Identification

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Name
Alprazolam
Accession Number
DB00404  (APRD00280, DB05925, DB05690)
Type
Small Molecule
Groups
Approved, Illicit, Investigational
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.

Structure
Thumb
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
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AlprazolamTablet1 mgOralPro Doc Limitee2004-04-01Not applicableCanada
AlprazolamTablet2 mgOralJamp Pharma CorporationNot applicableNot applicableCanada
AlprazolamTablet, extended release3 mg/1OralZydus Pharmaceuticals Usa, Inc.2008-10-28Not applicableUs
AlprazolamTablet1 mgOralJamp Pharma CorporationNot applicableNot applicableCanada
AlprazolamTablet, extended release2 mg/1OralZydus Pharmaceuticals Usa, Inc.2008-10-28Not applicableUs
AlprazolamTablet0.5 mgOralJamp Pharma CorporationNot applicableNot applicableCanada
AlprazolamTablet0.50 mgOralSanis Health Inc2010-04-30Not applicableCanada
AlprazolamTablet, extended release1 mg/1OralZydus Pharmaceuticals Usa, Inc.2008-10-28Not applicableUs
AlprazolamTablet0.25 mgOralJamp Pharma CorporationNot applicableNot applicableCanada
AlprazolamTablet0.25 mgOralSanis Health Inc2010-04-30Not applicableCanada
Additional Data Available
  • Application Number
    Application Number

    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

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

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AlprazolamTablet0.5 mg/1OralRemedy Repack2007-09-052018-10-19Us
AlprazolamTablet1 mg/1OralGreenstone, Llc1981-10-16Not applicableUs
AlprazolamTablet, orally disintegrating0.25 mg/1OralPreferreed Pharmaceuticals Inc.2010-03-162017-04-19Us
AlprazolamTablet1 mg/1OralContract Pharmacy Services Pa2007-03-28Not applicableUs
AlprazolamTablet0.25 mg/1OralAurobindo Pharma2015-07-31Not applicableUs
AlprazolamTablet0.25 mg/1OralAphena Pharma Solutions - Tennessee, LLC1993-10-01Not applicableUs
AlprazolamTablet0.25 mg/1OralActavis Pharma, Inc.1993-10-01Not applicableUs
AlprazolamTablet1 mg/1OralBionpharma Inc.2015-10-012019-03-31Us
AlprazolamTablet0.5 mg/1OralMc Kesson Packaging Services A Buisness Unit Of Mc Kesson Corporation2007-08-302011-10-31Us
AlprazolamTablet0.5 mg/1OralNucare Pharmaceuticals,inc.2007-03-28Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    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

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

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Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
GabazolamineAlprazolam (0.25 mg/1) + Choline (125 mg/1)KitOralPhysician Therapeutics Llc2011-07-07Not applicableUs
Gabazolamine-0.5Alprazolam (0.5 mg/1) + Choline (125 mg/1)KitOralPhysician Therapeutics Llc2011-07-07Not applicableUs
Sentrazolam AMAlprazolam (0.25 mg/1) + Choline (250 mg/1)KitOralPhysician Therapeutics Llc2011-07-07Not applicableUs
International/Other Brands
Alplax / Alprazolan / Alpronax / Alprox / Alviz / Cassadan / Esparon / Ralozam / Restyl / Solanax / Staccato alprazolam (Alexza) / Tafil / Trankimazin / Tranquinal / Xanor
Categories
UNII
YU55MQ3IZY
CAS number
28981-97-7
Weight
Average: 308.765
Monoisotopic: 308.082874143
Chemical Formula
C17H13ClN4
InChI Key
VREFGVBLTWBCJP-UHFFFAOYSA-N
InChI
InChI=1S/C17H13ClN4/c1-11-20-21-16-10-19-17(12-5-3-2-4-6-12)14-9-13(18)7-8-15(14)22(11)16/h2-9H,10H2,1H3
IUPAC Name
12-chloro-3-methyl-9-phenyl-2,4,5,8-tetraazatricyclo[8.4.0.0²,⁶]tetradeca-1(10),3,5,8,11,13-hexaene
SMILES
CC1=NN=C2CN=C(C3=CC=CC=C3)C3=C(C=CC(Cl)=C3)N12

Pharmacology

Indication

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
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
UGamma-aminobutyric acid receptor subunit alpha-1Not AvailableHumans
UGamma-aminobutyric acid receptor subunit alpha-6Not AvailableHumans
UTranslocator proteinNot AvailableHumans
AGABA-A receptor (anion channel)
positive allosteric modulator
Humans
UGamma-aminobutyric acid receptor subunit alpha-3Not AvailableHumans
UGamma-aminobutyric acid receptor subunit alpha-4Not AvailableHumans
UGamma-aminobutyric acid receptor subunit alpha-5Not AvailableHumans
UGamma-aminobutyric acid receptor subunit alpha-2Not AvailableHumans
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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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

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

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
DrugInteraction
(R)-warfarinThe metabolism of Alprazolam can be decreased when combined with (R)-warfarin.
(S)-WarfarinThe metabolism of Alprazolam can be decreased when combined with (S)-Warfarin.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when Alprazolam is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3-isobutyl-1-methyl-7H-xanthineThe therapeutic efficacy of Alprazolam can be decreased when used in combination with 3-isobutyl-1-methyl-7H-xanthine.
3,5-diiodothyropropionic acidThe metabolism of Alprazolam can be decreased when combined with 3,5-diiodothyropropionic acid.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when Alprazolam is combined with 4-Bromo-2,5-dimethoxyamphetamine.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Alprazolam.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when Alprazolam is combined with 4-Methoxyamphetamine.
5-androstenedioneThe metabolism of Alprazolam can be decreased when combined with 5-androstenedione.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of adverse effects can be increased when Alprazolam is combined with 5-methoxy-N,N-dimethyltryptamine.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
  • Avoid alcohol.
  • Avoid excessive quantities of coffee or tea (Caffeine).
  • Avoid taking with grapefruit juice.
  • Take with food.

References

Synthesis Reference

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

General References
  1. 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. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
External Links
Human Metabolome Database
HMDB0014548
KEGG Drug
D00225
KEGG Compound
C06817
PubChem Compound
2118
PubChem Substance
46507078
ChemSpider
2034
BindingDB
50001728
ChEBI
2611
ChEMBL
CHEMBL661
Therapeutic Targets Database
DAP000239
PharmGKB
PA448333
HET
08H
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Alprazolam
ATC Codes
N05BA12 — Alprazolam
AHFS Codes
  • 28:24.08 — Benzodiazepines
PDB Entries
3u5j / 6huo
FDA label
Download (381 KB)
MSDS
Download (47.3 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedTreatmentType 1 Insulin-Dependent Diabetes Mellitus1
0Unknown StatusBasic SciencePsychotropic Drugs Effects1
1CompletedNot AvailableAlzheimer's Disease (AD) / Huntington's Disease (HD)1
1CompletedNot AvailableHealthy Volunteers10
1CompletedNot AvailablePharmacokinetics1
1CompletedBasic ScienceAnxiety Disorders1
1CompletedBasic ScienceHealthy Volunteers6
1CompletedBasic SciencePrescription Drug Abuse (Not Dependent) / Recreational Drug Use1
1CompletedDiagnosticCannabis Use Disorders1
1CompletedDiagnosticDepressive Disorder and Anxiety Disorders / Healthy Volunteers1
1CompletedOtherAnxiety Disorders3
1CompletedOtherDriving Performance1
1CompletedOtherMigraine1
1CompletedPreventionPost-Operative Delirium1
1CompletedTreatmentAbuse Liability of Staccato Alprazolam1
1CompletedTreatmentAnxiety2
1CompletedTreatmentSocial Anxiety Disorder (SAD) / Social Phobia1
1RecruitingOtherFood-Drug Interactions1
1TerminatedTreatmentHealthy Volunteers1
1WithdrawnBasic ScienceHealthy Volunteers2
2CompletedTreatmentAnxiety Disorders / Panic Disorders1
2CompletedTreatmentDental Anxiety1
2CompletedTreatmentEpilepsies1
2CompletedTreatmentGeneralized Anxiety Disorder (GAD)1
2RecruitingTreatmentEpilepsies1
2RecruitingTreatmentGeneralized Anxiety Disorder (GAD)1
2, 3CompletedPreventionDiagnostic Esophagogastroduodenoscopy1
2, 3CompletedTreatmentPost Traumatic Stress Disorder (PTSD)1
3TerminatedTreatmentAnxiety Disorders / Dementias / Depression / Psychosomatic Disorders / Schizophrenic Disorders1
4CompletedBasic ScienceDriving Behavior1
4CompletedBasic ScienceHealthy Volunteers1
4CompletedDiagnosticAnxiety Disorders1
4CompletedOtherPsychomotor Impairment1
4CompletedTreatmentAnxiety2
4CompletedTreatmentGeneralized Anxiety Disorder (GAD)1
4CompletedTreatmentGeneralized Anxiety Disorder (GAD) / Panic Disorders1
4CompletedTreatmentInferior Alveolar Nerve Block Failure1
4CompletedTreatmentPanic Disorders2
4Not Yet RecruitingTreatmentAnxiety Disease / Gynecologic Diseases1
4TerminatedTreatmentPanic Disorders3
4WithdrawnTreatmentAnxiety Disorders1
Not AvailableCompletedNot AvailableType 1 Insulin-Dependent Diabetes Mellitus1
Not AvailableCompletedBasic ScienceAOD Effects and Consequences1
Not AvailableNot Yet RecruitingTreatmentCoronary Angiography / Sedative Premedication1

Pharmacoeconomics

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

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

    Learn more

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

Taxonomy

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

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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...
Gene Name
GABRA1
Uniprot ID
P14867
Uniprot Name
Gamma-aminobutyric acid receptor subunit alpha-1
Molecular Weight
51801.395 Da
References
  1. 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]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Inhibitory extracellular ligand-gated ion channel activity
Specific Function
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name
GABRA6
Uniprot ID
Q16445
Uniprot Name
Gamma-aminobutyric acid receptor subunit alpha-6
Molecular Weight
51023.69 Da
References
  1. 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]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Cholesterol binding
Specific Function
Can bind protoporphyrin IX and may play a role in the transport of porphyrins and heme (By similarity). Promotes the transport of cholesterol across mitochondrial membranes and may play a role in l...
Gene Name
TSPO
Uniprot ID
P30536
Uniprot Name
Translocator protein
Molecular Weight
18827.81 Da
References
  1. 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]
Kind
Protein group
Organism
Humans
Pharmacological action
Yes
Actions
Positive allosteric modulator
General Function
Inhibitory extracellular ligand-gated ion channel activity
Specific Function
Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...

Components:
References
  1. Riss J, Cloyd J, Gates J, Collins S: Benzodiazepines in epilepsy: pharmacology and pharmacokinetics. Acta Neurol Scand. 2008 Aug;118(2):69-86. doi: 10.1111/j.1600-0404.2008.01004.x. Epub 2008 Mar 31. [PubMed:18384456]
  2. Verster JC, Volkerts ER: Clinical pharmacology, clinical efficacy, and behavioral toxicity of alprazolam: a review of the literature. CNS Drug Rev. 2004 Spring;10(1):45-76. [PubMed:14978513]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Inhibitory extracellular ligand-gated ion channel activity
Specific Function
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name
GABRA3
Uniprot ID
P34903
Uniprot Name
Gamma-aminobutyric acid receptor subunit alpha-3
Molecular Weight
55164.055 Da
References
  1. 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]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Inhibitory extracellular ligand-gated ion channel activity
Specific Function
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name
GABRA4
Uniprot ID
P48169
Uniprot Name
Gamma-aminobutyric acid receptor subunit alpha-4
Molecular Weight
61622.645 Da
References
  1. 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]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Transporter activity
Specific Function
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name
GABRA5
Uniprot ID
P31644
Uniprot Name
Gamma-aminobutyric acid receptor subunit alpha-5
Molecular Weight
52145.645 Da
References
  1. 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]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Inhibitory extracellular ligand-gated ion channel activity
Specific Function
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name
GABRA2
Uniprot ID
P47869
Uniprot Name
Gamma-aminobutyric acid receptor subunit alpha-2
Molecular Weight
51325.85 Da
References
  1. Verster JC, Volkerts ER: Clinical pharmacology, clinical efficacy, and behavioral toxicity of alprazolam: a review of the literature. CNS Drug Rev. 2004 Spring;10(1):45-76. [PubMed:14978513]

Enzymes

Kind
Protein
Organism
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  3. Williams JA, Ring BJ, Cantrell VE, Jones DR, Eckstein J, Ruterbories K, Hamman MA, Hall SD, Wrighton SA: Comparative metabolic capabilities of CYP3A4, CYP3A5, and CYP3A7. Drug Metab Dispos. 2002 Aug;30(8):883-91. [PubMed:12124305]
  4. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
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. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
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. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  3. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
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]

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 August 24, 2019 06:28