CAS 151319-34-5|Zaleplon|N-(3-{3-cyanopyrazolo[1,5-a]pyrimidin-7-yl}phenyl)-N-ethylacetamide|Zaleplon|N-(3-{3-cyanopyrazolo[1,5-a]pyrimidin-7-yl}phenyl)-N-ethylacetamide|Sonata|CL-284846|N-[3-(3-Cya...

General Information

Structure

Molecular Formula

C₁₇H₁₅N₅O

Molecular Mass

305.3339

Exact Mass

305.12766013

Charge

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

InChIKey

HUNXMJYCHXQEGX-UHFFFAOYSA-N

Canonic Smiles

CCN(c1cccc(c1)c1ccnc2n1ncc2C#N)C(=O)C

Isomeric Smiles

O=C(N(c1cc(c2n3ncc(c3ncc2)C#N)ccc1)CC)C

Calculated Properties

JChem

LogD (pH = 7.4)

1.53

LogD (pH = 5.5)

1.53

Log P

1.53

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

-0.50

Polar Surface Area

74.29

Polarizability

32.09

Molar Refractivity

97.24

LOG S

-3.80

Data Source

Names and Identifiers

Synonyms

ZaleplonZaleplonN-[3-(3-Cyanopyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-N-ethylacetamideSonataCL-284846DEA No. 2781zaleplonN-[3-(3-Cyanopyrazolo-[1,5-a]pyrimidin-7-yl)phenyl)-N-ethylacetamidezaleplon3'-(3-Cyanopyrazolo(1,5-a)pyrimidin-7-yl)-N-ethylacetanilide

IUPAC name

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

IUPAC Traditional name

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

Brand Name

ZalaplonSonata

International Nonproprietary Name (INN)

zaleplon

Names and Identifiers

Registration numbers

CAS Number

151319-34-5

MDL Number

MFCD00867990

PubChem CID

5719

PubChem SID

1609643014650826787246409

MetaboLights Database

MTBLS2406MTBLS867MTBLS673MTBLS3943

ACToR Database

Beilstein Number

BindingDB Database

CHEMBL

Drug Central Database

BRENDA Database

DrugBank ID

Wikipedia Title

LINCS Database

Patent number

KEGG ID

SureChEMBL Database

BKMS React Database

CHEBI ID

KEGG DRUG Database

CompTox Database

BRENDA Ligand Database

84232

Registration numbers

Properties

Safety Information

Acute toxicity (oral, dermal, inhalation), category 4

Skin irritation, category 2

Eye irritation, category 2

Skin sensitisation, category 1

Specific Target Organ Toxicity – Single exposure, category 3

Pharmacology Properties

Benzodiazepine receptor agonist, but lacks Bz-associated side-effects

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

DrugBank

DB00962

Drug Groups

illicit; approved; investigational

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 schedule IV drug in the United States.

Indication

For the treatment of short-term treatment of insomnia in adults.

Pharmacology

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 (GABA_BZ) receptor complex. Subunit modulation of the GABA_BZ 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 GABA_A-receptor chloride ionophore complex at benzodiazepine(BZ) omega-1 (BZ1, ο1) receptors.

Toxicity

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

Affected Organisms

Humans and other mammals

Biotransformation

Zaleplon is primarily metabolized by aldehyde oxidase.

Absorption

Absorption Zaleplon is rapidly and almost completely absorbed following oral administration.

Half Life

Approximately 1 hour

Protein Binding

Approximately 60% (in vitro plasma protein binding).

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.

Distribution

* 1.4 L/kg

Clearance

* 1 L/h/kg

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. [Pubmed]

• 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]

• Ramakrishnan K, Scheid DC: Treatment options for insomnia. Am Fam Physician. 2007 Aug 15;76(4):517-26. [Pubmed]

• Barbera J, Shapiro C: Benefit-risk assessment of zaleplon in the treatment of insomnia. Drug Saf. 2005;28(4):301-18. [Pubmed]

• Dooley M, Plosker GL: Zaleplon: a review of its use in the treatment of insomnia. Drugs. 2000 Aug;60(2):413-45. [Pubmed]

• 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]

• 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]

External Links

• [Wikipedia]

• [RxList]

• [PDRhealth]

• [Drugs.com]

Sigma Aldrich

Z0502

Biochem/physiol Actions
Zaleplon is a non-benzodiazepine agonist at the benzodiazepine site of the GABAA receptor; sedative; hypnotic.

TRC

Z145000

Selective non-benzodiazepine GABAA receptor agonist.

ChEBI

CHEBI:10102

A pyrazolo[1,5-a]pyrimidine having a nitrile group at position 3 and a 3-(N-ethylacetamido)phenyl substituent at the 7-position.

Molecule Details

References

PubChem Literature

From Data Sources

• Barbera J, Shapiro C: Benefit-risk assessment of zaleplon in the treatment of insomnia. Drug Saf. 2005;28(4):301-18. Pubmed

• 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

• 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

• 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

• Ramakrishnan K, Scheid DC: Treatment options for insomnia. Am Fam Physician. 2007 Aug 15;76(4):517-26. Pubmed

• Dooley M, Plosker GL: Zaleplon: a review of its use in the treatment of insomnia. Drugs. 2000 Aug;60(2):413-45. Pubmed

• Beer, B., et al.: J. Clin. Pharmacol., 34, 335 (1993)

• Elie, R., et al.: J. Clin. Psychiatry, 60, 536 (1993)

• Heydorn, W.E., et al.:

• Rosen, A.S., et al.: Biopharm. Drug Dispos., 20, 171 (1993)

• Allen, D., et al.: Eur. J. Clin. Pharmacol., 45, 313 (1993)

• Beer, B. et al., CNS Drug Rev., 1997, 3, 207, (rev)

• Beer, B. et al., J. Clin. Pharmacol., 1994, 34, 335, (pharmacol)

• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 698

• Dooley, M. et al., Drugs, 2000, 60, 413-445, (rev)

• Vanover, K.E. et al., Psychopharmacology, 1994, 115, 289, (pharmacol)

• Allen, D. et al., Eur. J. Clin. Pharmacol., 1993, 45, 313, (pharmacol, man)

• Hurst, M. et al., CNS Drugs, 1999, 11, 387-392

• Vanover, K.E. et al., Drug Dev. Res., 1994, 33, 39, (pharmacol)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

IUPAC name

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

IUPAC Traditional name

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

Brand Name

ZalaplonSonata

International Nonproprietary Name (INN)

zaleplon

Registration numbers

CAS Number

151319-34-5

MDL Number

MFCD00867990

PubChem CID

5719

PubChem SID

1609643014650826787246409

MetaboLights Database

MTBLS2406MTBLS867MTBLS673MTBLS3943

ACToR Database

Beilstein Number

BindingDB Database

CHEMBL

Drug Central Database

BRENDA Database

DrugBank ID

Wikipedia Title

LINCS Database

Patent number

KEGG ID

SureChEMBL Database

BKMS React Database

CHEBI ID

KEGG DRUG Database

CompTox Database

BRENDA Ligand Database

84232

Molecule Details

DrugBank

DB00962

Drug Groups

illicit; approved; investigational

Description

Indication

For the treatment of short-term treatment of insomnia in adults.

Pharmacology

Toxicity

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

Affected Organisms

Humans and other mammals

Biotransformation

Zaleplon is primarily metabolized by aldehyde oxidase.

Absorption

Absorption Zaleplon is rapidly and almost completely absorbed following oral administration.

Half Life

Approximately 1 hour

Protein Binding

Approximately 60% (in vitro plasma protein binding).

Elimination

Distribution

* 1.4 L/kg

Clearance

* 1 L/h/kg

References

• 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]

• Ramakrishnan K, Scheid DC: Treatment options for insomnia. Am Fam Physician. 2007 Aug 15;76(4):517-26. [Pubmed]

• Barbera J, Shapiro C: Benefit-risk assessment of zaleplon in the treatment of insomnia. Drug Saf. 2005;28(4):301-18. [Pubmed]

• Dooley M, Plosker GL: Zaleplon: a review of its use in the treatment of insomnia. Drugs. 2000 Aug;60(2):413-45. [Pubmed]

• 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]

• 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]

External Links

• [Wikipedia]

• [RxList]

• [PDRhealth]

• [Drugs.com]

Sigma Aldrich

Z0502

Biochem/physiol Actions
Zaleplon is a non-benzodiazepine agonist at the benzodiazepine site of the GABAA receptor; sedative; hypnotic.

TRC

Z145000

Selective non-benzodiazepine GABAA receptor agonist.

ChEBI

CHEBI:10102

A pyrazolo[1,5-a]pyrimidine having a nitrile group at position 3 and a 3-(N-ethylacetamido)phenyl substituent at the 7-position.

References

PubChem Literature

From Data Sources

• Barbera J, Shapiro C: Benefit-risk assessment of zaleplon in the treatment of insomnia. Drug Saf. 2005;28(4):301-18. Pubmed

• 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

• 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

• 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

• Ramakrishnan K, Scheid DC: Treatment options for insomnia. Am Fam Physician. 2007 Aug 15;76(4):517-26. Pubmed

• Dooley M, Plosker GL: Zaleplon: a review of its use in the treatment of insomnia. Drugs. 2000 Aug;60(2):413-45. Pubmed

• Beer, B., et al.: J. Clin. Pharmacol., 34, 335 (1993)

• Elie, R., et al.: J. Clin. Psychiatry, 60, 536 (1993)

• Heydorn, W.E., et al.:

• Rosen, A.S., et al.: Biopharm. Drug Dispos., 20, 171 (1993)

• Allen, D., et al.: Eur. J. Clin. Pharmacol., 45, 313 (1993)

• Beer, B. et al., CNS Drug Rev., 1997, 3, 207, (rev)

• Beer, B. et al., J. Clin. Pharmacol., 1994, 34, 335, (pharmacol)

• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 698

• Dooley, M. et al., Drugs, 2000, 60, 413-445, (rev)

• Vanover, K.E. et al., Psychopharmacology, 1994, 115, 289, (pharmacol)

• Allen, D. et al., Eur. J. Clin. Pharmacol., 1993, 45, 313, (pharmacol, man)

• Hurst, M. et al., CNS Drugs, 1999, 11, 387-392

• Vanover, K.E. et al., Drug Dev. Res., 1994, 33, 39, (pharmacol)

Bioactivity

PubChem BioAssay

Properties

Safety Information

Acute toxicity (oral, dermal, inhalation), category 4

Skin irritation, category 2

Eye irritation, category 2

Skin sensitisation, category 1

Specific Target Organ Toxicity – Single exposure, category 3

Pharmacology Properties

Benzodiazepine receptor agonist, but lacks Bz-associated side-effects

Molecule

ID:838