Zaleplon
C17H15N5O 305.33
Acetamide, N-[3-(3-cyanopyrazolo[1,5-
]pyrimidin-7-yl)phenyl]-N-ethyl-;
3¢-(3-Cyanopyrazolo[1,5-]pyrimidin-7-yl)-N-ethylacetanilide
[151319-34-5].
(zal' e plon).
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C17H15N5O 305.33
Acetamide, N-[3-(3-cyanopyrazolo[1,5-
]pyrimidin-7-yl)phenyl]-N-ethyl-;
3¢-(3-Cyanopyrazolo[1,5-
]pyrimidin-7-yl)-N-ethylacetanilide
[151319-34-5].DEFINITION
Zaleplon contains NLT 98.0% and NMT 102.0% of C17H15N5O, calculated on the anhydrous basis.
IDENTIFICATION
• B.
The retention time of the major peak of the Sample solution corresponds to that of the Standard solution, as obtained in the Assay.
ASSAY
• Procedure
Buffer:
0.3 g/L of ammonium formate in water. Adjust with formic acid to a pH of 4.0.
Mobile phase:
Acetonitrile and Buffer (7:18)
Diluent:
Acetonitrile and water (1:1)
System suitability solution:
0.5 mg/mL of USP Zaleplon RS and 0.5 µg/mL each of USP Zaleplon Related Compound A RS and USP Zaleplon Related Compound B RS in Diluent
Standard solution:
50 µg/mL of USP Zaleplon RS in Diluent
Sample solution:
50 µg/mL of Zaleplon in Diluent
Chromatographic system
Mode:
LC
Detector:
UV 245 nm
Column:
4-mm × 10-cm; 3-µm packing L1
Flow rate:
1 mL/min
Injection size:
10 µL
Run time:
2 times the retention time of zaleplon
System suitability
Samples:
System suitability solution and Standard solution
Suitability requirements
[Note—The relative retention times for zaleplon and zaleplon related compound B are 1.0 and 1.2, respectively. ]
Resolution:
NLT 2.0 between zaleplon and zaleplon related compound B, System suitability solution
Tailing factor:
NMT 1.5, Standard solution
Relative standard deviation:
NMT 1.0%, Standard solution
Analysis
Samples:
Standard solution and Sample solution
Calculate the percentage of C17H15N5O in the portion of Zaleplon taken:
Result = (rU/rS) × (CS/CU) × 100
| rU | = | = peak response of zaleplon from the Sample solution |
| rS | = | = peak response of zaleplon from the Standard solution |
| CS | = | = concentration of USP Zaleplon RS in the Standard solution (µg/mL) |
| CU | = | = concentration of Zaleplon in the Sample solution (µg/mL) |
Acceptance criteria:
98.0%–102.0% on the anhydrous basis
IMPURITIES
Organic Impurities
• Procedure
Diluent:
Acetonitrile and water (1:1)
Solution A:
Use the Buffer in the Assay.
Solution B:
Acetonitrile
Mobile phase:
See the gradient table below.
| Time (min) |
Solution A (%) |
Solution B (%) |
|---|---|---|
| 0 | 80 | 20 |
| 11.0 | 68 | 32 |
| 17.0 | 60 | 40 |
| 30.0 | 60 | 40 |
| 31.0 | 80 | 20 |
| 35.0 | 80 | 20 |
System suitability solution:
Proceed as directed in the Assay.
Standard solution:
0.5 µg/mL of USP Zaleplon RS in Diluent
Sample solution:
0.5 mg/mL of Zaleplon in Diluent
Chromatographic system
Mode:
LC
Detector:
UV 245 nm
Column:
4.6-mm × 25-cm; 5-µm packing L1
Flow rate:
1 mL/min
Injection size:
10 µL
System suitability
Samples:
System suitability solution and Standard solution
Suitability requirements
Resolution:
NLT 14.0 between zaleplon related compound A and zaleplon, and NLT 2.0 between zaleplon and zaleplon related compound B; System suitability solution
Relative standard deviation:
NMT 5.0%, Standard solution
Analysis
Samples:
Standard solution and Sample solution
Calculate the percentage of any individual impurity in the portion of Zaleplon taken:
Result = (rU/rS) × (CS/CU) × (1/F) × 100
| rU | = | = peak response of an individual impurity from the Sample solution |
| rS | = | = peak response of zaleplon from the Standard solution |
| CS | = | = concentration of USP Zaleplon RS in the Standard solution (mg/mL) |
| CU | = | = concentration of Zaleplon in the Sample solution (mg/mL) |
| F | = | = relative response factor for the corresponding impurity peak (see Impurity Table 1) |
Acceptance criteria
Individual impurities:
See Impurity Table 1.
Total impurities:
NMT 0.5%
Impurity Table 1
| Name | Relative Retention Time |
Relative Response Factor |
Acceptance Criteria, NMT (%) |
|---|---|---|---|
| Cyanopyrazolaminea | 0.18 | 1.0 | 0.10 |
| Zaleplon related compound Ab |
0.58 | 0.76 | 0.10 |
| Zaleplon | 1.0 | — | — |
| Zaleplon related compound Bc |
1.08 | 0.92 | 0.10 |
| Any unspecified individual impurity |
— | 1.0 | 0.10 |
|
a
3-Aminopyrazole-4-carbonitrile.
b
(E)-N-{3-[3-(Dimethylamino)acryloyl]phenyl}-N-ethylacetamide.
c
N-[3-(3-Cyanopyrazolo[1,5-
]pyrimidin-5-yl)phenyl]-N-ethylacetamide.
|
|||
SPECIFIC TESTS
• Water Determination, Method I 
921
:
NMT 2.0%
921:
NMT 2.0%
ADDITIONAL REQUIREMENTS
• Packaging and Storage:
Preserve in light-resistant containers, and store at room temperature.
• USP Reference Standards 11
11
USP Zaleplon RS
USP Zaleplon Related Compound A RS
(E)-N-{3-[3-(Dimethylamino)acryloyl]phenyl}-N-ethylacetamide.
C15H20N2O2 260.33
(E)-N-{3-[3-(Dimethylamino)acryloyl]phenyl}-N-ethylacetamide.
C15H20N2O2 260.33
USP Zaleplon Related Compound B RS
N-[3-(3-Cyanopyrazolo[1,5-]pyrimidin-5-yl)phenyl]-N-ethylacetamide.
C17H15N5O 305.33
N-[3-(3-Cyanopyrazolo[1,5-
]pyrimidin-5-yl)phenyl]-N-ethylacetamide.
C17H15N5O 305.33
Auxiliary Information—
Please check for your question in the FAQs before contacting USP.
| Topic/Question | Contact | Expert Committee |
|---|---|---|
| Monograph | Hariram Ramanathan, M.S.
Associate Scientific Liaison 1-301-816-8313 |
(SM42010) Monographs - Small Molecules 4 |
| Reference Standards | RS Technical Services 1-301-816-8129 rstech@usp.org |
USP35–NF30 Page 5057
Pharmacopeial Forum: Volume No. 36(4) Page 938