Mupirocin Calcium
(mue pir' oh sin kal' see um).
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1075.34Nonanoic acid, 9-[[3-Methyl-1-oxo-4-[tetrahydro-3,4-dihydroxy-5-[[3-(2-hydroxy-1-methylpropyl)oxiranyl]methyl]-2H-pyran-2-yl]-2-butenyl]oxy-, calcium salt (2:1), dihydrate, [2S-[2
(E),3
,4,5[2R*,3R*(1R*,2R*)]]]-.
(
E,2S,3R,4R,5S)-5-[(2S,3S,4S,5S)-2,3-Epoxy-5-hydroxy-4-methylhexyl]tetrahydro-3,4-dihydroxy--methyl-2H-pyran-2-crotonic acid, ester with 9-hydroxynonanoic acid, calcium salt (2:1), dihydrate
[115074-43-6].» Mupirocin Calcium contains the equivalent of not less than 865 µg and not more than 936 µg of mupirocin (C26H44O9) per mg.
Packaging and storage—
Preserve in tight containers. Store at 25
, excursions permitted between 15 and 30.
, excursions permitted between 15 and 30.
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Identification—
A:
Infrared Absorption 
197M
—[note—Do not dry or grind extensively. ]
197M—[note—Do not dry or grind extensively. ]
B:
The retention time of the major peak in the chromatogram of the Assay preparation corresponds to that in the chromatogram of the Standard preparation, as obtained in the Assay.
C:
When moistened with hydrochloric acid, it meets the requirements of the flame test for Calcium 191.
191.
Water, Method I 921:
not less than 3.0% and not more than 4.5%.
921:
not less than 3.0% and not more than 4.5%.
Chloride 221—
Dissolve 50 mg in a mixture of 1 mL of 2 N nitric acid and 15 mL of methanol. Add 1 mL of silver nitrate TS: the turbidity does not exceed that produced by 0.70 mL of 0.020 N hydrochloric acid (0.5%).
221—
Dissolve 50 mg in a mixture of 1 mL of 2 N nitric acid and 15 mL of methanol. Add 1 mL of silver nitrate TS: the turbidity does not exceed that produced by 0.70 mL of 0.020 N hydrochloric acid (0.5%).
Related compounds—
0.1 M Ammonium acetate—
Prepare as directed in the Assay.
Mobile phase—
Prepare a filtered and degassed mixture of 0.1 M Ammonium acetate and tetrahydrofuran (70:30). Make adjustments if necessary (see System Suitability under Chromatography 621).
621).
pH 4 Acetate buffer—
Transfer about 13.6 g of sodium acetate to a 1000-mL volumetric flask, and dissolve in about 900 mL of water. Adjust with glacial acetic acid to a pH of 4.0, and dilute with water to volume.
Diluent—
Prepare a mixture of pH 4 Acetate buffer and methanol (1:1).
Standard solution—
Transfer about 25 mg of USP Mupirocin Lithium RS, accurately weighed, to a 200-mL volumetric flask, dissolve in and dilute with Diluent to volume, and mix.
Test solution—
Transfer about 50 mg of Mupirocin Calcium, accurately weighed, to a 10-mL volumetric flask, dissolve in and dilute with Diluent to volume, and mix.
Resolution solution—
Adjust 10 mL of the Standard solution with 6 N hydrochloric acid to a pH of 2.0, allow to stand for 20 hours, and adjust with 5 N sodium hydroxide to a pH of 4.0.
Chromatographic system (see Chromatography 621)—
The liquid chromatograph is equipped with a 240-nm detector and a 4.6-mm × 25-cm column that contains 5-µm packing L7. The flow rate is about 1 mL per minute. Chromatograph the Resolution solution, and record the peak responses as directed for Procedure: two peaks are observed at retention times of about 0.63 and 0.67 relative to mupirocin. These peaks correspond to mupirocin rearrangement products. The resolution, R, between the second of these two peaks and the peak corresponding to mupirocin is not less than 7.0. Chromatograph the Standard solution, and record the peak responses as directed for Procedure: the column efficiency for the mupirocin peak is not less than 3000 theoretical plates; the tailing factor for the mupirocin peak is not more than 2; and the relative standard deviation of the mupirocin peak for replicate injections is not more than 5%.
621)—
The liquid chromatograph is equipped with a 240-nm detector and a 4.6-mm × 25-cm column that contains 5-µm packing L7. The flow rate is about 1 mL per minute. Chromatograph the Resolution solution, and record the peak responses as directed for Procedure: two peaks are observed at retention times of about 0.63 and 0.67 relative to mupirocin. These peaks correspond to mupirocin rearrangement products. The resolution, R, between the second of these two peaks and the peak corresponding to mupirocin is not less than 7.0. Chromatograph the Standard solution, and record the peak responses as directed for Procedure: the column efficiency for the mupirocin peak is not less than 3000 theoretical plates; the tailing factor for the mupirocin peak is not more than 2; and the relative standard deviation of the mupirocin peak for replicate injections is not more than 5%.
Procedure—
Separately inject equal volumes (about 20 µL) of the Standard solution and the Test solution into the chromatograph, and measure the peak area responses for all of the peaks. Calculate the percentage of each related compound in the portion of Mupirocin Calcium taken by the formula:
(CS / CU)(ri / rS)(P/1000)(100)
in which CS is the concentration, in mg per mL, of USP Mupirocin Lithium RS in the Standard solution; CU is the concentration, in mg per mL, of Mupirocin Calcium in the Test solution; ri is the peak area for any impurity obtained from the Test solution; rS is the peak area for mupirocin obtained from the Standard solution; and P/1000 is the potency of mupirocin, converted to mg per mg, of USP Mupirocin Lithium RS. Disregard any peak with an area less than 0.05 times the area of the mupirocin peak in the chromatogram obtained from the Standard solution.
| Peak Identification |
Relative Retention Time |
Limit (%, w/w) |
|---|---|---|
| Pseudomonic acid D1 | 0.75 | NMT 2.5 |
| Mupirocin | 1.0 | — |
| Any other unspecified impurity |
— | NMT 1 |
| Total impurities | — | NMT 4.5 |
|
1
(E)-9-{(E)-4-[(2S,3R,4R,5S)-3,4-Dihydroxy-5-({(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl}methyl)tetrahydro-2H-pyran-2-yl]-3-methylbut-2-enoyloxy}non-4-enoic acid.
|
||
Assay—
0.1 M Ammonium acetate—
Transfer about 7.7 g of ammonium acetate to a 1000-mL volumetric flask, dissolve in about 900 mL of water, adjust with glacial acetic acid to a pH of 5.7, and dilute with water to volume.
Mobile phase—
Prepare a filtered and degassed mixture of 0.1 M Ammonium acetate and tetrahydrofuran (68:32). Make adjustments if necessary (see System Suitability under Chromatography 621).
621).
Standard preparation—
Transfer about 25 mg of USP Mupirocin Lithium RS, accurately weighed, to a 200-mL volumetric flask, dissolve in 5 mL of methanol, dilute with 0.1 M Ammonium acetate to volume, and mix.
Assay preparation—
Transfer about 25 mg of Mupirocin Calcium, accurately weighed, to a 200-mL volumetric flask, dissolve in 5 mL of methanol, dilute with 0.1 M Ammonium acetate to volume, and mix.
Resolution solution—
Adjust 10 mL of the Standard preparation with 6 N hydrochloric acid to a pH of 2.0, and allow to stand for 20 hours.
Chromatographic system (see Chromatography 621)—
The liquid chromatograph is equipped with a 230-nm detector and a 4.6-mm × 25-cm column that contains 5-µm packing L7. The flow rate is about 1 mL per minute. Chromatograph the Resolution solution, and record the peak responses as directed for Procedure: the resolution, R, of the second of the two peaks corresponding to mupirocin rearrangement products and the peak corresponding to mupirocin is not less than 7.0. Chromatograph the Standard preparation, and record the peak responses as directed for Procedure: the relative standard deviation for replicate injections is not more than 1.0%.
621)—
The liquid chromatograph is equipped with a 230-nm detector and a 4.6-mm × 25-cm column that contains 5-µm packing L7. The flow rate is about 1 mL per minute. Chromatograph the Resolution solution, and record the peak responses as directed for Procedure: the resolution, R, of the second of the two peaks corresponding to mupirocin rearrangement products and the peak corresponding to mupirocin is not less than 7.0. Chromatograph the Standard preparation, and record the peak responses as directed for Procedure: the relative standard deviation for replicate injections is not more than 1.0%.
Procedure—
Separately inject equal volumes (about 20 µL) of the Standard preparation and the Assay preparation into the chromatograph, and measure the peak area responses for the major peaks. Calculate the quantity, in µg, of mupirocin (C26H44O9) in each mg of Mupirocin Calcium taken by the formula:
P(CS / CU)(rU / rS)
in which P is the potency, in µg, of mupirocin in each mg of USP Mupirocin Lithium RS; CS is the concentration, in mg per mL, of USP Mupirocin Lithium RS in the Standard preparation; CU is the concentration, in mg per mL, of Mupirocin Calcium in the Assay preparation; and rU and rS are the mupirocin peak area responses obtained from the Assay preparation and the Standard preparation, respectively.
Auxiliary Information—
Please check for your question in the FAQs before contacting USP.
| Topic/Question | Contact | Expert Committee |
|---|---|---|
| Monograph | Ahalya Wise, M.S.
Senior Scientific Liaison 1-301-816-8161 |
(SM12010) Monographs - Small Molecules 1 |
| Reference Standards | RS Technical Services 1-301-816-8129 rstech@usp.org |
USP35–NF30 Page 3963
Pharmacopeial Forum: Volume No. 34(1) Page 101