Identification

Name
Alprazolam
Accession Number
DB00404
Description

Alprazolam is a triazolobenzodiazepine indicated for the treatment of anxiety and panic disorders.Label It is mainly metabolized by CYP3As and so is contraindicated with CYP3A inhibitors like ketoconazole and itraconazole.Label Benzodiazepine treatment should be stopped gradually by tapering down a patient's dose to avoid withdrawal symptoms.4 Alprazolam's adverse effects are generally related to the sedation it can cause.4 Alprazolam has been mixed with alcohol as a drug of abuse to potentiate the sedative effects of the drug which may lead to coma and death.4 Alprazolam was given FDA approval on October 16, 19817.

Type
Small Molecule
Groups
Approved, Illicit, Investigational
Structure
Thumb
Weight
Average: 308.765
Monoisotopic: 308.082874143
Chemical Formula
C17H13ClN4
Synonyms
  • 8-Chloro-1-methyl-6-phenyl-4H-s-triazolo(4,3-a)(1,4)benzodiazepine
  • Alprazolam
External IDs
  • AZ-002
  • TUS-1
  • U 31,889
  • U-31,889
  • U-31889

Pharmacology

Indication

Alprazolam is indicated for the management of anxiety disorder, anxiety associated with depression, panic disorder, and panic disorder with agoraphobia.Label Alprazolam may also be prescribed off label for insomnia, premenstrual syndrome, and depression.3

Associated Conditions
Contraindications & Blackbox Warnings
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Pharmacodynamics

Alprazolam is indicated to treat anxiety and panic disorders.Label The mechanism by which its cell receptor interactions translate to a clinical effect is not known.Label,3,4

Alprazolam exerts its effects through interaction with BNZ-1, BNZ-2, and GABA-A receptors.3,4 Alprazolam binding to BNZ-1 is thought to influence sedation and anti-anxiety, BNZ-2 may influence memory, coordination, muscle relaxation, and anticonvulsive activity, and GABA-A may calm patients by increasing the affinity of GABA-A receptors for GABA3,4.

The metabolism of alprazolam is mediated largely through the action of CYP3As and so alprazolam is contraindicated with CYP3A inhibitors such as ketoconazole and itraconazole.Label

Alprazolam, like other benzodiazepines, can cause dependancy and so when stopping treatment doses should be tapered down gradually4. Alprazolam's adverse effects are generally related to the sedating effects of the drug.4 This effect has lead to abuse of alprazolam with alcohol to potentiate its sedating effect, which may lead to coma and death.4

Mechanism of action

Alprazolam is a triazolobenzodiazepine used to treat certain anxiety and panic disorders.Label Alprazolam acts on benzodiazepine receptors BNZ-1 and BNZ-2.Label,3,2 The active metabolites 4-hydroxyalprazolam acts on these receptors with 0.20 times the potency of alprazolam and alpha-hydroxyalprazolam acts on these receptors with 0.66 times the potency.Label

The effect of alprazolam on BNZ-1 mediates the sedation and anti-anxiety effects of the drug while the action on BNZ-2 mediates effects on memory, coordination, muscle relaxation, and anticonvulsive activity.3,4

Alprazolam also couple with GABA-A receptors to enhance GABA binding to its receptor.3 This interaction mediates inhibition of the nervous system and results in a calming effect.3

The molecular mechanisms as well as the clinical effects of alprazolam have both been well demonstrated, however the means by which the molecular mechanism translates to a clinical effect is still not understood.Label,3,4

TargetActionsOrganism
AGABA(A) Receptor
positive allosteric modulator
Humans
AGABA(A) Receptor Benzodiazepine Binding Site
ligand
Humans
Absorption

Oral bioavailability of a standard release tablet of alprazolam is 84-91% with a time to maximum concentration of 1.8 hours.2 A 1mg oral dose of alprazolam leads to a maximum plasma concentration of 12-22mcg/L.2 Alprazolam is rapidly absorbed in the gastrointestinal tract.2

Data for the area under the curve and the effect of taking alprazolam with food are not readily available.Label

Volume of distribution

Volume of distribution following oral administration is 0.8-1.3L/kg.2 Alprazolam crosses the blood-brain barrier.4

Protein binding

Alprazolam is 80% protein bound in serum.Label The majority of this protein binding is to serum albumin.Label,1 Alprazolam is also bound to alpha1-acid glycoprotein with low frequency.2

Metabolism

Alprazolam is metabolized to less effective metabolites by various CYPs including CYP3A4, CYP3A5, CYP3A7, and CYP2C9.Label,5,6,9 The majority of alprazolam metabolism is mediated by hydroxylation via CYP3As.Label,5,6,2,9 4-hydroxyalprazolam has 20% the binding affinity of the parent drug, alpha-hydroxyalprazolam has 66% the affinity, and the benzophenone metabolite has <1% the affinity.Label,2

Hover over products below to view reaction partners

Route of elimination

Alprazolam is mainly eliminated in the urine.Label A large portion of the dose is eliminated as unmetabolized alprazolam.2 <10% of the dose is eliminated as alpha-hydroxy-alprazolam and 4-hydroxy-alprazolam.2

Half-life

11.2 hours in healthy patients.Label The half life is 16.3h in the elderly, 5.8-65.3h in patients with alcoholic liver disease, 9.9-40.4h in obese patients.Label The half life is 25% higher in Asian patients compared to Caucasians.Label Other studies have shown the half life to be 9-16h.2

Clearance

Oral clearance is 0.90±0.21mL/min/kg but this increases to 2.13±0.54mL/min/kg when given with CYP3A inducers.Label Other studies have demonstrated a clearance of 0.70-1.5mL/min/kg.2

Adverse Effects
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Toxicity

Alprazolam overdose can present as sleepiness, confusion, poor coordination, slow reflexes, coma, and death.Label Taking alprazolam with alcohol lowers the threshold for overdose.Label Patients should have their respiration, pulse, and blood pressure monitored.Label Patients can be treated by gastric lavage and intravenous fluids.Label. If hypotension occurs, patients may be treated with vasopressors.Label In known, or suspected overdoses, patients can be given the benzodiazepine receptor antagonist flumazenil in addition to other methods of management.Label

Oral LD50 in rats is 331-2171mg/kg.Label

Alprazolam is a pregnancy category D teratogen meaning there is evidence of risk to the fetus of a mother taking alprazolam but in some cases the benefit may outweigh the risk.Label,8 Children born to these mothers are also at risk of withdrawal symptoms, flaccidity, and respiratory issues.Label

Benzodiazepines are expressed in human breast milk and so nursing is generally not recommended in mothers taking alprazolam.Label

Alprazolam is not associated with carcinogenicity, mutagenicity, or impairment of fertility.Label

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

Interactions

Drug Interactions
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.
DrugInteraction
AbacavirAlprazolam may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbametapirThe serum concentration of Alprazolam can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Alprazolam can be increased when combined with Abatacept.
AcalabrutinibThe metabolism of Alprazolam can be decreased when combined with Acalabrutinib.
AcarboseAcarbose may decrease the excretion rate of Alprazolam which could result in a higher serum level.
AceclofenacAceclofenac may decrease the excretion rate of Alprazolam which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Alprazolam which could result in a higher serum level.
AcetaminophenThe metabolism of Alprazolam can be decreased when combined with Acetaminophen.
AcetazolamideThe metabolism of Alprazolam can be decreased when combined with Acetazolamide.
AcetophenazineThe risk or severity of adverse effects can be increased when Alprazolam is combined with Acetophenazine.
Additional Data Available
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  • Severity
    Severity
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    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level
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  • Action
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Food Interactions
  • Avoid alcohol. Alcohol may potentiate the CNS depressant effects of this drug.
  • Avoid grapefruit products.
  • Limit caffeine intake.
  • Take with or without food. Food increases the Cmax of extended release alprazolam by 25%, but the AUC and half life are not affected.

Products

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Product Images
International/Other Brands
Alplax / Alprazolan / Alpronax / Alprox / Alviz / Cassadan / Esparon / Ralozam / Restyl / Solanax / Staccato alprazolam (Alexza) / Tafil / Trankimazin / Tranquinal / Xanor
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AlprazolamTablet1 mgOralPro Doc Limitee2004-04-01Not applicableCanada flag
AlprazolamTablet1 mgOralJamp Pharma CorporationNot applicableNot applicableCanada flag
AlprazolamTablet, extended release1 mg/1OralZydus Pharmaceuticals Usa, Inc.2008-10-28Not applicableUS flag
AlprazolamTablet0.50 mgOralSanis Health Inc2010-04-30Not applicableCanada flag
AlprazolamTablet0.5 mgOralJamp Pharma CorporationNot applicableNot applicableCanada flag
AlprazolamTablet, extended release3 mg/1OralZydus Pharmaceuticals Usa, Inc.2008-10-28Not applicableUS flag
AlprazolamTablet0.25 mgOralSanis Health Inc2010-04-30Not applicableCanada flag
AlprazolamTablet, extended release0.5 mg/1OralZydus Pharmaceuticals Usa, Inc.2008-10-28Not applicableUS flag
AlprazolamTablet2 mgOralJamp Pharma CorporationNot applicableNot applicableCanada flag
AlprazolamTablet0.25 mgOralJamp Pharma CorporationNot applicableNot applicableCanada flag
Additional Data Available
  • Application Number
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    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AlprazolamTablet0.5 mg/1OralPD-Rx Pharmaceuticals, Inc.2018-07-09Not applicableUS flag
AlprazolamTablet2 mg/1OralAidarex Pharmaceuticals LLC2007-03-28Not applicableUS flag
AlprazolamTablet0.25 mg/1OralAmerican Health Packaging2019-10-21Not applicableUS flag
AlprazolamTablet2 mg/1OralNucare Pharmaceuticals, Inc.1995-01-032019-12-31US flag
AlprazolamTablet0.5 mg/1OralREMEDYREPACK INC.2007-09-052018-03-14US flag
AlprazolamTablet2 mg/1OralActavis Pharma, Inc.1993-10-01Not applicableUS flag
AlprazolamTablet0.5 mg/1OralPreferred Pharmaceuticals, Inc.1999-12-29Not applicableUS flag
AlprazolamTablet, extended release3 mg/1OralEon Labs, Inc.2006-06-302012-03-31US flag
AlprazolamTablet0.25 mg/1OralMcKesson Corporation dba SKY Packaging1995-12-29Not applicableUS flag
AlprazolamTablet0.25 mg/1OralCardinal Health2009-12-312019-04-30US flag
Additional Data Available
  • Application Number
    Application Number
    Available for Purchase

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code
    Available for Purchase

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Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
GabazolamineAlprazolam (0.25 mg/1) + Choline (125 mg/1)KitOralPhysician Therapeutics Llc2011-07-07Not applicableUS flag
Gabazolamine-0.5Alprazolam (0.5 mg/1) + Choline (125 mg/1)KitOralPhysician Therapeutics Llc2011-07-07Not applicableUS flag
Sentrazolam AMAlprazolam (0.25 mg/1) + Choline (250 mg/1)KitOralPhysician Therapeutics Llc2011-07-07Not applicableUS flag

Categories

ATC Codes
N05BA12 — Alprazolam
Drug Categories
Chemical TaxonomyProvided by Classyfire
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-triazole / 1,2,4-triazolo[4,3-a][1,4]benzodiazepine / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle / Azole / Benzenoid / Heteroaromatic compound / Hydrocarbon derivative
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organochlorine compound, triazolobenzodiazepine (CHEBI:2611)

Chemical Identifiers

UNII
YU55MQ3IZY
CAS number
28981-97-7
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

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. Dangkoob F, Housaindokht MR, Asoodeh A, Rajabi O, Rouhbakhsh Zaeri Z, Verdian Doghaei A: Spectroscopic and molecular modeling study on the separate and simultaneous bindings of alprazolam and fluoxetine hydrochloride to human serum albumin (HSA): with the aim of the drug interactions probing. Spectrochim Acta A Mol Biomol Spectrosc. 2015 Feb 25;137:1106-19. doi: 10.1016/j.saa.2014.08.149. Epub 2014 Oct 7. [PubMed:25300043]
  2. Greenblatt DJ, Wright CE: Clinical pharmacokinetics of alprazolam. Therapeutic implications. Clin Pharmacokinet. 1993 Jun;24(6):453-71. doi: 10.2165/00003088-199324060-00003. [PubMed:8513649]
  3. George TT, Tripp J: Alprazolam . [PubMed:30844192]
  4. 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]
  5. 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]
  6. 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]
  7. FDA Approved Drug Products: Xanax [Link]
  8. FDA Pregnancy Categories [Link]
  9. Flockhart Table of Drug Interactions [Link]
  10. FDA Approved Drug Products: XANAX (Alprazolam) tablets [Link]
Human Metabolome Database
HMDB0014548
KEGG Drug
D00225
KEGG Compound
C06817
PubChem Compound
2118
PubChem Substance
46507078
ChemSpider
2034
BindingDB
50001728
RxNav
596
ChEBI
2611
ChEMBL
CHEMBL661
ZINC
ZINC000000000903
Therapeutic Targets Database
DAP000239
PharmGKB
PA448333
PDBe Ligand
08H
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Alprazolam
AHFS Codes
  • 28:24.08 — Benzodiazepines
PDB Entries
3u5j / 6huo
FDA label
Download (381 KB)
MSDS
Download (47.3 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedBasic ScienceDriving Behavior1
4CompletedBasic ScienceHealthy Volunteers1
4CompletedDiagnosticAnxiety Disorders1
4CompletedOtherPsychomotor Impairment1
4CompletedTreatmentAnxiety2
4CompletedTreatmentGeneralized Anxiety Disorder (GAD)1
4CompletedTreatmentGeneralized Anxiety Disorder (GAD) / Panic Disorders1
4CompletedTreatmentInferior Alveolar Nerve Block Failure1
4CompletedTreatmentPanic Disorders2
4Not Yet RecruitingTreatmentAgitation on Recovery From Sedation1

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
Tablet
Tablet250 mcg
Solution, concentrateOral1 mg/1mL
TabletOral.25 mg/1
TabletOral.5 mg/1
TabletOral0.25 mg/1
TabletOral0.5 mg/1
TabletOral1 mg/1
TabletOral1.00 mg/1
TabletOral2 mg
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
Tablet0.5 MG
Tablet1 MG
Tablet0.25 MG
Solution / dropsOral0.75 MG/ML
Tablet0.50 MG
Tablet1.0 MG
Tablet500 mcg
Tablet, orally disintegratingOral0.25 mg/1
Tablet, orally disintegratingOral0.5 mg/1
Tablet, orally disintegratingOral1 mg/1
Tablet, orally disintegratingOral2 mg/1
Tablet, coatedOral1 mg
Tablet, coatedOral250 mcg
Tablet, coatedOral500 mcg
KitOral
TabletOral
TabletOral0.50 MG
TabletOral250 mcg
TabletOral500 mcg
Tablet, extended releaseOral0.5 MG
Tablet, extended releaseOral1 MG
Tablet, extended releaseOral2 MG
Tablet, extended releaseOral3 MG
TabletOral0.5 mg
TabletOral1 mg
SolutionOral0.75 mg
TabletOral0.25 mg
TabletSublingual
Tablet, extended releaseOral
Tablet, extended releaseOral500 mcg
TabletSublingual1 mg
TabletSublingual0.5 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)Region
US6221392No2001-04-242018-04-09US flag
US6024981No2000-02-152018-04-09US flag
Additional Data Available
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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.
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

Targets

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:
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]
  3. 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. [PubMed:29950725]
  4. 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. [PubMed:23038269]
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:
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. [PubMed:23038269]
  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. [PubMed:29950725]

Enzymes

Kind
Protein
Organism
Humans
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. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
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. 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]
  3. Flockhart Table of Drug Interactions [Link]
  4. FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
  5. FDA Approved Drug Products: XANAX (Alprazolam) tablets [Link]
Kind
Protein
Organism
Humans
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
Humans
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. Allqvist A, Miura J, Bertilsson L, Mirghani RA: Inhibition of CYP3A4 and CYP3A5 catalyzed metabolism of alprazolam and quinine by ketoconazole as racemate and four different enantiomers. Eur J Clin Pharmacol. 2007 Feb;63(2):173-9. doi: 10.1007/s00228-006-0230-z. Epub 2007 Jan 3. [PubMed:17200836]
  2. Park JY, Kim KA, Park PW, Lee OJ, Kang DK, Shon JH, Liu KH, Shin JG: Effect of CYP3A5*3 genotype on the pharmacokinetics and pharmacodynamics of alprazolam in healthy subjects. Clin Pharmacol Ther. 2006 Jun;79(6):590-9. doi: 10.1016/j.clpt.2006.02.008. [PubMed:16765147]
  3. Hirota N, Ito K, Iwatsubo T, Green CE, Tyson CA, Shimada N, Suzuki H, Sugiyama Y: In vitro/in vivo scaling of alprazolam metabolism by CYP3A4 and CYP3A5 in humans. Biopharm Drug Dispos. 2001 Mar;22(2):53-71. [PubMed:11745908]
  4. Flockhart Table of Drug Interactions [Link]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Dangkoob F, Housaindokht MR, Asoodeh A, Rajabi O, Rouhbakhsh Zaeri Z, Verdian Doghaei A: Spectroscopic and molecular modeling study on the separate and simultaneous bindings of alprazolam and fluoxetine hydrochloride to human serum albumin (HSA): with the aim of the drug interactions probing. Spectrochim Acta A Mol Biomol Spectrosc. 2015 Feb 25;137:1106-19. doi: 10.1016/j.saa.2014.08.149. Epub 2014 Oct 7. [PubMed:25300043]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Not Available
Specific Function
Functions as transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in...

Components:
References
  1. Greenblatt DJ, Wright CE: Clinical pharmacokinetics of alprazolam. Therapeutic implications. Clin Pharmacokinet. 1993 Jun;24(6):453-71. doi: 10.2165/00003088-199324060-00003. [PubMed:8513649]

Drug created on June 13, 2005 07:24 / Updated on December 02, 2020 10:11

Ddi 4