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Alprazolam

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Also known as Alprazolam civNiravamNSC-760140U 31,889U-31,889U-31889XanaxXanax xrSID26719699SID29215419SID144205245C0164731

Summary

Alprazolam (CHEMBL661) is an approved small-molecule anxiolytic drug (ATC N05BA12) targeting GABRA1, GABRA2, and GABRA3; indicated across 16 conditions including panic disorder and anxiety.

At a glance

  • Status: Approved (max clinical phase 4)
  • Modality: Small molecule
  • ATC class: N05BA12
  • Targets: 4 (GABRA1, GABRA2, GABRA3…)
  • Indications: 16 conditions
  • Clinical trials: 67
  • Chemistry: 308.8 Da · C17H13ClN4

Identifiers

Drug identity and classification

FieldValue
ChEMBL IDCHEMBL661
NameAlprazolam
TypeSmall molecule
Max phase4
FDA approvedyes
PubChem CID2118
ChEBICHEBI:2611
ATCN05BA12
Molecular formulaC17H13ClN4
Molecular weight308.8
InChIKeyVREFGVBLTWBCJP-UHFFFAOYSA-N

SMILES: CC1=NN=C2N1C3=C(C=C(C=C3)Cl)C(=NC2)C4=CC=CC=C4

IUPAC name: 8-chloro-1-methyl-6-phenyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine

ChEBI definition: A member of the class of triazolobenzodiazepines that is 4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine carrying methyl, phenyl and chloro substituents at positions 1, 6 and 8 respectively. Alprazolam is only found in individuals that have taken this drug.

Pharmacological roles (ChEBI): anxiolytic drug, anticonvulsant, muscle relaxant, sedative, GABA agonist.

Other ChEBI roles (chemical / environmental): xenobiotic.

Also known as: Alprazolam, Alprazolam civ, Niravam, NSC-760140, U 31,889, U-31,889, U-31889, Xanax, Xanax xr, SID26719699, SID29215419, ALPRAZOLAM

Patent coverage: 39,075 distinct patent families (130,677 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 130,621 (100%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

GeneTargetActionpAffinityCancer dependencyUniProt
GABRA1GABAA receptor α1 subunitPositive7.430%P14867
GABRA2GABAA receptor α2 subunitPositive7.920%P47869
GABRA3GABAA receptor α3 subunitPositive7.160%P34903
GABRA5GABAA receptor α5 subunitPositive80.9%P31644

Broader ChEMBL bioactivity targets: 18 (assay-derived). Sample: Bromodomain-containing protein 4, Nuclear receptor ROR-gamma, Prelamin-A/C, 15-hydroxyprostaglandin dehydrogenase [NAD(+)], GABA-A receptor; anion channel, Gamma-aminobutyric acid receptor subunit alpha-1, GABA-A receptor; alpha-1/beta-2/gamma-2, GABA A receptor alpha-3/beta-2/gamma-2, GABA A receptor alpha-2/beta-2/gamma-2, Cannabinoid receptor 1.

Bioactivity

ChEMBL activities: 16 potent at pChembl ≥ 5 of 19 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

TargetpChemblTypeValueUnitActivity ID
GABRG29.22Ki0.6nMCHEMBL_ACT_24843247
GABRA19.1Ki0.8nMCHEMBL_ACT_24843226
GABRG28.85Ki1.4nMCHEMBL_ACT_24843268
GABRG28.82Ki1.5nMCHEMBL_ACT_24843289
O090288.48Ki3.3nMCHEMBL_ACT_350409
P628138.38AC504.2nMCHEMBL_ACT_25131170
GABRA58EC5010nMCHEMBL_ACT_350417
GABRA27.92EC5012nMCHEMBL_ACT_350413
LMNA7.9Potency12.6nMCHEMBL_ACT_3663624
GABRA17.43EC5037nMCHEMBL_ACT_350411
GABRA37.16EC5069nMCHEMBL_ACT_350415
P514505.7Potency1995nMCHEMBL_ACT_4963354
BRD45.61Kd2460nMCHEMBL_ACT_8055999
P514505.6Potency2512nMCHEMBL_ACT_5011534
CNR15.48AC503346nMCHEMBL_ACT_25181936
OPRK15.13AC507485nMCHEMBL_ACT_25129970

Target pathways

Aggregated over 4 target gene(s): GABRA1, GABRA2, GABRA3, GABRA5.

Top Reactome pathways

2 total, by targets touching each:

PathwayTargetsGenes
GABA receptor activation4GABRA1, GABRA2, GABRA3, GABRA5
Signaling by ERBB41GABRA1

Dominant GO biological processes

GO termTargets
gamma-aminobutyric acid signaling pathway4
synaptic transmission, GABAergic4
chloride transmembrane transport4
inhibitory synapse assembly4
monoatomic ion transport4
chloride transport4
monoatomic ion transmembrane transport4
regulation of postsynaptic membrane potential4
regulation of presynaptic membrane potential2
behavioral fear response1
signal transduction1
associative learning1
inner ear receptor cell development1
innervation1
cochlea development1

Indications & clinical

Indications

16 indications (4 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

IndicationTrial phaseMONDOEFO
panic disorder4MONDO:0005383EFO:0004262
anxiety4MONDO:0011918EFO:0005230
anxiety disorder4MONDO:0005618EFO:0006788
generalized anxiety disorder4MONDO:0001942EFO:1001892
dementia3MONDO:0001627HP:0000726
depressive disorder3MONDO:0002050MONDO:0002050
visual epilepsy3MONDO:0001386HP:0001250
post-traumatic stress disorder2MONDO:0005146EFO:0001358
epilepsy2MONDO:0005027EFO:0000474
drug dependence1MONDO:0005303EFO:0003890
social phobia1MONDO:0001247EFO:1001917
asthma1MONDO:0004979MONDO:0004979
type 1 diabetes mellitus1MONDO:0005147MONDO:0005147
migraine disorder1MONDO:0005277MONDO:0005277

2 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 67.

Phase distribution

PhaseTrials
PHASE130
PHASE415
Not specified6
PHASE25
PHASE2/PHASE33
PHASE33
PHASE1/PHASE23
EARLY_PHASE12

Top trials by phase / activity

NCTPhaseStatusTitle
NCT06874452PHASE4RECRUITINGAn Extension Test of Whether to Use Oral Anti-anxiety Drugs (Alprazolam) When Patients Choose Second Eye Cataract Surgery After Unblinding, and Analyze Their Anxiety, Satisfaction and Pain Satisfaction
NCT00266409PHASE4COMPLETEDTrial to Compare Time to Response in the Symptoms of Anxiety to Concomitant Treatment With Niravam™ and an SSRI or SNRI to Treatment With an SSRI or SNRI Alone in Subjects With Generalized Anxiety Disorder or Panic Disorder
NCT00662259PHASE4COMPLETEDDrug Treatment Validation of Functional Magnetic Resonance Imaging in Generalized Anxiety Disorder
NCT00703885PHASE4COMPLETEDPharmacofMRI (Functional Magnetic Resonance Imaging) of Anxiolytic Medications (Alprazolam)
NCT00803400PHASE4COMPLETEDEfficacy of Aerobic Exercise Added to Alprazolam in Panic Disorder Treatment
NCT01322867PHASE4COMPLETEDA Bioequivalence Study Of A New Alprazolam Dropped Formulation Versus Alprazolam Tablets
NCT01486615PHASE4COMPLETEDPremedication With Melatonin and Alprazolam Combination Versus Alprazolam or Melatonin Alone
NCT01546090PHASE4COMPLETEDEffect of Alprazolam on the Success of Inferior Alveolar Nerve (IAN) Block
NCT01546896PHASE4WITHDRAWNEffects of Buspar on Depressive Symptom Improvement and Neuroprotection in Patients With Anxiety Disorder
NCT01549691PHASE4COMPLETEDReassessment of Premedication in Surgery
NCT03327506PHASE4UNKNOWNPreoperative Hypnosis Versus Premedication in Gynecological Surgery
NCT04184141PHASE4UNKNOWNPreoperative Use of Alprazolam and Hydroxyzine in Anxiety
NCT06097676PHASE4COMPLETEDAn Abuse Potential Study of Orally Administered HORIZANT in Healthy, Non-dependent, Recreational Drug Users
NCT06357104PHASE4COMPLETEDDetoxification From the Lipid Tract
NCT07154147PHASE4COMPLETEDOral vs IV Sedation for Cataract Surgery in Older Adults
NCT05076617PHASE3ENROLLING_BY_INVITATIONA Study to Test the Safety and Tolerability of Staccato Alprazolam in Study Participants 12 Years of Age and Older With Stereotypical Prolonged Seizures
NCT05077904PHASE3RECRUITINGA Study to Test the Efficacy and Safety of Staccato Alprazolam in Study Participants 12 Years of Age and Older With Stereotypical Prolonged Seizures
NCT00356278PHASE2/PHASE3COMPLETEDD-cycloserine and Virtual Reality Exposure to Treat Iraq War Veterans With PTSD
NCT01949038PHASE2/PHASE3COMPLETEDAlprazolam as Conscious Sedation for Upper Gastrointestinal Endoscopy
NCT02374567PHASE3TERMINATEDPharmacovigilance in Gerontopsychiatric Patients
NCT03130842PHASE2/PHASE3COMPLETEDPremedication With Alprazolam and Midazolam for Upper Gastrointestinal Endoscopy
NCT05006079PHASE2RECRUITINGOpioid/Benzodiazepine Polydrug Abuse: Aim 3
NCT06757140PHASE1/PHASE2RECRUITINGOpioid Drug Interaction Study
NCT00004373PHASE2COMPLETEDPhase II Double-Blind, Placebo-Controlled Study of the Reinforcing Effects of Alprazolam in Patients With Anxiety
NCT00245609PHASE2COMPLETEDTrial of Pregabalin, Alprazolam, and Placebo in Subjects With Anxiety Prior to Dental Procedure
NCT03478982PHASE2COMPLETEDInpatient, Dose-Ranging Study of Staccato Alprazolam in Epilepsy With Predictable Seizure Pattern
NCT03635437PHASE1/PHASE2COMPLETEDEvaluation of Safety and Diabetes Status Upon Oral Treatment With GABA in Patients With Longstanding Type-1 Diabetes
NCT03702803PHASE2UNKNOWNEfficacy and Safety Study of a IMSS Developed Phytopharmaceutical for the Treatment of Anxiety.
NCT04715269PHASE1/PHASE2UNKNOWNRole of Alprazolam in the Management of Acute Coronary Syndrome
NCT00426608PHASE1COMPLETEDTo Investigate Effects GSK561679 on Part of the Body’s System That Controls the Balance of Many of the Hormones.
NCT00555139PHASE1COMPLETEDA Study To Compare The Putative Anxiolytic Effect Of 2 New Drugs In Subjects With Social Anxiety Disorder
NCT00580190PHASE1TERMINATEDEvaluation Of PF-00572778 And Alprazolam On Naloxone Challenge In Healthy Subjects
NCT00603980PHASE1COMPLETEDStaccato Alprazolam Abuse Liability
NCT00647894PHASE1COMPLETEDFasting Study of Alprazolam Extended-Release Tablets 1 mg to Xanax XR Tablets 1 mg
NCT00810316PHASE1COMPLETEDEvaluate Pharmacokinetics Of Two Different Pharmaceutical Oral Formulations Of Alprazolam And A Clonazepam Tablet In Mexican Healthy Population
NCT00860119PHASE1COMPLETEDBioequivalence of Alprazolam Sublingual vs Oral Tablets
NCT00878514PHASE1COMPLETEDBioequivalence Study Comparing Two Alprazolam 1 mg Tablets Under Fed Conditions
NCT00878865PHASE1COMPLETEDBioequivalence Study Comparing Two Alprazolam 1 mg Tablets
NCT00975481PHASE1COMPLETEDA Study To Evaluate The Abuse Potential Of Single Oral Doses Of Dimebon (Latrepirdine) In Healthy Recreational Polydrug Users
NCT01046162PHASE1WITHDRAWNA Study Of Two Oral Preparations Of 2 Mg Alprazolam In Healthy Volunteers Under Fasting Conditions

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline, but PharmGKB curates 3 clinical and 5 variant annotation(s) for this drug (gene-keyed; see PharmGKB).

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

75 molecules share ≥1 primary target. Top 60 by shared-target count:

MoleculeSourceStatusShared targets
APALUTAMIDEChEMBLPhase 4 (approved)GABRA1, GABRA2, GABRA3, GABRA5
BREXANOLONEChEMBLPhase 4 (approved)GABRA1, GABRA2, GABRA3, GABRA5
CHLORDIAZEPOXIDEChEMBLPhase 4 (approved)GABRA1, GABRA2, GABRA3, GABRA5
CLONAZEPAMChEMBLPhase 4 (approved)GABRA1, GABRA2, GABRA3, GABRA5
DIAZEPAMChEMBLPhase 4 (approved)GABRA1, GABRA2, GABRA3, GABRA5
ENZALUTAMIDEChEMBLPhase 4 (approved)GABRA1, GABRA2, GABRA3, GABRA5
FLUMAZENILChEMBLPhase 4 (approved)GABRA1, GABRA2, GABRA3, GABRA5
FLUNITRAZEPAMChEMBLPhase 4 (approved)GABRA1, GABRA2, GABRA3, GABRA5
GANAXOLONEChEMBLPhase 4 (approved)GABRA1, GABRA2, GABRA3, GABRA5
LIOTHYRONINEChEMBLPhase 4 (approved)GABRA1, GABRA2, GABRA3, GABRA5
PROPOFOLChEMBLPhase 4 (approved)GABRA1, GABRA2, GABRA3, GABRA5
TRIAZOLAMChEMBLPhase 4 (approved)GABRA1, GABRA2, GABRA3, GABRA5
ALFAXALONEChEMBL + PubChemPhase 2 (approved)GABRA1, GABRA2, GABRA3, GABRA5
ABECARNILChEMBLPhase 2GABRA1, GABRA2, GABRA3, GABRA5
AZD7325ChEMBLPhase 2GABRA1, GABRA2, GABRA3, GABRA5
BAICALEINChEMBLPhase 2GABRA1, GABRA2, GABRA3, GABRA5
BASMISANILChEMBLPhase 2GABRA1, GABRA2, GABRA3, GABRA5
BRETAZENILChEMBLPhase 2GABRA1, GABRA2, GABRA3, GABRA5
DELORAZEPAMChEMBLPhase 2GABRA1, GABRA2, GABRA3, GABRA5
FLAVONEChEMBLPhase 2GABRA1, GABRA2, GABRA3, GABRA5
MK-0777ChEMBLPhase 2GABRA1, GABRA2, GABRA3, GABRA5
PROGABIDEChEMBLPhase 2GABRA1, GABRA2, GABRA3, GABRA5
ESZOPICLONEChEMBLPhase 4 (approved)GABRA1, GABRA2, GABRA3
ZOLPIDEMChEMBLPhase 4 (approved)GABRA1, GABRA2, GABRA3
DARIGABATChEMBLPhase 2GABRA1, GABRA3, GABRA5
CRIZOTINIBChEMBL + PubChemPhase 4 (approved)GABRA1, GABRA2
ASENAPINEChEMBLPhase 4 (approved)GABRA1, GABRA2
AZELASTINEChEMBLPhase 4 (approved)GABRA1, GABRA2
BENPERIDOLChEMBLPhase 4 (approved)GABRA1, GABRA2
CANDESARTAN CILEXETILChEMBLPhase 4 (approved)GABRA1, GABRA2
CHLORAMBUCILChEMBLPhase 4 (approved)GABRA1, GABRA2
CLOZAPINEChEMBLPhase 4 (approved)GABRA1, GABRA2
EPINASTINEChEMBLPhase 4 (approved)GABRA1, GABRA2
ETOMIDATEChEMBLPhase 4 (approved)GABRA1, GABRA2
GLAFENINEChEMBLPhase 4 (approved)GABRA1, GABRA2
SIMVASTATINChEMBLPhase 4 (approved)GABRA1, GABRA2
TIPRANAVIRChEMBLPhase 4 (approved)GABRA1, GABRA2
TROGLITAZONEChEMBLPhase 4 (approved)GABRA1, GABRA2
ZALEPLONChEMBLPhase 4 (approved)GABRA1, GABRA2
SURAMINChEMBLPhase 3GABRA1, GABRA2
TIRATRICOLChEMBLPhase 3GABRA1, GABRA2
PANADIPLONChEMBLPhase 2GABRA1, GABRA3
SARIPIDEMChEMBLPhase 2GABRA1, GABRA5
ZOTEPINEChEMBLPhase 2GABRA1, GABRA2
AfatinibPubChemApprovedGABRA1, GABRA2
ApixabanPubChemApprovedGABRA1, GABRA2
BinimetinibPubChemApprovedGABRA1, GABRA2
chenodiolPubChemApprovedGABRA1, GABRA2
FulvestrantPubChemApprovedGABRA1, GABRA2
gentian violetPubChemApprovedGABRA1, GABRA2
ImipenemPubChemApprovedGABRA1, GABRA2
LactulosePubChemApprovedGABRA1, GABRA2
levocarnitinePubChemApprovedGABRA1, GABRA2
podofiloxPubChemApprovedGABRA1, GABRA2
Propylene GlycolPubChemApprovedGABRA1, GABRA2
PyrazinamidePubChemApprovedGABRA1, GABRA2
PyridoxinePubChemApprovedGABRA1, GABRA2
RiociguatPubChemApprovedGABRA1, GABRA2
saxagliptinPubChemApprovedGABRA1, GABRA2
ThiaminePubChemApprovedGABRA1, GABRA2

About this page

Generated deterministically by Sugi Atlas from primary biomedical databases via BioBTree. Every record on this page traces to a primary source.

Generated
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Sources 30

This page pulls from 30 datasets indexed by BioBTree:

chebichembl_activitychembl_moleculechembl_targetcivic_evidenceclingen_dosageclinical_trialsdepmapefoensemblentrezgogoparentgtopdbgtopdb_interactiongtopdb_ligandhgncmeshmondomsigdbpatent_compoundpharmgkbpharmgkb_guidelinepubchempubchem_activityreactomereactomeparentrefseqtranscriptuniprot