Identification

Name
Alprazolam
Accession Number
DB00404  (APRD00280, DB05925)
Type
Small Molecule
Groups
Approved, Illicit, Investigational
Description

A triazolobenzodiazepine compound with antianxiety and sedative-hypnotic actions, that is efficacious in the treatment of panic disorders, with or without agoraphobia, and in generalized anxiety disorders. (From AMA Drug Evaluations Annual, 1994, p238)

Structure
Thumb
Synonyms
  • 8-Chloro-1-methyl-6-phenyl-4H-S-triazolo(4,3-a)(1,4)benzodiazepine
  • Alprazolam
External IDs
TUS-1 / U 31,889 / U-31,889 / U-31889
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AlprazolamTablet0.50 mgOralSanis Health Inc2010-04-30Not applicableCanada
AlprazolamTablet, extended release0.5 mg/1OralZydus Pharmaceuticals Usa, Inc.2008-10-28Not applicableUs
AlprazolamTablet0.5 mgOralJamp Pharma CorporationNot applicableNot applicableCanada
AlprazolamTablet, extended release2 mg/1OralZydus Pharmaceuticals Usa, Inc.2008-10-28Not applicableUs
AlprazolamTablet1 mgOralPro Doc Limitee2004-04-01Not applicableCanada
AlprazolamTablet0.25 mgOralSanis Health Inc2010-04-30Not applicableCanada
AlprazolamTablet2 mgOralJamp Pharma CorporationNot applicableNot applicableCanada
AlprazolamTablet0.25 mgOralJamp Pharma CorporationNot applicableNot applicableCanada
AlprazolamTablet, extended release1 mg/1OralZydus Pharmaceuticals Usa, Inc.2008-10-28Not applicableUs
AlprazolamTablet1 mgOralJamp Pharma CorporationNot applicableNot applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AlprazolamTablet1 mg/1OralLake Erie Medical Dba Quality Care Produts Llc2011-11-152014-06-01Us
AlprazolamTablet, extended release3 mg/1OralEon Labs, Inc.2006-06-302012-03-31Us
AlprazolamTablet0.25 mg/1OralA S Medication Solutions2010-06-18Not applicableUs
AlprazolamTablet0.25 mg/1OralContract Pharmacy Services Pa2007-03-28Not applicableUs
AlprazolamTablet0.5 mg/1OralAmerican Health Packaging2018-10-01Not applicableUs
AlprazolamTablet1 mg/1OralNucare Pharmaceuticals, Inc.2015-10-01Not applicableUs
AlprazolamTablet.25 mg/1OralUnit Dose Services1995-12-29Not applicableUs
AlprazolamTablet, extended release3 mg/1OralTeva2007-06-042009-02-28Us
AlprazolamTablet.25 mg/1OralA-S Medication Solutions1995-12-292017-08-31Us
AlprazolamTablet0.25 mg/1OralActavis Pharma, Inc.1993-10-01Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
GabazolamineAlprazolam (0.25 mg/1) + Choline (125 mg/1)KitPhysician Therapeutics Llc2011-07-07Not applicableUs
Gabazolamine-0.5Alprazolam (0.5 mg/1) + Choline (125 mg/1)KitPhysician Therapeutics Llc2011-07-07Not applicableUs
Sentrazolam AMAlprazolam (0.25 mg/1) + Choline (250 mg/1)KitPhysician Therapeutics Llc2011-07-07Not applicableUs
International/Other Brands
Alplax / Alprazolan / Alpronax / Alprox / Alviz / Cassadan / Esparon / Ralozam / Restyl / Solanax / Tafil / Trankimazin / Tranquinal / Xanax / Xanor
Categories
UNII
YU55MQ3IZY
CAS number
28981-97-7
Weight
Average: 308.765
Monoisotopic: 308.082874143
Chemical Formula
C17H13ClN4
InChI Key
VREFGVBLTWBCJP-UHFFFAOYSA-N
InChI
InChI=1S/C17H13ClN4/c1-11-20-21-16-10-19-17(12-5-3-2-4-6-12)14-9-13(18)7-8-15(14)22(11)16/h2-9H,10H2,1H3
IUPAC Name
12-chloro-3-methyl-9-phenyl-2,4,5,8-tetraazatricyclo[8.4.0.0²,⁶]tetradeca-1(10),3,5,8,11,13-hexaene
SMILES
CC1=NN=C2CN=C(C3=CC=CC=C3)C3=C(C=CC(Cl)=C3)N12

Pharmacology

Indication

For the management of anxiety disorder or the short-term relief of symptoms of anxiety and for the treatment of panic disorder, with or without agoraphobia.

Associated Conditions
Pharmacodynamics

Alprazolam, a benzodiazepine, is used to treat panic disorder and anxiety disorder. Unlike chlordiazepoxide, clorazepate, and prazepam, alprazolam has a shorter half-life and metabolites with minimal activity. Like other triazolo benzodiazepines such as triazolam, alprazolam may have significant drug interactions involving the hepatic cytochrome P-450 3A4 isoenzyme. Clinically, all benzodiazepines cause a dose-related central nervous system depressant activity varying from mild impairment of task performance to hypnosis. Unlike other benzodiazepines, alprazolam may also have some antidepressant activity, although clinical evidence of this is lacking.

Mechanism of action

Benzodiazepines bind nonspecifically to benzodiazepine receptors BNZ1, which mediates sleep, and BNZ2, which affects muscle relaxation, anticonvulsant activity, motor coordination, and memory. As benzodiazepine receptors are thought to be coupled to gamma-aminobutyric acid-A (GABAA) receptors, this enhances the effects of GABA by increasing GABA affinity for the GABA receptor. Binding of the inhibitory neurotransmitter GABA to the site opens the chloride channel, resulting in a hyperpolarized cell membrane that prevents further excitation of the cell.

TargetActionsOrganism
AGABA-A receptor (anion channel)
positive allosteric modulator
Human
Absorption

Readily absorbed from the gastrointestinal tract. Bioavailability is 80-90%.

Volume of distribution
Not Available
Protein binding

80% (mainly to albumin)

Metabolism

Hepatic. Hydroxylated in the liver to α-hydroxyalprazolam, which is also active. This and other metabolites are later excreted in urine as glucuronides.

Route of elimination

Alprazolam and its metabolites are excreted primarily in the urine.

Half life

6.3-26.9 hours

Clearance
  • 2.13 +/- 0.54 mL/min/kg [CYP3A inducers]
  • 0.90 +/- 0.21 mL/min/kg [without CYP3A inducers]
Toxicity

Oral, mouse: LD50=1020 mg/kg. Symptoms of overdose include confusion, coma, impaired coordination, sleepiness, and slowed reaction time.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of Alprazolam can be decreased when combined with (R)-warfarin.
(S)-WarfarinThe metabolism of Alprazolam can be decreased when combined with (S)-Warfarin.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when Alprazolam is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3-isobutyl-1-methyl-7H-xanthineThe therapeutic efficacy of Alprazolam can be decreased when used in combination with 3-isobutyl-1-methyl-7H-xanthine.
3,4-MethylenedioxyamphetamineThe risk or severity of adverse effects can be increased when Alprazolam is combined with 3,4-Methylenedioxyamphetamine.
3,5-diiodothyropropionic acidThe metabolism of Alprazolam can be decreased when combined with 3,5-diiodothyropropionic acid.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when Alprazolam is combined with 4-Bromo-2,5-dimethoxyamphetamine.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Alprazolam.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when Alprazolam is combined with 4-Methoxyamphetamine.
5-androstenedioneThe metabolism of Alprazolam can be decreased when combined with 5-androstenedione.
Food Interactions
  • Avoid alcohol.
  • Avoid excessive quantities of coffee or tea (Caffeine).
  • Avoid taking with grapefruit juice.
  • Take with food.

References

Synthesis Reference

Hester, J.B., Jr.; US. Patent 3,681,343; August 1,1972; assigned to The Upjohn Company. Hester, J.B., Jr.; US.Patent 3,781,289; December 25,1973;assigned to The Upjohn Company. Hester, J.B., Jr.; U S . Patent 3,709898; January 9,1973; assigned to The Upjohn Company.

General References
  1. Risse SC, Whitters A, Burke J, Chen S, Scurfield RM, Raskind MA: Severe withdrawal symptoms after discontinuation of alprazolam in eight patients with combat-induced posttraumatic stress disorder. J Clin Psychiatry. 1990 May;51(5):206-9. [PubMed:2335496]
  2. Wolf B, Griffiths RR: Physical dependence on benzodiazepines: differences within the class. Drug Alcohol Depend. 1991 Dec 31;29(2):153-6. [PubMed:1686752]
  3. Haque W, Watson DJ, Bryant SG: Death following suspected alprazolam withdrawal seizures: a case report. Tex Med. 1990 Jan;86(1):44-7. [PubMed:2300914]
  4. Hori A: Pharmacotherapy for personality disorders. Psychiatry Clin Neurosci. 1998 Feb;52(1):13-9. [PubMed:9682928]
  5. Garcia-Algar O, Lopez-Vilchez MA, Martin I, Mur A, Pellegrini M, Pacifici R, Rossi S, Pichini S: Confirmation of gestational exposure to alprazolam by analysis of biological matrices in a newborn with neonatal sepsis. Clin Toxicol (Phila). 2007;45(3):295-8. [PubMed:17453885]
External Links
Human Metabolome Database
HMDB0014548
KEGG Drug
D00225
KEGG Compound
C06817
PubChem Compound
2118
PubChem Substance
46507078
ChemSpider
2034
BindingDB
50001728
ChEBI
2611
ChEMBL
CHEMBL661
Therapeutic Targets Database
DAP000239
PharmGKB
PA448333
HET
08H
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Alprazolam
ATC Codes
N05BA12 — Alprazolam
AHFS Codes
  • 28:24.08 — Benzodiazepines
PDB Entries
3u5j
FDA label
Download (63.6 KB)
MSDS
Download (47.3 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedTreatmentDiabetes, Diabetes Mellitus Type 11
0Unknown StatusBasic SciencePsychotropic Drugs Effects1
1CompletedNot AvailableAlzheimer's Disease (AD) / Huntington's Disease (HD)1
1CompletedNot AvailableHealthy Volunteers10
1CompletedNot AvailablePharmacokinetics1
1CompletedBasic ScienceAnxiety Disorders1
1CompletedBasic ScienceHealthy Volunteers5
1CompletedBasic SciencePrescription Drug Abuse (Not Dependent) / Recreational Drug Use1
1CompletedDiagnosticCannabis Use Disorders1
1CompletedDiagnosticDepressive Disorder and Anxiety Disorders / Healthy Volunteers1
1CompletedOtherAnxiety Disorders3
1CompletedOtherMigraines1
1CompletedPreventionPost-Operative Delirium1
1CompletedTreatmentAbuse Liability of Staccato Alprazolam1
1CompletedTreatmentFeeling Anxious2
1CompletedTreatmentSocial Anxiety Disorder (SAD) / Social Phobia1
1TerminatedTreatmentHealthy Volunteers1
1WithdrawnBasic ScienceHealthy Volunteers2
2CompletedTreatmentAnxiety Disorders / Panic Disorders1
2CompletedTreatmentDental Anxiety1
2CompletedTreatmentGeneralized Anxiety Disorder (GAD)1
2RecruitingTreatmentGeneralized Anxiety Disorder (GAD)1
2, 3CompletedPreventionDiagnostic Esophagogastroduodenoscopy1
2, 3CompletedTreatmentPost Traumatic Stress Disorder (PTSD)1
3TerminatedTreatmentAnxiety Disorders / Dementias / Depression / Psychosomatic Disorders / Schizophrenic Disorders1
4CompletedBasic ScienceDriving Behavior1
4CompletedBasic ScienceHealthy Volunteers1
4CompletedDiagnosticAnxiety Disorders1
4CompletedTreatmentFeeling Anxious2
4CompletedTreatmentGeneralized Anxiety Disorder (GAD) / Panic Disorders1
4CompletedTreatmentInferior Alveolar Nerve Block Failure1
4CompletedTreatmentPanic Disorders2
4Not Yet RecruitingTreatmentAnxiety Disease / Gynecologic Diseases1
4RecruitingOtherPsychomotor Impairment1
4TerminatedTreatmentPanic Disorders3
4Unknown StatusTreatmentGeneralized Anxiety Disorder (GAD)1
4WithdrawnTreatmentAnxiety Disorders1
Not AvailableCompletedNot AvailableDiabetes, Diabetes Mellitus Type 11
Not AvailableCompletedBasic ScienceAOD Effects and Consequences1
Not AvailableNot Yet RecruitingTreatmentCoronary Angiography / Sedative Premedication1

Pharmacoeconomics

Manufacturers
  • Roxane laboratories inc
  • Actavis elizabeth llc
  • Amneal pharmaceuticals ny llc
  • Apotex inc
  • Barr laboratories inc
  • Corepharma llc
  • Impax laboratories inc
  • Mylan pharmaceuticals inc
  • Sandoz inc
  • Teva pharmaceuticals usa
  • Vintage pharmaceuticals llc
  • Watson laboratories inc florida
  • Zydus pharmaceuticals usa inc
  • Pharmacia and upjohn
  • Par pharmaceutical inc
  • Schwarz pharma inc
  • Alphapharm party ltd
  • Dava international inc
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Sun pharma global inc
  • Teva pharmaceuticals usa inc
  • Watson laboratories inc
  • Pharmacia and upjohn co
Packagers
  • Actavis Group
  • Aidarex Pharmacuticals LLC
  • Alphapharm Party Ltd.
  • Amerisource Health Services Corp.
  • Amneal Pharmaceuticals
  • Apotheca Inc.
  • A-S Medication Solutions LLC
  • AzurPharma Inc.
  • Barr Pharmaceuticals
  • Bryant Ranch Prepack
  • Cardinal Health
  • Caremark LLC
  • Centaur Pharmaceuticals Pvt Ltd.
  • Cima Laboratories Inc.
  • Corepharma LLC
  • DAVA Pharmaceuticals
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Emcure Pharmaceuticals Ltd.
  • Eon Labs
  • Global Pharmaceuticals
  • Greenstone LLC
  • H.J. Harkins Co. Inc.
  • Heartland Repack Services LLC
  • Innoviant Pharmacy Inc.
  • Ivax Pharmaceuticals
  • Kaiser Foundation Hospital
  • Keltman Pharmaceuticals Inc.
  • Lake Erie Medical and Surgical Supply
  • Liberty Pharmaceuticals
  • Major Pharmaceuticals
  • Mckesson Corp.
  • Medisca Inc.
  • Medvantx Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mylan
  • Novopharm Ltd.
  • Nucare Pharmaceuticals Inc.
  • Palmetto Pharmaceuticals Inc.
  • Par Pharmaceuticals
  • PD-Rx Pharmaceuticals Inc.
  • Pfizer Inc.
  • Pharmacia Inc.
  • Pharmedix
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Prepak Systems Inc.
  • Qualitest
  • Rebel Distributors Corp.
  • Redpharm Drug
  • Remedy Repack
  • Rising Pharmaceuticals
  • Roxane Labs
  • Sandhills Packaging Inc.
  • Sandoz
  • Southwood Pharmaceuticals
  • Stat Rx Usa
  • Sun Pharmaceutical Industries Ltd.
  • Teva Pharmaceutical Industries Ltd.
  • UDL Laboratories
  • Ultratab Labs Inc.
  • Va Cmop Dallas
  • Vintage Pharmaceuticals Inc.
  • Zydus Pharmaceuticals
Dosage forms
FormRouteStrength
Solution, concentrateOral1 mg/1mL
TabletOral.25 mg/1
TabletOral.5 mg/1
TabletOral0.25 mg/1
TabletOral0.5 mg/1
TabletOral0.50 mg
TabletOral1 mg/1
TabletOral1.00 mg/1
TabletOral2 mg/1
TabletOral2.00 mg/1
Tablet, extended releaseOral0.5 mg/1
Tablet, extended releaseOral1 mg/1
Tablet, extended releaseOral2 mg/1
Tablet, extended releaseOral3 mg/1
TabletOral2 mg
Tablet, orally disintegratingOral0.25 mg/1
Tablet, orally disintegratingOral0.5 mg/1
Tablet, orally disintegratingOral1 mg/1
Tablet, orally disintegratingOral2 mg/1
TabletOral.25 mg
TabletOral.5 mg
Kit
TabletOral0.25 mg
TabletOral0.5 mg
TabletOral1 mg
Prices
Unit descriptionCostUnit
ALPRAZolam Intensol 1 mg/ml Concentrate 30ml Bottle67.03USD bottle
Niravam 2 mg Dispersible Tablet8.53USD dispersible tablet
Xanax xr 3 mg tablet7.25USD tablet
Xanax XR 3 mg 24 Hour tablet7.1USD tablet
Niravam 2 mg tablet6.86USD tablet
Niravam 1 mg Dispersible Tablet5.42USD dispersible tablet
Xanax xr 2 mg tablet4.84USD tablet
Xanax XR 2 mg 24 Hour tablet4.73USD tablet
Niravam 0.5 mg Dispersible Tablet4.2USD dispersible tablet
Niravam 1 mg tablet4.04USD tablet
Xanax 2 mg tablet3.82USD tablet
ALPRAZolam 3 mg 24 Hour tablet3.67USD tablet
Xanax XR 1 mg 24 Hour tablet3.64USD tablet
Xanax xr 1 mg tablet3.64USD tablet
Niravam 0.25 mg Dispersible Tablet3.45USD dispersible tablet
Niravam 0.5 mg tablet3.02USD tablet
Xanax XR 0.5 mg 24 Hour tablet3.01USD tablet
Xanax xr 0.5 mg tablet2.93USD tablet
ALPRAZolam 2 mg 24 Hour tablet2.53USD tablet
Niravam 0.25 mg tablet2.43USD tablet
ALPRAZolam 1 mg 24 Hour tablet2.33USD tablet
Xanax 1 mg tablet2.29USD tablet
Alprazolam 1 mg/ml oral conc2.23USD ml
Xanax 0.5 mg tablet1.3USD tablet
Alprazolam 2 mg tablet1.22USD tablet
Xanax 0.25 mg tablet1.09USD tablet
ALPRAZolam 0.5 mg 24 Hour tablet1.07USD tablet
Alprazolam 1 mg tablet0.78USD tablet
Alprazolam 0.5 mg tablet0.67USD tablet
Alprazolam 0.25 mg tablet0.55USD tablet
Apo-Alpraz 0.5 mg Tablet0.1USD tablet
Mylan-Alprazolam 0.5 mg Tablet0.1USD tablet
Novo-Alprazol 0.5 mg Tablet0.1USD tablet
Apo-Alpraz 0.25 mg Tablet0.08USD tablet
Mylan-Alprazolam 0.25 mg Tablet0.08USD tablet
Novo-Alprazol 0.25 mg Tablet0.08USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6221392No2001-04-242018-04-09Us
US6024981No2000-02-152018-04-09Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)228-229.5 °CHester, J.B., Jr.; US. Patent3,681,343; August 1,1972; assigned to The Upjohn Company. Hester, J.B., Jr.; US.Patent3,781,289; December 25,1973;assigned to The Upjohn Company. Hester, J.B., Jr.; U S . Patent 3,709898; January 9,1973; assigned t o The Upjohn Company.
water solubility40 mg/L at pH 7; 12 mg/mL at pH 1.2Not Available
logP2.12BIOBYTE (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.0324 mg/mLALOGPS
logP2.23ALOGPS
logP2.37ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)18.3ChemAxon
pKa (Strongest Basic)5.08ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.07 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity98.88 m3·mol-1ChemAxon
Polarizability32.22 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9794
Caco-2 permeable+0.8867
P-glycoprotein substrateNon-substrate0.5099
P-glycoprotein inhibitor INon-inhibitor0.7301
P-glycoprotein inhibitor IIInhibitor0.8354
Renal organic cation transporterInhibitor0.7688
CYP450 2C9 substrateNon-substrate0.7907
CYP450 2D6 substrateNon-substrate0.9164
CYP450 3A4 substrateSubstrate0.7353
CYP450 1A2 substrateInhibitor0.8758
CYP450 2C9 inhibitorInhibitor0.8076
CYP450 2D6 inhibitorNon-inhibitor0.8137
CYP450 2C19 inhibitorInhibitor0.6519
CYP450 3A4 inhibitorNon-inhibitor0.6308
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8913
Ames testNon AMES toxic0.8957
CarcinogenicityNon-carcinogens0.6779
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.3717 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.973
hERG inhibition (predictor II)Non-inhibitor0.8733
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-0kdi-4792000000-9f1cdda14e36000955d3
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a59-0079000000-e4c35fb4df41aa5cc62e
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0bt9-0169000000-0e6779728f3bdec2acf1
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a4i-0910000000-9efa6a8a3dea17fc1ce7

Taxonomy

Description
This compound belongs to the class of organic compounds known as 1,2,4-triazolo[4,3-a][1,4]benzodiazepines. These are aromatic compounds containing a 1,4-benzodiazepine fused to and sharing a nitrogen atom with a 1,2,4-triazole ring.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzodiazepines
Sub Class
1,4-benzodiazepines
Direct Parent
1,2,4-triazolo[4,3-a][1,4]benzodiazepines
Alternative Parents
Benzene and substituted derivatives / Aryl chlorides / Triazoles / Heteroaromatic compounds / Ketimines / Propargyl-type 1,3-dipolar organic compounds / Azacyclic compounds / Organopnictogen compounds / Organochlorides / Hydrocarbon derivatives
Substituents
1,2,4-triazolo[4,3-a][1,4]benzodiazepine / Aryl chloride / Aryl halide / Monocyclic benzene moiety / Benzenoid / Azole / 1,2,4-triazole / Heteroaromatic compound / Ketimine / Propargyl-type 1,3-dipolar organic compound
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organochlorine compound, triazolobenzodiazepine (CHEBI:2611)

Targets

Kind
Protein group
Organism
Human
Pharmacological action
Yes
Actions
Positive allosteric modulator
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:
References
  1. 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]
  2. Verster JC, Volkerts ER: Clinical pharmacology, clinical efficacy, and behavioral toxicity of alprazolam: a review of the literature. CNS Drug Rev. 2004 Spring;10(1):45-76. [PubMed:14978513]

Enzymes

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 un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
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 un...
Gene Name
CYP3A7
Uniprot ID
P24462
Uniprot Name
Cytochrome P450 3A7
Molecular Weight
57525.03 Da
References
  1. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
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 react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  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. 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]
  4. 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 un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  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. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]

Drug created on June 13, 2005 07:24 / Updated on November 20, 2018 00:42