U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C17H15N5O
Molecular Weight 305.3339
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ZALEPLON

SMILES

CCN(C(C)=O)C1=CC(=CC=C1)C2=CC=NC3=C(C=NN23)C#N

InChI

InChIKey=HUNXMJYCHXQEGX-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C17H15N5O
Molecular Weight 305.3339
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including https://www.drugbank.ca/drugs/DB00962

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. 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. Zaleplon is marketed under the brand names Sonata, Starnoc, and Andante.

Approval Year

Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
62 ng/mL
5 mg single, intravenous
dose: 5 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ZALEPLON plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
14.5 ng/mL
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ZALEPLON plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
86.1 ng × h/mL
5 mg single, intravenous
dose: 5 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ZALEPLON plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
26.9 ng × h/mL
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ZALEPLON plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.05 h
5 mg single, intravenous
dose: 5 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ZALEPLON plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
1.08 h
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ZALEPLON plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
40%
ZALEPLON plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
75 mg single, oral
Highest studied dose
Dose: 75 mg
Route: oral
Route: single
Dose: 75 mg
Sources:
healthy, 18 - 44
Health Status: healthy
Age Group: 18 - 44
Sex: M+F
Sources:
200 mg single, oral
Overdose
Dose: 200 mg
Route: oral
Route: single
Dose: 200 mg
Sources:
unhealthy
Other AEs: Loss of consciousness...
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy
Disc. AE: Sleep driving, Suicide...
Other AEs: Abnormal thinking, Abnormal behavior...
AEs leading to
discontinuation/dose reduction:
Sleep driving
Suicide
Anaphylactic reaction (severe)
Anaphylactoid reaction (severe)
Angioedema (grade 3-5)
Other AEs:
Abnormal thinking
Abnormal behavior
Amnesia
Depression worsened
Suicidal tendency
Sources:
AEs

AEs

AESignificanceDosePopulation
Loss of consciousness
200 mg single, oral
Overdose
Dose: 200 mg
Route: oral
Route: single
Dose: 200 mg
Sources:
unhealthy
Abnormal behavior
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy
Abnormal thinking
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy
Amnesia
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy
Depression worsened
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy
Suicidal tendency
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy
Sleep driving Disc. AE
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy
Suicide Disc. AE
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy
Angioedema grade 3-5
Disc. AE
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy
Anaphylactic reaction severe
Disc. AE
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy
Anaphylactoid reaction severe
Disc. AE
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer






Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
yes
yes
yes (co-administration study)
Comment: Rifampicin is a strong CYP3A4 inducer. Multiple dosing of rifampicin (600 mg qd for 13 days) reduces both Cmax and AUC of zaleplon to 25% of its respective value, caused by a 5 fold increase in zaleplon oral clearance.
Page: 6.0
PubMed

PubMed

TitleDatePubMed
The new Z-drugs as sedatives and hypnotics.
2005-06-18
Screening and confirmatory method for benzodiazepines and hypnotics in oral fluid by LC-MS/MS.
2005-06-10
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005-06
Contribution of alpha 1GABAA and alpha 5GABAA receptor subtypes to the discriminative stimulus effects of ethanol in squirrel monkeys.
2005-05
Determination of 14 benzodiazepines and hydroxy metabolites, zaleplon and zolpidem as tert-butyldimethylsilyl derivatives compared with other common silylating reagents in whole blood by gas chromatography-mass spectrometry.
2005-04-25
Diagnosis and treatment of chronic insomnia: a review.
2005-03
A NICE missed opportunity?
2005-03
Short-term treatment with hypnotic drugs for insomnia: going beyond the evidence.
2005-03
Making decisions in the absence of high quality clinical evidence: we need to bring some science into the judgement.
2005-03
NICE review: not nice for patients!
2005-03
NICE: The National Institute of Clinical Excellence -- or Eccentricity? Reflections on the Z-drugs as hypnotics.
2005-03
Long-term use of sedative hypnotics in older patients with insomnia.
2005-03
Eszopiclone (Lunesta), a new hypnotic.
2005-02-28
Validated liquid chromatographic ultraviolet method for the quantitation of Etoricoxib in human plasma using liquid-liquid extraction.
2005-02-25
Benefit-risk assessment of zaleplon in the treatment of insomnia.
2005
Direct injection, column switching-liquid chromatographic technique for the estimation of rabeprazole in bioequivalence study.
2004-12-25
Perchance, to sleep...and then stay asleep.
2004-12
What's wrong with prescribing hypnotics?
2004-12
Characterization of the interaction of indiplon, a novel pyrazolopyrimidine sedative-hypnotic, with the GABAA receptor.
2004-11
In vivo pharmacological characterization of indiplon, a novel pyrazolopyrimidine sedative-hypnotic.
2004-11
Hypnotic efficacy of zaleplon for daytime sleep in rested individuals.
2004-08-01
"A comparison of the effectiveness of two hypnotic agents for the treatment of insomnia".
2004-08
Sleeping pills without regrets. They've long been the risky quick fixes of sleep medicine. Soon some sleeping pills may be sold as long-term solutions.
2004-08
Zaleplon overdose associated with sleepwalking and complex behavior.
2004-08
Residual effects of sleep medication on driving ability.
2004-08
Validated semiquantitative/quantitative screening of 51 drugs in whole blood as silylated derivatives by gas chromatography-selected ion monitoring mass spectrometry and gas chromatography electron capture detection.
2004-07-05
Treatment of primary insomnia.
2004-07-01
Comparative efficacy of newer hypnotic drugs for the short-term management of insomnia: a systematic review and meta-analysis.
2004-07
Sleep-inducing pharmaceuticals: a comparison of melatonin, zaleplon, zopiclone, and temazepam.
2004-06
Newer hypnotic drugs for the short-term management of insomnia: a systematic review and economic evaluation.
2004-06
An assessment of quality of sleep and the use of drugs with sedating properties in hospitalized adult patients.
2004-03-24
Electroencephalographic properties of zaleplon, a non-benzodiazepine sedative/hypnotic, in rats.
2004-03
Performance following a sudden awakening from daytime nap induced by zaleplon.
2004-01
Potent inhibition of human liver aldehyde oxidase by raloxifene.
2004-01
The pharmacology and mechanisms of action of new generation, non-benzodiazepine hypnotic agents.
2004
Residual effects of hypnotics: epidemiology and clinical implications.
2004
Effects of zolpidem and zaleplon on sleep, respiratory patterns and performance at a simulated altitude of 4,000 m.
2004
Comparative pharmacokinetics and pharmacodynamics of short-acting hypnosedatives: zaleplon, zolpidem and zopiclone.
2004
Changes in GABA(A) receptor gene expression associated with selective alterations in receptor function and pharmacology after ethanol withdrawal.
2003-12-17
Impact of melatonin, zaleplon, zopiclone, and temazepam on psychomotor performance.
2003-12
Effects of imatinib mesylate (STI571, Glivec) on the pharmacokinetics of simvastatin, a cytochrome p450 3A4 substrate, in patients with chronic myeloid leukaemia.
2003-11-17
Separation and identification of zaleplon metabolites in human urine using capillary electrophoresis with laser-induced fluorescence detection and liquid chromatography-mass spectrometry.
2003-10-03
Effect of zaleplon, a non-benzodiazepine hypnotic, on melatonin secretion in rabbits.
2003-10
[Drug treatment of sleep disorders in the elderly].
2003-09
Mixed drug intoxication involving zaleplon ("Sonata").
2003-07-08
Preference of insomniac patients between a single dose of zolpidem 10 mg versus zaleplon 10 mg.
2003-07
Ziprasidone metabolism, aldehyde oxidase, and clinical implications.
2003-06
Zaleplon and driving impairment.
2003-05
Pharmacokinetics and drug interactions of the sedative hypnotics.
2003
Zaleplon improves sleep quality in maintenance hemodialysis patients.
2003
Patents

Sample Use Guides

The recommended dose of Sonata (Zaleplon) for most nonelderly adults is 10 mg. For certain low weight individuals, 5 mg may be a sufficient dose. Although the risk of certain adverse events associated with the use of Sonata appears to be dose dependent, the 20 mg dose has been shown to be adequately tolerated and may be considered for the occasional patient who does not benefit from a trial of a lower dose. Doses above 20 mg have not been adequately evaluated and are not recommended. Sonata should be taken immediately before bedtime or after the patient has gone to bed and has experienced difficulty falling asleep.
Route of Administration: Oral
Zaleplon (1x10(-8) to 3x10(-6) M) exhibited marked efficacy in potentiating GABA-evoked Cl  currents in voltage-clamped Xenopus oocytes expressing human a1b2g2 GABAA receptors.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:05:44 GMT 2025
Edited
by admin
on Mon Mar 31 18:05:44 GMT 2025
Record UNII
S62U433RMH
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ZALEPLON CIV
USP-RS  
Preferred Name English
ZALEPLON
EMA EPAR   INN   JAN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
ZALEPLON [MART.]
Common Name English
ZAL-846
Code English
ZALEPLON [USP MONOGRAPH]
Common Name English
ACETAMIDE, N-(3-(3-CYANOPYRAZOLO(1,5-.ALPHA.)PYRIMIDIN-7-YL)PHENYL)-N-ETHYL-
Common Name English
ZALEPLON CIV [USP-RS]
Common Name English
LJC10846
Code English
ZALEPLON [USAN]
Common Name English
L-846
Code English
3'-(3-CYANOPYRAZOLO(1,5-.ALPHA.)PYRIMIDIN-7-YL)-N-ETHYLACETANILIDE
Common Name English
ZALEPLON [MI]
Common Name English
CL 284,846
Code English
LJC-10846
Code English
ZERENE
Brand Name English
SKP-1041
Code English
CL-284846
Code English
ZALEPLON [VANDF]
Common Name English
zaleplon [INN]
Common Name English
Zaleplon [WHO-DD]
Common Name English
ZALEPLON [ORANGE BOOK]
Common Name English
SONATA
Brand Name English
L846
Code English
ZALEPLON [JAN]
Common Name English
ZALEPLON [EMA EPAR]
Common Name English
Classification Tree Code System Code
EMA ASSESSMENT REPORTS SONATA (AUTHORIZED: SLEEP INITIATION AND MAINTENANCE DISORDERS)
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
EMA ASSESSMENT REPORTS ZERENE (WITHDRAWN: SLEEP INITIATION AND MAINTENANCE DISORDERS)
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
NDF-RT N0000183360
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
NCI_THESAURUS C29756
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
DEA NO. 2781
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
WHO-VATC QN05CF03
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
LIVERTOX NBK548924
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
WHO-ATC N05CF03
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
Code System Code Type Description
NCI_THESAURUS
C29551
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
PRIMARY
LACTMED
Zaleplon
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
PRIMARY
FDA UNII
S62U433RMH
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
PRIMARY
SMS_ID
100000088001
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
PRIMARY
CAS
151319-34-5
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
PRIMARY
WIKIPEDIA
ZALEPLON
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
PRIMARY
CHEBI
10102
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
PRIMARY
RXCUI
74667
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
PRIMARY RxNorm
MESH
C085665
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
PRIMARY
ChEMBL
CHEMBL1521
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
PRIMARY
IUPHAR
4345
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
PRIMARY
DRUG BANK
DB00962
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
PRIMARY
RS_ITEM_NUM
1724350
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
PRIMARY
DRUG CENTRAL
2857
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
PRIMARY
USAN
GG-36
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
PRIMARY
DAILYMED
S62U433RMH
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
PRIMARY
EVMPD
SUB00132MIG
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
PRIMARY
EPA CompTox
DTXSID5023748
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
PRIMARY
PUBCHEM
5719
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
PRIMARY
MERCK INDEX
m11579
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
PRIMARY Merck Index
INN
7312
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
PRIMARY
Related Record Type Details
TARGET->MODULATOR
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
USP
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METABOLITE -> PARENT
METABOLITE INACTIVE -> PARENT
MAJOR
URINE
METABOLITE INACTIVE -> PARENT
MINOR
URINE
METABOLITE INACTIVE -> PARENT
MINOR
URINE
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IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
Process impurity; may not be found in all manufacturing processes
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
Process impurity; may not be found in all manufacturing processes
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
Process impurity; may not be found in all manufacturing processes.
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC