Zaleplon
Identification
- Summary
Zaleplon is a sedative used for short term treatment of insomnia in adults.
- Brand Names
- Sonata
- Generic Name
- Zaleplon
- DrugBank Accession Number
- DB00962
- Background
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 schedule IV drug in the United States.
- Type
- Small Molecule
- Groups
- Approved, Illicit, Investigational
- Structure
- Weight
- Average: 305.3339
Monoisotopic: 305.127660127 - Chemical Formula
- C17H15N5O
- Synonyms
- 3'-(3-Cyanopyrazolo(1,5-a)pyrimidin-7-yl)-N-ethylacetanilide
- Zaleplon
- External IDs
- CL 284,846
- CL-284846
- DEA No. 2781
- L846
- LJC 10846
- LJC-10846
- SKP-1041
- ZAL-846
Pharmacology
- Indication
For the treatment of short-term treatment of insomnia in adults.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Insomnia •••••••••••• - Contraindications & Blackbox Warnings
- Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API
- Pharmacodynamics
Zaleplon is a nonbenzodiazepine hypnotic from the pyrazolopyrimidine class and is indicated for the short-term treatment of insomnia. While Zaleplon is a hypnotic agent with a chemical structure unrelated to benzodiazepines, barbiturates, or other drugs with known hypnotic properties, it interacts with the gamma-aminobutyric acid-benzodiazepine (GABABZ) receptor complex. Subunit modulation of the GABABZ receptor chloride channel macromolecular complex is hypothesized to be responsible for some of the pharmacological properties of benzodiazepines, which include sedative, anxiolytic, muscle relaxant, and anticonvulsive effects in animal models. Zaleplon also binds selectively to the CNS GABAA-receptor chloride ionophore complex at benzodiazepine(BZ) omega-1 (BZ1, ο1) receptors.
- Mechanism of action
Zaleplon exerts its action through subunit modulation of the GABABZ receptor chloride channel macromolecular complex. Zaleplon also binds selectively to the brain omega-1 receptor located on the alpha subunit of the GABA-A/chloride ion channel receptor complex and potentiates t-butyl-bicyclophosphorothionate (TBPS) binding.
Target Actions Organism AGamma-aminobutyric acid receptor subunit alpha-1 potentiatorHumans - Absorption
Absorption Zaleplon is rapidly and almost completely absorbed following oral administration.
- Volume of distribution
- 1.4 L/kg
- Protein binding
Approximately 60% (in vitro plasma protein binding).
- Metabolism
Zaleplon is primarily metabolized by aldehyde oxidase.
Hover over products below to view reaction partners
- Route of elimination
Zaleplon is metabolized primarily by the liver and undergoes significant presystemic metabolism. After oral administration, zaleplon is extensively metabolized, with less than 1% of the dose excreted unchanged in urine. Renal excretion of unchanged zaleplon accounts for less than 1% of the administered dose.
- Half-life
Approximately 1 hour
- Clearance
- 1 L/h/kg
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Side effects include abdominal pain, amnesia, dizziness, drowsiness, eye pain, headache, memory loss, menstrual pain, nausea, sleepiness, tingling, weakness
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Zaleplon is combined with 1,2-Benzodiazepine. Abacavir Zaleplon may decrease the excretion rate of Abacavir which could result in a higher serum level. Abametapir The serum concentration of Zaleplon can be increased when it is combined with Abametapir. Abatacept The metabolism of Zaleplon can be increased when combined with Abatacept. Acalabrutinib The metabolism of Zaleplon can be decreased when combined with Acalabrutinib. - Food Interactions
- Avoid alcohol. Ingesting alcohol may increase the CNS depressant effects of zaleplon.
- Do not take with or immediately after a high-fat meal. The effects of zaleplon are reduced when taken with a high-fat meal.
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Images
- International/Other Brands
- Zalaplon
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Sonata Capsule 5 mg/1 Oral Physicians Total Care, Inc. 2007-09-05 Not applicable US Sonata Capsule 5 mg Oral Meda Ab 2016-09-08 2015-10-21 EU Sonata Capsule 10 mg Oral Meda Ab 2016-09-08 2015-10-21 EU Sonata Capsule 5 mg Oral Meda Ab 2016-09-08 2015-10-21 EU Sonata Capsule 10 mg Oral Meda Ab 2016-09-08 2015-10-21 EU - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Zaleplon Capsule 5 mg/1 Oral Unichem Pharmaceuticals (USA), Inc. 2009-05-05 Not applicable US Zaleplon Capsule 10 mg/1 Oral H.J. Harkins Company 2010-12-15 Not applicable US Zaleplon Capsule 5 mg/1 Oral Mylan Pharmaceuticals 2008-06-06 2016-06-30 US Zaleplon Capsule 10 mg/1 Oral A-S Medication Solutions 2008-06-06 2017-11-21 US Zaleplon Capsule 10 mg/1 Oral Preferred Pharmaceuticals Inc. 2018-08-06 Not applicable US
Categories
- ATC Codes
- N05CF03 — Zaleplon
- Drug Categories
- Acetates
- Acids, Acyclic
- Amides
- Anticonvulsants
- Benzodiazepine hypnotics and sedatives
- Central Nervous System Agents
- Central Nervous System Depressants
- Central Nervous System Depression
- 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
- GABA Agents
- GABA Agonists
- GABA Modulators
- GABA-A Receptor Agonists
- gamma-Aminobutyric Acid A Receptor Agonist
- Hypnotics (Nonbenzodiazepine)
- Hypnotics and Sedatives
- Miscellaneous Anxiolytics Sedatives and Hypnotics
- Nervous System
- Neurotransmitter Agents
- Psycholeptics
- Chemical TaxonomyProvided by Classyfire
- 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 show 2 more
- Substituents
- 4-phenylpyrimidine / 5-phenylpyrimidine / Acetamide / Acetanilide / Anilide / Aromatic heteropolycyclic compound / Azacycle / Azole / Benzenoid / Carbonitrile show 17 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- nitrile, pyrazolopyrimidine (CHEBI:10102)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- S62U433RMH
- CAS number
- 151319-34-5
- InChI Key
- HUNXMJYCHXQEGX-UHFFFAOYSA-N
- InChI
- 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
- IUPAC Name
- N-(3-{3-cyanopyrazolo[1,5-a]pyrimidin-7-yl}phenyl)-N-ethylacetamide
- SMILES
- CCN(C(C)=O)C1=CC=CC(=C1)C1=CC=NC2=C(C=NN12)C#N
References
- Synthesis Reference
Farhan Aslam, "Polymorphs of zaleplon and methods for the preparation thereof." U.S. Patent US20020072527, issued June 13, 2002.
US20020072527- General References
- 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. [Article]
- 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. [Article]
- Ramakrishnan K, Scheid DC: Treatment options for insomnia. Am Fam Physician. 2007 Aug 15;76(4):517-26. [Article]
- Barbera J, Shapiro C: Benefit-risk assessment of zaleplon in the treatment of insomnia. Drug Saf. 2005;28(4):301-18. [Article]
- Dooley M, Plosker GL: Zaleplon: a review of its use in the treatment of insomnia. Drugs. 2000 Aug;60(2):413-45. [Article]
- 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. [Article]
- Patat A, Paty I, Hindmarch I: Pharmacodynamic profile of Zaleplon, a new non-benzodiazepine hypnotic agent. Hum Psychopharmacol. 2001 Jul;16(5):369-392. [Article]
- External Links
- Human Metabolome Database
- HMDB0015097
- KEGG Drug
- D00530
- KEGG Compound
- C07484
- PubChem Compound
- 5719
- PubChem Substance
- 46508267
- ChemSpider
- 5517
- BindingDB
- 86521
- 74667
- ChEBI
- 10102
- ChEMBL
- CHEMBL1521
- ZINC
- ZINC000000006300
- Therapeutic Targets Database
- DAP000266
- PharmGKB
- PA451952
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Zaleplon
- FDA label
- Download (66.1 KB)
- MSDS
- Download (57.6 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Basic Science Memory / Sleep 1 4 Completed Supportive Care Cognitive Functioning / Pharmacologic Actions / Sleep 1 3 Terminated Treatment Anxiety Disorders / Dementia / Depression / Psychosomatic Disorders / Schizophrenia 1 2 Completed Treatment Clinical Depression / Human Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS) 1 2 Completed Treatment Insomnia 1
Pharmacoeconomics
- Manufacturers
- King pharmaceuticals research and development inc sub king pharmaceuticals inc
- Aurobindo pharma ltd
- Cipla ltd
- Mylan pharmaceuticals inc
- Orchid healthcare div orchid chemicals and pharmaceuticals ltd
- Roxane laboratories inc
- Sandoz inc
- Teva pharmaceuticals usa
- Unichem laboratories ltd
- Upsher smith laboratories inc
- West ward pharmaceutical corp
- Packagers
- A-S Medication Solutions LLC
- Aurobindo Pharma Ltd.
- Cipla Ltd.
- Corepharma LLC
- DAVA Pharmaceuticals
- DispenseXpress Inc.
- Dispensing Solutions
- Diversified Healthcare Services Inc.
- Greenstone LLC
- Innoviant Pharmacy Inc.
- King Pharmaceuticals Inc.
- Mylan
- Northstar Rx LLC
- Nucare Pharmaceuticals Inc.
- Physicians Total Care Inc.
- Rebel Distributors Corp.
- Roxane Labs
- Teva Pharmaceutical Industries Ltd.
- Unichem Laboratories Ltd.
- USL Pharma Inc.
- West-Ward Pharmaceuticals
- Dosage Forms
Form Route Strength Capsule Oral Capsule, coated Oral 5 mg Capsule Oral 10 mg Capsule Oral 5 mg Capsule Oral 10 mg/1 Capsule Oral 5 mg/1 Capsule, gelatin coated Oral 10 mg/1 Capsule, gelatin coated Oral 5 mg/1 - Prices
Unit description Cost Unit Sonata 10 mg capsule 6.83USD capsule Sonata 5 mg capsule 5.26USD capsule Zaleplon 5 mg capsule 2.13USD capsule Zaleplon 10 mg capsule 2.09USD capsule DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 157-159 °C Not Available logP 0.9 Not Available - Predicted Properties
Property Value Source Water Solubility 0.0403 mg/mL ALOGPS logP 2 ALOGPS logP 1.53 Chemaxon logS -3.9 ALOGPS pKa (Strongest Basic) 0.28 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 74.29 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 97.24 m3·mol-1 Chemaxon Polarizability 32.09 Å3 Chemaxon Number of Rings 3 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 + 0.9751 Caco-2 permeable + 0.5973 P-glycoprotein substrate Non-substrate 0.6094 P-glycoprotein inhibitor I Non-inhibitor 0.5232 P-glycoprotein inhibitor II Inhibitor 0.8239 Renal organic cation transporter Non-inhibitor 0.745 CYP450 2C9 substrate Non-substrate 0.8607 CYP450 2D6 substrate Non-substrate 0.8551 CYP450 3A4 substrate Substrate 0.6341 CYP450 1A2 substrate Non-inhibitor 0.5 CYP450 2C9 inhibitor Inhibitor 0.5986 CYP450 2D6 inhibitor Non-inhibitor 0.9507 CYP450 2C19 inhibitor Non-inhibitor 0.5238 CYP450 3A4 inhibitor Non-inhibitor 0.8396 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.7673 Ames test Non AMES toxic 0.5372 Carcinogenicity Non-carcinogens 0.6481 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.6277 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9806 hERG inhibition (predictor II) Non-inhibitor 0.8931
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 190.4219393 predictedDarkChem Lite v0.1.0 [M-H]- 189.3782393 predictedDarkChem Lite v0.1.0 [M-H]- 165.6831 predictedDeepCCS 1.0 (2019) [M+H]+ 190.7502393 predictedDarkChem Lite v0.1.0 [M+H]+ 190.7896393 predictedDarkChem Lite v0.1.0 [M+H]+ 168.0411 predictedDeepCCS 1.0 (2019) [M+Na]+ 190.7797393 predictedDarkChem Lite v0.1.0 [M+Na]+ 190.1029393 predictedDarkChem Lite v0.1.0 [M+Na]+ 174.82384 predictedDeepCCS 1.0 (2019)
Targets
![](https://go.drugbank.com/assets/locked/DrugTargets2-682eb846d210ae4bf33ca03febccfb57bb1c61318e699b729e5df4dfab2c5b67.png)
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Potentiator
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- Patat A, Paty I, Hindmarch I: Pharmacodynamic profile of Zaleplon, a new non-benzodiazepine hypnotic agent. Hum Psychopharmacol. 2001 Jul;16(5):369-392. [Article]
- Barbera J, Shapiro C: Benefit-risk assessment of zaleplon in the treatment of insomnia. Drug Saf. 2005;28(4):301-18. [Article]
- 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. [Article]
- 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. [Article]
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
- Tanoue C, Sugihara K, Uramaru N, Tayama Y, Watanabe Y, Horie T, Ohta S, Kitamura S: Prediction of human metabolism of the sedative-hypnotic zaleplon using chimeric mice transplanted with human hepatocytes. Xenobiotica. 2013 Nov;43(11):956-62. doi: 10.3109/00498254.2013.788232. Epub 2013 May 8. [Article]
- Renwick AB, Mistry H, Ball SE, Walters DG, Kao J, Lake BG: Metabolism of Zaleplon by human hepatic microsomal cytochrome P450 isoforms. Xenobiotica. 1998 Apr;28(4):337-48. doi: 10.1080/004982598239452 . [Article]
- Foye, William O.;Williams, David A.;Lemke, Thomas L. (2002). Foye's Principles of Medicinal Chemistry (5th ed.). Lippincott Williams & Wilkins. [ISBN:0683307371]
- Flockhart Table of Drug Interactions [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
- Flockhart Table of Drug Interactions [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
- Flockhart Table of Drug Interactions [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Xanthine dehydrogenase activity
- Specific Function
- Oxidase with broad substrate specificity, oxidizing aromatic azaheterocycles, such as N1-methylnicotinamide and N-methylphthalazinium, as well as aldehydes, such as benzaldehyde, retinal, pyridoxal...
- Gene Name
- AOX1
- Uniprot ID
- Q06278
- Uniprot Name
- Aldehyde oxidase
- Molecular Weight
- 147916.735 Da
References
- 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. [Article]
- Obach RS: Potent inhibition of human liver aldehyde oxidase by raloxifene. Drug Metab Dispos. 2004 Jan;32(1):89-97. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55