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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2018-05-20 20:50:41 UTC
HMDB IDHMDB0014548
Secondary Accession Numbers
  • HMDB14548
Metabolite Identification
Common NameAlprazolam
DescriptionAlprazolam is only found in individuals that have used or taken this drug. It is a triazolobenzodiazepine compound with antianxiety and sedative-hypnotic actions, that is efficacious in the treatment of panic disorders, with or without agoraphobia, and in generalized anxiety disorders. (From AMA Drug Evaluations Annual, 1994, p238)Benzodiazepines bind nonspecifically to benzodiazepine receptors BNZ1, which mediates sleep, and BNZ2, which affects muscle relaxation, anticonvulsant activity, motor coordination, and memory. As benzodiazepine receptors are thought to be coupled to gamma-aminobutyric acid-A (GABAA) receptors, this enhances the effects of GABA by increasing GABA affinity for the GABA receptor. Binding of the inhibitory neurotransmitter GABA to the site opens the chloride channel, resulting in a hyperpolarized cell membrane that prevents further excitation of the cell.
Structure
Thumb
Synonyms
ValueSource
8-chloro-1-Methyl-6-phenyl-4H-S-triazolo(4,3-a)(1,4)benzodiazepineChEBI
XanaxChEBI
TUS-1HMDB
Alphapharm brand OF alprazolamMeSH
Alprazolam orion brandMeSH
Alprazolam pfizer brandMeSH
Apotex brand OF alprazolamMeSH
KalmaMeSH
Kenral brand OF alprazolamMeSH
Nu alprazMeSH
Pfizer brand OF alprazolamMeSH
Temmler brand OF alprazolamMeSH
TrankimazinMeSH
Alprazolam kenral brandMeSH
Alprazolam novopharm brandMeSH
Alprazolam nu-pharm brandMeSH
apo AlprazMeSH
apo-AlprazMeSH
Arzneimittelwerk dresden brand OF alprazolamMeSH
CassadanMeSH
NuAlprazMeSH
Alprazolam alphapharm brandMeSH
ApoAlprazMeSH
novo AlprazolMeSH
novo-AlprazolMeSH
NovoAlprazolMeSH
Nu pharm brand OF alprazolamMeSH
Nu-pharm brand OF alprazolamMeSH
Alprazolam apotex brandMeSH
Alprazolam temmler brandMeSH
AlprazolanMeSH
AlproxMeSH
D-65MTMeSH
D65MTMeSH
EsparonMeSH
Novopharm brand OF alprazolamMeSH
Nu-alprazMeSH
Orion brand OF alprazolamMeSH
RalozamMeSH
TafilMeSH
Chemical FormulaC17H13ClN4
Average Molecular Weight308.765
Monoisotopic Molecular Weight308.082874143
IUPAC Name12-chloro-3-methyl-9-phenyl-2,4,5,8-tetraazatricyclo[8.4.0.0²,⁶]tetradeca-1(10),3,5,8,11,13-hexaene
Traditional Nameneurol
CAS Registry Number28981-97-7
SMILES
CC1=NN=C2CN=C(C3=CC=CC=C3)C3=C(C=CC(Cl)=C3)N12
InChI Identifier
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
InChI KeyVREFGVBLTWBCJP-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzodiazepines
Sub Class1,4-benzodiazepines
Direct Parent1,2,4-triazolo[4,3-a][1,4]benzodiazepines
Alternative Parents
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
  • Organic 1,3-dipolar compound
  • Azacycle
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Imine
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point228 - 228.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.032 g/LNot Available
LogP4.9Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.032 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity98.88 m³·mol⁻¹ChemAxon
Polarizability32.22 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-4090000000-d08d3360d39ebeeb87f8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0a4i-0910000000-9efa6a8a3dea17fc1ce7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a59-0079000000-e4c35fb4df41aa5cc62eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0bt9-0169000000-0e6779728f3bdec2acf1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0a4i-0910000000-9efa6a8a3dea17fc1ce7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0009000000-be2bb3a7878fa113efc8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0039000000-7bd62157388fecd0e430View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0o93-3390000000-307fd2f8dd5a9c4f7eacView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0029000000-ceec7f24f309605ec6fbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0097000000-d61397bd13173381fc0dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-3290000000-370bd9e4b8fa73925c04View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0kdi-4792000000-9f1cdda14e36000955d3View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00404 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00404 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00404
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2034
KEGG Compound IDC06817
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAlprazolam
METLIN IDNot Available
PubChem Compound2118
PDB ID08H
ChEBI ID2611
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Wolf B, Griffiths RR: Physical dependence on benzodiazepines: differences within the class. Drug Alcohol Depend. 1991 Dec 31;29(2):153-6. [PubMed:1686752 ]
  2. Haque W, Watson DJ, Bryant SG: Death following suspected alprazolam withdrawal seizures: a case report. Tex Med. 1990 Jan;86(1):44-7. [PubMed:2300914 ]
  3. Risse SC, Whitters A, Burke J, Chen S, Scurfield RM, Raskind MA: Severe withdrawal symptoms after discontinuation of alprazolam in eight patients with combat-induced posttraumatic stress disorder. J Clin Psychiatry. 1990 May;51(5):206-9. [PubMed:2335496 ]
  4. Hori A: Pharmacotherapy for personality disorders. Psychiatry Clin Neurosci. 1998 Feb;52(1):13-9. [PubMed:9682928 ]
  5. Garcia-Algar O, Lopez-Vilchez MA, Martin I, Mur A, Pellegrini M, Pacifici R, Rossi S, Pichini S: Confirmation of gestational exposure to alprazolam by analysis of biological matrices in a newborn with neonatal sepsis. Clin Toxicol (Phila). 2007;45(3):295-8. [PubMed:17453885 ]