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

• ChemBase ID: 838
• Molecular Formular: C17H15N5O
• Molecular Mass: 305.3339
• Monoisotopic Mass: 305.12766013
• SMILES: O=C(N(c1cc(c2n3ncc(c3ncc2)C#N)ccc1)CC)C
• Canonical SMILES: CCN(c1cccc(c1)c1ccnc2n1ncc2C#N)C(=O)C
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(3-{3-cyanopyrazolo[1,5-a]pyrimidin-7-yl}phenyl)-N-ethylacetamide
• IUPAC Traditional name: N-(3-{3-cyanopyrazolo[1,5-a]pyrimidin-7-yl}phenyl)-N-ethylacetamide; zaleplon
• Brand Name: Sonata; Zalaplon
• Synonyms: N-[3-(3-Cyanopyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-N-ethylacetamide; Sonata; DEA No. 2781; zaleplon; Zaleplon; CL-284846; N-[3-(3-Cyanopyrazolo-[1,5-a]pyrimidin-7-yl)phenyl)-N-ethylacetamide; Zaleplon

Database IDs

• CAS Number: 151319-34-5
• MDL Number: MFCD00867990
• PubChem SID: 46508267; 160964301
• PubChem CID: 5719

CALCULATED PROPERTIES

JChem

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 1.534877
• LogD (pH = 7.4): 1.5348797
• Log P: 1.5348797
• Molar Refractivity: 97.2364 cm^3
• Polarizability: 33.73101 Å^3
• Polar Surface Area: 74.29 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.0
• LOG S: -3.88
• Solubility (Water): 4.03e-02 g/l

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; DMSO: ~20 mg/mL; H2O: insoluble; Methanol
• Apperance: white solid; White to Off-White Solid
• Melting Point: 186-187°C
• Hydrophobicity(logP): 0.9

Safety Information

• Storage Condition: Controlled Substance, -20°C Freezer; desiccated; protect from light
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Drug Control: USDEA Schedule IV; psychotrope; regulated under CDSA - not available from Sigma-Aldrich Canada
• Storage Temperature: 2-8°C

Pharmacology Properties

• Mechanism of Action: Benzodiazepine receptor agonist, but lacks Bz-associated side-effects

Product Information

• Purity: ≥98% (HPLC)
• Application(s): Hypnotic; Psychosedative; Sedative; Sedatives; Tranquilizer
• Empirical Formula (Hill Notation): C17H15N5O

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.

Toronto Research Chemicals - Z145000

Selective non-benzodiazepine GABAA receptor agonist.

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