Midazolam

Identification

Summary

Midazolam is a short-acting benzodiazepine with rapid onset that is commonly used in seizures, anesthesia and anxiety disorders.

Brand Names

Buccolam, Busulfex, Nayzilam, Seizalam

Generic Name

Midazolam

DrugBank Accession Number

DB00683

Background

Midazolam is a short-acting hypnotic-sedative drug with anxiolytic, muscle relaxant, anticonvulsant, sedative, hypnotic, and amnesic properties.⁶ It belongs to a class of drugs called benzodiazepines. This drug is unique from others in this class due to its rapid onset of effects and short duration of action.⁶ Midazolam is available by oral, rectal, intranasal, intramuscular (IM), and intravenous (IV) routes and has been used in various biomedical applications, including dentistry, cardiac surgery, and endoscopic procedures as pre-anesthetic medication, and as an adjunct to local anesthesia.²¹

This drug was initially approved by the US FDA in 1985, and has been approved for various indications since.¹⁹ In late 2018, the intramuscular preparation was approved by the FDA for the treatment of status epilepticus in adults.¹⁹ In May 2019, the nasal spray of midazolam was approved for the acute treatment of distinctive intermittent, stereotypic seizure episodes in patients 12 years of age and older.⁸ Midazolam is considered a schedule IV drug in the United States due to the low potential for abuse and low risk of dependence.¹⁰

Type

Small Molecule

Groups

Approved, Illicit

Structure

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Midazolam (DB00683)

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Weight

Average: 325.767
Monoisotopic: 325.078203343

Chemical Formula

C₁₈H₁₃ClFN₃

Synonyms

• Midazolam
• Midazolamum

External IDs

• Dea No. 2884
• Ro 21-3981/001
• Ro 21-3981/003

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Pharmacology

Indication

Midazolam has different indications depending on its formulation by the FDA.

Nasal

For the nasal spray formulation, midazolam is indicated for the acute treatment of intermittent, stereotypic episodes of frequent seizure activity (i.e., seizure clusters, acute repetitive seizures) that are distinct from a patient’s usual seizure pattern in patients with epilepsy 12 years of age and older.¹³

Intravenous

For the intravenous injection formulation, midazolam is indicated as an agent for sedation/anxiolysis/amnesia and prior to or during diagnostic, therapeutic or endoscopic procedures, such as bronchoscopy, gastroscopy, cystoscopy, coronary angiography, cardiac catheterization, oncology procedures, radiologic procedures, suture of lacerations and other procedures either alone or in combination with other CNS depressants.¹⁴ The sedative, anxiolytic and amnestic use of midazolam can also be employed pre-operatively.¹⁴ It can also be indicated for induction of general anesthesia, before administration of other anesthetic agents or as a component of intravenous supplementation of nitrous oxide and oxygen for a balanced anesthesia.¹⁴ A relatively narrower dose range of midazolam and a shorter period of induction can be achieved if midazolam is combined with narcotic premedication.¹⁴ Finally, midazolam can be indicated as a continous intravenous infusion for sedation of intubated and mechanically ventilated patients as a component of anesthesia or during treatment in a critical care setting.¹⁴

Intramuscular

For the intramusuclar injection formulation, midazolam is indicated for preoperative sedation/anxiolysis/amnesia or for treatment of status epilepticus in adults.^14,15

Oral

Midazolam 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. It is only approved in monitored settings only and not for chronic or home use.¹¹

In Europe, a buccal formulation of midazolam is also approved for the treatment of prolonged, acute, convulsive seizures in infants, toddlers, children and adolescents (from 3 months to < 18 years). For infants between 3-6 months of age treatment should be in a hospital setting where monitoring is possible and resuscitation equipment is available.¹⁶

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Treatment of	Epileptic seizure		••••••••••••	••••••••••• •••••	••••••• ••••••• •••••••	•••••
Treatment of	Status epilepticus		••••••••••••	•••••		•••••••••

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Associated Therapies

• Anaesthesia
• Anxiolytic therapy therapy
• Sedation for mechanically-ventilated patients
• Preoperative amnesia therapy
• Preoperative sedation therapy

Contraindications & Blackbox Warnings

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Pharmacodynamics

General effects

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 benzodiazepine drugs, include sedative, anxiolytic, amnestic, muscle relaxant, as well as hypnotic activities.²⁰ Benzodiazepines enhance the inhibitory action of the amino acid neurotransmitter gamma-aminobutyric acid (GABA). Receptors for GABA are targeted by many important drugs that affect GABA function and are commonly used in the treatment of anxiety disorder, epilepsy, insomnia, spasticity, and aggressive behavior.⁷

Sedation and memory

The onset of sedation after intramuscular administration in adults is 15 minutes, with maximal sedation occurring 30-60 minutes after injection.^Label In one study of adults, when tested the following day, 73% of the patients who were administered midazolam intramuscularly had no recollection of memory cards shown 30 minutes following drug administration; 40% had no recollection of the memory cards shown 60 minutes after drug administration. Onset time of sedative effects in pediatric patients begins within 5 minutes and peaks at 15-30 minutes depending upon the dose administered. In the pediatric population, up to 85% had no memory of pictures shown after receiving intramuscular midazolam compared to 5% of the placebo control group.²⁰

Sedation in both adult and pediatric patients is reached within 3 to 5 minutes post intravenous (IV) injection. The time of onset is affected by the dose administered and the simultaneous administration of narcotic pre-medication. Seventy-one (71%) percent of the adult patients in clinical endoscopy studies had no memory of insertion of the endoscope; 82% of the patients had no memory of withdrawal of the endoscope.¹⁴

Anesthesia induction

When midazolam is administered intravenously (IV) for anesthetic induction, induction of anesthesia occurs in about 1.5 minutes when narcotic pre-medication has been given and in 2 to 2.5 minutes without narcotic pre-medication/ other sedative pre-medication. Impairment in a memory test was observed in 90% of the patients.¹⁴

Mechanism of action

The actions of benzodiazepines such as midazolam are mediated through the inhibitory neurotransmitter gamma-aminobutyric acid (GABA), which is one of the major inhibitory neurotransmitters in the central nervous system. Benzodiazepines increase the activity of GABA, thereby producing a sedating effect, relaxing skeletal muscles, and inducing sleep, anesthesia, and amnesia. Benzodiazepines bind to the benzodiazepine site on GABA-A receptors, which potentiates the effects of GABA by increasing the frequency of chloride channel opening.²⁰ These receptors have been identified in different body tissues including the heart and skeletal muscle, although mainly appear to be present in the central nervous system.⁶

Target	Actions	Organism
AGABA(A) Receptor	positive allosteric modulator	Humans
AGABA(A) Receptor Benzodiazepine Binding Site	ligand	Humans
UAdenosine receptor A2a	potentiator	Humans

Absorption

Intramuscular

Following IM administration of a single 10 mg midazolam dose to healthy subjects, midazolam was absorbed with median T_max (range) of 0.5 (0.25 to 0.5) hours; midazolam's mean (±SD) C_max and AUC_0-∞ were 113.9 (±30.9) ng/mL and 402.7 (±97.0) ng∙h/mL, respectively.¹⁵

Rectal

After rectal administration midazolam is absorbed rapidly. Maximum plasma concentration is reached within 30 minutes. The absolute bioavailability is approximately 50%.²¹

Intranasal Administration

Following the nasal administration of a single 5 mg midazolam dose to healthy adults, midazolam was absorbed with a median T_max (range) of 17.3 (7.8 to 28.2) minutes; midazolam's mean (±SD) C_max and AUC_0-∞ were 54.7 (±30.4) ng/mL and 126.2 (±59) ng∙h/mL, respectively. The mean absolute bioavailability is approximately 44%.¹³

Oral

In pediatric patients from 6 months to <16 years old, the mean T_max values across dose groups (0.25, 0.5, and 1.0 mg/kg) range from 0.17 to 2.65 hours. Midazolam also exhibits linear pharmacokinetics within this dose range (up to a maximum dose of 40 mg). Linearity was also demonstrated across the doses within the age group of 2 years to <12 years having 18 patients at each of the three doses. Due to first-pass metabolism, only 40-50% of the administered oral dose reaches the circulation.⁶ The absolute bioavailability of midazolam is about 36%, which is not affected by pediatric age or weight. C_max and AUC_0-∞ were also calculated to range from 28 to 201 ng/mL and 67.6 to 821 ng∙h/mL respectively.¹¹

Buccal

After oromucosal administration midazolam is absorbed rapidly. Maximum plasma concentration is reached within 30 minutes in children. The absolute bioavailability of oromucosal midazolam is about 75% in adults. The bioavailability of oromucosal midazolam has been estimated at 87% in children with severe malaria and convulsions. C_max and AUC_0-∞ were also calculated to range from 87 to 148 ng/mL and 168 to 254 ng∙h/mL respectively.¹⁶

Volume of distribution

Female gender, old age, and obesity may increase the volume of distribution. Midazolam may also cross the placenta and has been detected in human milk and cerebrospinal fluid.^Label,20

Intravenous administration

In pediatric patients (6 months to <16 years) receiving 0.15 mg/kg IV midazolam, the mean steady-state volume of distribution ranged from 1.24 to 2.02 L/kg.¹¹ For healthy adult patients, the volume of distribution determined from six single-dose pharmacokinetic studies ranged from 1.0 to 3.1 L/kg.¹⁴

Intramuscular administration

The mean (±SD) apparent volume of distribution (Vz/F) of midazolam following a single IM dose of 10 mg midazolam was 2117 (±845.1) mL/kg in healthy subjects.¹⁵

Intranasal

The estimated total volume of distribution of midazolam is 226.5 L.¹³

Buccal

The steady-state volume of distribution following oromucosal administration is estimated to be 5.3 l/kg.¹⁶

Protein binding

In adults and pediatric patients, midazolam is approximately 97% bound to plasma protein, principally albumin. In healthy volunteers, 1-hydroxy midazolam is bound to the extent of 89%.¹³

Metabolism

In vitro studies with human liver microsomes indicate that the biotransformation of midazolam is mediated by the cytochrome P450-3A4 (CYP3A4). This enzyme is present in gastrointestinal tract mucosa, as well as in the liver. The 1-hydroxy-midazolam (also termed alpha-hydroxymidazolam) metabolite comprises 60% to 70% of the biotransformation products of midazolam, while 4-hydroxy-midazolam constitutes 5% or less. Small amounts of a dihydroxy derivative have also been detected, but not quantified.¹⁵ Midazolam also undergoes N-glucuronidation via UGT1A4 after the process of hepatic oxidation by cytochrome enzymes.⁶

Studies of the intravenous administration of 1-hydroxy-midazolam in humans suggest that 1-hydroxymidazolam is at least as potent as the parent compound, and may contribute to the net pharmacologic activity of midazolam. In vitro studies have demonstrated that the affinities of 1- and 4-hydroxy-midazolam for the benzodiazepine receptor are approximately 20% and 7%, respectively, relative to midazolam.¹⁵

Hover over products below to view reaction partners

• Midazolam
  • 1-hydroxymidazolam
    • 1-hydroxymidazolam-N-glucuronide
    • 1-hydroxymidazolam-O-glucuronide
    • 1,4-dihydroxymidazolam
  • 4-hydroxymidazolam
    • 4-hydroxymidazolam-N-glucuronide
    • 4-hydroxymidazolam-O-glucuronide
    • 1,4-dihydroxymidazolam
  • Midazolam-N-glucuronide

Route of elimination

The α-hydroxymidazolam glucuronide conjugate of midazolam is excreted in the urine. No significant amount of parent drug or metabolites is found in urine before beta-glucuronidase and sulfatase deconjugation, suggesting that the urinary metabolites are excreted mainly as conjugates. The amount of midazolam excreted unchanged in the urine when given intravenously is less than 0.5%. 45% to 57% of the dose was excreted in the urine as 1-hydroxymethyl midazolam conjugate.¹⁵ The principal urinary excretion products are glucuronide conjugates of hydroxylated derivatives.¹⁵

Plasma clearance of midazolam is higher in patients that remain in the supine position, because of a 40-60 percent increase in hepatic blood flow during supination. Pregnancy may also increase the metabolism of midazolam.⁶

Half-life

Intravenous: Six single-dose pharmacokinetic studies involving healthy adults yield an elimination half-life of 1.8 to 6.4 hours (mean of approximately 3 hours).¹⁴

Intramuscular Following IM administration of 10 mg midazolam, the mean (±SD) elimination half-life of midazolam was 4.2 (±1.87) hours.¹⁵

Intranasal Following the administration of NAYZILAM in clinical trials, median midazolam and 1-hydroxy-midazolam elimination half-lives ranged from 2.1 to 6.2 hours and 2.7 to 7.2 hours, respectively, independent of dose.¹³

Oral The mean elimination half-life of midazolam ranged from 2.2 to 6.8 hours following single oral doses of 0.25, 0.5, and 1.0 mg/kg of midazolam HCl syrup.¹¹

*Buccal The initial and terminal elimination half-lives are 27 and 204 minutes, respectively.¹⁶

Clearance

Intramuscular

Following IM administration of 10 mg midazolam, the apparent total body clearance (CL/F) of midazolam was 367.3 (±73.5) mL/hr/kg.¹⁵

Intravenous:

Six single-dose pharmacokinetic studies involving healthy adults yield a total clearance (Cl) of 0.25 to 0.54 L/hr/kg.¹⁴

Intranasal

Midazolam clearance was calculated to be 1.9 mL/min/kg

Oral Following a group of patients receiving the 0.15 mg/kg IV dose, the mean total clearance ranged from 9.3 to 11.0 mL/min/kg.¹¹

*Buccal Plasma clearance of midazolam in children following oromucosal administration is 30 ml/kg/min.¹⁶

Adverse Effects

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Toxicity

LD₅₀=215 mg/kg, in rats.^MSDS

Overdose

Signs of overdose include sedation, somnolence, confusion, impaired coordination, diminished reflexes, coma, and deleterious effects on vital signs. Serious cardiorespiratory adverse reactions have occurred, sometimes ending in death or permanent neurologic effects, after the administration of midazolam.^Label

A note on cardiac and respiratory depression

After administration of midazolam, continuous monitoring of respiratory and cardiac function is recommended until the patient is in stable condition. Serious and life-threatening cardiorespiratory adverse reactions, including hypoventilation, airway obstruction, apnea, and hypotension have been reported with the use of midazolam. Patients should be monitored in a setting with immediate access to resuscitative drugs if they are required. Resuscitation equipment and personnel trained in their use and skilled in airway management should be available when midazolam is administered.^Label

The usual recommended intramuscular pre-medicating doses of midazolam do not depress the ventilatory response to carbon dioxide stimulation to a clinically significant extent in adults. Intravenous induction doses of midazolam depress the ventilatory response to carbon dioxide stimulation for at least 15 minutes longer than the duration of ventilatory depression following administration of thiopental in adults. Impairment of ventilatory response to carbon dioxide is more severe in adult patients diagnosed with chronic obstructive pulmonary disease (COPD).²⁰

A note on dependence

When midazolam is used in long-term sedation in the ICU (intensive care unit) or other settings, physical dependence on midazolam may develop. The risk of dependence increases with dose and duration of treatment; this risk is also greater in patients with a medical history of substance abuse.¹⁰

Special caution should be exercised when administering midazolam in the following populations

High-risk patients include adults over 60 years of age, chronically ill or debilitated patients, which may include patients with chronic respiratory insufficiency, patients with chronic renal failure, impaired hepatic function or with impaired cardiac function, pediatric patients (especially those with cardiovascular instability). These high-risk patients require lower dosages and should be monitored on a continuous basis for early signs of alterations of vital functions, so that appropriate management may be administered.¹⁰

Mutagenesis

Midazolam was negative for genotoxicity during in vitro and in vivo assays.^Label

Impairment of Fertility

When midazolam (0, 1, 4, or 16 mg/kg) was given orally to male and female rats before and during mating and continuing in females throughout gestation and lactation, no adverse effects on male or female fertility were observed. Midazolam plasma exposures (AUC) at the highest dose tested were approximately 6 times that in humans at the recomended human dose.^Label

Pathways

Not Available

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Interactions

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This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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1,2-Benzodiazepine	The risk or severity of sedation and CNS depression can be increased when Midazolam is combined with 1,2-Benzodiazepine.
Abacavir	Midazolam may decrease the excretion rate of Abacavir which could result in a higher serum level.
Abametapir	The serum concentration of Midazolam can be increased when it is combined with Abametapir.
Abatacept	The metabolism of Midazolam can be increased when combined with Abatacept.
Abemaciclib	The serum concentration of Abemaciclib can be increased when it is combined with Midazolam.

Food Interactions

• Avoid alcohol. Midazolam may make your sleepiness or dizziness worse.
• Avoid grapefruit products. Bioavailability of midazolam can increase.

Products

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Midazolam hydrochloride	W7TTW573JJ	59467-96-8	PLYSCVSCYOQVRP-UHFFFAOYSA-N
Midazolam maleate	77520S18SE	59467-94-6	XYGVIBXOJOOCFR-BTJKTKAUSA-N

International/Other Brands

Anquil (General Pharma) / Benzosed (Pharmaceutical) / Dalam (Richmond) / Damizol (Specifar) / Demizolam (Dem Ilaç) / Doricum (Roche) / Dormicum (Roche) / Dormid (Scott) / Dormipron (Chalver) / Dormire (Cristália) / Dormitol (Square) / Dormixal (Demo) / Dormonid (Roche) / Drimnorth (Northia) / Epistatus (IFET) / Flormidal (Galenika) / Fulsed (Ranbaxy) / Fulsed Injection (Terapia) / Garen (Bio-Pharma) / Gobbizolam (Gobbi) / Hipnazolam (EMS) / Hipnoz (Pharos) / Hypnofast (Incepta) / Hypnovel (Roche) / Ipnovel (Roche) / Nocturna (Lafi) / Setam (Rimsa) / Talentum (Fisiopharma) / Terap (Sanitas) / Versed (Roche)

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Buccolam	Solution	5 mg	Buccal	Neuraxpharm Pharmaceuticals S.L.	2022-05-04	Not applicable
Buccolam	Solution	7.5 mg	Buccal	Neuraxpharm Pharmaceuticals S.L.	2016-09-08	Not applicable
Buccolam	Solution	10 mg	Buccal	Neuraxpharm Pharmaceuticals S.L.	2022-05-04	Not applicable
Buccolam	Solution	2.5 mg	Buccal	Neuraxpharm Pharmaceuticals S.L.	2022-05-04	Not applicable
Buccolam	Solution	5 mg	Buccal	Neuraxpharm Pharmaceuticals S.L.	2016-09-08	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Apo-midazolam Injectable 1 mg/ml	Liquid	1 mg / mL	Intramuscular; Intravenous	Apotex Corporation	2001-04-10	2013-08-02
Apo-midazolam Injectable 5 mg/ml	Liquid	5 mg / mL	Intramuscular; Intravenous	Apotex Corporation	2001-04-10	2013-08-02
Midazolam	Injection, solution	5 mg/1mL	Intramuscular; Intravenous	Steriscience Specialties Private Limited	2023-07-31	Not applicable
Midazolam	Injection, solution	5 mg/1mL	Intramuscular; Intravenous	Cardinal Health	2000-07-14	2016-10-31
Midazolam	Injection, solution	1 mg/1mL	Intramuscular; Intravenous	HF Acquisition Co LLC, DBA HealthFirst	2018-09-16	2020-08-01

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Midazolam HCl	Midazolam hydrochloride (0.5 mg/1mL)	Injection, solution	Intravenous	Cantrell Drug Company	2014-09-03	Not applicable
Midazolam HCl	Midazolam hydrochloride (1 mg/1mL)	Injection, solution	Intravenous	Cantrell Drug Company	2013-06-28	Not applicable
MIDOLAM 15 MG/3 ML IM/IV REKTAL COZELTI ICEREN AMPUL, 5 ADET	Midazolam (15 mg/3ml)	Injection	Intramuscular; Intravenous	PHARMADA İLAÇ SAN. VE TİC. A.Ş.	2020-03-17	2024-01-23
MIDOLAM 5 MG/1 ML IM/IV REKTAL COZELTI ICEREN AMPUL, 5 ADET	Midazolam (5 mg/1ml)	Injection	Intramuscular; Intravenous	PHARMADA İLAÇ SAN. VE TİC. A.Ş.	2020-03-17	2024-01-23
MIDOLAM 50 MG/10 ML IM/IV REKTAL COZELTI ICEREN AMPUL, 5 ADET	Midazolam (50 mg/10ml)	Injection	Intramuscular; Intravenous	PHARMADA İLAÇ SAN. VE TİC. A.Ş.	2019-11-26	2024-01-23

Categories

ATC Codes

N05CD08 — Midazolam

• N05CD — Benzodiazepine derivatives
• N05C — HYPNOTICS AND SEDATIVES
• N05 — PSYCHOLEPTICS
• N — NERVOUS SYSTEM

Drug Categories

• Adjuvants, Anesthesia
• Anesthetics
• Anti-Anxiety Agents
• Benzodiazepine hypnotics and sedatives
• Benzodiazepines and benzodiazepine derivatives
• Central Nervous System Agents
• Central Nervous System Depressants
• Cytochrome P-450 CYP3A Inhibitors
• Cytochrome P-450 CYP3A Substrates
• Cytochrome P-450 CYP3A4 Inhibitors
• Cytochrome P-450 CYP3A4 Inhibitors (strength unknown)
• Cytochrome P-450 CYP3A4 Substrates
• Cytochrome P-450 CYP3A5 Substrates
• Cytochrome P-450 CYP3A7 Substrates
• Cytochrome P-450 Enzyme Inhibitors
• Cytochrome P-450 Substrates
• Drugs that are Mainly Renally Excreted
• GABA Agents
• GABA Modulators
• Heterocyclic Compounds, Fused-Ring
• Hypnotics and Sedatives
• Nervous System
• Neurotransmitter Agents
• P-glycoprotein substrates
• Psycholeptics
• Psychotropic Drugs
• Tranquilizing Agents
• Triazolobenzodiazepines
• UGT1A4 substrates
• UGT2B7 substrates

Chemical TaxonomyProvided by Classyfire

Description

This compound belongs to the class of organic compounds known as imidazo[1,5-a][1,4]benzodiazepines. These are compounds containing an imidazole ring and a 1,4-benzodiazepine ring system, both sharing one nitrogen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodiazepines

Sub Class

1,4-benzodiazepines

Direct Parent

Imidazo[1,5-a][1,4]benzodiazepines

Alternative Parents

Fluorobenzenes / 1,4-diazepines / N-substituted imidazoles / Aryl fluorides / Aryl chlorides / Heteroaromatic compounds / Ketimines / Propargyl-type 1,3-dipolar organic compounds / Azacyclic compounds / Organopnictogen compounds / Organofluorides / Organochlorides / Hydrocarbon derivatives

show 3 more

Substituents

Aromatic heteropolycyclic compound / Aryl chloride / Aryl fluoride / Aryl halide / Azacycle / Azole / Benzenoid / Fluorobenzene / Halobenzene / Heteroaromatic compound / Hydrocarbon derivative / Imidazo[1,5-a][1,4]benzodiazepine / Imidazole / Imine / Ketimine / Monocyclic benzene moiety / N-substituted imidazole / Organic 1,3-dipolar compound / Organic nitrogen compound / Organochloride / Organofluoride / Organohalogen compound / Organonitrogen compound / Organopnictogen compound / Para-diazepine / Propargyl-type 1,3-dipolar organic compound

show 16 more

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

diazepine (CHEBI:6931)

Affected organisms

• Humans and other mammals

Chemical Identifiers

UNII

R60L0SM5BC

CAS number

59467-70-8

InChI Key

DDLIGBOFAVUZHB-UHFFFAOYSA-N

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

IUPAC Name

12-chloro-9-(2-fluorophenyl)-3-methyl-2,4,8-triazatricyclo[8.4.0.0^{2,6}]tetradeca-1(10),3,5,8,11,13-hexaene

SMILES

CC1=NC=C2CN=C(C3=CC=CC=C3F)C3=C(C=CC(Cl)=C3)N12

References

Synthesis Reference

US6262260

General References

1. Skerritt JH, Johnston GA: Enhancement of GABA binding by benzodiazepines and related anxiolytics. Eur J Pharmacol. 1983 May 6;89(3-4):193-8. [Article]
2. Isojarvi JI, Tokola RA: Benzodiazepines in the treatment of epilepsy in people with intellectual disability. J Intellect Disabil Res. 1998 Dec;42 Suppl 1:80-92. [Article]
3. Garratt JC, Gent JP, Feely M, Haigh JR: Can benzodiazepines be classified by characterising their anticonvulsant tolerance-inducing potential? Eur J Pharmacol. 1988 Jan 5;145(1):75-80. [Article]
4. Tokunaga S, Takeda Y, Shinomiya K, Hirase M, Kamei C: Effects of some H1-antagonists on the sleep-wake cycle in sleep-disturbed rats. J Pharmacol Sci. 2007 Feb;103(2):201-6. Epub 2007 Feb 8. [Article]
5. Vermeeren A: Residual effects of hypnotics: epidemiology and clinical implications. CNS Drugs. 2004;18(5):297-328. [Article]
6. Nordt SP, Clark RF: Midazolam: a review of therapeutic uses and toxicity. J Emerg Med. 1997 May-Jun;15(3):357-65. [Article]
7. Jembrek MJ, Vlainic J: GABA Receptors: Pharmacological Potential and Pitfalls. Curr Pharm Des. 2015;21(34):4943-59. [Article]
8. Wheless JW: A critical evaluation of midazolam nasal spray for the treatment of patients with seizure clusters. Expert Rev Neurother. 2021 Nov;21(11):1195-1205. doi: 10.1080/14737175.2021.1890033. Epub 2021 Mar 12. [Article]
9. Siegel GJ, Agranoff BW, Albers RW et al. (1999). Basic Neurochemistry: Molecular, Cellular and Medical Aspects (6th ed.). Lippincott Williams.
10. Drug Scheduling: United States Drug Enforcement Administration (DEA) [Link]
11. DailyMed: Midazolam [Link]
12. NAYZILAM® (midazolam) nasal spray - FDA Label [Link]
13. FDA Approved Drug Products: NAYZILAM (midazolam) nasal spray, CIV Jan 2023 [Link]
14. DailyMed: Midazolam injection [Link]
15. FDA Approved Drug Products: SEIZALAM® (midazolam injection), for intramuscular use [Link]
16. EMA Approved Drug Products: BUCCOLAM oromucosal solution [Link]
17. Health Canada Approved Drug Products: Midazolam Intramuscular or Intravenous Injection (January 2023) [Link]
18. Midazolam Chemical Handbook [Link]
19. CENTER FOR DRUG EVALUATION AND RESEARCH APPLICATION NUMBER: 211321Orig1s000 [Link]
20. Intravenous Midazolam FDA label [File]
21. MedSafe NZ: Midazolam Inj [File]

External Links

Human Metabolome Database

HMDB0014821

KEGG Drug

D00550

KEGG Compound

C07524

PubChem Compound

4192

PubChem Substance

46507611

ChemSpider

4047

BindingDB

21363

RxNav

6960

ChEBI

6931

ChEMBL

CHEMBL655

ZINC

ZINC000095626706

Therapeutic Targets Database

DAP000241

PharmGKB

PA450496

Guide to Pharmacology

GtP Drug Page

PDBe Ligand

08J

RxList

RxList Drug Page

Drugs.com

Drugs.com Drug Page

Wikipedia

Midazolam

PDB Entries

3u5k / 5te8

FDA label

Download (250 KB)

MSDS

Download (68.9 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Active Not Recruiting	Other	Major Depressive Disorder (MDD) / Major depressive disorder, recurrent episode	1
4	Active Not Recruiting	Treatment	Depression, Bipolar / Suicidal Thoughts / Unipolar Depression	1
4	Active Not Recruiting	Treatment	Driving Performance After Minor Ambulatory Surgery / Minor Surgical Procedures With Monitored Anesthesia Care	1
4	Completed	Not Available	Anaesthesia / Nerve Block / Orthopaedic Disorders	1
4	Completed	Not Available	Disorders of Gallbladder, Biliary Tract and Pancrease	1

Pharmacoeconomics

Manufacturers

• Apothecon inc div bristol myers squibb
• App pharmaceuticals llc
• Astrazeneca pharmaceuticals lp
• Baxter healthcare corp anesthesia and critical care
• Baxter healthcare corp anesthesia critical care
• Bedford laboratories div ben venue laboratories inc
• Ben venue laboratories inc
• Claris lifesciences ltd
• Hospira inc
• International medicated systems ltd
• International medication systems ltd
• Taylor pharmaceuticals
• Wockhardt ltd
• Hlr technology
• Apotex inc richmond hill
• Hi tech pharmacal co inc
• Paddock laboratories inc
• Ranbaxy laboratories ltd
• Roxane laboratories inc
• Hoffmann la roche inc

Packagers

• Akorn Inc.
• APP Pharmaceuticals
• A-S Medication Solutions LLC
• B&B Pharmaceuticals
• Baxter International Inc.
• Bedford Labs
• Ben Venue Laboratories Inc.
• Cardinal Health
• Cura Pharmaceutical Co. Inc.
• Dispensing Solutions
• Ebewe Pharma
• Hi Tech Pharmacal Co. Inc.
• Hospira Inc.
• Mikart Inc.
• Novex Pharma
• Paddock Labs
• Patheon Inc.
• Pharmedium
• Physicians Total Care Inc.
• Ranbaxy Laboratories
• Roxane Labs
• Wockhardt Ltd.

Dosage Forms

Form	Route	Strength
Liquid	Intramuscular; Intravenous	1 mg / mL
Solution	Intramuscular; Intravenous	1 mg
Solution	Buccal	10 mg
Solution	Buccal	2.5 mg
Solution	Buccal	5 mg
Solution	Buccal	7.5 mg
Solution	Parenteral	16.680 mg
Injection	Intramuscular; Intravenous	15 mg/3ml
Injection	Intramuscular; Intravenous	50 mg/10ml
Injection	Intramuscular; Intravenous	5 mg/5ml
Solution	Intramuscular; Intravenous
Injection, solution	Intramuscular; Intravenous; Rectal
Injection	Intravenous
Injection	Intramuscular; Intravenous	15 MG
Injection	Intramuscular; Intravenous	5 mg/ml
Injection	Intramuscular; Intravenous	5 MG
Injection	Intramuscular; Intravenous
Tablet	Oral	10.200 mg
Solution	Intramuscular; Intravenous; Rectal	1 mg
Injection, solution	Parenteral
Solution	Intravenous	5 mg
Injection	Intramuscular; Intravenous; Rectal	15 MG/3ML
Solution	Intramuscular; Intravenous; Rectal	5 MG/5ML
Injection	Intramuscular; Intravenous; Rectal	5 MG/ML
Tablet, film coated	Oral	15 mg
Tablet, film coated	Oral	7.5 mg
Tablet	Oral	7.5 MG
Solution	Intramuscular; Intravenous; Rectal	15 mg
Solution	Intramuscular; Intravenous; Rectal	50 mg
Solution	Intramuscular; Intravenous	5 mg
Solution	Intramuscular; Intravenous	15 mg
Solution	Oral	2.5 MG
Solution	Oral	5 MG
Solution	Oral	7.5 MG
Solution	Oral	10 mg
Injection, solution
Solution	Intravenous	5.000 mg
Solution	Parenteral	5.0 mg
Injection, solution	Intramuscular; Intravenous; Rectal	5 mg
Injection	Intramuscular; Intravenous	1 mg/mL
Injection, solution	Intramuscular; Intravenous
Injection, solution	Intramuscular; Intravenous	10 mg/2mL
Injection, solution	Intramuscular; Intravenous	2 mg/2mL
Injection, solution	Intramuscular; Intravenous	5 mg/5mL
Solution	Parenteral	15 mg
Solution	Intramuscular; Parenteral	15 mg
Solution	Intramuscular; Intravenous	50 mg
Solution	Intramuscular; Intravenous	500000 mg
Solution	Intravenous
Tablet, coated	Oral	7.5 mg
Injection, solution		1 MG/ML
Injection, solution	Parenteral; Rectal	1 MG/ML
Injection, solution	Rectal	5 MG/ML
Injection, solution	Intravenous	0.5 mg/1mL
Injection, solution	Intravenous	1 mg/1mL
Injection	Intramuscular; Intravenous	1 mg/1mL
Injection	Intramuscular; Intravenous	10 mg/2mL
Injection	Intramuscular; Intravenous	2 mg/2mL
Injection	Intramuscular; Intravenous	5 mg/1mL
Injection, solution	Intramuscular; Intravenous	1 mg/1mL
Injection, solution	Intramuscular; Intravenous	5 mg/1mL
Syrup	Oral	10 mg/5mL
Syrup	Oral	2 mg/1mL
Injection, solution		5 MG/ML
Injection	Intravenous	1 mg/1mL
Liquid	Intramuscular; Intravenous	5 mg / mL
Solution	Intramuscular; Intravenous	1 mg / mL
Solution	Intramuscular; Intravenous	5 mg / mL
Solution	Intravenous	1 mg / mL
Injection, solution	Parenteral	1 mg/ml
Solution
Tablet, film coated	Oral
Injection, solution	Intramuscular; Intravenous; Rectal	1 mg/mL
Injection, solution	Intramuscular; Intravenous; Rectal	5 mg/ml
Injection	Intravenous	1 mg/ml
Injection	Parenteral	1 MG/ML
Injection, solution	Parenteral	2 mg/ml
Injection	Intravenous	5 mg/ml
Injection, solution	Parenteral	5 mg/ml
Injection	Parenteral	5 MG/ML
Solution	Intravenous	50 mg
Injection
Injection, solution	Intravenous	5 mg
Troche	Sublingual
Injection, solution	Intramuscular	10 mg/0.7mL
Spray	Nasal	5 mg/0.1mL
Solution	Oral	2 MG/ML
Solution	Oral
Solution	Intravenous	5.60 mg
Solution	Parenteral	5.000 mg
Solution	Intramuscular; Intravenous; Rectal
Injection, solution	Intramuscular	5 mg/1mL
Solution	Intramuscular; Intravenous; Rectal	5 mg
Solution	Parenteral	5.560 mg
Solution	Parenteral	5.00 mg
Solution	Parenteral	5.00000 mg
Solution	Parenteral	16.68 mg
Solution	Parenteral	15.000 mg
Solution	Intramuscular; Intravenous; Rectal	5 mg/mL
Solution	Intramuscular; Intravenous; Rectal	1 mg/mL
Solution	Intramuscular	5.00 mg

Prices

Unit description	Cost	Unit
Midazolam 5 mg/ml	3.9USD	ml
Midazolam-nacl 2 mg/ml inj	2.31USD	ml
Midazolam hcl 5 mg/ml vial	1.18USD	ml
Midazolam-nacl 1 mg/ml inj	1.13USD	ml
Midazolam hcl 2 mg/ml syrup	1.08USD	ml
Midazolam 1 mg/ml isecure syr	0.73USD	ml
Midazolam hcl 1 mg/ml vial	0.26USD	ml

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)	Region
US9289432	No	2016-03-22	2028-01-18
US9687495	No	2017-06-27	2028-01-18
US8217033	No	2012-07-10	2028-01-18
US8809322	No	2014-08-19	2028-01-18
US10966990	No	2021-04-06	2038-06-20

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	161-164	L45093
boiling point (°C)	496.9±55.0	L45093
water solubility	54mg/L	L45093
logP	2.73	L45093

Predicted Properties

Property	Value	Source
Water Solubility	0.00987 mg/mL	ALOGPS
logP	3.89	ALOGPS
logP	3.97	Chemaxon
logS	-4.5	ALOGPS
pKa (Strongest Basic)	6.19	Chemaxon
Physiological Charge	0	Chemaxon
Hydrogen Acceptor Count	2	Chemaxon
Hydrogen Donor Count	0	Chemaxon
Polar Surface Area	30.18 Å2	Chemaxon
Rotatable Bond Count	1	Chemaxon
Refractivity	99.43 m3·mol-1	Chemaxon
Polarizability	32.71 Å3	Chemaxon
Number of Rings	4	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	Yes	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	1.0
Blood Brain Barrier	+	0.9724
Caco-2 permeable	+	0.8866
P-glycoprotein substrate	Non-substrate	0.5074
P-glycoprotein inhibitor I	Inhibitor	0.5587
P-glycoprotein inhibitor II	Inhibitor	0.8388
Renal organic cation transporter	Inhibitor	0.7476
CYP450 2C9 substrate	Non-substrate	0.7366
CYP450 2D6 substrate	Non-substrate	0.9116
CYP450 3A4 substrate	Substrate	0.7194
CYP450 1A2 substrate	Inhibitor	0.8586
CYP450 2C9 inhibitor	Inhibitor	0.7132
CYP450 2D6 inhibitor	Non-inhibitor	0.6887
CYP450 2C19 inhibitor	Inhibitor	0.6554
CYP450 3A4 inhibitor	Non-inhibitor	0.5214
CYP450 inhibitory promiscuity	High CYP Inhibitory Promiscuity	0.9001
Ames test	Non AMES toxic	0.8024
Carcinogenicity	Non-carcinogens	0.7703
Biodegradation	Not ready biodegradable	1.0
Rat acute toxicity	3.1488 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9827
hERG inhibition (predictor II)	Non-inhibitor	0.7379

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-002g-5092000000-4478c9440e5f31cecc49
Mass Spectrum (Electron Ionization)	MS	splash10-03di-3839000000-42781254e15bcd5b31b6
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	splash10-03di-0910000000-98021a5812f1663e9397
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-004i-0009000000-2411220f611ba30ef225
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-004i-0009000000-c724b297ae99edb399d3
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-004l-0098000000-b57c162c4eeaad9ef111
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-0006-0090000000-a3133528f5491f4c9a6b
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-05fs-0290000000-ee126555f849ecfff795
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-004i-0009000000-4ae622c7b53369b0cfb1
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-004i-0019000000-00c3c9e2813a454acda1
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-002f-0093000000-a8ca99ef6c84536bff07
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-0006-0091000000-3edc4aa6f67d99b789a8
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-0abd-0290000000-aa5e16437618ad2adb86
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-05fs-0490000000-a323090224c5b01e3990
MS/MS Spectrum - , positive	LC-MS/MS	splash10-004i-0189000000-6e704a4a2a65211394ab
MS/MS Spectrum - , positive	LC-MS/MS	splash10-03di-0910000000-98021a5812f1663e9397
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-004i-0009000000-000181022f4b8c3d9499
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-00di-0009000000-9530bcfae2ea7c6b7304
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-004i-0009000000-17a8419ced6a72f33e66
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-00di-0029000000-af8686767ab034b02afd
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0l4i-0092000000-3d68ea331540f8a06eba
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0umm-0090000000-fa5eb1375abc7482e578
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å2)	Source type	Source
[M-H]-	174.5475601	predicted	DarkChem Lite v0.1.0
[M-H]-	173.7339	predicted	DeepCCS 1.0 (2019)
[M+H]+	175.4209601	predicted	DarkChem Lite v0.1.0
[M+H]+	176.09192	predicted	DeepCCS 1.0 (2019)
[M+Na]+	174.8217601	predicted	DarkChem Lite v0.1.0
[M+Na]+	182.9479	predicted	DeepCCS 1.0 (2019)

Targets

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Details1. GABA(A) Receptor (Protein Group)

Kind

Protein group

Organism

Humans

Pharmacological action

Yes

Actions

Positive allosteric modulator

Curator comments

The GABA(A) receptor is pentameric (i.e. comprising 5 subunit proteins) and therefore has a multitude of potential isoforms. The above target is a collection of all possible GABA(A) subunits that may participate in the formation of the pentameric receptor and is not meant to imply direct a drug-protein interaction for each individual subunit.

General Function

Inhibitory extracellular ligand-gated ion channel activity

Specific Function

Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...

---

Components:

Name	UniProt ID
Gamma-aminobutyric acid receptor subunit alpha-1	P14867
Gamma-aminobutyric acid receptor subunit alpha-2	P47869
Gamma-aminobutyric acid receptor subunit alpha-3	P34903
Gamma-aminobutyric acid receptor subunit alpha-4	P48169
Gamma-aminobutyric acid receptor subunit alpha-5	P31644
Gamma-aminobutyric acid receptor subunit alpha-6	Q16445
Gamma-aminobutyric acid receptor subunit beta-1	P18505
Gamma-aminobutyric acid receptor subunit beta-2	P47870
Gamma-aminobutyric acid receptor subunit beta-3	P28472
Gamma-aminobutyric acid receptor subunit delta	O14764
Gamma-aminobutyric acid receptor subunit epsilon	P78334
Gamma-aminobutyric acid receptor subunit gamma-1	Q8N1C3
Gamma-aminobutyric acid receptor subunit gamma-2	P18507
Gamma-aminobutyric acid receptor subunit gamma-3	Q99928
Gamma-aminobutyric acid receptor subunit pi	O00591
Gamma-aminobutyric acid receptor subunit theta	Q9UN88

References

1. Sigel E, Steinmann ME: Structure, function, and modulation of GABA(A) receptors. J Biol Chem. 2012 Nov 23;287(48):40224-31. doi: 10.1074/jbc.R112.386664. Epub 2012 Oct 4. [Article]
2. Zhu S, Noviello CM, Teng J, Walsh RM Jr, Kim JJ, Hibbs RE: Structure of a human synaptic GABAA receptor. Nature. 2018 Jul;559(7712):67-72. doi: 10.1038/s41586-018-0255-3. Epub 2018 Jun 27. [Article]

Details2. GABA(A) Receptor Benzodiazepine Binding Site (Protein Group)

Kind

Protein group

Organism

Humans

Pharmacological action

Yes

Actions

Ligand

Curator comments

Benzodiazepines modulate GABA(A) function by binding at the interface between alpha (α) and gamma (γ) subunits. Of the 6 α-subunits, only 4 (α-1, -2, -3, and -5) participate in the formation of this binding site. The above target is a collection of all α- and γ-subunits that are known to participate in the formation of the benzodiazepine binding site.

General Function

Inhibitory extracellular ligand-gated ion channel activity

Specific Function

Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...

---

Components:

Name	UniProt ID
Gamma-aminobutyric acid receptor subunit alpha-1	P14867
Gamma-aminobutyric acid receptor subunit alpha-2	P47869
Gamma-aminobutyric acid receptor subunit alpha-3	P34903
Gamma-aminobutyric acid receptor subunit alpha-5	P31644
Gamma-aminobutyric acid receptor subunit gamma-1	Q8N1C3
Gamma-aminobutyric acid receptor subunit gamma-2	P18507
Gamma-aminobutyric acid receptor subunit gamma-3	Q99928

References

1. Zhu S, Noviello CM, Teng J, Walsh RM Jr, Kim JJ, Hibbs RE: Structure of a human synaptic GABAA receptor. Nature. 2018 Jul;559(7712):67-72. doi: 10.1038/s41586-018-0255-3. Epub 2018 Jun 27. [Article]
2. Sigel E, Steinmann ME: Structure, function, and modulation of GABA(A) receptors. J Biol Chem. 2012 Nov 23;287(48):40224-31. doi: 10.1074/jbc.R112.386664. Epub 2012 Oct 4. [Article]

Details3. Adenosine receptor A2a

Kind

Protein

Organism

Humans

Pharmacological action

Unknown

Actions

Potentiator

General Function

Identical protein binding

Specific Function

Receptor for adenosine. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase.

Gene Name

ADORA2A

Uniprot ID

P29274

Uniprot Name

Adenosine receptor A2a

Molecular Weight

44706.925 Da

References

1. Seubert CN, Morey TE, Martynyuk AE, Cucchiara RF, Dennis DM: Midazolam selectively potentiates the A(2A) - but not A1- receptor--mediated effects of adenosine: role of nucleoside transport inhibition and clinical implications. Anesthesiology. 2000 Feb;92(2):567-77. doi: 10.1097/00000542-200002000-00041. [Article]

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Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55