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Details

Stereochemistry ACHIRAL
Molecular Formula C18H13ClFN3.ClH
Molecular Weight 362.2288
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MIDAZOLAM HYDROCHLORIDE

SMILES

Cc1ncc2CN=C(c3ccccc3F)c4cc(ccc4-n12)Cl.Cl

InChI

InChIKey=PLYSCVSCYOQVRP-UHFFFAOYSA-N
InChI=1S/C18H13ClFN3.ClH/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;1H

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.4609
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C18H13ClFN3
Molecular Weight 325.7679
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

Curator's Comment:: Midazolam is a benzodiazepine. It works in the central nervous system (brain) to cause sleepiness, muscle relaxation, and short-term memory loss, and to reduce anxiety.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Midazolam

Approved Use

Midazolam 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 Date

503884800000
Primary
Midazolam

Approved Use

Midazolam 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 Date

503884800000
Primary
Midafresa

Approved Use

Epilepsy

Launch Date

1418774400000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
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
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
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
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

Funbound

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse events​
5 mg single, intranasal
MTD
Dose: 5 mg
Route: intranasal
Route: single
Dose: 5 mg
Sources:
unknown, 18 - 65 years
Health Status: unknown
Age Group: 18 - 65 years
Sex: unknown
Sources:
Other AEs: Nausea, Hypotension...
Other AEs:
Nausea
Hypotension
Sources:
5 mg 1 times / month multiple, intranasal
Recommended
Dose: 5 mg, 1 times / month
Route: intranasal
Route: multiple
Dose: 5 mg, 1 times / month
Sources:
unhealthy, > 12 years
Health Status: unhealthy
Age Group: > 12 years
Sex: unknown
Sources:
Disc. AE: Nasal discomfort, Somnolence...
Other AEs: Nasal discomfort, Somnolence...
AEs leading to
discontinuation/dose reduction:
Nasal discomfort (1 patient)
Somnolence (1 patient)
Other AEs:
Nasal discomfort (12.4%)
Somnolence (9.3%)
Sources:
5 mg single, intranasal
Recommended
Dose: 5 mg
Route: intranasal
Route: single
Dose: 5 mg
Sources:
unknown, adult and children
Health Status: unknown
Age Group: adult and children
Sex: M+F
Sources:
Other AEs: Hypoxemia, Hypotension...
Other AEs:
Hypoxemia (90 patients)
Hypotension (5 patients)
Sources:
5 mg single, intranasal
Recommended
Dose: 5 mg
Route: intranasal
Route: single
Dose: 5 mg
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Other AEs: Somnolence, Headache...
Other AEs:
Somnolence (10%)
Headache (7%)
Dysarthria (2%)
Nasal discomfort (5%)
Throat irritation (2%)
Rhinorrhea (3%)
Lacrimation increased (1%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Hypotension
5 mg single, intranasal
MTD
Dose: 5 mg
Route: intranasal
Route: single
Dose: 5 mg
Sources:
unknown, 18 - 65 years
Health Status: unknown
Age Group: 18 - 65 years
Sex: unknown
Sources:
Nausea
5 mg single, intranasal
MTD
Dose: 5 mg
Route: intranasal
Route: single
Dose: 5 mg
Sources:
unknown, 18 - 65 years
Health Status: unknown
Age Group: 18 - 65 years
Sex: unknown
Sources:
Nasal discomfort 1 patient
Disc. AE
5 mg 1 times / month multiple, intranasal
Recommended
Dose: 5 mg, 1 times / month
Route: intranasal
Route: multiple
Dose: 5 mg, 1 times / month
Sources:
unhealthy, > 12 years
Health Status: unhealthy
Age Group: > 12 years
Sex: unknown
Sources:
Somnolence 1 patient
Disc. AE
5 mg 1 times / month multiple, intranasal
Recommended
Dose: 5 mg, 1 times / month
Route: intranasal
Route: multiple
Dose: 5 mg, 1 times / month
Sources:
unhealthy, > 12 years
Health Status: unhealthy
Age Group: > 12 years
Sex: unknown
Sources:
Nasal discomfort 12.4%
5 mg 1 times / month multiple, intranasal
Recommended
Dose: 5 mg, 1 times / month
Route: intranasal
Route: multiple
Dose: 5 mg, 1 times / month
Sources:
unhealthy, > 12 years
Health Status: unhealthy
Age Group: > 12 years
Sex: unknown
Sources:
Somnolence 9.3%
5 mg 1 times / month multiple, intranasal
Recommended
Dose: 5 mg, 1 times / month
Route: intranasal
Route: multiple
Dose: 5 mg, 1 times / month
Sources:
unhealthy, > 12 years
Health Status: unhealthy
Age Group: > 12 years
Sex: unknown
Sources:
Hypotension 5 patients
5 mg single, intranasal
Recommended
Dose: 5 mg
Route: intranasal
Route: single
Dose: 5 mg
Sources:
unknown, adult and children
Health Status: unknown
Age Group: adult and children
Sex: M+F
Sources:
Hypoxemia 90 patients
5 mg single, intranasal
Recommended
Dose: 5 mg
Route: intranasal
Route: single
Dose: 5 mg
Sources:
unknown, adult and children
Health Status: unknown
Age Group: adult and children
Sex: M+F
Sources:
Lacrimation increased 1%
5 mg single, intranasal
Recommended
Dose: 5 mg
Route: intranasal
Route: single
Dose: 5 mg
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Somnolence 10%
5 mg single, intranasal
Recommended
Dose: 5 mg
Route: intranasal
Route: single
Dose: 5 mg
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Dysarthria 2%
5 mg single, intranasal
Recommended
Dose: 5 mg
Route: intranasal
Route: single
Dose: 5 mg
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Throat irritation 2%
5 mg single, intranasal
Recommended
Dose: 5 mg
Route: intranasal
Route: single
Dose: 5 mg
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Rhinorrhea 3%
5 mg single, intranasal
Recommended
Dose: 5 mg
Route: intranasal
Route: single
Dose: 5 mg
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Nasal discomfort 5%
5 mg single, intranasal
Recommended
Dose: 5 mg
Route: intranasal
Route: single
Dose: 5 mg
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Headache 7%
5 mg single, intranasal
Recommended
Dose: 5 mg
Route: intranasal
Route: single
Dose: 5 mg
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Overview

Overview

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes [Ki 3.7 uM]
yes [Ki 5.8 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
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%;
Page: 11,12
minor
minor
minor
no
no
no
no
no
no
no
no
no
no
no
no
no
yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Anticonvulsants for soman-induced seizure activity.
1999 Mar-Apr
Myoclonic movements in very low birth weight premature infants associated with midazolam intravenous bolus administration.
1999 Sep
Mice lacking the long splice variant of the gamma 2 subunit of the GABA(A) receptor are more sensitive to benzodiazepines.
2000 Jun
Anaesthetic agents inhibit gastrin-stimulated but not basal histamine release from rat stomach ECL cells.
2000 Jun
Midazolam attenuates ketamine-induced abnormal perception and thought process but not mood changes.
2000 Sep
Computerised advice on drug dosage to improve prescribing practice.
2001
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
Prediction of midazolam-CYP3A inhibitors interaction in the human liver from in vivo/in vitro absorption, distribution, and metabolism data.
2001 Apr
Bilateral frontal haemorrhages associated with continuous spinal analgesia.
2001 Feb
Transdermal delivery of antisense oligonucleotides can induce changes in gene expression in vivo.
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
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
Monitoring of end-tidal carbon dioxide partial pressure changes during infrarenal aortic cross-clamping: a non-invasive method to predict unclamping hypotension.
2001 Feb
Pharmacokinetic interaction of cytochrome P450 3A-related compounds with rhodamine 123, a P-glycoprotein substrate, in rats pretreated with dexamethasone.
2001 Feb
Propofol depressed neutrophil hydrogen peroxide production more than midazolam, whereas adhesion molecule expression was minimally affected by both anesthetics in rats with abdominal sepsis.
2001 Feb
The use of esmolol as an alternative to remifentanil during desflurane anesthesia for fast-track outpatient gynecologic laparoscopic surgery.
2001 Feb
In situ nasal absorption of midazolam in rats.
2001 Feb 1
[Premedication for endoscopy].
2001 Feb 2
[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
[The influence of age on hemodynamics and the dose requirements of propofol and buprenorphine in total intravenous anesthesia].
2001 Jan
Effect of diazepam and midazolam on the antinociceptive effect of morphine, metamizol and indomethacin in mice.
2001 Jan
The immunomodulatory effects of prolonged intravenous infusion of propofol versus midazolam in critically ill surgical patients.
2001 Jan
Continuous-flow nitrous oxide: searching for the ideal procedural anxiolytic for toddlers.
2001 Jan
A randomized clinical trial of continuous-flow nitrous oxide and midazolam for sedation of young children during laceration repair.
2001 Jan
Minimum local anesthetic volume blocking the femoral nerve in 50% of cases: a double-blinded comparison between 0.5% ropivacaine and 0.5% bupivacaine.
2001 Jan
A comparison of oral clonidine and oral midazolam as preanesthetic medications in the pediatric tonsillectomy patient.
2001 Jan
Parental perceptions of comfort during mechanical ventilation.
2001 Jan
Intranasal midazolam for treating febrile seizures in children. Safety is as important as efficacy.
2001 Jan 13
Intranasal midazolam for treating febrile seizures in children. Caution is required in applying hospital based evidence to primary care population.
2001 Jan 13
Intranasal midazolam for treating febrile seizures in children. Buccal midazolam should be preferred to nasal midazolam.
2001 Jan 13
Cyclodextrin solubilization of benzodiazepines: formulation of midazolam nasal spray.
2001 Jan 5
A retrospective study on the effectiveness of intranasal midazolam in pediatric burn patients.
2001 Jan-Feb
Patient status and time to intubation in the assessment of prehospital intubation performance.
2001 Jan-Mar
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
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
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
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
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
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 Fri Jun 25 22:05:59 UTC 2021
Edited
by admin
on Fri Jun 25 22:05:59 UTC 2021
Record UNII
W7TTW573JJ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MIDAZOLAM HYDROCHLORIDE
HSDB   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN  
Official Name English
VERSED
Brand Name English
RO 21-3981/003
Code English
BUCCOLAM
Brand Name English
MIDAZOLAM HYDROCHLORIDE [MART.]
Common Name English
MIDAZOLAM HYDROCHLORIDE CIV [USP-RS]
Common Name English
RO-213981001
Code English
MIDAZOLAM HYDROCHLORIDE [USAN]
Common Name English
MIDAZOLAM HYDROCHLORIDE [WHO-DD]
Common Name English
MIDAZOLAM HYDROCHLORIDE [ORANGE BOOK]
Common Name English
SEIZALAM
Brand Name English
8-CHLORO-6-(O-FLUOROPHENYL)-1-METHYL-4H-IMIDAZO(1,5-A)(1,4)BENZODIAZEPINE MONOHYDROCHLORIDE
Common Name English
4H-IMIDAZO(1,5-A)(1,4)BENZODIAZEPINE, 8-CHLORO-6-(2-FLUOROPHENYL)-1-METHYL-
Systematic Name English
MIDAZOLAM HYDROCHLORIDE [MI]
Common Name English
RO-21-3981/003
Code English
MIDAZOLAM HYDROCHLORIDE [VANDF]
Common Name English
MIDAZOLAM HYDROCHLORIDE CIV
USP-RS  
Common Name English
MIDAZOLAM HCL
Common Name English
MIDAZOLAM HYDROCHLORIDE [HSDB]
Common Name English
SHP-615
Code English
NSC-751451
Code English
SHP615
Code English
Classification Tree Code System Code
NCI_THESAURUS C1012
Created by admin on Fri Jun 25 22:05:59 UTC 2021 , Edited by admin on Fri Jun 25 22:05:59 UTC 2021
EU-Orphan Drug Midazolam Hydrochloride
Created by admin on Fri Jun 25 22:05:59 UTC 2021 , Edited by admin on Fri Jun 25 22:05:59 UTC 2021
EMA ASSESSMENT REPORTS BUCCOLAM (AUTHORIZED: EPILEPSY)
Created by admin on Fri Jun 25 22:05:59 UTC 2021 , Edited by admin on Fri Jun 25 22:05:59 UTC 2021
Code System Code Type Description
ECHA (EC/EINECS)
261-776-6
Created by admin on Fri Jun 25 22:05:59 UTC 2021 , Edited by admin on Fri Jun 25 22:05:59 UTC 2021
PRIMARY
DRUG BANK
DBSALT000118
Created by admin on Fri Jun 25 22:05:59 UTC 2021 , Edited by admin on Fri Jun 25 22:05:59 UTC 2021
PRIMARY
EPA CompTox
59467-96-8
Created by admin on Fri Jun 25 22:05:59 UTC 2021 , Edited by admin on Fri Jun 25 22:05:59 UTC 2021
PRIMARY
PUBCHEM
43032
Created by admin on Fri Jun 25 22:05:59 UTC 2021 , Edited by admin on Fri Jun 25 22:05:59 UTC 2021
PRIMARY
EVMPD
SUB03289MIG
Created by admin on Fri Jun 25 22:05:59 UTC 2021 , Edited by admin on Fri Jun 25 22:05:59 UTC 2021
PRIMARY
MERCK INDEX
M7531
Created by admin on Fri Jun 25 22:05:59 UTC 2021 , Edited by admin on Fri Jun 25 22:05:59 UTC 2021
PRIMARY Merck Index
USP_CATALOG
1443602
Created by admin on Fri Jun 25 22:05:59 UTC 2021 , Edited by admin on Fri Jun 25 22:05:59 UTC 2021
PRIMARY USP-RS
FDA UNII
W7TTW573JJ
Created by admin on Fri Jun 25 22:05:59 UTC 2021 , Edited by admin on Fri Jun 25 22:05:59 UTC 2021
PRIMARY
NCI_THESAURUS
C654
Created by admin on Fri Jun 25 22:05:59 UTC 2021 , Edited by admin on Fri Jun 25 22:05:59 UTC 2021
PRIMARY
RXCUI
203128
Created by admin on Fri Jun 25 22:05:59 UTC 2021 , Edited by admin on Fri Jun 25 22:05:59 UTC 2021
PRIMARY RxNorm
CAS
59467-96-8
Created by admin on Fri Jun 25 22:05:59 UTC 2021 , Edited by admin on Fri Jun 25 22:05:59 UTC 2021
PRIMARY
ChEMBL
CHEMBL655
Created by admin on Fri Jun 25 22:05:59 UTC 2021 , Edited by admin on Fri Jun 25 22:05:59 UTC 2021
PRIMARY
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