Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Zaleplon: Difference between pages

{{Short description|Medication used to treat insomnia}}

{{More citations needed|date=June 2018}}

{{Use dmy dates|date=April 2024}}

{{cs1 config|name-list-style=vanc|display-authors=6}}

{{Infobox drug

| Watchedfields = changed

| verifiedrevid = 470635467

| imageL = Zaleplon skeletal.svg

| widthL = 110

| altL =

| imageR = Zaleplon-from-xtal-Mercury-3D-bs.png

| widthR = 180

| altR =

<!--Clinical data-->

| pronounce =

| tradename = Sonata, others

| Drugs.com = {{drugs.com|monograph|zaleplon}}

| MedlinePlus = a601251

| DailyMedID = Zaleplon

| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->

| pregnancy_AU_comment =

| pregnancy_category =

| dependency_liability =

| addiction_liability = Moderate

| routes_of_administration = [[By mouth]]

| class = [[nonbenzodiazepine]]

| ATC_prefix = N05

| ATC_suffix = CF03

| ATC_supplemental =

<!-- -->

| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled -->

| legal_AU_comment =

| legal_BR = B1

| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=31 March 2023 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=3 August 2023 |access-date=16 August 2023 |publisher=[[Diário Oficial da União]] |language=pt-BR |publication-date=4 April 2023}}</ref>

| legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII -->

| legal_CA_comment =

| legal_DE = <!-- Anlage I, II, III or Unscheduled -->

| legal_DE_comment =

| legal_NZ = <!-- Class A, B, C -->

| legal_NZ_comment =

| legal_UK = Class C

| legal_UK_comment =

| legal_US = Schedule IV

| legal_US_comment = <ref name="Sonata FDA label" />

| legal_EU =

| legal_EU_comment =

| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV -->

| legal_UN_comment =

| legal_status = <!-- For countries not listed above -->

<!---->

| bioavailability = 30% (oral)<ref name="pharmokinetics">{{cite journal | vauthors = Rosen AS, Fournié P, Darwish M, Danjou P, Troy SM | title = Zaleplon pharmacokinetics and absolute bioavailability | journal = Biopharmaceutics & Drug Disposition | volume = 20 | issue = 3 | pages = 171–175 | date = April 1999 | pmid = 10211871 | doi = 10.1002/(sici)1099-081x(199904)20:3<171::aid-bdd169>3.0.co;2-k }}</ref>

| protein_bound =

| metabolism = [[Liver]] aldehyde oxidase (91%), [[CYP3A4]] (9%)<ref name="fda">{{cite web |title=20859 S009, 011 FDA Approved Labeling Text 12.10.07 |url=https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/020859s011lbl.pdf |publisher=[[Food and Drug Administration|FDA]] |access-date=21 March 2023}}</ref>

| metabolites =

| onset =

| elimination_half-life = 1 hr<ref name="pharmokinetics"/>

| duration_of_action =

| excretion = [[Kidney]]

<!-- -->

| CAS_number_Ref = {{cascite|correct|??}}

| = 34

| CAS_supplemental =

| PubChem = 5719

| IUPHAR_ligand = 4345

| = {{|correct|}}

| DrugBank = DB00962

| = {{|correct|chemspider}}

| ChemSpiderID = 5517

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = S62U433RMH

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D00530

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 10102

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 1521

| NIAID_ChemDB =

| PDB_ligand =

| synonyms =

<!-- Chemical and physical data -->

| IUPAC_name = ''N''-(3-(3-cyanopyrazolo[1,5-''a''] pyrimidin-7-yl)phenyl)-''N''-ethylacetamide

| C = 17

| H = 15

| N = 5

| O = 1

| SMILES = CCN(C(C)=O)c1cccc(-c2ccnc3c(C#N)cnn23)c1

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChI_comment =

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = HUNXMJYCHXQEGX-UHFFFAOYSA-N

| density =

| density_notes =

| melting_point =

| melting_high =

| melting_notes =

| boiling_point =

| boiling_notes =

| solubility =

| sol_units =

| specific_rotation =

'''Zaleplon''', sold under the brand name '''Sonata''' among others, is a [[sedative]] and [[hypnotic]] which is used to treat [[insomnia]]. It is a [[nonbenzodiazepine]] or [[Z-drug]] of the [[pyrazolopyrimidine]] class.<ref>{{cite journal | vauthors = Elie R, Rüther E, Farr I, Emilien G, Salinas E | title = Sleep latency is shortened during 4 weeks of treatment with zaleplon, a novel nonbenzodiazepine hypnotic. Zaleplon Clinical Study Group | journal = The Journal of Clinical Psychiatry | volume = 60 | issue = 8 | pages = 536–44 | date = August 1999 | pmid = 10485636 | doi = 10.4088/JCP.v60n0806 }}</ref> It was developed by [[King Pharmaceuticals]] and approved for medical use in the United States in 1999.<ref name="Sonata FDA label">{{cite web | title=Sonata (zaleplon) Capsules CIV | website=DailyMed | url=https://dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=451261 | access-date=21 March 2023}}</ref>

== Medical uses ==

Zaleplon is slightly effective in treating insomnia,<ref name=TB2012>{{cite journal | vauthors = Huedo-Medina TB, Kirsch I, Middlemass J, Klonizakis M, Siriwardena AN | title = Effectiveness of non-benzodiazepine hypnotics in treatment of adult insomnia: meta-analysis of data submitted to the Food and Drug Administration | journal = BMJ | volume = 345 | pages = e8343 | date = December 2012 | pmid = 23248080 | pmc = 3544552 | doi = 10.1136/bmj.e8343 }}</ref> primarily characterized by difficulty falling asleep. Zaleplon significantly reduces the time required to fall asleep by improving sleep latency and may therefore facilitate sleep induction rather than sleep maintenance.<ref name="Bhandari 2020">{{cite book | vauthors = Bhandari P, Sapra A | chapter = Zaleplon |date=2020| chapter-url= http://www.ncbi.nlm.nih.gov/books/NBK551571/ |title = StatPearls|place=Treasure Island (FL)|publisher=StatPearls Publishing|pmid=31855398|access-date=8 July 2020}}</ref><ref>{{cite journal | vauthors = Ebbens MM, Verster JC | title = Clinical evaluation of zaleplon in the treatment of insomnia | journal = Nature and Science of Sleep | volume = 2 | pages = 115–126 | date = 20 July 2010 | pmid = 23616704 | pmc = 3630939 | doi = 10.2147/nss.s6853 | doi-access = free }}</ref><ref name="Dooley 413–445">{{cite journal | vauthors = Dooley M, Plosker GL | title = Zaleplon: a review of its use in the treatment of insomnia | journal = Drugs | volume = 60 | issue = 2 | pages = 413–445 | date = August 2000 | pmid = 10983740 | doi = 10.2165/00003495-200060020-00014 | s2cid = 195691571 }}</ref> Due to its ultrashort elimination half-life, zaleplon may not be effective in reducing premature awakenings; however, it may be administered to alleviate [[Middle-of-the-night insomnia|middle-of-the-night awakenings]].<ref name="Bhandari 2020"/> However, zaleplon has not been empirically shown to increase total sleep time.<ref name="Dooley 413–445"/><ref name="Bhandari 2020"/>

Zaleplon does not significantly affect driving performance the morning following bedtime administration or 4 hours after middle-of-the-night administration. <ref>{{cite journal | vauthors = Verster JC, Veldhuijzen DS, Volkerts ER | title = Residual effects of sleep medication on driving ability | journal = Sleep Medicine Reviews | volume = 8 | issue = 4 | pages = 309–25 | date = August 2004 | pmid = 15233958 | doi = 10.1016/j.smrv.2004.02.001 | hdl = 1874/11902 | s2cid = 22856696 | hdl-access = free }}</ref> It may have advantages over [[benzodiazepines]] with fewer adverse effects.<ref name=Bar2005>{{cite journal | vauthors = Barbera J, Shapiro C | title = Benefit-risk assessment of zaleplon in the treatment of insomnia | journal = Drug Safety | volume = 28 | issue = 4 | pages = 301–18 | year = 2005 | pmid = 15783240 | doi = 10.2165/00002018-200528040-00003 | s2cid = 24222535 }}</ref>

=== Special populations ===

Zaleplon is not recommended for chronic use in the elderly.<ref>{{cite journal | title = American Geriatrics Society updated Beers Criteria for potentially inappropriate medication use in older adults | journal = Journal of the American Geriatrics Society | volume = 60 | issue = 4 | pages = 616–31 | date = April 2012 | pmid = 22376048 | pmc = 3571677 | doi = 10.1111/j.1532-5415.2012.03923.x | author1 = American Geriatrics Society 2012 Beers Criteria Update Expert Panel }}</ref> The elderly are more sensitive to the adverse effects of zaleplon such as cognitive side effects. Zaleplon may increase the risk of injury among the elderly. It should not be used during pregnancy or lactation. Clinicians should devote more attention when prescribing for patients with a history of alcohol or drug abuse, psychotic illness, or depression.<ref>{{cite journal | vauthors = Antai-Otong D | title = The art of prescribing. Risks and benefits of non-benzodiazepine receptor agonists in the treatment of acute primary insomnia in older adults | journal = Perspectives in Psychiatric Care | volume = 42 | issue = 3 | pages = 196–200 | date = August 2006 | pmid = 16916422 | doi = 10.1111/j.1744-6163.2006.00070.x | doi-access = free }}</ref>

In addition, some contend the efficacy and safety of long-term use of these agents remains to be enumerated, but nothing concrete suggests long-term use poses any direct harm to a person.<ref name="Bain KT 2006 168–92">{{cite journal | vauthors = Bain KT | title = Management of chronic insomnia in elderly persons | journal = The American Journal of Geriatric Pharmacotherapy | volume = 4 | issue = 2 | pages = 168–92 | date = June 2006 | pmid = 16860264 | doi = 10.1016/j.amjopharm.2006.06.006 }}</ref>

== Adverse effects ==

The adverse effects of zaleplon are similar to the adverse effects of benzodiazepines, although with less next-day sedation,<ref name="Wagner J 1998 680–91">{{cite journal | vauthors = Wagner J, Wagner ML, Hening WA | title = Beyond benzodiazepines: alternative pharmacologic agents for the treatment of insomnia | journal = The Annals of Pharmacotherapy | volume = 32 | issue = 6 | pages = 680–91 | date = June 1998 | pmid = 9640488 | doi = 10.1345/aph.17111 | s2cid = 34250754 }}</ref> and in two studies zaleplon use was found not to cause an increase in traffic accidents, as compared to other [[hypnotics]] currently on the market.<ref>{{cite journal | vauthors = Menzin J, Lang KM, Levy P, Levy E | title = A general model of the effects of sleep medications on the risk and cost of motor vehicle accidents and its application to France | journal = PharmacoEconomics | volume = 19 | issue = 1 | pages = 69–78 | date = January 2001 | pmid = 11252547 | doi = 10.2165/00019053-200119010-00005 | s2cid = 45013069 }}</ref><ref>{{cite journal | vauthors = Vermeeren A, Riedel WJ, van Boxtel MP, Darwish M, Paty I, Patat A | title = Differential residual effects of zaleplon and zopiclone on actual driving: a comparison with a low dose of alcohol | journal = Sleep | volume = 25 | issue = 2 | pages = 224–31 | date = March 2002 | pmid = 11905433 }}</ref>

Sleeping pills, including zaleplon, have been associated with an increased risk of death.<ref>{{cite journal | vauthors = Kripke DF | title = Mortality Risk of Hypnotics: Strengths and Limits of Evidence | journal = Drug Safety | volume = 39 | issue = 2 | pages = 93–107 | date = February 2016 | pmid = 26563222 | doi = 10.1007/s40264-015-0362-0 | s2cid = 7946506 | doi-access = free }}</ref>

Some evidence suggests zaleplon is not as chemically reinforcing and exhibits far fewer [[rebound effects]] when compared with other nonbenzodiazepines, or [[Z-drug]]s.<ref>{{cite journal | vauthors = Lader MH | title = Implications of hypnotic flexibility on patterns of clinical use | journal = International Journal of Clinical Practice. Supplement | issue = 116 | pages = 14–9 | date = January 2001 | pmid = 11219327 }}</ref>

== Interactions ==

The [[CYP3A4]] [[liver enzyme]] is a minor metabolic pathway for zaleplon, normally metabolizing about 9% of the drug.<ref name="fda" /> CYP3A4 inducers such as [[rifampicin]], [[phenytoin]], [[carbamazepine]], and

[[phenobarbital]] can reduce the effectiveness of zaleplon, and therefore the FDA suggests that other hypnotic drugs be considered in patients taking a CYP3A4 inducer.<ref name="fda" />

Additional sedation has been observed when zaleplon is combined with [[thioridazine]], but it is not clear whether this was due to merely an additive effect of taking two sedative drugs at once or a true drug-drug interaction.<ref name="Wang">{{cite journal | vauthors = Wang JS, DeVane CL | title = Pharmacokinetics and drug interactions of the sedative hypnotics | journal = Psychopharmacology Bulletin | volume = 37 | issue = 1 | pages = 10–29 | year = 2003 | pmid = 14561946 | doi = 10.1007/BF01990373 | s2cid = 1543185 | url = http://www.medworksmedia.com/psychopharmbulletin/pdf/12/010-029_PB%20W03_Wang_final.pdf | access-date = 28 December 2008 | archive-url = https://web.archive.org/web/20070709230745/http://www.medworksmedia.com/psychopharmbulletin/pdf/12/010-029_PB%20W03_Wang_final.pdf | archive-date = 9 July 2007 | url-status = dead }}</ref> [[Diphenhydramine]], a weak inhibitor of aldehyde oxidase, has not been found to affect the pharmacokinetics of zaleplon.<ref name="Wang"/>

== Pharmacology ==

===Mechanism of action===

Zaleplon is a high-selectivity,<ref>Binding assays show no binding (IsC50 > 10,000 micromolar) with regards to the 5HT1, 5HT1A, 5-HT2A, 5-HT3, D1, D2, alpha-1 adrenoceptor, alpha-2 adrenoceptor, or M1 receptors. {{cite journal | vauthors = Noguchi H, Kitazumi K, Mori M, Shiba T | title = Binding and neuropharmacological profile of zaleplon, a novel nonbenzodiazepine sedative/hypnotic | journal = European Journal of Pharmacology | volume = 434 | issue = 1–2 | pages = 21–28 | date = January 2002 | pmid = 11755161 | doi = 10.1016/S0014-2999(01)01502-3 }}</ref> high-affinity ligand of positive modulator sites of GABA_A receptors, which enhances GABAergic inhibition of neurotransmission in the central nervous system. The ultrashort [[half-life]] gives zaleplon a unique advantage over other hypnotics because of its lack of next-day residual effects on driving and other performance-related skills.<ref>{{cite journal | vauthors = Patat A, Paty I, Hindmarch I | title = Pharmacodynamic profile of Zaleplon, a new non-benzodiazepine hypnotic agent | journal = Human Psychopharmacology | volume = 16 | issue = 5 | pages = 369–392 | date = July 2001 | pmid = 12404558 | doi = 10.1002/hup.310 | s2cid = 21096374 }}</ref><ref>{{cite journal | vauthors = Rowlett JK, Spealman RD, Lelas S, Cook JM, Yin W | title = Discriminative stimulus effects of zolpidem in squirrel monkeys: role of GABA(A)/alpha1 receptors | journal = Psychopharmacology | volume = 165 | issue = 3 | pages = 209–215 | date = January 2003 | pmid = 12420154 | doi = 10.1007/s00213-002-1275-z | s2cid = 37632215 }}</ref> Unlike nonselective benzodiazepine drugs and zopiclone, which distort the [[sleep pattern]], zaleplon appears to induce sleep without disrupting the normal [[sleep architecture]].<ref>{{cite journal | vauthors = Noguchi H, Kitazumi K, Mori M, Shiba T | title = Binding and neuropharmacological profile of zaleplon, a novel nonbenzodiazepine sedative/hypnotic | journal = European Journal of Pharmacology | volume = 434 | issue = 1–2 | pages = 21–28 | date = January 2002 | pmid = 11755161 | doi = 10.1016/S0014-2999(01)01502-3 }}</ref>

A [[meta-analysis]] of randomized, controlled [[clinical trials]] which compared benzodiazepines against zaleplon or other Z-drugs such as zolpidem, zopiclone, and eszopiclone has found few clear and consistent differences between zaleplon and the benzodiazepines in terms of [[sleep onset latency]], total sleep duration, number of awakenings, quality of sleep, adverse events, [[Drug tolerance|tolerance]], [[rebound insomnia]], and daytime [[alertness]].<ref>{{cite journal | vauthors = Dündar Y, Dodd S, Strobl J, Boland A, Dickson R, Walley T | title = Comparative efficacy of newer hypnotic drugs for the short-term management of insomnia: a systematic review and meta-analysis | journal = Human Psychopharmacology | volume = 19 | issue = 5 | pages = 305–22 | date = July 2004 | pmid = 15252823 | doi = 10.1002/hup.594 | s2cid = 10888200 }}</ref>

Zaleplon should be understood as an ultrashort-acting sedative-hypnotic drug for the treatment of insomnia. Zaleplon increases [[EEG]] power density in the δ-frequency band and a decrease in the energy of the θ-frequency band<ref>{{cite journal | vauthors = Noguchi H, Kitazumi K, Mori M, Shiba T | title = Electroencephalographic properties of zaleplon, a non-benzodiazepine sedative/hypnotic, in rats | journal = Journal of Pharmacological Sciences | volume = 94 | issue = 3 | pages = 246–51 | date = March 2004 | pmid = 15037809 | doi = 10.1254/jphs.94.246 | doi-access = free }}</ref><ref>{{cite journal | vauthors = Petroski RE, Pomeroy JE, Das R, Bowman H, Yang W, Chen AP, Foster AC | title = Indiplon is a high-affinity positive allosteric modulator with selectivity for alpha1 subunit-containing GABAA receptors | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 317 | issue = 1 | pages = 369–77 | date = April 2006 | pmid = 16399882 | doi = 10.1124/jpet.105.096701 | s2cid = 46510829 }}</ref>

=== Pharmacokinetics ===

Zaleplon is primarily metabolised by [[aldehyde oxidase]] into 5-oxozaleplon, and its half-life may be affected by substances which inhibit or induce aldehyde oxidase. According to urine analysis, about 9% of zaleplon is metabolized by [[CYP3A4]] to form desethylzaleplon, which is quickly metabolized by aldehyde oxidase to 5-oxodesethylzaleplon.<ref name="fda" /><ref name="pharmokinetics"/> All of these metabolites are inactive.<ref name="pharmokinetics"/> When taken orally, zaleplon reaches maximum concentration in about 45 minutes.<ref name="pharmokinetics"/>

== Chemistry ==

Zaleplon is classified as a [[pyrazolopyrimidine]].<ref name="PubChemZaleplon">{{cite web |title=Zaleplon |url=https://pubchem.ncbi.nlm.nih.gov/compound/zaleplon |website=pubchem.ncbi.nlm.nih.gov |publisher=U.S. National Library of Medicine |access-date=10 June 2018 |language=en}}</ref> Pure zaleplon in its solid state is a white to off-white powder with very low [[solubility]] in water, as well as low solubility in [[ethanol]] and [[propylene glycol]].<ref name="fda"/> It has a constant [[octanol-water partition coefficient]] of log P = 1.23 in the [[pH]] range between 1 and 7.<ref name="fda"/>

=== Synthesis ===

[[File:Zaleplon synthesis.svg|thumb|center|900px|Zaleplon synthesis<ref>J. P. Dusza et al., {{US patent|4626538}} (1986 to Am. Cyanamid).</ref><ref>http://en.cnki.com.cn/Article_en/CJFDTotal-ZYSG200205002.htm 《China Pharmacist》 2002-05 Synthesis of Zaleplon.</ref>]]

The synthesis starts with the condensation of [[3-acetylacetanilide]]<ref>{{cite journal | vauthors = Banasik M, Komura H, Shimoyama M, Ueda K | title = Specific inhibitors of poly(ADP-ribose) synthetase and mono(ADP-ribosyl)transferase | journal = The Journal of Biological Chemistry | volume = 267 | issue = 3 | pages = 1569–1575 | date = January 1992 | pmid = 1530940 | doi = 10.1016/S0021-9258(18)45983-2 | doi-access = free }}</ref><ref>{{cite journal | vauthors = Dehmel F, Weinbrenner S, Julius H, Ciossek T, Maier T, Stengel T, Fettis K, Burkhardt C, Wieland H, Beckers T | title = Trithiocarbonates as a novel class of HDAC inhibitors: SAR studies, isoenzyme selectivity, and pharmacological profiles | journal = Journal of Medicinal Chemistry | volume = 51 | issue = 13 | pages = 3985–4001 | date = July 2008 | pmid = 18558669 | doi = 10.1021/jm800093c }}</ref> ('''1''') with ''N'',''N''-dimethylformamide dimethyl acetal ([[DMFDMA]])<ref>{{Cite journal |doi=10.1021/jo00193a045|title = Convenient preparation of N,N-dimethylacetamide dimethyl acetal|journal = The Journal of Organic Chemistry|volume = 49|issue = 19|pages = 3659–3660|year = 1984| vauthors = Salomon RG, Raychaudhuri SR }}</ref> to give the eneamide ('''2'''). The anilide nitrogen is then alkylated by means of [[sodium hydride]] and [[ethyl iodide]] to give '''3'''. The first step in the condensation with 3-amino-4-cyanopyrazole can be visualized as involving an [[addition-elimination reaction]] sequence on the eneamide function to give a transient intermediate such as '''5'''. Cyclization then leads to formation of the fused [[pyrimidine]] ring to afford zaleplon ('''6''').

==Society and culture==

=== Recreational use ===

Zaleplon has the potential to be a drug of recreational use, and has been found to have an addictive potential similar to benzodiazepine and benzodiazepine-like hypnotics.<ref>{{cite web|url=http://dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=6299|title=Sonata®(zaleplon)Capsules}}</ref>

Some individuals use a different delivery method than prescribed, such as [[Insufflation (medicine)|insufflation]], to induce effects faster.<ref>{{cite journal | vauthors = Paparrigopoulos T, Tzavellas E, Karaiskos D, Liappas I | title = Intranasal zaleplon abuse | journal = The American Journal of Psychiatry | volume = 165 | issue = 11 | pages = 1489–90 | date = November 2008 | pmid = 18981079 | doi = 10.1176/appi.ajp.2008.08030452 | url = http://ajp.psychiatryonline.org/cgi/content/full/165/11/1489-a | access-date = 5 April 2011 | archive-date = 5 July 2010 | archive-url = https://web.archive.org/web/20100705104126/http://ajp.psychiatryonline.org/cgi/content/full/165/11/1489-a | url-status = dead }}</ref> [[File:Sonata10mg.JPG|thumb|right|180px| Sonata 10-mg capsules]]

[[Anterograde amnesia]] can occur and can cause one to lose track of the amount of zaleplon already ingested, prompting the ingesting of more than originally planned.<ref>{{cite journal | vauthors = Rush CR, Frey JM, Griffiths RR | title = Zaleplon and triazolam in humans: acute behavioral effects and abuse potential | journal = Psychopharmacology | volume = 145 | issue = 1 | pages = 39–51 | date = July 1999 | pmid = 10445371 | doi = 10.1007/s002130051030 | s2cid = 12061258 }}</ref><ref>{{cite journal | vauthors = Ator NA | title = Zaleplon and triazolam: drug discrimination, plasma levels, and self-administration in baboons | journal = Drug and Alcohol Dependence | volume = 61 | issue = 1 | pages = 55–68 | date = December 2000 | pmid = 11064184 | doi = 10.1016/S0376-8716(00)00123-X }}</ref>

=== Aviation use ===

The [[Federal Aviation Administration]] allows zaleplon with a 12-hour wait period and no more than twice a week, which makes it the sleep medication with the shortest allowed waiting period after use.<ref name=aviationMedicine>{{cite web|url=https://www.aviationmedicine.com/medication-database|title=Medication Database – AMAS}}</ref> The substances with the 2nd shortest period, which is of 24 hours, are zolpidem and [[ramelteon]].<ref name=aviationMedicine />

=== Military use ===

The [[United States Air Force]] uses zaleplon as one of the hypnotics approved as a "[[no-go pill]]" to help aviators and special-duty personnel sleep in support of mission readiness (with a four-hour restriction on subsequent flight operation). "Ground tests" are required prior to authorization being issued to use the medication in an operational situation.<ref name=Caldwell>{{cite journal | vauthors = Caldwell JA, Caldwell JL | title = Fatigue in military aviation: an overview of US military-approved pharmacological countermeasures | journal = Aviation, Space, and Environmental Medicine | volume = 76 | issue = 7 Suppl | pages = C39-51 | date = July 2005 | pmid = 16018329 | url = http://docserver.ingentaconnect.com/deliver/connect/asma/00956562/v76n7x1/s10.pdf?expires=1335744234&id=68546495&titleid=8218&accname=Guest+User&checksum=D97BA65A8E7071CC3766CF365ED85FA3 | format = pdf }}</ref> The other hypnotics used as "no-go pills" are [[temazepam]] and [[zolpidem]], which both have longer mandatory recovery periods.<ref name=Caldwell />

== References ==

{{Reflist}}

{{Hypnotics and sedatives}}

{{Insomnia pharmacotherapies}}

{{GABAAR PAMs}}

{{Portal bar | Medicine}}

{{Authority control}}

[[Category:Acetanilides]]

[[Category:GABAA receptor positive allosteric modulators]]

[[Category:Nitriles]]

[[Category:Drugs developed by Pfizer]]

[[Category:Nonbenzodiazepines]]

[[Category:Pyrazolopyrimidines]]