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

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Alprazolam (DB00404)

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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

• Anxiety
• Generalized Anxiety Disorder (GAD)
• Panic Disorders

Contraindications & Blackbox Warnings

Learn about our commercial Contraindications & Blackbox Warnings data.

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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 GABA^3,4.

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 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

• Alprazolam
  • alpha-Hydroxyalprazolam
    • alpha,4-dihydroxy-alprazolam
  • 4-hydroxyalprazolam
    • Alprazolam benzophenone metabolite
    • alpha,4-dihydroxy-alprazolam
  • Beta-Hydroxyalprazolam

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

Learn about our commercial Adverse Effects data.

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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.

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• Withdrawn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

Drug	Interaction
Unlock Additional Data
Abacavir	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.
Acalabrutinib	The metabolism of Alprazolam can be decreased when combined with Acalabrutinib.
Acarbose	Acarbose may decrease the excretion rate of Alprazolam which could result in a higher serum level.
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.

Additional Data Available

Extended Description
Extended Description
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Extended description of the mechanism of action and particular properties of each drug interaction.
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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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A rating for the strength of the evidence supporting each drug interaction.
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Action
Action
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An effect category for each drug interaction. Know how this interaction affects the subject drug.
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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

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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
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Alprazolam	Tablet	0.50 mg	Oral	Sanis Health Inc	2010-04-30	Not applicable
Alprazolam	Tablet, extended release	1 mg/1	Oral	Zydus Pharmaceuticals Usa, Inc.	2008-10-28	Not applicable
Alprazolam	Tablet	0.5 mg	Oral	Jamp Pharma Corporation	Not applicable	Not applicable
Alprazolam	Tablet, extended release	3 mg/1	Oral	Zydus Pharmaceuticals Usa, Inc.	2008-10-28	Not applicable
Alprazolam	Tablet	0.25 mg	Oral	Sanis Health Inc	2010-04-30	Not applicable
Alprazolam	Tablet, extended release	0.5 mg/1	Oral	Zydus Pharmaceuticals Usa, Inc.	2008-10-28	Not applicable
Alprazolam	Tablet	2 mg	Oral	Jamp Pharma Corporation	Not applicable	Not applicable
Alprazolam	Tablet	0.25 mg	Oral	Jamp Pharma Corporation	Not applicable	Not applicable
Alprazolam	Tablet	1 mg	Oral	Pro Doc Limitee	2004-04-01	Not applicable
Alprazolam	Tablet, extended release	2 mg/1	Oral	Zydus Pharmaceuticals Usa, Inc.	2008-10-28	Not applicable

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
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
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Alprazolam	Tablet	0.25 mg/1	Oral	Nucare Pharmaceuticals,inc.	2007-03-28	Not applicable
Alprazolam	Tablet, extended release	1 mg/1	Oral	Preferred Pharmaceuticals, Inc.	2012-11-15	2019-05-08
Alprazolam	Tablet, extended release	0.5 mg/1	Oral	Teva	2007-06-04	2009-02-28
Alprazolam	Tablet	1.00 mg/1	Oral	Boca Pharmacal, Inc.	2010-10-15	2017-02-28
Alprazolam	Tablet	0.5 mg/1	Oral	bryant ranch prepack	1993-10-01	Not applicable
Alprazolam	Tablet	0.25 mg/1	Oral	PD-Rx Pharmaceuticals, Inc.	2007-03-28	Not applicable
Alprazolam	Tablet, extended release	0.5 mg/1	Oral	bryant ranch prepack	2011-06-07	Not applicable
Alprazolam	Tablet	0.5 mg/1	Oral	American Health Packaging	2019-05-01	Not applicable
Alprazolam	Tablet	0.25 mg/1	Oral	PD-Rx Pharmaceuticals, Inc.	1981-10-16	Not applicable
Alprazolam	Tablet	2 mg/1	Oral	Physicians Total Care, Inc.	2009-09-16	Not applicable

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
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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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
Gabazolamine-0.5	Alprazolam (0.5 mg/1) + Choline (125 mg/1)	Kit	Oral	Physician Therapeutics Llc	2011-07-07	Not applicable
Sentrazolam AM	Alprazolam (0.25 mg/1) + Choline (250 mg/1)	Kit	Oral	Physician Therapeutics Llc	2011-07-07	Not applicable

Categories

ATC Codes

N05BA12 — Alprazolam

• N05BA — Benzodiazepine derivatives
• N05B — ANXIOLYTICS
• N05 — PSYCHOLEPTICS
• N — NERVOUS SYSTEM

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

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]

External Links

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

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 Disorders	1
4	Completed	Treatment	Inferior Alveolar Nerve Block Failure	1
4	Completed	Treatment	Panic Disorders	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
Tablet		250 mcg
Solution, concentrate	Oral	1 mg/1mL
Tablet	Oral	.25 mg/1
Tablet	Oral	.5 mg/1
Tablet	Oral	0.25 mg/1
Tablet	Oral	0.5 mg/1
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		0.5 MG
Tablet		1 MG
Tablet		0.25 MG
Solution / drops	Oral	0.75 MG/ML
Tablet		0.50 MG
Tablet		1.0 MG
Tablet		500 mcg
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
Tablet, coated	Oral	1 mg
Tablet, coated	Oral	250 mcg
Tablet, coated	Oral	500 mcg
Kit	Oral
Tablet	Oral
Tablet	Oral	0.50 MG
Tablet	Oral	250 mcg
Tablet	Oral	500 mcg
Tablet, extended release	Oral	0.5 MG
Tablet, extended release	Oral	1 MG
Tablet, extended release	Oral	2 MG
Tablet, extended release	Oral	3 MG
Tablet	Oral	0.5 mg
Tablet	Oral	1 mg
Solution	Oral	0.75 mg
Tablet	Oral	0.25 mg
Tablet	Sublingual
Tablet, extended release	Oral
Tablet, extended release	Oral	500 mcg
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
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US6221392	No	2001-04-24	2018-04-09
US6024981	No	2000-02-15	2018-04-09

Additional Data Available

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Filed On
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The date on which a patent was filed with the relevant government.
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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

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

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	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

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Drug created on June 13, 2005 07:24 / Updated on November 30, 2020 13:38