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Synopsis

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Chemistry

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Also known as: 151319-34-5, Sonata, Cl-284846, Skp-1041, N-[3-(3-cyanopyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-n-ethylacetamide, Zal-846

Molecular Formula

C₁₇H₁₅N₅O

Molecular Weight

305.33 g/mol

InChI Key

HUNXMJYCHXQEGX-UHFFFAOYSA-N

FDA UNII

S62U433RMH

Zaleplon is a nonbenzodiazepine from the pyrazolopyrimidine class with hypnotic, sedative, anxiolytic, and muscle relaxant properties. Zaleplon interacts with the gamma-aminobutyric acid (GABA) -A receptor, thereby affecting the chloride channel ionophore complex and potentiating the inhibitory effects of GABA. In addition, zaleplon binds selectively to the brain omega-1 receptor situated on the alpha subunit of the GABA-A/chloride ion channel receptor complex and potentiates t-butyl-bicyclophosphorothionate (TBPS) binding.

Zaleplon is a gamma-Aminobutyric Acid A Receptor Agonist. The mechanism of action of zaleplon is as a GABA A Agonist. The physiologic effect of zaleplon is by means of Central Nervous System Depression.

1 2D Structure

Zaleplon

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

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

2.1.2 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

2.1.3 InChI Key

HUNXMJYCHXQEGX-UHFFFAOYSA-N

2.1.4 Canonical SMILES

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

2.2 Other Identifiers

2.2.1 UNII

S62U433RMH

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 3'-(3-cyanopyrazolo(1,5-alpha)pyrimidin-7-yl)-n-ethylacetanilide

2. Cl 284,846

3. Cl 284846

4. Cl-284846

5. Cl284,846

6. L 846

7. L-846

8. N-(3-(3-cyanopyrazolo(1,5-a)pyrimidin-7-yl)phenyl)-n-ethylacetamide

9. Skp-1041

10. Sonata

11. Starnoc

12. Zelepion

2.3.2 Depositor-Supplied Synonyms

1. 151319-34-5

2. Sonata

3. Cl-284846

4. Skp-1041

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

6. Zal-846

7. Cl 284,846

8. Ljc 10846

9. L846

10. Cl 284846

11. Ljc-10846

12. L-846

13. Dea No. 2781

14. Zaleplon Civ

15. 3'-(3-cyanopyrazolo(1,5-a)pyrimidin-7-yl)-n-ethylacetanilide

16. N-(3-(3-cyanopyrazolo(1,5-a)pyrimidin-7-yl)phenyl)-n-ethylacetamide

17. S62u433rmh

18. Chebi:10102

19. N-(3-(3-cyanopyrazolo[1,5-a]pyrimidin-7-yl)phenyl)-n-ethylacetamide

20. Ncgc00160525-01

21. Dsstox_cid_3748

22. Dsstox_rid_77183

23. Dsstox_gsid_23748

24. Zal 846

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

26. Staccato-zaleplon

27. Smr000238180

28. Sonata (tn)

29. Cas-151319-34-5

30. Unii-s62u433rmh

31. Zaleplon Ap

32. Zaleplon [usan:usp:inn:ban]

33. 3'-(3-cyanopyrazolo(1,5-alpha)pyrimidin-7-yl)-n-ethylacetanilide

34. Az-007

35. Zaleplon [usan]

36. Zaleplon [inn]

37. Zaleplon [jan]

38. Zaleplon [mi]

39. Zaleplon [vandf]

40. Zaleplon [mart.]

41. Zaleplon [who-dd]

42. Acetamide, N-(3-(3-cyanopyrazolo(1,5-a)pyrimidin-7-yl)phenyl)-n-ethyl-

43. Zaleplon (jan/usp/inn)

44. Chembl1521

45. Zaleplon [ema Epar]

46. Schembl29118

47. Mls000759451

48. Mls001424238

49. Bidd:gt0046

50. Zaleplon [orange Book]

51. Zaleplon Civ [usp-rs]

52. Gtpl4345

53. Zinc6300

54. Dtxsid5023748

55. Zaleplon [usp Monograph]

56. Bdbm86521

57. Zaleplon 1.0 Mg/ml In Methanol

58. Hms2052j11

59. Hms3394j11

60. Hms3713h08

61. Act04427

62. Bcp21340

63. Cas_5719

64. Nsc_5719

65. Tox21_111872

66. N-[3-(3-cyanopyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-n-ethyl-acetamide

67. Zaleplon, >=98% (hplc), Solid

68. Acetamide, N-(3-(3-cyanopyrazolo(1,5-alpha)pyrimidin-7-yl)phenyl)-n-ethyl-

69. Akos000280863

70. Tox21_111872_1

71. Ac-2082

72. Ccg-101187

73. Db00962

74. Nc00437

75. Ss-4571

76. Ncgc00160525-02

77. Hy-14265

78. Db-015068

79. A12993

80. C07484

81. D00530

82. Ab00640003_03

83. 319z345

84. A809159

85. Q145052

86. Sr-01000759426

87. Sr-01000759426-3

88. Zaleplon, United States Pharmacopeia (usp) Reference Standard

89. N-[3-(cyanopyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-n-ethylacetamide

90. 3'-(3-cyanopyrazolo(1,5-.alpha.)pyrimidin-7-yl)-n-ethylacetanilide

91. N-[3-(3-cyanopyrazolo-[1,5-a]-pyrimidin-7-yl)-phenyl]-n-ethyl Acetamide

92. Acetamide, N-(3-(3-cyanopyrazolo(1,5-.alpha.)pyrimidin-7-yl)phenyl)-n-ethyl-

93. Zaleplon Solution, 1.0 Mg/ml In Methanol, Ampule Of 1 Ml, Certified Reference Material

94. 1007130-22-4

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₇H₁₅N₅O
Molecular Weight	305.33 g/mol
XLogP3	1
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	3
Exact Mass	305.12766012 g/mol
Monoisotopic Mass	305.12766012 g/mol
Topological Polar Surface Area	74.3 Å²
Heavy Atom Count	23
Formal Charge	0
Complexity	487
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 4
Drug Name	Sonata
PubMed Health	Zaleplon (By mouth)
Drug Classes	Nonbarbiturate Hypnotic
Drug Label	Zaleplon is a nonbenzodiazepine hypnotic from the pyrazolopyrimidine class. The chemical name of zaleplon is N-[3-(3-cyanopyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-N-ethylacetamide. Its empirical formula is C17H15N5O, and its molecular weight is 305.34....
Active Ingredient	Zaleplon
Dosage Form	Capsule
Route	Oral
Strength	5mg; 10mg
Market Status	Prescription
Company	Pfizer

2 of 4
Drug Name	Zaleplon
PubMed Health	Zaleplon (By mouth)
Drug Classes	Nonbarbiturate Hypnotic
Drug Label	Zaleplon is a nonbenzodiazepine hypnotic from the pyrazolopyrimidine class. The chemical name of zaleplon is N-[3-(3-cyanopyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-N-ethylacetamide. Its empirical formula is C17H15N5O, and its molecular weight is 305.34....
Active Ingredient	Zaleplon
Dosage Form	Capsule
Route	Oral
Strength	5mg; 10mg
Market Status	Prescription
Company	Upsher Smith; Unichem; Aurobindo Pharma; Cipla; Hikma Pharms; Roxane; Teva Pharms; Orchid Hlthcare; Mylan

3 of 4
Drug Name	Sonata
PubMed Health	Zaleplon (By mouth)
Drug Classes	Nonbarbiturate Hypnotic
Drug Label	Zaleplon is a nonbenzodiazepine hypnotic from the pyrazolopyrimidine class. The chemical name of zaleplon is N-[3-(3-cyanopyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-N-ethylacetamide. Its empirical formula is C17H15N5O, and its molecular weight is 305.34....
Active Ingredient	Zaleplon
Dosage Form	Capsule
Route	Oral
Strength	5mg; 10mg
Market Status	Prescription
Company	Pfizer

4 of 4
Drug Name	Zaleplon
PubMed Health	Zaleplon (By mouth)
Drug Classes	Nonbarbiturate Hypnotic
Drug Label	Zaleplon is a nonbenzodiazepine hypnotic from the pyrazolopyrimidine class. The chemical name of zaleplon is N-[3-(3-cyanopyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-N-ethylacetamide. Its empirical formula is C17H15N5O, and its molecular weight is 305.34....
Active Ingredient	Zaleplon
Dosage Form	Capsule
Route	Oral
Strength	5mg; 10mg
Market Status	Prescription
Company	Upsher Smith; Unichem; Aurobindo Pharma; Cipla; Hikma Pharms; Roxane; Teva Pharms; Orchid Hlthcare; Mylan

4.2 Drug Indication

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

FDA Label

Sonata is indicated for the treatment of patients with insomnia who have difficulty falling asleep. It is indicated only when the disorder is severe, disabling or subjecting the individual to extreme distress.

5 Pharmacology and Biochemistry

5.1 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, 1) receptors.

5.2 MeSH Pharmacological Classification

Anticonvulsants

Drugs used to prevent SEIZURES or reduce their severity. (See all compounds classified as Anticonvulsants.)

Hypnotics and Sedatives

Drugs used to induce drowsiness or sleep or to reduce psychological excitement or anxiety. (See all compounds classified as Hypnotics and Sedatives.)

GABA Modulators

Substances that do not act as agonists or antagonists but do affect the GAMMA-AMINOBUTYRIC ACID receptor-ionophore complex. GABA-A receptors (RECEPTORS, GABA-A) appear to have at least three allosteric sites at which modulators act: a site at which BENZODIAZEPINES act by increasing the opening frequency of GAMMA-AMINOBUTYRIC ACID-activated chloride channels; a site at which BARBITURATES act to prolong the duration of channel opening; and a site at which some steroids may act. GENERAL ANESTHETICS probably act at least partly by potentiating GABAergic responses, but they are not included here. (See all compounds classified as GABA Modulators.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

ZALEPLON

5.3.2 FDA UNII

S62U433RMH

5.3.3 Pharmacological Classes

GABA A Agonists [MoA]; gamma-Aminobutyric Acid A Receptor Agonist [EPC]; Central Nervous System Depression [PE]

5.4 ATC Code

N05CF03

N - Nervous system

N05 - Psycholeptics

N05C - Hypnotics and sedatives

N05CF - Benzodiazepine related drugs

N05CF03 - Zaleplon

5.5 Absorption, Distribution and Excretion

Absorption

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

Route of 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.

Volume of Distribution

1.4 L/kg

Clearance

1 L/h/kg

5.6 Metabolism/Metabolites

Zaleplon is primarily metabolized by aldehyde oxidase.

Zaleplon has known human metabolites that include Dementhylazed-zaleplon.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

5.7 Biological Half-Life

Approximately 1 hour

5.8 Mechanism of Action

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.

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01

Aurobindo Pharma Limited

India

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Israel

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India

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Argentina

Israel

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API Reference Price

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Number of Transactions

Total Quantity (KGS)

Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

Importing Country	Total Quantity (KGS)	Average Price (USD/KGS)	Number of Transactions

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INTERMEDIATES SUPPLIERS

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Europe

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DRUG PRODUCT COMPOSITIONS

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DOSAGE - CAPSULE;ORAL - 10MG

USFDA APPLICATION NUMBER - 20859

DOSAGE - CAPSULE;ORAL - 5MG

USFDA APPLICATION NUMBER - 20859

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Fillers, Diluents & Binders

Direct Compression

Thickeners and Stabilizers

Granulation

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Coating Systems & Additives

Co-Processed Excipients

Topical

Controlled & Modified Release

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US Medicaid Prescriptions

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CHEMISTRY

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ACTIVE PHARMA INGREDIENTS

14 API Suppliers

9 USDMF

3 EU WC

4 NDC API

6 Listed Suppliers

$ API Reference Price

INTERMEDIATES

3 Intermediates Suppliers

FINISHED DOSAGE FORMULATIONS

33 FDF Dossiers

22 FDA Orange Book

6 Europe

5 Listed Dossiers

DRUG PRODUCT COMPOSITIONS

CAPSULE;ORAL - 10MG

CAPSULE;ORAL - 5MG

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18 BASF

5 DFE Pharma

2 Finar

6 Gangwal Chemicals

1 Ideal Cures Pvt Ltd

2 Ingredion Pharma Solutions

26 Kerry

3 Lonza Capsugel

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2 Nomisma Healthcare

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17 Roquette

2 Seppic

3 Shanghai Shenmei Pharmaceutical Technology Co., Ltd

9 Sigachi Industries

1 Valens Pharmachem

2 Vasa Pharmachem

EXCIPIENTS BY APPLICATIONS

61 Fillers, Diluents & Binders

29 Direct Compression

22 Thickeners and Stabilizers

17 Granulation

16 Lubricants & Glidants

15 Coating Systems & Additives

15 Co-Processed Excipients

12 Topical

11 Controlled & Modified Release

9 Disintegrants & Superdisintegrants

8 Film Formers & Plasticizers

8 Empty Capsules

8 Taste Masking

6 Solubilizers

5 Chewable & Orodispersible Aids

4 Emulsifying Agents

4 Parenteral

3 Coloring Agents

1 API Stability Enhancers

1 Surfactant & Foaming Agents

1 Rheology Modifiers

DIGITAL CONTENT

8 NEWS #PharmaBuzz

GLOBAL SALES INFORMATION

1 US Medicaid Prescriptions

14 Finished Drug Prices

PATENTS & EXCLUSIVITIES

2 Health Canada Patents