Alprazolam
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
Structure for Alprazolam (DB00404)
- 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
Accelerate your drug discovery research with the industry’s only fully connected ADMET dataset, ideal for:Accelerate your drug discovery research with our fully connected ADMET dataset- 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
Contraindications & Blackbox WarningsWith our commercial data, access important information on dangerous risks, contraindications, and adverse effects.Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects- 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
Target Actions Organism AGABA(A) Receptor positive allosteric modulatorHumans AGABA(A) Receptor Benzodiazepine Binding Site ligandHumans - 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
Reduce medical errorsand improve treatment outcomes with our comprehensive & structured data on drug adverse effects.Reduce medical errors & improve treatment outcomes with our adverse effects data- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Alprazolam may decrease the excretion rate of Abacavir which could result in a higher serum level. Abametapir The serum concentration of Alprazolam can be increased when it is combined with Abametapir. Abatacept The metabolism of Alprazolam can be increased when combined with Abatacept. Abiraterone The metabolism of Alprazolam can be decreased when combined with Abiraterone. Acalabrutinib The metabolism of Alprazolam can be decreased when combined with Acalabrutinib. Aceclofenac Aceclofenac may decrease the excretion rate of Alprazolam which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Alprazolam which could result in a higher serum level. Acetaminophen The metabolism of Alprazolam can be decreased when combined with Acetaminophen. Acetazolamide The metabolism of Alprazolam can be decreased when combined with Acetazolamide. Acetophenazine The risk or severity of adverse effects can be increased when Alprazolam is combined with Acetophenazine. 
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- 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
Comprehensive & structured drug product infoFrom application numbers to product codes, connect different identifiers through our commercial datasets.Easily connect various identifiers back to our datasets- 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
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Alprazolam Tablet, extended release 3 mg/1 Oral Zydus Pharmaceuticals Usa, Inc. 2008-10-28 Not applicable US 
Alprazolam Tablet 2 mg Oral Jamp Pharma Corporation Not applicable Not applicable Canada 
Alprazolam Tablet, extended release 0.5 mg/1 Oral Zydus Pharmaceuticals Usa, Inc. 2008-10-28 Not applicable US Alprazolam Tablet 0.25 mg Oral Jamp Pharma Corporation Not applicable Not applicable Canada Alprazolam Tablet 1 mg Oral Pro Doc Limitee 2004-04-01 Not applicable Canada Alprazolam Tablet, extended release 2 mg/1 Oral Zydus Pharmaceuticals Usa, Inc. 2008-10-28 Not applicable US Alprazolam Tablet 1 mg Oral Jamp Pharma Corporation Not applicable Not applicable Canada Alprazolam Tablet 0.50 mg Oral Sanis Health Inc 2010-04-30 Not applicable Canada Alprazolam Tablet, extended release 1 mg/1 Oral Zydus Pharmaceuticals Usa, Inc. 2008-10-28 Not applicable US Alprazolam Tablet 0.5 mg Oral Jamp Pharma Corporation Not applicable Not applicable Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Alprazolam Tablet 0.25 mg/1 Oral Aphena Pharma Solutions - Tennessee, LLC 1993-10-01 Not applicable US Alprazolam Tablet 1 mg/1 Oral Golden State Medical Supply Inc 2007-03-28 2022-06-30 US Alprazolam Tablet 0.5 mg/1 Oral Nucare Pharmaceuticals, Inc. 1995-12-29 Not applicable US Alprazolam Tablet, extended release 0.5 mg/1 Oral Physicians Total Care, Inc. 2009-06-01 2011-06-30 US Alprazolam Tablet 0.25 mg/1 Oral Nucare Pharmaceuticals,inc. 2007-03-28 Not applicable US Alprazolam Tablet, extended release 1 mg/1 Oral Apotex Corp 2008-11-12 2008-11-13 US Alprazolam Tablet 1 mg/1 Oral A-S Medication Solutions 1995-12-29 2018-06-30 US Alprazolam Tablet 0.5 mg/1 Oral Qualitest 2008-09-25 2016-12-31 US 
Alprazolam Tablet 0.5 mg/1 Oral Boca Pharmacal, Inc. 2010-10-15 2017-02-28 US Alprazolam Tablet 0.25 mg/1 Oral Vintage Pharmaceuticals 2008-09-25 2009-08-19 US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Gabazolamine Alprazolam (0.25 mg/1) + Choline (125 mg/1) Kit Oral Physician Therapeutics Llc 2011-07-07 Not applicable US Gabazolamine-0.5 Alprazolam (0.5 mg/1) + Choline (125 mg/1) Kit Oral Physician Therapeutics Llc 2011-07-07 Not applicable US Sentrazolam AM Alprazolam (0.25 mg/1) + Choline (250 mg/1) Kit Oral Physician Therapeutics Llc 2011-07-07 Not applicable US
Categories
- ATC Codes
- N05BA12 — Alprazolam
- Drug Categories
- Alcohols
- Amines
- Amino Alcohols
- Anti-Anxiety Agents
- Benzazepines
- Benzene Derivatives
- Benzodiazepines and benzodiazepine derivatives
- Biogenic Amines
- Biogenic Monoamines
- Catechols
- Central Nervous System Agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP2C9 Substrates
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 CYP3A5 Substrates
- Cytochrome P-450 CYP3A7 Substrates
- Cytochrome P-450 Substrates
- Drugs that are Mainly Renally Excreted
- Ethanolamines
- GABA Agents
- GABA Modulators
- Heterocyclic Compounds, Fused-Ring
- Hypnotics and Sedatives
- Nervous System
- Neurotransmitter Agents
- Phenols
- Psycholeptics
- Psychotropic Drugs
- Tranquilizing Agents
- Triazolobenzodiazepines
- 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
- 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]
- 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]
- George TT, Tripp J: Alprazolam . [PubMed:30844192]
- 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]
- 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]
- 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]
- FDA Approved Drug Products: Xanax [Link]
- FDA Pregnancy Categories [Link]
- Flockhart Table of Drug Interactions [Link]
- FDA Approved Drug Products: XANAX (Alprazolam) tablets [Link]
- External Links
- Human Metabolome Database
- HMDB0014548
- KEGG Drug
- D00225
- KEGG Compound
- C06817
- PubChem Compound
- 2118
- PubChem Substance
- 46507078
- ChemSpider
- 2034
- BindingDB
- 50001728
- 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
Phase Status Purpose Conditions Count 4 Completed Basic Science Driving Behavior 1 4 Completed Basic Science Healthy Volunteers 1 4 Completed Diagnostic Anxiety Disorders 1 4 Completed Other Psychomotor Impairment 1 4 Completed Treatment Anxiety 2 4 Completed Treatment Generalized Anxiety Disorder (GAD) 1 4 Completed Treatment Generalized Anxiety Disorder (GAD) / Panic Disorder 1 4 Completed Treatment Inferior Alveolar Nerve Block Failure 1 4 Completed Treatment Panic Disorder 2 4 Not Yet Recruiting Treatment Agitation on Recovery From Sedation 1
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
Form Route Strength Tablet Sublingual Tablet Solution, concentrate Oral 1 mg/1mL Tablet Oral .25 mg/1 Tablet Oral .5 mg/1 Tablet Oral 0.25 mg Tablet Oral 0.25 mg/1 Tablet Oral 0.5 mg/1 Tablet Oral 0.50 mg Tablet Oral 1 mg/1 Tablet Oral 1.00 mg/1 Tablet Oral 2 mg Tablet Oral 2 mg/1 Tablet Oral 2.00 mg/1 Tablet, extended release Oral 0.5 mg/1 Tablet, extended release Oral 1 mg/1 Tablet, extended release Oral 2 mg/1 Tablet, extended release Oral 3 mg/1 Tablet, extended release Oral Solution / drops Oral Tablet Oral Tablet 1 mg Tablet, orally disintegrating Oral 0.25 mg/1 Tablet, orally disintegrating Oral 0.5 mg/1 Tablet, orally disintegrating Oral 1 mg/1 Tablet, orally disintegrating Oral 2 mg/1 Kit Oral Capsule Tablet Oral 0.5 mg Tablet Oral 1 mg Solution Oral Tablet Sublingual 1 mg Tablet Sublingual 0.5 mg - Prices
Unit description Cost Unit ALPRAZolam Intensol 1 mg/ml Concentrate 30ml Bottle 67.03USD bottle Niravam 2 mg Dispersible Tablet 8.53USD dispersible tablet Xanax xr 3 mg tablet 7.25USD tablet Xanax XR 3 mg 24 Hour tablet 7.1USD tablet Niravam 2 mg tablet 6.86USD tablet Niravam 1 mg Dispersible Tablet 5.42USD dispersible tablet Xanax xr 2 mg tablet 4.84USD tablet Xanax XR 2 mg 24 Hour tablet 4.73USD tablet Niravam 0.5 mg Dispersible Tablet 4.2USD dispersible tablet Niravam 1 mg tablet 4.04USD tablet Xanax 2 mg tablet 3.82USD tablet ALPRAZolam 3 mg 24 Hour tablet 3.67USD tablet Xanax XR 1 mg 24 Hour tablet 3.64USD tablet Xanax xr 1 mg tablet 3.64USD tablet Niravam 0.25 mg Dispersible Tablet 3.45USD dispersible tablet Niravam 0.5 mg tablet 3.02USD tablet Xanax XR 0.5 mg 24 Hour tablet 3.01USD tablet Xanax xr 0.5 mg tablet 2.93USD tablet ALPRAZolam 2 mg 24 Hour tablet 2.53USD tablet Niravam 0.25 mg tablet 2.43USD tablet ALPRAZolam 1 mg 24 Hour tablet 2.33USD tablet Xanax 1 mg tablet 2.29USD tablet Alprazolam 1 mg/ml oral conc 2.23USD ml Xanax 0.5 mg tablet 1.3USD tablet Alprazolam 2 mg tablet 1.22USD tablet Xanax 0.25 mg tablet 1.09USD tablet ALPRAZolam 0.5 mg 24 Hour tablet 1.07USD tablet Alprazolam 1 mg tablet 0.78USD tablet Alprazolam 0.5 mg tablet 0.67USD tablet Alprazolam 0.25 mg tablet 0.55USD tablet Apo-Alpraz 0.5 mg Tablet 0.1USD tablet Mylan-Alprazolam 0.5 mg Tablet 0.1USD tablet Novo-Alprazol 0.5 mg Tablet 0.1USD tablet Apo-Alpraz 0.25 mg Tablet 0.08USD tablet Mylan-Alprazolam 0.25 mg Tablet 0.08USD tablet Novo-Alprazol 0.25 mg Tablet 0.08USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US6221392 No 2001-04-24 2018-04-09 US US6024981 No 2000-02-15 2018-04-09 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 228-229.5 °C Hester, 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
Property Value Source Water Solubility 0.0324 mg/mL ALOGPS logP 2.23 ALOGPS logP 2.37 ChemAxon logS -4 ALOGPS pKa (Strongest Acidic) 18.3 ChemAxon pKa (Strongest Basic) 5.08 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 3 ChemAxon Hydrogen Donor Count 0 ChemAxon Polar Surface Area 43.07 Å2 ChemAxon Rotatable Bond Count 1 ChemAxon Refractivity 98.88 m3·mol-1 ChemAxon Polarizability 32.22 Å3 ChemAxon Number of Rings 4 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9794 Caco-2 permeable + 0.8867 P-glycoprotein substrate Non-substrate 0.5099 P-glycoprotein inhibitor I Non-inhibitor 0.7301 P-glycoprotein inhibitor II Inhibitor 0.8354 Renal organic cation transporter Inhibitor 0.7688 CYP450 2C9 substrate Non-substrate 0.7907 CYP450 2D6 substrate Non-substrate 0.9164 CYP450 3A4 substrate Substrate 0.7353 CYP450 1A2 substrate Inhibitor 0.8758 CYP450 2C9 inhibitor Inhibitor 0.8076 CYP450 2D6 inhibitor Non-inhibitor 0.8137 CYP450 2C19 inhibitor Inhibitor 0.6519 CYP450 3A4 inhibitor Non-inhibitor 0.6308 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.8913 Ames test Non AMES toxic 0.8957 Carcinogenicity Non-carcinogens 0.6779 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.3717 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.973 hERG inhibition (predictor II) Non-inhibitor 0.8733
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Mass Spectrum (Electron Ionization) MS splash10-0kdi-4792000000-9f1cdda14e36000955d3 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available LC-MS/MS Spectrum - LC-ESI-qTof , Positive LC-MS/MS Not Available LC-MS/MS Spectrum - LC-ESI-QTOF , positive LC-MS/MS splash10-0a59-0079000000-e4c35fb4df41aa5cc62e MS/MS Spectrum - , positive LC-MS/MS splash10-0bt9-0169000000-0e6779728f3bdec2acf1 MS/MS Spectrum - , positive LC-MS/MS splash10-0a4i-0910000000-9efa6a8a3dea17fc1ce7
Targets
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- 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
- 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]
- 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]
- 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]
- 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
- 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]
- 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
- 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
- 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]
- 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]
- Flockhart Table of Drug Interactions [Link]
- FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
- 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
- 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
- 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]
- 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]
- 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]
- 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
- 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
- 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 13:24 / Updated on April 13, 2021 00:29