
Binding, partial agonism, and potentiation of alpha(1)-adrenergic receptor function by benzodiazepines: A potential site of allosteric modulation. | 1999 Dec |
|
Anticonvulsants for soman-induced seizure activity. | 1999 Mar-Apr |
|
Flumazenil antagonizes midazolam-induced airway narrowing during nasal breathing in humans. | 1999 May |
|
A double-blind placebo controlled trial of oral midazolam as premedication before flexible sigmoidoscopy. | 1999 Nov |
|
No reduction in the sufentanil requirement of elderly patients undergoing ventilatory support in the medical intensive care unit. | 1999 Oct |
|
Anaesthetic agents inhibit gastrin-stimulated but not basal histamine release from rat stomach ECL cells. | 2000 Jun |
|
Computerised advice on drug dosage to improve prescribing practice. | 2001 |
|
Propofol vs midazolam for ICU sedation : a Canadian multicenter randomized trial. | 2001 Apr |
|
Using intranasal midazolam spray to prevent claustrophobia induced by MR imaging. | 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 |
|
Triazolam discrimination in squirrel monkeys distinguishes high-efficacy agonists from other benzodiazepines and non-benzodiazepine drugs. | 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 |
|
Pharmacoeconomic assessment of propofol 2% used for prolonged sedation. | 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 |
|
Cardiovascular effects of sevoflurane, isoflurane, halothane, and fentanyl-midazolam in children with congenital heart disease: an echocardiographic study of myocardial contractility and hemodynamics. | 2001 Feb |
|
[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 |
|
[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 |
|
Influence of patient posture on oxygen saturation during fibre-optic bronchoscopy. | 2001 Jan |
|
Digitally assisted acromioplasty: the effect of interscalene block on this new surgical technique. | 2001 Jan |
|
Continuous-flow nitrous oxide: searching for the ideal procedural anxiolytic for toddlers. | 2001 Jan |
|
Etomidate for pediatric sedation prior to fracture reduction. | 2001 Jan |
|
Adrenocortical dysfunction following etomidate induction in emergency department patients. | 2001 Jan |
|
Speed of recovery and side-effect profile of sevoflurane sedation compared with midazolam. | 2001 Jan |
|
Awake craniotomy for removal of intracranial tumor: considerations for early discharge. | 2001 Jan |
|
A comparison of oral clonidine and oral midazolam as preanesthetic medications in the pediatric tonsillectomy patient. | 2001 Jan |
|
A method for the simultaneous evaluation of the activities of seven major human drug-metabolizing cytochrome P450s using an in vitro cocktail of probe substrates and fast gradient liquid chromatography tandem mass spectrometry. | 2001 Jan |
|
Parental perceptions of comfort during mechanical ventilation. | 2001 Jan |
|
Intranasal midazolam for treating febrile seizures in children. Buccal midazolam should be preferred to nasal midazolam. | 2001 Jan 13 |
|
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 |
|
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 |
|
Evaluation of the safety and efficacy of repeated sedations for the radiotherapy of young children with cancer: a prospective study of 1033 consecutive sedations. | 2001 Mar 1 |
|
Management of background pain and anxiety in critically burned children requiring protracted mechanical ventilation. | 2001 Mar-Apr |
|
Onset and duration of action of rocuronium--from tracheal intubation, through intense block to complete recovery. | 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
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8173965
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.
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142441
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DBSALT002303
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59467-94-6
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CHEMBL655
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100000076068
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C167002
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261-775-0
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m7531
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77520S18SE
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5384200
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ACTIVE MOIETY
PARENT (SALT/SOLVATE)
SUBSTANCE RECORD