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Identification
NameMidazolam
Accession NumberDB00683  (APRD00680)
TypeSmall Molecule
GroupsApproved, Illicit
Description

A short-acting hypnotic-sedative drug with anxiolytic and amnestic properties. It is used in dentistry, cardiac surgery, endoscopic procedures, as preanesthetic medication, and as an adjunct to local anesthesia. The short duration and cardiorespiratory stability makes it useful in poor-risk, elderly, and cardiac patients. It is water-soluble at pH less than 4 and lipid-soluble at physiological pH. [PubChem] Midazolam is a schedule IV drug in the United States.

Structure
Thumb
Synonyms
Buccolam
Dormicum
Midazolam
Midazolamum
External Identifiers
  • Dea No. 2884
  • Ro 21-3981/001
  • Ro 21-3981/003
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Midazolam Injectionsolution5 mgintramuscular; intravenousMylan Pharmaceuticals UlcNot applicableNot applicableCanada
Midazolam Injectionsolution1 mgintramuscular; intravenousMylan Pharmaceuticals UlcNot applicableNot applicableCanada
Midazolam Injectionsolution5 mgintramuscular; intravenousPfizer Canada Inc2015-03-31Not applicableCanada
Midazolam Injectionsolution1 mgintramuscular; intravenousSandoz Canada Incorporated1999-07-21Not applicableCanada
Midazolam Injectionsolution1 mgintramuscular; intravenousPfizer Canada Inc2015-03-31Not applicableCanada
Midazolam Injectionsolution5 mgintramuscular; intravenousNovopharm Limited2001-12-17Not applicableCanada
Midazolam Injectionsolution1 mgintramuscular; intravenousNovopharm Limited2001-12-17Not applicableCanada
Midazolam Injectionsolution1 mgintramuscular; intravenousFresenius Kabi Canada Ltd2001-03-26Not applicableCanada
Midazolam Injectionliquid5 mgintramuscular; intravenousFresenius Kabi Canada Ltd2001-03-26Not applicableCanada
Midazolam Injectionsolution5 mgintramuscular; intravenousSandoz Canada Incorporated1999-07-21Not applicableCanada
Midazolam Injection BPsolution5 mgintramuscular; intravenousHospira Healthcare CorporationNot applicableNot applicableCanada
Midazolam Injection BPsolution1 mgintramuscular; intravenousHospira Healthcare CorporationNot applicableNot applicableCanada
Midazolam Injection Sdzsolution5 mgintramuscular; intravenousSandoz Canada Incorporated2012-07-26Not applicableCanada
Midazolam Injection Sdzsolution1 mgintramuscular; intravenousSandoz Canada Incorporated2012-07-26Not applicableCanada
Midazolam Injection USPsolution1 mgintramuscular; intravenousHospira Healthcare CorporationNot applicableNot applicableCanada
Midazolam Injection USPsolution1 mgintramuscular; intravenousHospira Healthcare Corporation2015-03-30Not applicableCanada
Midazolam Injection USPsolution5 mgintramuscular; intravenousHospira Healthcare Corporation2016-02-16Not applicableCanada
Midazolam Injection USPsolution5 mgintramuscular; intravenousHospira Healthcare Corporation2016-02-09Not applicableCanada
PMS-midazolamliquid5 mgintramuscular; intravenousPharmascience IncNot applicableNot applicableCanada
PMS-midazolamliquid1 mgintramuscular; intravenousPharmascience IncNot applicableNot applicableCanada
Versed Inj 1mg/mlliquid1 mgintramuscular; intravenousHoffmann La Roche Limited1989-12-312004-07-07Canada
Versed Inj 5mg/mlliquid5 mgintramuscular; intravenousHoffmann La Roche Limited1988-12-312004-06-28Canada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-midazolam Injectable 1 mg/mlliquid1 mgintramuscular; intravenousApotex Inc2001-04-102013-08-02Canada
Apo-midazolam Injectable 5 mg/mlliquid5 mgintramuscular; intravenousApotex Inc2001-04-102013-08-02Canada
Midazolaminjection1 mg/mLintramuscular; intravenousCardinal Health2000-06-20Not applicableUs
Midazolaminjection, solution1 mg/mLintramuscular; intravenousSagent Pharmaceuticals2012-03-19Not applicableUs
Midazolaminjection, solution1 mg/mLintramuscular; intravenousAPP Pharmaceuticals, LLC2000-07-10Not applicableUs
Midazolaminjection, solution2 mg/2mLintramuscular; intravenousBD Rx Inc.2014-10-03Not applicableUs
Midazolaminjection5 mg/mLintramuscular; intravenousCardinal Health2000-06-20Not applicableUs
Midazolaminjection, solution5 mg/mLintramuscular; intravenousThe Medicines Company2000-07-14Not applicableUs
Midazolaminjection, solution5 mg/mLintramuscular; intravenousBD Rx Inc.2014-10-03Not applicableUs
Midazolaminjection1 mg/mLintramuscular; intravenousWest Ward Pharmaceutical Corp.2000-06-20Not applicableUs
Midazolaminjection, solution1 mg/mLintramuscular; intravenousAPP Pharmaceuticals, LLC2000-07-14Not applicableUs
Midazolaminjection, solution1 mg/mLintramuscular; intravenousCardinal Health2000-07-14Not applicableUs
Midazolaminjection, solution5 mg/mLintramuscular; intravenousThe Medicines Company2000-07-14Not applicableUs
Midazolaminjection5 mg/mLintramuscular; intravenousAkorn, Inc.2005-05-06Not applicableUs
Midazolaminjection, solution5 mg/mLintramuscular; intravenousCardinal Health2000-07-14Not applicableUs
Midazolaminjection, solution5 mg/mLintramuscular; intravenousThe Medicines Company2000-07-14Not applicableUs
Midazolaminjection1 mg/mLintramuscular; intravenousAkorn, Inc.2005-05-06Not applicableUs
Midazolaminjection, solution1 mg/mLintramuscular; intravenousThe Medicines Company2000-07-10Not applicableUs
Midazolaminjection5 mg/mLintramuscular; intravenousWest Ward Pharmaceutical Corp.2000-06-20Not applicableUs
Midazolaminjection1 mg/mLintramuscular; intravenousA S Medication Solutions Llc2000-06-20Not applicableUs
Midazolaminjection5 mg/mLintramuscular; intravenousCaraco Pharmaceutical Laboratories, Ltd.2012-08-08Not applicableUs
Midazolaminjection5 mg/mLintramuscular; intravenousWest Ward Pharmaceutical Corp.2000-06-20Not applicableUs
Midazolaminjection5 mg/mLintramuscular; intravenousA S Medication Solutions Llc2000-06-20Not applicableUs
Midazolaminjection1 mg/mLintramuscular; intravenousCaraco Pharmaceutical Laboratories, Ltd.2012-08-08Not applicableUs
Midazolaminjection, solution1 mg/mLintramuscular; intravenousThe Medicines Company2000-07-14Not applicableUs
Midazolaminjection5 mg/mLintramuscular; intravenousWest Ward Pharmaceutical Corp.2000-06-20Not applicableUs
Midazolaminjection5 mg/mLintramuscular; intravenousSagent Pharmaceuticals2012-03-19Not applicableUs
Midazolaminjection1 mg/mLintramuscular; intravenousWest Ward Pharmaceutical Corp.2000-06-20Not applicableUs
Midazolaminjection1 mg/mLintramuscular; intravenousSagent Pharmaceuticals2012-03-19Not applicableUs
Midazolaminjection1 mg/mLintramuscular; intravenousCardinal Health2000-06-20Not applicableUs
Midazolaminjection, solution5 mg/mLintramuscular; intravenousThe Medicines Company2000-07-14Not applicableUs
Midazolaminjection, solution5 mg/mLintramuscular; intravenousSagent Pharmaceuticals2012-03-19Not applicableUs
Midazolaminjection5 mg/mLintramuscular; intravenousCardinal Health2000-06-20Not applicableUs
Midazolaminjection, solution1 mg/mLintramuscular; intravenousThe Medicines Company2000-07-14Not applicableUs
Midazolaminjection, solution10 mg/2mLintramuscular; intravenousBD Rx Inc.2014-10-03Not applicableUs
Midazolaminjection1 mg/mLintramuscular; intravenousWest Ward Pharmaceutical Corp.2000-06-20Not applicableUs
Midazolam Hydrochlorideinjection, solution1 mg/mLintramuscular; intravenousA S Medication Solutions Llc2000-06-20Not applicableUs
Midazolam Hydrochlorideinjection1 mg/mLintramuscular; intravenousWockhardt Limited2008-05-30Not applicableUs
Midazolam Hydrochlorideinjection1 mg/mLintramuscular; intravenousWockhardt USA LLC.2008-05-30Not applicableUs
Midazolam Hydrochloridesyrup2 mg/mLoralAtlantic Biologicals Corps2002-07-05Not applicableUs
Midazolam Hydrochloridesyrup2 mg/mLoralRoxane Laboratories, Inc2002-04-30Not applicableUs
Midazolam Hydrochlorideinjection1 mg/mLintramuscular; intravenousCardinal Health2010-03-04Not applicableUs
Midazolam Hydrochlorideinjection, solution5 mg/mLintramuscular; intravenousA S Medication Solutions Llc2000-06-20Not applicableUs
Midazolam Hydrochlorideinjection, solution5 mg/mLintramuscular; intravenousDispensing Solutions, Inc.2011-05-03Not applicableUs
Midazolam Hydrochloridesyrup2 mg/mLoralPaddock Laboratories, LLC2005-05-02Not applicableUs
Midazolam Hydrochloridesyrup2 mg/mLoralRanbaxy Pharmaceuticlas Inc2002-07-05Not applicableUs
Midazolam Hydrochlorideinjection, solution5 mg/mLintramuscular; intravenousDispensing Solutions, Inc.2011-05-02Not applicableUs
Midazolam Hydrochlorideinjection, solution5 mg/mLintramuscular; intravenousHospira, Inc.2000-06-20Not applicableUs
Midazolam Hydrochlorideinjection1 mg/mLintramuscular; intravenousCardinal Health2010-03-04Not applicableUs
Midazolam Hydrochlorideinjection5 mg/mLintramuscular; intravenousGeneral Injectables & Vaccines, Inc2010-08-01Not applicableUs
Midazolam Hydrochloridesyrup2 mg/mLoralPrecision Dose Inc.2015-05-26Not applicableUs
Midazolam Hydrochlorideinjection, solution1 mg/mLintramuscular; intravenousHospira, Inc.2000-06-20Not applicableUs
Midazolam Hydrochlorideinjection10 mg/2mLintramuscular; intravenousCardinal Health2000-06-21Not applicableUs
Midazolam Hydrochlorideinjection, solution1 mg/mLintramuscular; intravenousCardinal Health2002-06-13Not applicableUs
Midazolam Hydrochlorideinjection, solution5 mg/mLintramuscular; intravenousHospira, Inc.2002-07-22Not applicableUs
Midazolam Hydrochlorideinjection5 mg/mLintramuscular; intravenousCardinal Health2000-06-21Not applicableUs
Midazolam Hydrochlorideinjection, solution1 mg/mLintramuscular; intravenousCardinal Health2002-07-22Not applicableUs
Midazolam Hydrochloridesyrup2 mg/mLoralPrecision Dose Inc.2015-05-26Not applicableUs
Midazolam Hydrochlorideinjection, solution5 mg/mLintramuscular; intravenousHospira, Inc.2002-06-13Not applicableUs
Midazolam Hydrochlorideinjection5 mg/mLintramuscular; intravenousCardinal Health2000-06-21Not applicableUs
Midazolam Hydrochlorideinjection5 mg/mLintramuscular; intravenousWockhardt Limited2008-11-10Not applicableUs
Midazolam Hydrochlorideinjection, solution1 mg/mLintramuscular; intravenousCardinal Health2002-07-22Not applicableUs
Midazolam Hydrochloridesyrup10 mg/5mLoralPrecision Dose Inc.2010-10-112016-08-31Us
Midazolam Hydrochlorideinjection5 mg/mLintramuscular; intravenousWockhardt USA LLC.2008-11-10Not applicableUs
Midazolam Hydrochlorideinjection1 mg/mLintramuscular; intravenousBaxter Healthcare Corporation2010-03-042015-12-29Us
Midazolam Hydrochlorideinjection, solution1 mg/mLintramuscular; intravenousHospira, Inc.2002-06-13Not applicableUs
Midazolam Hydrochlorideinjection2 mg/2mLintramuscular; intravenousCardinal Health2000-06-21Not applicableUs
Midazolam Hydrochlorideinjection1 mg/mLintramuscular; intravenousWockhardt Limited2008-11-10Not applicableUs
Midazolam Hydrochlorideinjection1 mg/mLintramuscular; intravenousWockhardt USA LLC.2008-11-10Not applicableUs
Midazolam Hydrochlorideinjection5 mg/mLintramuscular; intravenousBaxter Healthcare Corporation2010-03-042015-12-29Us
Midazolam Hydrochlorideinjection1 mg/mLintramuscular; intravenousPhysicians Total Care, Inc.2006-12-12Not applicableUs
Midazolam Hydrochlorideinjection5 mg/mLintramuscular; intravenousWockhardt Limited2008-05-30Not applicableUs
Midazolam Hydrochlorideinjection5 mg/mLintramuscular; intravenousWockhardt USA LLC.2008-05-30Not applicableUs
Midazolam Hydrochlorideinjection, solution1 mg/mLintramuscular; intravenousHospira, Inc.2002-07-22Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Midazolam HClinjection, solution.5 mg/mLintravenousCantrell Drug Company2013-01-30Not applicableUs
Midazolam HClinjection, solution1 mg/mLintravenousCantrell Drug Company2010-08-02Not applicableUs
International Brands
NameCompany
AnquilGeneral Pharma
BenzosedPharmaceutical
DalamRichmond
DamizolSpecifar
DemizolamDem Ilaç
DoricumRoche
DormicumRoche
DormidScott
DormipronChalver
DormireCristália
DormitolSquare
DormixalDemo
DormonidRoche
DrimnorthNorthia
EpistatusIFET
FlormidalGalenika
FulsedRanbaxy
Fulsed InjectionTerapia
GarenBio-Pharma
GobbizolamGobbi
HipnazolamEMS
HipnozPharos
HypnofastIncepta
HypnovelRoche
IpnovelRoche
NocturnaLafi
SetamRimsa
TalentumFisiopharma
TerapSanitas
VersedRoche
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Midazolam Hydrochloride
Thumb
  • InChI Key: PLYSCVSCYOQVRP-UHFFFAOYSA-N
  • Monoisotopic Mass: 361.054881082
  • Average Mass: 362.228
DBSALT000118
Categories
UNIIR60L0SM5BC
CAS number59467-70-8
WeightAverage: 325.767
Monoisotopic: 325.078203343
Chemical FormulaC18H13ClFN3
InChI KeyInChIKey=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[8.4.0.0²,⁶]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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzodiazepines
Sub Class1,4-benzodiazepines
Direct ParentImidazo[1,5-a][1,4]benzodiazepines
Alternative Parents
Substituents
  • Imidazo[1,5-a][1,4]benzodiazepine
  • Halobenzene
  • Fluorobenzene
  • Para-diazepine
  • Benzenoid
  • N-substituted imidazole
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl fluoride
  • Aryl chloride
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Ketimine
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organofluoride
  • Organochloride
  • Organohalogen compound
  • Imine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationThe midazolam injection is indicated for preoperative sedation/anziolysis/amnesia. It is also an agent for sedation/anziolysis/amnesia prior to or during diagnostic, therapeutic, or endoscopic procedures. Midazolam can also be given intravenously for induction of general anaesthesia.
PharmacodynamicsMidazolam 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 (gamma)-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.
Mechanism of actionIt is thought that 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 brain. Benzodiazepines increase the activity of GABA, thereby producing a calming effect, relaxing skeletal muscles, and inducing sleep. Benzodiazepines bind to the benzodiazepine site on GABA-A receptors, which potentiates the effects of GABA by increasing the frequency of chloride channel opening.
Related Articles
AbsorptionRapidly absorbed after oral administration. The absolute bioavailability of the midazolam syrup in pediatric patients is about 36%. The absolute bioavailability, if given intramuscularly (IM), is greater than 90%. Cmax, IM = 90 ng/mL; Tmax, IM = 0.5 hours. Following IM administered, Cmax for midazolam and its 1-hydroxy metabolite were approxiately one-half of those achieved after intravenous injection.
Volume of distribution
  • 1.24 to 2.02 L/kg [pediatric patients (6 months to <16 years) receiving 0.15 mg/kg IV midazolam,]
  • 1 to 3.1 L/kg [intravenously administered, healthy adults]
    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.
Protein binding97% protein bound.
Metabolism

Midazolam is primarily metabolized in the liver and gut by human cytochrome P450 IIIA4 (CYP3A4) to its pharmacologic active metabolite, (alpha)-hydroxymidazolam (also known as 1-hydroxy-midazolam), and 4-hydroxymidazolam (makes up 5% or less of the biotransformation products). 1-hydroxy-midazolam is at least as potent as the parent compound and may contributed to the overall 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. It also undergoes N-glucuronidation via UGT1A4.

SubstrateEnzymesProduct
Midazolam
Alpha-hydroxymidazolamDetails
Midazolam
4-hydroxymidazolamDetails
Route of eliminationMidazolam is primarily metabolized in the liver and gut by human cytochrome P450 IIIA4 (CYP3A4) to its pharmacologic active metabolite, α-hydroxymidazolam, followed by glucuronidation of the α–hydroxyl metabolite which is present in unconjugated and conjugated forms in human plasma. The α- hydroxymidazolam glucuronide is then excreted in urine. No significant amount of parent drug or metabolites is extractable from urine before beta-glucuronidase and sulfatase deconjugation, indicating 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.
Half lifeIntravenous, healthy adults = 1.8 to 6.4 hours (mean of 3 hours)
Clearance
  • 9.3 to 11 mL/min/kg [pediatric patients (6 months to <16 years old)]
  • 0.25 to 0.54 L/hr/kg [intravenous, healthy adults]
ToxicityLD50=825 mg/kg (Orally in rats). Signs of overdose include sedation, somnolence, confusion, impaired coordination, diminished reflexes, coma, and deleterious effects on vital signs.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9724
Caco-2 permeable+0.8866
P-glycoprotein substrateNon-substrate0.5074
P-glycoprotein inhibitor IInhibitor0.5587
P-glycoprotein inhibitor IIInhibitor0.8388
Renal organic cation transporterInhibitor0.7476
CYP450 2C9 substrateNon-substrate0.7366
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.7194
CYP450 1A2 substrateInhibitor0.8586
CYP450 2C9 inhibitorInhibitor0.7132
CYP450 2D6 inhibitorNon-inhibitor0.6887
CYP450 2C19 inhibitorInhibitor0.6554
CYP450 3A4 inhibitorNon-inhibitor0.5214
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.9001
Ames testNon AMES toxic0.8024
CarcinogenicityNon-carcinogens0.7703
BiodegradationNot ready biodegradable1.0
Rat acute toxicity3.1488 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9827
hERG inhibition (predictor II)Non-inhibitor0.7379
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
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
Dosage forms
FormRouteStrength
Liquidintramuscular; intravenous1 mg
Liquidintramuscular; intravenous5 mg
Injectionintramuscular; intravenous1 mg/mL
Injectionintramuscular; intravenous5 mg/mL
Injection, solutionintramuscular; intravenous10 mg/2mL
Injection, solutionintramuscular; intravenous2 mg/2mL
Injection, solutionintravenous.5 mg/mL
Injection, solutionintravenous1 mg/mL
Injectionintramuscular; intravenous10 mg/2mL
Injectionintramuscular; intravenous2 mg/2mL
Injection, solutionintramuscular; intravenous1 mg/mL
Injection, solutionintramuscular; intravenous5 mg/mL
Syruporal10 mg/5mL
Syruporal2 mg/mL
Solutionintramuscular; intravenous1 mg
Solutionintramuscular; intravenous5 mg
Prices
Unit descriptionCostUnit
Midazolam 5 mg/ml3.9USD ml
Midazolam-nacl 2 mg/ml inj2.31USD ml
Midazolam hcl 5 mg/ml vial1.18USD ml
Midazolam-nacl 1 mg/ml inj1.13USD ml
Midazolam hcl 2 mg/ml syrup1.08USD ml
Midazolam 1 mg/ml isecure syr0.73USD ml
Midazolam hcl 1 mg/ml vial0.26USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point159 °CPhysProp
water solubility0.024 mg/mLThorsteinn Loftsson and Dagný Hreinsdóttir, 2006
Predicted Properties
PropertyValueSource
Water Solubility0.00987 mg/mLALOGPS
logP3.89ALOGPS
logP3.33ChemAxon
logS-4.5ALOGPS
pKa (Strongest Basic)6.57ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area30.18 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity99.43 m3·mol-1ChemAxon
Polarizability32.7 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
MSMass Spectrum (Electron Ionization)splash10-03di-3839000000-42781254e15bcd5b31b6View in MoNA
References
Synthesis Reference

Madhup K. Dhaon, “Process for the preparation of midazolam.” U.S. Patent US6262260, issued August, 1979.

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. [PubMed:6135616 ]
  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. [PubMed:10030438 ]
  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. [PubMed:2894998 ]
  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. [PubMed:17287588 ]
  5. Vermeeren A: Residual effects of hypnotics: epidemiology and clinical implications. CNS Drugs. 2004;18(5):297-328. [PubMed:15089115 ]
External Links
ATC CodesN05CD08
AHFS Codes
  • 28:24.08
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (73.7 KB)
Interactions
Drug Interactions
Drug
AmodiaquineThe serum concentration of Amodiaquine can be increased when it is combined with Midazolam.
AprepitantThe serum concentration of Midazolam can be increased when it is combined with Aprepitant.
AtazanavirThe serum concentration of Midazolam can be increased when it is combined with Atazanavir.
AtorvastatinThe serum concentration of Midazolam can be increased when it is combined with Atorvastatin.
AzelastineMidazolam may increase the central nervous system depressant (CNS depressant) activities of Azelastine.
BaclofenThe risk or severity of adverse effects can be increased when Baclofen is combined with Midazolam.
BatimastatThe serum concentration of Midazolam can be increased when it is combined with Batimastat.
BexaroteneThe serum concentration of Midazolam can be decreased when it is combined with Bexarotene.
BoceprevirThe serum concentration of Midazolam can be increased when it is combined with Boceprevir.
BosentanThe serum concentration of Midazolam can be decreased when it is combined with Bosentan.
BrimonidineBrimonidine may increase the central nervous system depressant (CNS depressant) activities of Midazolam.
BuprenorphineMidazolam may increase the central nervous system depressant (CNS depressant) activities of Buprenorphine.
ClarithromycinThe serum concentration of Midazolam can be increased when it is combined with Clarithromycin.
ClozapineThe risk or severity of adverse effects can be increased when Midazolam is combined with Clozapine.
CobicistatThe serum concentration of Midazolam can be increased when it is combined with Cobicistat.
ConivaptanThe serum concentration of Midazolam can be increased when it is combined with Conivaptan.
DabrafenibThe serum concentration of Midazolam can be decreased when it is combined with Dabrafenib.
DarunavirThe serum concentration of Midazolam can be increased when it is combined with Darunavir.
DasatinibThe serum concentration of Midazolam can be increased when it is combined with Dasatinib.
DeferasiroxThe serum concentration of Midazolam can be decreased when it is combined with Deferasirox.
DoxylamineDoxylamine may increase the central nervous system depressant (CNS depressant) activities of Midazolam.
DronabinolDronabinol may increase the central nervous system depressant (CNS depressant) activities of Midazolam.
DroperidolDroperidol may increase the central nervous system depressant (CNS depressant) activities of Midazolam.
ErythromycinThe serum concentration of Midazolam can be increased when it is combined with Erythromycin.
EthanolMidazolam may increase the central nervous system depressant (CNS depressant) activities of Ethanol.
FluconazoleThe metabolism of Midazolam can be decreased when combined with Fluconazole.
FosamprenavirThe serum concentration of Midazolam can be increased when it is combined with Fosamprenavir.
FosaprepitantThe serum concentration of Midazolam can be increased when it is combined with Fosaprepitant.
Fusidic AcidThe serum concentration of Midazolam can be increased when it is combined with Fusidic Acid.
Ginkgo bilobaThe serum concentration of Midazolam can be decreased when it is combined with Ginkgo biloba.
HydrocodoneMidazolam may increase the central nervous system depressant (CNS depressant) activities of Hydrocodone.
HydroxyzineHydroxyzine may increase the central nervous system depressant (CNS depressant) activities of Midazolam.
IdelalisibThe serum concentration of Midazolam can be increased when it is combined with Idelalisib.
IndinavirThe serum concentration of Midazolam can be increased when it is combined with Indinavir.
IsoflurophateThe serum concentration of Midazolam can be increased when it is combined with Isoflurophate.
ItraconazoleThe serum concentration of Midazolam can be increased when it is combined with Itraconazole.
IvacaftorThe serum concentration of Midazolam can be increased when it is combined with Ivacaftor.
KetoconazoleThe serum concentration of Midazolam can be increased when it is combined with Ketoconazole.
LorazepamThe risk or severity of adverse effects can be increased when Lorazepam is combined with Midazolam.
LuliconazoleThe serum concentration of Midazolam can be increased when it is combined with Luliconazole.
Magnesium SulfateMagnesium Sulfate may increase the central nervous system depressant (CNS depressant) activities of Midazolam.
MethadoneMidazolam may increase the central nervous system depressant (CNS depressant) activities of Methadone.
MethotrimeprazineMidazolam may increase the central nervous system depressant (CNS depressant) activities of Methotrimeprazine.
MetyrosineMidazolam may increase the sedative activities of Metyrosine.
MifepristoneThe serum concentration of Midazolam can be increased when it is combined with Mifepristone.
MinocyclineMinocycline may increase the central nervous system depressant (CNS depressant) activities of Midazolam.
MirtazapineMidazolam may increase the central nervous system depressant (CNS depressant) activities of Mirtazapine.
MitotaneThe serum concentration of Midazolam can be decreased when it is combined with Mitotane.
NabiloneNabilone may increase the central nervous system depressant (CNS depressant) activities of Midazolam.
NelfinavirThe serum concentration of Midazolam can be increased when it is combined with Nelfinavir.
NetupitantThe serum concentration of Midazolam can be increased when it is combined with Netupitant.
OlanzapineThe risk or severity of adverse effects can be increased when Olanzapine is combined with Midazolam.
OrphenadrineMidazolam may increase the central nervous system depressant (CNS depressant) activities of Orphenadrine.
PalbociclibThe serum concentration of Midazolam can be increased when it is combined with Palbociclib.
ParaldehydeMidazolam may increase the central nervous system depressant (CNS depressant) activities of Paraldehyde.
ParoxetineThe risk or severity of adverse effects can be increased when Midazolam is combined with Paroxetine.
PerampanelPerampanel may increase the central nervous system depressant (CNS depressant) activities of Midazolam.
PhenytoinThe metabolism of Midazolam can be increased when combined with Phenytoin.
PramipexoleMidazolam may increase the sedative activities of Pramipexole.
PropofolThe serum concentration of Propofol can be increased when it is combined with Midazolam.
RitonavirThe serum concentration of Midazolam can be increased when it is combined with Ritonavir.
RopiniroleMidazolam may increase the sedative activities of Ropinirole.
RotigotineMidazolam may increase the sedative activities of Rotigotine.
RufinamideThe risk or severity of adverse effects can be increased when Rufinamide is combined with Midazolam.
SaquinavirThe serum concentration of Midazolam can be increased when it is combined with Saquinavir.
SiltuximabThe serum concentration of Midazolam can be decreased when it is combined with Siltuximab.
SimeprevirThe serum concentration of Midazolam can be increased when it is combined with Simeprevir.
Sodium oxybateMidazolam may increase the central nervous system depressant (CNS depressant) activities of Sodium oxybate.
St. John's WortThe serum concentration of Midazolam can be decreased when it is combined with St. John&#39;s Wort.
StiripentolThe serum concentration of Midazolam can be increased when it is combined with Stiripentol.
SuvorexantMidazolam may increase the central nervous system depressant (CNS depressant) activities of Suvorexant.
TapentadolTapentadol may increase the central nervous system depressant (CNS depressant) activities of Midazolam.
TeduglutideThe serum concentration of Midazolam can be increased when it is combined with Teduglutide.
TelaprevirThe serum concentration of Midazolam can be increased when it is combined with Telaprevir.
TelithromycinThe serum concentration of Midazolam can be increased when it is combined with Telithromycin.
ThalidomideMidazolam may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
TheophyllineThe therapeutic efficacy of Midazolam can be decreased when used in combination with Theophylline.
TipranavirThe serum concentration of Midazolam can be increased when it is combined with Tipranavir.
TocilizumabThe serum concentration of Midazolam can be decreased when it is combined with Tocilizumab.
YohimbineThe therapeutic efficacy of Midazolam can be decreased when used in combination with Yohimbine.
ZolpidemMidazolam may increase the central nervous system depressant (CNS depressant) activities of Zolpidem.
Food Interactions
  • Grapefruit juice slows the product's absorption and significantly increases its bioavailability.

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
potentiator
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. Functions as receptor for diazepines and various anesthetics, such as pentobarbital; these are bound at a separate allosteric effector binding site. Functions as ligand-gated chloride channel (By si...
Gene Name:
GABRA1
Uniprot ID:
P14867
Molecular Weight:
51801.395 Da
References
  1. Mohler H, Fritschy JM, Rudolph U: A new benzodiazepine pharmacology. J Pharmacol Exp Ther. 2002 Jan;300(1):2-8. [PubMed:11752090 ]
  2. Riss J, Cloyd J, Gates J, Collins S: Benzodiazepines in epilepsy: pharmacology and pharmacokinetics. Acta Neurol Scand. 2008 Aug;118(2):69-86. doi: 10.1111/j.1600-0404.2008.01004.x. Epub 2008 Mar 31. [PubMed:18384456 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
potentiator
General Function:
Inhibitory extracellular ligand-gated ion channel activity
Specific Function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name:
GABRA2
Uniprot ID:
P47869
Molecular Weight:
51325.85 Da
References
  1. Mohler H, Fritschy JM, Rudolph U: A new benzodiazepine pharmacology. J Pharmacol Exp Ther. 2002 Jan;300(1):2-8. [PubMed:11752090 ]
  2. Riss J, Cloyd J, Gates J, Collins S: Benzodiazepines in epilepsy: pharmacology and pharmacokinetics. Acta Neurol Scand. 2008 Aug;118(2):69-86. doi: 10.1111/j.1600-0404.2008.01004.x. Epub 2008 Mar 31. [PubMed:18384456 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
potentiator
General Function:
Inhibitory extracellular ligand-gated ion channel activity
Specific Function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name:
GABRA3
Uniprot ID:
P34903
Molecular Weight:
55164.055 Da
References
  1. Mohler H, Fritschy JM, Rudolph U: A new benzodiazepine pharmacology. J Pharmacol Exp Ther. 2002 Jan;300(1):2-8. [PubMed:11752090 ]
  2. Riss J, Cloyd J, Gates J, Collins S: Benzodiazepines in epilepsy: pharmacology and pharmacokinetics. Acta Neurol Scand. 2008 Aug;118(2):69-86. doi: 10.1111/j.1600-0404.2008.01004.x. Epub 2008 Mar 31. [PubMed:18384456 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
potentiator
General Function:
Inhibitory extracellular ligand-gated ion channel activity
Specific Function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name:
GABRA4
Uniprot ID:
P48169
Molecular Weight:
61622.645 Da
References
  1. Mohler H, Fritschy JM, Rudolph U: A new benzodiazepine pharmacology. J Pharmacol Exp Ther. 2002 Jan;300(1):2-8. [PubMed:11752090 ]
  2. Riss J, Cloyd J, Gates J, Collins S: Benzodiazepines in epilepsy: pharmacology and pharmacokinetics. Acta Neurol Scand. 2008 Aug;118(2):69-86. doi: 10.1111/j.1600-0404.2008.01004.x. Epub 2008 Mar 31. [PubMed:18384456 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
potentiator
General Function:
Transporter activity
Specific Function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name:
GABRA5
Uniprot ID:
P31644
Molecular Weight:
52145.645 Da
References
  1. Mohler H, Fritschy JM, Rudolph U: A new benzodiazepine pharmacology. J Pharmacol Exp Ther. 2002 Jan;300(1):2-8. [PubMed:11752090 ]
  2. Riss J, Cloyd J, Gates J, Collins S: Benzodiazepines in epilepsy: pharmacology and pharmacokinetics. Acta Neurol Scand. 2008 Aug;118(2):69-86. doi: 10.1111/j.1600-0404.2008.01004.x. Epub 2008 Mar 31. [PubMed:18384456 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
potentiator
General Function:
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. Functions as receptor for diazepines and various anesthetics, such as pentobarbital; these are bound at a separate allosteric effector binding site. Functions as ligand-gated chloride channel (By si...
Gene Name:
GABRB1
Uniprot ID:
P18505
Molecular Weight:
54234.085 Da
References
  1. Mohler H, Fritschy JM, Rudolph U: A new benzodiazepine pharmacology. J Pharmacol Exp Ther. 2002 Jan;300(1):2-8. [PubMed:11752090 ]
  2. Riss J, Cloyd J, Gates J, Collins S: Benzodiazepines in epilepsy: pharmacology and pharmacokinetics. Acta Neurol Scand. 2008 Aug;118(2):69-86. doi: 10.1111/j.1600-0404.2008.01004.x. Epub 2008 Mar 31. [PubMed:18384456 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
potentiator
General Function:
Gaba-gated chloride 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. Functions as receptor for diazepines and various anesthetics, such as pentobarbital; these are bound at a separate allosteric effector binding site. Functions as ligand-gated chloride channel.
Gene Name:
GABRB3
Uniprot ID:
P28472
Molecular Weight:
54115.04 Da
References
  1. Mohler H, Fritschy JM, Rudolph U: A new benzodiazepine pharmacology. J Pharmacol Exp Ther. 2002 Jan;300(1):2-8. [PubMed:11752090 ]
  2. Riss J, Cloyd J, Gates J, Collins S: Benzodiazepines in epilepsy: pharmacology and pharmacokinetics. Acta Neurol Scand. 2008 Aug;118(2):69-86. doi: 10.1111/j.1600-0404.2008.01004.x. Epub 2008 Mar 31. [PubMed:18384456 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
potentiator
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. Functions as receptor for diazepines and various anesthetics, such as pentobarbital; these are bound at a separate allosteric effector binding site. Functions as ligand-gated chloride channel.
Gene Name:
GABRB2
Uniprot ID:
P47870
Molecular Weight:
59149.895 Da
References
  1. Mohler H, Fritschy JM, Rudolph U: A new benzodiazepine pharmacology. J Pharmacol Exp Ther. 2002 Jan;300(1):2-8. [PubMed:11752090 ]
  2. Riss J, Cloyd J, Gates J, Collins S: Benzodiazepines in epilepsy: pharmacology and pharmacokinetics. Acta Neurol Scand. 2008 Aug;118(2):69-86. doi: 10.1111/j.1600-0404.2008.01004.x. Epub 2008 Mar 31. [PubMed:18384456 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
potentiator
General Function:
Inhibitory extracellular ligand-gated ion channel activity
Specific Function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name:
GABRA6
Uniprot ID:
Q16445
Molecular Weight:
51023.69 Da
References
  1. Mohler H, Fritschy JM, Rudolph U: A new benzodiazepine pharmacology. J Pharmacol Exp Ther. 2002 Jan;300(1):2-8. [PubMed:11752090 ]
  2. Riss J, Cloyd J, Gates J, Collins S: Benzodiazepines in epilepsy: pharmacology and pharmacokinetics. Acta Neurol Scand. 2008 Aug;118(2):69-86. doi: 10.1111/j.1600-0404.2008.01004.x. Epub 2008 Mar 31. [PubMed:18384456 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
potentiator
General Function:
Inhibitory extracellular ligand-gated ion channel activity
Specific Function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name:
GABRG1
Uniprot ID:
Q8N1C3
Molecular Weight:
53594.49 Da
References
  1. Mohler H, Fritschy JM, Rudolph U: A new benzodiazepine pharmacology. J Pharmacol Exp Ther. 2002 Jan;300(1):2-8. [PubMed:11752090 ]
  2. Riss J, Cloyd J, Gates J, Collins S: Benzodiazepines in epilepsy: pharmacology and pharmacokinetics. Acta Neurol Scand. 2008 Aug;118(2):69-86. doi: 10.1111/j.1600-0404.2008.01004.x. Epub 2008 Mar 31. [PubMed:18384456 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
potentiator
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. Functions as receptor for diazepines and various anesthetics, such as pentobarbital; these are bound at a separate allosteric effector binding site. Functions as ligand-gated chloride channel.
Gene Name:
GABRG2
Uniprot ID:
P18507
Molecular Weight:
54161.78 Da
References
  1. Mohler H, Fritschy JM, Rudolph U: A new benzodiazepine pharmacology. J Pharmacol Exp Ther. 2002 Jan;300(1):2-8. [PubMed:11752090 ]
  2. Riss J, Cloyd J, Gates J, Collins S: Benzodiazepines in epilepsy: pharmacology and pharmacokinetics. Acta Neurol Scand. 2008 Aug;118(2):69-86. doi: 10.1111/j.1600-0404.2008.01004.x. Epub 2008 Mar 31. [PubMed:18384456 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
potentiator
General Function:
Inhibitory extracellular ligand-gated ion channel activity
Specific Function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name:
GABRG3
Uniprot ID:
Q99928
Molecular Weight:
54288.16 Da
References
  1. Mohler H, Fritschy JM, Rudolph U: A new benzodiazepine pharmacology. J Pharmacol Exp Ther. 2002 Jan;300(1):2-8. [PubMed:11752090 ]
  2. Riss J, Cloyd J, Gates J, Collins S: Benzodiazepines in epilepsy: pharmacology and pharmacokinetics. Acta Neurol Scand. 2008 Aug;118(2):69-86. doi: 10.1111/j.1600-0404.2008.01004.x. Epub 2008 Mar 31. [PubMed:18384456 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
potentiator
General Function:
Gaba-a receptor activity
Specific Function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name:
GABRD
Uniprot ID:
O14764
Molecular Weight:
50707.835 Da
References
  1. Mohler H, Fritschy JM, Rudolph U: A new benzodiazepine pharmacology. J Pharmacol Exp Ther. 2002 Jan;300(1):2-8. [PubMed:11752090 ]
  2. Riss J, Cloyd J, Gates J, Collins S: Benzodiazepines in epilepsy: pharmacology and pharmacokinetics. Acta Neurol Scand. 2008 Aug;118(2):69-86. doi: 10.1111/j.1600-0404.2008.01004.x. Epub 2008 Mar 31. [PubMed:18384456 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
potentiator
General Function:
Inhibitory extracellular ligand-gated ion channel activity
Specific Function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name:
GABRE
Uniprot ID:
P78334
Molecular Weight:
57971.175 Da
References
  1. Mohler H, Fritschy JM, Rudolph U: A new benzodiazepine pharmacology. J Pharmacol Exp Ther. 2002 Jan;300(1):2-8. [PubMed:11752090 ]
  2. Riss J, Cloyd J, Gates J, Collins S: Benzodiazepines in epilepsy: pharmacology and pharmacokinetics. Acta Neurol Scand. 2008 Aug;118(2):69-86. doi: 10.1111/j.1600-0404.2008.01004.x. Epub 2008 Mar 31. [PubMed:18384456 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
potentiator
General Function:
Gaba-a receptor activity
Specific Function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel. In the uterus, the function of the receptor appears to be related to tissue contractility. The binding of this pI subunit with other GABA(A) receptor subunits alters the sensitivity of recombinant receptors to ...
Gene Name:
GABRP
Uniprot ID:
O00591
Molecular Weight:
50639.735 Da
References
  1. Mohler H, Fritschy JM, Rudolph U: A new benzodiazepine pharmacology. J Pharmacol Exp Ther. 2002 Jan;300(1):2-8. [PubMed:11752090 ]
  2. Riss J, Cloyd J, Gates J, Collins S: Benzodiazepines in epilepsy: pharmacology and pharmacokinetics. Acta Neurol Scand. 2008 Aug;118(2):69-86. doi: 10.1111/j.1600-0404.2008.01004.x. Epub 2008 Mar 31. [PubMed:18384456 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
potentiator
General Function:
Gaba-a receptor activity
Specific Function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel. Rho-1 GABA receptor could play a role in retinal neurotransmission.
Gene Name:
GABRR1
Uniprot ID:
P24046
Molecular Weight:
55882.91 Da
References
  1. Mohler H, Fritschy JM, Rudolph U: A new benzodiazepine pharmacology. J Pharmacol Exp Ther. 2002 Jan;300(1):2-8. [PubMed:11752090 ]
  2. Riss J, Cloyd J, Gates J, Collins S: Benzodiazepines in epilepsy: pharmacology and pharmacokinetics. Acta Neurol Scand. 2008 Aug;118(2):69-86. doi: 10.1111/j.1600-0404.2008.01004.x. Epub 2008 Mar 31. [PubMed:18384456 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
potentiator
General Function:
Gaba-a receptor activity
Specific Function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel. Rho-2 GABA receptor could play a role in retinal neurotransmission.
Gene Name:
GABRR2
Uniprot ID:
P28476
Molecular Weight:
54150.41 Da
References
  1. Mohler H, Fritschy JM, Rudolph U: A new benzodiazepine pharmacology. J Pharmacol Exp Ther. 2002 Jan;300(1):2-8. [PubMed:11752090 ]
  2. Riss J, Cloyd J, Gates J, Collins S: Benzodiazepines in epilepsy: pharmacology and pharmacokinetics. Acta Neurol Scand. 2008 Aug;118(2):69-86. doi: 10.1111/j.1600-0404.2008.01004.x. Epub 2008 Mar 31. [PubMed:18384456 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
potentiator
General Function:
Gaba-a receptor activity
Specific Function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name:
GABRR3
Uniprot ID:
A8MPY1
Molecular Weight:
54271.1 Da
References
  1. Mohler H, Fritschy JM, Rudolph U: A new benzodiazepine pharmacology. J Pharmacol Exp Ther. 2002 Jan;300(1):2-8. [PubMed:11752090 ]
  2. Riss J, Cloyd J, Gates J, Collins S: Benzodiazepines in epilepsy: pharmacology and pharmacokinetics. Acta Neurol Scand. 2008 Aug;118(2):69-86. doi: 10.1111/j.1600-0404.2008.01004.x. Epub 2008 Mar 31. [PubMed:18384456 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
potentiator
General Function:
Transmembrane signaling receptor activity
Specific Function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name:
GABRQ
Uniprot ID:
Q9UN88
Molecular Weight:
72020.875 Da
References
  1. Mohler H, Fritschy JM, Rudolph U: A new benzodiazepine pharmacology. J Pharmacol Exp Ther. 2002 Jan;300(1):2-8. [PubMed:11752090 ]
  2. Riss J, Cloyd J, Gates J, Collins S: Benzodiazepines in epilepsy: pharmacology and pharmacokinetics. Acta Neurol Scand. 2008 Aug;118(2):69-86. doi: 10.1111/j.1600-0404.2008.01004.x. Epub 2008 Mar 31. [PubMed:18384456 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Foti RS, Rock DA, Wienkers LC, Wahlstrom JL: Selection of alternative CYP3A4 probe substrates for clinical drug interaction studies using in vitro data and in vivo simulation. Drug Metab Dispos. 2010 Jun;38(6):981-7. doi: 10.1124/dmd.110.032094. Epub 2010 Mar 4. [PubMed:20203109 ]
  2. Pelkonen O, Maenpaa J, Taavitsainen P, Rautio A, Raunio H: Inhibition and induction of human cytochrome P450 (CYP) enzymes. Xenobiotica. 1998 Dec;28(12):1203-53. [PubMed:9890159 ]
  3. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  4. Zhou S, Chan E, Lim LY, Boelsterli UA, Li SC, Wang J, Zhang Q, Huang M, Xu A: Therapeutic drugs that behave as mechanism-based inhibitors of cytochrome P450 3A4. Curr Drug Metab. 2004 Oct;5(5):415-42. [PubMed:15544435 ]
  5. Williams JA, Ring BJ, Cantrell VE, Jones DR, Eckstein J, Ruterbories K, Hamman MA, Hall SD, Wrighton SA: Comparative metabolic capabilities of CYP3A4, CYP3A5, and CYP3A7. Drug Metab Dispos. 2002 Aug;30(8):883-91. [PubMed:12124305 ]
  6. Galetin A, Clarke SE, Houston JB: Quinidine and haloperidol as modifiers of CYP3A4 activity: multisite kinetic model approach. Drug Metab Dispos. 2002 Dec;30(12):1512-22. [PubMed:12433827 ]
  7. Obach RS, Reed-Hagen AE: Measurement of Michaelis constants for cytochrome P450-mediated biotransformation reactions using a substrate depletion approach. Drug Metab Dispos. 2002 Jul;30(7):831-7. [PubMed:12065442 ]
  8. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Oxygen binding
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Molecular Weight:
57108.065 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  2. Patki KC, Von Moltke LL, Greenblatt DJ: In vitro metabolism of midazolam, triazolam, nifedipine, and testosterone by human liver microsomes and recombinant cytochromes p450: role of cyp3a4 and cyp3a5. Drug Metab Dispos. 2003 Jul;31(7):938-44. [PubMed:12814972 ]
  3. Wandel C, Bocker R, Bohrer H, Browne A, Rugheimer E, Martin E: Midazolam is metabolized by at least three different cytochrome P450 enzymes. Br J Anaesth. 1994 Nov;73(5):658-61. [PubMed:7826796 ]
  4. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015 ]
  5. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Oxygen binding
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A7
Uniprot ID:
P24462
Molecular Weight:
57525.03 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  2. Gorski JC, Hall SD, Jones DR, VandenBranden M, Wrighton SA: Regioselective biotransformation of midazolam by members of the human cytochrome P450 3A (CYP3A) subfamily. Biochem Pharmacol. 1994 Apr 29;47(9):1643-53. [PubMed:8185679 ]
  3. Ghosal A, Satoh H, Thomas PE, Bush E, Moore D: Inhibition and kinetics of cytochrome P4503A activity in microsomes from rat, human, and cdna-expressed human cytochrome P450. Drug Metab Dispos. 1996 Sep;24(9):940-7. [PubMed:8886602 ]
  4. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015 ]
  5. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
Molecular Weight:
56277.81 Da
References
  1. Ekins S, Vandenbranden M, Ring BJ, Gillespie JS, Yang TJ, Gelboin HV, Wrighton SA: Further characterization of the expression in liver and catalytic activity of CYP2B6. J Pharmacol Exp Ther. 1998 Sep;286(3):1253-9. [PubMed:9732386 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  3. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Oxygen binding
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP4B1
Uniprot ID:
P13584
Molecular Weight:
58990.64 Da
References
  1. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Protein homodimerization activity
Specific Function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Isoform 2 lacks transferase activity but acts as a negative regulator of isoform 1 (By similarity).
Gene Name:
UGT1A4
Uniprot ID:
P22310
Molecular Weight:
60024.535 Da
References
  1. Klieber S, Hugla S, Ngo R, Arabeyre-Fabre C, Meunier V, Sadoun F, Fedeli O, Rival M, Bourrie M, Guillou F, Maurel P, Fabre G: Contribution of the N-glucuronidation pathway to the overall in vitro metabolic clearance of midazolam in humans. Drug Metab Dispos. 2008 May;36(5):851-62. doi: 10.1124/dmd.107.019539. Epub 2008 Feb 6. [PubMed:18256203 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:
CYP2E1
Uniprot ID:
P05181
Molecular Weight:
56848.42 Da
References
  1. Tassaneeyakul W, Birkett DJ, Miners JO: Inhibition of human hepatic cytochrome P4502E1 by azole antifungals, CNS-active drugs and non-steroidal anti-inflammatory agents. Xenobiotica. 1998 Mar;28(3):293-301. [PubMed:9574817 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitorinducer
General Function:
Xenobiotic-transporting atpase activity
Specific Function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular Weight:
141477.255 Da
References
  1. Schuetz EG, Beck WT, Schuetz JD: Modulators and substrates of P-glycoprotein and cytochrome P4503A coordinately up-regulate these proteins in human colon carcinoma cells. Mol Pharmacol. 1996 Feb;49(2):311-8. [PubMed:8632764 ]
  2. Katoh M, Nakajima M, Yamazaki H, Yokoi T: Inhibitory effects of CYP3A4 substrates and their metabolites on P-glycoprotein-mediated transport. Eur J Pharm Sci. 2001 Feb;12(4):505-13. [PubMed:11231118 ]
  3. Schwab D, Fischer H, Tabatabaei A, Poli S, Huwyler J: Comparison of in vitro P-glycoprotein screening assays: recommendations for their use in drug discovery. J Med Chem. 2003 Apr 24;46(9):1716-25. [PubMed:12699389 ]
  4. Takano M, Hasegawa R, Fukuda T, Yumoto R, Nagai J, Murakami T: Interaction with P-glycoprotein and transport of erythromycin, midazolam and ketoconazole in Caco-2 cells. Eur J Pharmacol. 1998 Oct 9;358(3):289-94. [PubMed:9822896 ]
  5. Kim RB, Wandel C, Leake B, Cvetkovic M, Fromm MF, Dempsey PJ, Roden MM, Belas F, Chaudhary AK, Roden DM, Wood AJ, Wilkinson GR: Interrelationship between substrates and inhibitors of human CYP3A and P-glycoprotein. Pharm Res. 1999 Mar;16(3):408-14. [PubMed:10213372 ]
  6. Polli JW, Wring SA, Humphreys JE, Huang L, Morgan JB, Webster LO, Serabjit-Singh CS: Rational use of in vitro P-glycoprotein assays in drug discovery. J Pharmacol Exp Ther. 2001 Nov;299(2):620-8. [PubMed:11602674 ]
  7. Mahar Doan KM, Humphreys JE, Webster LO, Wring SA, Shampine LJ, Serabjit-Singh CJ, Adkison KK, Polli JW: Passive permeability and P-glycoprotein-mediated efflux differentiate central nervous system (CNS) and non-CNS marketed drugs. J Pharmacol Exp Ther. 2002 Dec;303(3):1029-37. [PubMed:12438524 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Secondary active organic cation transmembrane transporter activity
Specific Function:
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)-N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine...
Gene Name:
SLC22A1
Uniprot ID:
O15245
Molecular Weight:
61153.345 Da
References
  1. Zhang L, Schaner ME, Giacomini KM: Functional characterization of an organic cation transporter (hOCT1) in a transiently transfected human cell line (HeLa). J Pharmacol Exp Ther. 1998 Jul;286(1):354-61. [PubMed:9655880 ]
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:11