Zaleplon (CED0006279)

Record Information

Version

1.0

Creation Date

2009-07-15 20:46:17 UTC

Update Date

2026-05-14 16:54:14 UTC

SynCED ID

CED0006279

Secondary Accession Numbers

CHEM002118
T3D2673

Identification

Common Name

Zaleplon

Class

Small Molecule

Description

Zaleplon is an exogenous organic compound with the formula C17H15N5O and an average molecular weight of 305.33 g/mol. It exists as a solid at room temperature. Zaleplon belongs to the pyrimidines and pyrimidine derivatives, a subclass of diazines within the organic compounds. This compound is utilized as a sedative, anxiolytic drug, anticonvulsant, and central nervous system depressant. It is found in healthcare, pharmaceuticals, and veterinary products as a hypnotic and sedative. Other recorded sources include household cleaning and consumer products, such as tobacco smoke filters, other smoking requisites, non-electric simulated smoking devices, and cigar cigarettes, as well as electrical and electronic equipment, including radio transmission systems and electrically stimulated smoking devices. The recorded route of exposure is oral. Zaleplon targets the translocator protein (TSPO) and the gamma-aminobutyric acid receptor subunit alpha-1 (GABRA1). It exerts its action through subunit modulation of the GABABZ receptor chloride channel macromolecular complex. Specifically, zaleplon binds selectively to the brain alomega-1 receptor situated on the alpha subunit of the GABA-A/chloride ion channel receptor complex and potentiates t-butyl-bicyclophosphorothionate (TBPS) binding.

Contaminant Type

Amide
Amine
Anticonvulsant
Anxiolytic
Drug
Human Neurotoxin
Hypnotic and Sedative
Metabolite
Nitrile
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₁₇H₁₅N₅O

Average Molecular Mass

305.334 g/mol

Monoisotopic Mass

305.128 g/mol

CAS Registry Number

151319-34-5

IUPAC Name

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

Traditional Name

zaleplon

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

Classification

Not classified

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Solid

Appearance

White to off-white powder (RxList, A308).

Experimental Properties

Property	Value
Melting Point	157-159°C
Boiling Point	Not Available
Solubility	4.03e-02 g/L

Predicted Properties

Property	Value	Source
Water Solubility	0.04 g/L	ALOGPS
logP	2	ALOGPS
logP	1.53	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Basic)	0.3	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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-002o-3190000000-e824b41dc4a274647c52	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0179000000-1ba269c717f4cb21ab11	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0bti-0093000000-4fa0fb440741a86e6ec0	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0049000000-5aaa826ffa805612f3d8	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0bvr-0093000000-ee7356e7d1d88937a5a1	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0uy3-9070000000-ba55a55873577a61559b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-0039000000-f5fc7839e64ab7770cbd	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0imi-1192000000-a401fb58f718b462f3e8	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-01qc-2090000000-3a6f247edccc09a27d47	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0019000000-3c4d873dc10d23983dbb	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0096000000-14f38245f06af2128bbb	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-01pa-0090000000-87387933dc3858c721b3	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-0009000000-da3cbd45a045c0d9febd	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0092000000-215903c9317ecf06ce4e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0j5l-0191000000-41735f022846556481db	Not Available	View Spectrum
MS	MS Spectrum	splash10-01ot-3391000000-78a75199aa0ab8c426be	Not Available	View Spectrum

Toxicity Profile

Toxicity Values

Toxicity Value	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Toxicity Rating	Reference
949.0 Log mg/kg [530:1700]	Rat	LD50	oral	predicted	Not Available	Not Available

Toxicity / Toxin Class

Not Available

Mechanism of Toxicity

Zaleplon exerts its action through subunit modulation of the GABA_BZ 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. Organic nitriles decompose into cyanide ions both in vivo and in vitro. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (9)

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Minimum Risk Level

Not Available

Symptoms

Side effects include abdominal pain, amnesia, dizziness, drowsiness, eye pain, headache, memory loss, menstrual pain, nausea, sleepiness, tingling, weakness

Treatment

General symptomatic and supportive measures should be used along with immediate gastric lavage where appropriate. Intravenous fluids should be administered as needed. As in all cases of drug overdose, respiration, pulse, blood pressure, and other appropriate signs should be monitored and general supportive measures employed. Hypotension and CNS depression should be monitored and treated by appropriate medical intervention. (11)

Health Effects

Health Effect	Relationship	Direction	Description	Reference

Exposure Sources

Source ID	Source	Sector	Reference
CEDs000376	Hypnotics and sedatives?Hypnotics and sedatives are synthetic chemicals primarily used to induce sleep, reduce anxiety, and manage various psychiatric disorders.	Healthcare, pharmaceuticals & veterinary products	Not Available
CEDs000518	Electrically Stimulated Smoking Devices?Electrically stimulated smoking devices, commonly known as e-cigarettes or vape pens, utilize electrical components to heat a liquid solution, often containing nicotine, flavorings, and other additives, to produce an aerosol for inhalation.	Electrical & Electronic Equipment	PubChem
CEDs000530	Radio Transmission Systems?Radio transmission systems utilize a variety of synthetic chemicals in their manufacturing and maintenance processes.	Electrical & Electronic Equipment	PubChem
CEDs000556	Cigar Cigarettes?Cigar cigarettes are a source of synthetic chemical contamination due to the combustion of various tobacco blends and additives.	Household cleaning & consumer products	PubChem
CEDs000559	Non Electric Simulated Smoking Devices?Non-electric simulated smoking devices, often designed to mimic the experience of smoking without combustion, can be sources of synthetic chemical contamination due to the materials and chemicals used in their construction and operation.	Household cleaning & consumer products	PubChem
CEDs000560	Other Smoking Requisites?Other smoking requisites, including items such as lighters, matches, and rolling papers, can introduce synthetic chemical contamination through various components and additives.	Household cleaning & consumer products	PubChem
CEDs000569	Tobacco Smoke Filters?Tobacco smoke filters are designed to reduce the inhalation of harmful substances in cigarette smoke, including tar and other particulate matter.	Household cleaning & consumer products	PubChem
CEDs000580	Manufacture Preparation Of Tobacco Products?The manufacture and preparation of tobacco products involve various processes that can result in the introduction of synthetic chemicals into the environment.	Industrial manufacturing & chemical processing	PubChem
CEDs000611	Anti Perspirants Or Body Deoderants?Antiperspirants and body deodorants commonly contain synthetic chemicals such as aluminum compounds, parabens, and synthetic fragrances.	Personal care & cosmetics	PubChem
CEDs000614	Essential Oils Or Perfumes?Essential oils and perfumes are complex mixtures of volatile compounds derived from natural or synthetic sources, commonly used for their aromatic properties.	Personal care & cosmetics	PubChem
CEDs000632	Apparel?Apparel production often involves the use of various synthetic chemicals, including dyes, finishing agents, and preservatives.	Textiles, leather & furnishings	PubChem
CEDs000642	Footwear?Footwear production often involves the use of various synthetic chemicals, such as adhesives, dyes, and treatments, which can contribute to environmental contamination.	Textiles, leather & furnishings	PubChem
CEDs000650	Purses Luggage Hand Bags?Purses, luggage, and handbags are often manufactured using synthetic materials such as polyvinyl chloride (PVC), polyurethane, and various types of nylon.	Textiles, leather & furnishings	PubChem
CEDs000651	Purses Money Bags Wallets?Purses, money bags, and wallets are often manufactured using synthetic materials, including plastics, polyurethanes, and various treated fabrics.	Textiles, leather & furnishings	PubChem
CEDs000671	Airplanes And Helicopters?Airplanes and helicopters are significant sources of synthetic chemical contamination primarily through the use of aviation fuels, lubricants, and de-icing agents.	Aviation & Aerospace	PubChem
CEDs000685	Ceramics?Ceramics can be a source of synthetic chemical contamination through various additives and processing agents used in their production.	Building & Construction	PubChem
CEDs000696	Nanotechnology?Nanotechnology involves the manipulation of materials at the molecular or atomic level, typically within the range of 1 to 100 nanometers.	Industrial manufacturing & chemical processing	PubChem
CEDs000735	Explosives?Explosives are chemical compounds or mixtures designed to undergo rapid decomposition, releasing energy in the form of gas and heat.	Defense & military infrastructure	PubChem
CEDs000744	Water, Wastewater, & Sewage Treatment?Water, wastewater, and sewage treatment processes are critical for managing and mitigating pollutants in water systems.	Wastewater, sanitation & biosolids	PubChem

Pathways

2 pathwaysPathway Source: PathBank

Zaleplon Action Pathway

Zaleplon Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	LIM domain kinase 1	P53667	Humans	Predicted (SEA)	Prediction Confidence Score 0.36 Applicability Domain 0.38 Statistical Significance 0.0188 Supporting Reference Compounds 565 E-value 146.512
Click to view 3D structure	Glycogen synthase kinase-3 alpha	P49840	Humans	Predicted (SEA)	Prediction Confidence Score 0.358 Applicability Domain 0.365 Statistical Significance 0.0268 Supporting Reference Compounds 754 E-value 208.558
Click to view 3D structure	Serine/threonine-protein kinase MARK2	Q7KZI7	Humans	Predicted (SEA)	Prediction Confidence Score 0.357 Applicability Domain 0.38 Statistical Significance 0.0193 Supporting Reference Compounds 512 E-value 150.56
Click to view 3D structure	Serine/threonine-protein kinase pim-1	P11309	Humans	Predicted (SEA)	Prediction Confidence Score 0.357 Applicability Domain 0.365 Statistical Significance 0.0331 Supporting Reference Compounds 967 E-value 257.992
Click to view 3D structure	Serine/threonine-protein kinase PLK1	P53350	Humans	Predicted (SEA)	Prediction Confidence Score 0.355 Applicability Domain 0.365 Statistical Significance 0.0259 Supporting Reference Compounds 705 E-value 201.707
Click to view 3D structure	MAP kinase-activated protein kinase 2	P49137	Humans	Predicted (SEA)	Prediction Confidence Score 0.355 Applicability Domain 0.365 Statistical Significance 0.026 Supporting Reference Compounds 679 E-value 202.642
Click to view 3D structure	Cyclin-dependent kinase 1	P06493	Humans	Predicted (SEA)	Prediction Confidence Score 0.355 Applicability Domain 0.365 Statistical Significance 0.0248 Supporting Reference Compounds 715 E-value 193.3
Click to view 3D structure	RAC-alpha serine/threonine-protein kinase	P31749	Humans	Predicted (SEA)	Prediction Confidence Score 0.346 Applicability Domain 0.365 Statistical Significance 0.0347 Supporting Reference Compounds 797 E-value 270.215
Click to view 3D structure	Cyclin-dependent kinase 2	P24941	Humans	Predicted (SEA)	Prediction Confidence Score 0.343 Applicability Domain 0.365 Statistical Significance 0.0469 Supporting Reference Compounds 1029 E-value 364.957
Click to view 3D structure	Dual specificity tyrosine-phosphorylation-regulated kinase 1A	Q13627	Humans	Predicted (SEA)	Prediction Confidence Score 0.339 Applicability Domain 0.365 Statistical Significance 0.0431 Supporting Reference Compounds 906 E-value 335.608
Click to view 3D structure	Mitogen-activated protein kinase 13	O15264	Humans	Predicted (SEA)	Prediction Confidence Score 0.335 Applicability Domain 0.38 Statistical Significance 0.0307 Supporting Reference Compounds 558 E-value 239.231
Click to view 3D structure	Casein kinase II subunit alpha	P68400	Humans	Predicted (SEA)	Prediction Confidence Score 0.334 Applicability Domain 0.365 Statistical Significance 0.0325 Supporting Reference Compounds 593 E-value 253.244
Click to view 3D structure	Glycogen synthase kinase-3 beta	P49841	Humans	Predicted (SEA)	Prediction Confidence Score 0.333 Applicability Domain 0.365 Statistical Significance 0.0659 Supporting Reference Compounds 1157 E-value 513.026
Click to view 3D structure	Vascular endothelial growth factor receptor 2	P35968	Humans	Predicted (SEA)	Prediction Confidence Score 0.333 Applicability Domain 0.365 Statistical Significance 0.0829 Supporting Reference Compounds 1660 E-value 645.681
Click to view 3D structure	Aurora kinase B	Q96GD4	Humans	Predicted (SEA)	Prediction Confidence Score 0.332 Applicability Domain 0.365 Statistical Significance 0.0589 Supporting Reference Compounds 1017 E-value 458.221
Click to view 3D structure	Serine/threonine-protein kinase PAK 1	Q13153	Humans	Predicted (SEA)	Prediction Confidence Score 0.332 Applicability Domain 0.365 Statistical Significance 0.0348 Supporting Reference Compounds 595 E-value 270.915
Click to view 3D structure	Interleukin-1 receptor-associated kinase 4	Q9NWZ3	Humans	Predicted (SEA)	Prediction Confidence Score 0.332 Applicability Domain 0.365 Statistical Significance 0.0426 Supporting Reference Compounds 682 E-value 332.027
Click to view 3D structure	Ribosomal protein S6 kinase beta-1	P23443	Humans	Predicted (SEA)	Prediction Confidence Score 0.329 Applicability Domain 0.365 Statistical Significance 0.0398 Supporting Reference Compounds 590 E-value 309.996
Click to view 3D structure	Rho-associated protein kinase 1	Q13464	Humans	Predicted (SEA)	Prediction Confidence Score 0.329 Applicability Domain 0.365 Statistical Significance 0.0504 Supporting Reference Compounds 834 E-value 392.282
Click to view 3D structure	Serine/threonine-protein kinase D2	Q9BZL6	Humans	Predicted (SEA)	Prediction Confidence Score 0.329 Applicability Domain 0.365 Statistical Significance 0.0386 Supporting Reference Compounds 604 E-value 300.809
Click to view 3D structure	Cyclin-dependent kinase 5	Q00535	Humans	Predicted (SEA)	Prediction Confidence Score 0.329 Applicability Domain 0.365 Statistical Significance 0.0467 Supporting Reference Compounds 779 E-value 363.4
Click to view 3D structure	Serine/threonine-protein kinase MRCK alpha	Q5VT25	Humans	Predicted (SEA)	Prediction Confidence Score 0.329 Applicability Domain 0.365 Statistical Significance 0.0359 Supporting Reference Compounds 572 E-value 279.323
Click to view 3D structure	RAC-gamma serine/threonine-protein kinase	Q9Y243	Humans	Predicted (SEA)	Prediction Confidence Score 0.329 Applicability Domain 0.365 Statistical Significance 0.038 Supporting Reference Compounds 620 E-value 295.827
Click to view 3D structure	Serine/threonine-protein kinase Nek2	P51955	Humans	Predicted (SEA)	Prediction Confidence Score 0.329 Applicability Domain 0.365 Statistical Significance 0.0419 Supporting Reference Compounds 660 E-value 325.955
Click to view 3D structure	Serine/threonine-protein kinase Sgk2	Q9HBY8	Humans	Predicted (SEA)	Prediction Confidence Score 0.329 Applicability Domain 0.365 Statistical Significance 0.0284 Supporting Reference Compounds 493 E-value 221.247
Click to view 3D structure	Gamma-aminobutyric acid receptor subunit alpha-1	P14867	Humans	Known	Zaleplon exerts its action through subunit modulation of the GABA_BZ receptor chloride channel macromolecular complex.Zaleplon binds selectively to the brain alomega-1 receptor situated on the alpha subunit of the GABA-A/chloride ion channel receptor complex and potentiates t-butyl-bicyclophosphorothionate (TBPS) binding.
Click to view 3D structure	Translocator protein	P30536	Humans	Known	Zaleplon exerts its action through subunit modulation of the GABA_BZ receptor chloride channel macromolecular complex.Zaleplon binds selectively to the brain alomega-1 receptor situated on the alpha subunit of the GABA-A/chloride ion channel receptor complex and potentiates t-butyl-bicyclophosphorothionate (TBPS) binding.

Concentrations

Not Available

External Links

Identifiers

Not Available

References

Synthesis Reference

Farhan Aslam, “Polymorphs of zaleplon and methods for the preparation thereof.” U.S. Patent US20020072527, issued June 13, 2002.

MSDS

Link

General References

Wishart DS, Knox C, Guo AC, Cheng D, Shrivastava S, Tzur D, Gautam B, Hassanali M: DrugBank: a knowledgebase for drugs, drug actions and drug targets. Nucleic Acids Res. 2008 Jan;36(Database issue):D901-6. Epub 2007 Nov 29. [PubMed: 18048412]
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]
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]
Ramakrishnan K, Scheid DC: Treatment options for insomnia. Am Fam Physician. 2007 Aug 15;76(4):517-26. [PubMed: 17853625]
Barbera J, Shapiro C: Benefit-risk assessment of zaleplon in the treatment of insomnia. Drug Saf. 2005;28(4):301-18. [PubMed: 15783240]
Dooley M, Plosker GL: Zaleplon: a review of its use in the treatment of insomnia. Drugs. 2000 Aug;60(2):413-45. [PubMed: 10983740]
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]
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]
Wikipedia. Cyanide poisoning. Last Updated 30 March 2009. - http://en.wikipedia.org/wiki/Cyanide_poisoning
Drugs.com - http://www.drugs.com/cons/Zaleplon.html
RxList: The Internet Drug Index (2009). - http://www.rxlist.com/

Zaleplon (CED0006279)

Structure for CHEM002118: Zaleplon

Structure