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Zaleplon

July 24, 2017
Common Name

Zaleplon Description

Zaleplon is a sedative/hypnotic, mainly used for insomnia. It is known as a nonbenzodiazepine hypnotic. Zaleplon interacts with the GABA receptor complex and shares some of the pharmacological properties of the benzodiazepines. Zaleplon is a schedlie IV drug in the United States. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source 3'-(3-cyanopyrazolo(1,5-a)Pyrimidin-7-yl)-N-ethylacetanilideChEBI DEA no. 2781HMDB N-(3-(3-cyanopyrazolo(1,5-a)Pyrimidin-7-yl)phenyl)-N-ethylacetamideMeSH ZelepionMeSH SonataMeSH StarnocMeSH

Chemical Formlia

C17H15N5O Average Molecliar Weight

305.3339 Monoisotopic Molecliar Weight

305.127660127 IUPAC Name

N-(3-{3-cyanopyrazolo[1,5-a]pyrimidin-7-yl}phenyl)-N-ethylacetamide Traditional Name

zaleplon CAS Registry Number

151319-34-5 SMILES

CCN(C(C)=O)C1=CC=CC(=C1)C1=CC=NC2=C(C=NN12)C#N

InChI Identifier

InChI=1S/C17H15N5O/c1-3-21(12(2)23)15-6-4-5-13(9-15)16-7-8-19-17-14(10-18)11-20-22(16)17/h4-9,11H,3H2,1-2H3

InChI Key

HUNXMJYCHXQEGX-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of organic compounds known as phenylpyrimidines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrimidine ring through a CC or CN bond. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions. Kingdom

Organic compounds Super Class

Organoheterocyclic compounds Class

Diazines Sub Class

Pyrimidines and pyrimidine derivatives Direct Parent

Phenylpyrimidines Alternative Parents

  • Acetanilides
  • Pyrazolo[1,5-a]pyrimidines
  • Tertiary carboxylic acid amides
  • Pyrazoles
  • Heteroaromatic compounds
  • Acetamides
  • Nitriles
  • Azacyclic compounds
  • Organopnictogen compounds
  • Organic oxides
  • Hydrocarbon derivatives
  • Carbonyl compounds

    • Substituents

  • 4-phenylpyrimidine
  • 5-phenylpyrimidine
  • Acetanilide
  • Pyrazolo[1,5-a]pyrimidine
  • Anilide
  • Pyrazolopyrimidine
  • Monocyclic benzene moiety
  • Benzenoid
  • Azole
  • Heteroaromatic compound
  • Acetamide
  • Tertiary carboxylic acid amide
  • Pyrazole
  • Carboxamide group
  • Carboxylic acid derivative
  • Carbonitrile
  • Nitrile
  • Azacycle
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organic oxide
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound

    • Molecliar Framework

    Aromatic heteropolycyclic compounds External Descriptors

  • nitrile (CHEBI:10102 )
  • pyrazolopyrimidine (CHEBI:10102 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Anticonvlisants
  • Anxiolytics sedatives and hypnotics
  • Hypnotics and Sedatives

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Cytoplasm
  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point157 – 159 °CNot Available Boiling PointNot AvailableNot Available Water Solubility4.03e-02 g/LNot Available LogP0.9Not Available

    Predicted Properties

    Property Value Source Water Solubility0.04 mg/mLALOGPS logP2ALOGPS logP1.53ChemAxon logS-3.9ALOGPS pKa (Strongest Basic)0.3ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count4ChemAxon Hydrogen Donor Count0ChemAxon Polar Surface Area74.29 Å2ChemAxon Rotatable Bond Count3ChemAxon Refractivity97.24 m3·mol-1ChemAxon Polarizability32.09 Å3ChemAxon Number of Rings3ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key LC-MS/MS

    LC-MS/MS Spectrum – , positivesplash10-0a4i-0179000000-1ba269c717f4cb21ab11View in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available MS

    Mass Spectrum (Electron Ionization)splash10-01ot-3391000000-78a75199aa0ab8c426beView in MoNA

    Biological Properties Cellliar Locations

  • Cytoplasm
  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00962

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00962

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Predicted Concentrations

    Biofluid Value Original age Original sex Original condition Comments Blood0-3 uMAdlit (>18 years old)BothNormalPredicted based on drug qualities Blood0-2 umol/mmol creatinineAdlit (>18 years old)BothNormalPredicted based on drug qualities

    Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB00962 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    5517 KEGG Compound ID

    C07484 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Zaleplon NuGOwiki Link

    HMDB15097 Metagene Link

    HMDB15097 METLIN ID

    Not Available PubChem Compound

    5719 PDB ID

    Not Available ChEBI ID

    10102

    Product: Berberine (chloride)

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. Patat A, Paty I, Hindmarch I: Pharmacodynamic profile of Zaleplon, a new non-benzodiazepine hypnotic agent. Hum Psychopharmacol. 2001 Jul;16(5):369-392. [PubMed:12404558 ]
    2. Barbera J, Shapiro C: Benefit-risk assessment of zaleplon in the treatment of insomnia. Drug Saf. 2005;28(4):301-18. [PubMed:15783240 ]
    3. Noguchi H, Kitazumi K, Mori M, Shiba T: Electroencephalographic properties of zaleplon, a non-benzodiazepine sedative/hypnotic, in rats. J Pharmacol Sci. 2004 Mar;94(3):246-51. [PubMed:15037809 ]
    4. Holm KJ, Goa KL: Zolpidem: an update of its pharmacology, therapeutic efficacy and tolerability in the treatment of insomnia. Drugs. 2000 Apr;59(4):865-89. [PubMed:10804040 ]
    5. Dooley M, Plosker GL: Zaleplon: a review of its use in the treatment of insomnia. Drugs. 2000 Aug;60(2):413-45. [PubMed:10983740 ]
    6. Dundar Y, Dodd S, Strobl J, Boland A, Dickson R, Walley T: Comparative efficacy of newer hypnotic drugs for the short-term management of insomnia: a systematic review and meta-analysis. Hum Psychopharmacol. 2004 Jul;19(5):305-22. [PubMed:15252823 ]
    7. Ramakrishnan K, Scheid DC: Treatment options for insomnia. Am Fam Physician. 2007 Aug 15;76(4):517-26. [PubMed:17853625 ]

    Enzymes

    General function:
    Involved in oxidoreductase activity
    Specific function:
    Not Available
    Gene Name:
    AOX1
    Uniprot ID:
    Q06278
    Molecular weight:
    147916.735
    References
    1. Lake BG, Ball SE, Kao J, Renwick AB, Price RJ, Scatina JA: Metabolism of zaleplon by human liver: evidence for involvement of aldehyde oxidase. Xenobiotica. 2002 Oct;32(10):835-47. [PubMed:12419014 ]
    2. Obach RS: Potent inhibition of human liver aldehyde oxidase by raloxifene. Drug Metab Dispos. 2004 Jan;32(1):89-97. [PubMed:14709625 ]
    General function:
    Involved in monooxygenase 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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
    Gene Name:
    CYP3A4
    Uniprot ID:
    P08684
    Molecular weight:
    57255.585
    References
    1. 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 ]
    General function:
    Involved in monooxygenase 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 unrelated compounds, including steroids, fatty acids, and xenobiotics.
    Gene Name:
    CYP3A5
    Uniprot ID:
    P20815
    Molecular weight:
    57108.065
    General function:
    Involved in monooxygenase 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 unrelated compounds, including steroids, fatty acids, and xenobiotics.
    Gene Name:
    CYP3A7
    Uniprot ID:
    P24462
    Molecular weight:
    57525.03
    General function:
    Signal transduction mechanisms
    Specific function:
    Responsible for the manifestation of peripheral-type benzodiazepine recognition sites and is most likely to comprise binding domains for benzodiazepines and isoquinoline carboxamides. May play a role in the transport of porphyrins and heme. Plays a role in the transport of cholesterol across mitochondrial membranes in steroidogenic cells
    Gene Name:
    TSPO
    Uniprot ID:
    P30536
    Molecular weight:
    18778.7
    References
    1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
    2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
    General function:
    Involved in ion transport
    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:
    GABRA1
    Uniprot ID:
    P14867
    Molecular weight:
    51801.4
    References
    1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
    2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
    3. Patat A, Paty I, Hindmarch I: Pharmacodynamic profile of Zaleplon, a new non-benzodiazepine hypnotic agent. Hum Psychopharmacol. 2001 Jul;16(5):369-392. [PubMed:12404558 ]
    4. Barbera J, Shapiro C: Benefit-risk assessment of zaleplon in the treatment of insomnia. Drug Saf. 2005;28(4):301-18. [PubMed:15783240 ]
    5. Sanger DJ, Griebel G, Perrault G, Claustre Y, Schoemaker H: Discriminative stimulus effects of drugs acting at GABA(A) receptors: differential profiles and receptor selectivity. Pharmacol Biochem Behav. 1999 Oct;64(2):269-73. [PubMed:10515302 ]
    6. Terzano MG, Rossi M, Palomba V, Smerieri A, Parrino L: New drugs for insomnia: comparative tolerability of zopiclone, zolpidem and zaleplon. Drug Saf. 2003;26(4):261-82. [PubMed:12608888 ]

    PMID: 23716627

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