Bumetanide
(bue met' a nide).
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364.42Benzoic acid, 3-(aminosulfonyl)-5-(butylamino)-4-phenoxy-.
3-(Butylamino)-4-phenoxy-5-sulfamoylbenzoic acid
[28395-03-1].» Bumetanide contains not less than 98.0 percent and not more than 102.0 percent of C17H20N2O5S, calculated on the dried basis.
Packaging and storage—
Preserve in tight, light-resistant containers. Store at 25
, excursions permitted between 15 and 30.
, excursions permitted between 15 and 30.
USP Reference standards 
11
—
11—
USP Bumetanide RS 
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USP Bumetanide Related Compound A RS
3-Amino-4-phenoxy-5-sulfamoylbenzoic acid.
C13H12N2O5S 308.31
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3-Amino-4-phenoxy-5-sulfamoylbenzoic acid.
C13H12N2O5S 308.31
USP Bumetanide Related Compound B RS
3-Nitro-4-phenoxy-5-sulfamoylbenzoic acid.
C13H10N2O7S 338.29
3-Nitro-4-phenoxy-5-sulfamoylbenzoic acid.
C13H10N2O7S 338.29
USP Butyl 3-(butylamino)-4-phenoxy-5-sulfamoylbenzoate RS
C21H28N2O5S 420.53
C21H28N2O5S 420.53
Identification—
C:
The principal spot obtained from the chromatogram of the Test preparation exhibits an RF value corresponding to that in the chromatogram of Standard solution 1, as obtained in the test for Related compounds.
Loss on drying 731—
Dry it at 105 for 4 hours: it loses not more than 0.5% of its weight.
731—
Dry it at 105 for 4 hours: it loses not more than 0.5% of its weight.
Residue on ignition 281:
not more than 0.1%, a 1-g specimen being used.
281:
not more than 0.1%, a 1-g specimen being used.
Heavy metals, Method II 231:
0.002%.
231:
0.002%.
Related compounds—
Adsorbent:
0.25-mm layer of chromatographic silica gel mixture.
Test solution—
Dissolve an accurately weighed quantity of Bumetanide in methanol to obtain a solution having a concentration of about 25 mg per mL.
Standard solution 1—
Dissolve an accurately weighed quantity of USP Bumetanide RS in methanol to obtain a solution having a known concentration of about 25 mg per mL.
Standard solution 2—
Dilute a volume of Standard solution 1 quantitatively, and stepwise if necessary, with methanol to obtain a solution having a known concentration of about 0.05 mg per mL.
Standard solution 3—
Dissolve an accurately weighed quantity of USP Bumetanide Related Compound B RS in methanol, and dilute quantitatively, and stepwise if necessary, with methanol to obtain a solution having a known concentration of about 0.05 mg per mL.
Standard solution 4—
Dissolve an accurately weighed quantity of USP Bumetanide Related Compound A RS in methanol, and dilute quantitatively, and stepwise if necessary, with methanol to obtain a solution having a known concentration of about 0.025 mg per mL.
Standard solution 5—
Dissolve an accurately weighed quantity of USP Butyl 3-(butylamino)-4-phenoxy-5-sulfamoylbenzoate RS in methanol, and dilute quantitatively, and stepwise if necessary, with methanol to obtain a solution having a known concentration of about 0.025 mg per mL.
Application volume:
20 µL of each solution.
Developing solvent system:
a mixture of chloroform, cyclohexane, glacial acetic acid, and methanol (80:10:10:2.5).
Procedure—
Proceed as directed for Thin-Layer Chromatography under Chromatography 621. After drying the application spots, place the plate in an unlined and unsaturated chromatographic chamber. Examine the plate under short-wavelength UV light. Any secondary spots obtained from the chromatogram of the Test solution having RF values corresponding to the RF values of the principal spots obtained from the chromatograms of Standard solutions 3, 4, and 5 are not larger or more intense than the principal spots obtained from the chromatograms of Standard solutions 3, 4, and 5, respectively: not more than 0.2% of bumetanide related compound B is found; not more than 0.1% of bumetanide related compound A is found; and not more than 0.1% of butyl 3-(butylamino)-4-phenoxy-5-sulfamoylbenzoate is found. No other individual secondary spots obtained from the chromatogram of the Test solution are larger or more intense than the principal spot obtained from the chromatogram of Standard solution 2: not more than 0.2% of any other individual impurity is found; and not more than 0.4% of the sum of all other impurities is found (excluding bumetanide related compound A, bumetanide related compound B, and butyl 3-(butylamino)-4-phenoxy-5-sulfamoylbenzoate).
621. After drying the application spots, place the plate in an unlined and unsaturated chromatographic chamber. Examine the plate under short-wavelength UV light. Any secondary spots obtained from the chromatogram of the Test solution having RF values corresponding to the RF values of the principal spots obtained from the chromatograms of Standard solutions 3, 4, and 5 are not larger or more intense than the principal spots obtained from the chromatograms of Standard solutions 3, 4, and 5, respectively: not more than 0.2% of bumetanide related compound B is found; not more than 0.1% of bumetanide related compound A is found; and not more than 0.1% of butyl 3-(butylamino)-4-phenoxy-5-sulfamoylbenzoate is found. No other individual secondary spots obtained from the chromatogram of the Test solution are larger or more intense than the principal spot obtained from the chromatogram of Standard solution 2: not more than 0.2% of any other individual impurity is found; and not more than 0.4% of the sum of all other impurities is found (excluding bumetanide related compound A, bumetanide related compound B, and butyl 3-(butylamino)-4-phenoxy-5-sulfamoylbenzoate).
Assay—
Dissolve about 1 g of Bumetanide, accurately weighed, in 150 mL of alcohol in a 250-mL conical flask. Add phenol red TS, and titrate with 0.1 N sodium hydroxide VS. Perform a blank determination (see Titrimetry 541), and make any necessary correction. Each mL of 0.1 N sodium hydroxide is equivalent to 36.44 mg of C17H20N2O5S.
541), and make any necessary correction. Each mL of 0.1 N sodium hydroxide is equivalent to 36.44 mg of C17H20N2O5S.
Auxiliary Information—
Please check for your question in the FAQs before contacting USP.
| Topic/Question | Contact | Expert Committee |
|---|---|---|
| Monograph | Sujatha Ramakrishna, Ph.D.
Senior Scientific Liaison 1-301-816-8349 |
(SM22010) Monographs - Small Molecules 2 |
| Reference Standards | RS Technical Services 1-301-816-8129 rstech@usp.org |
USP35–NF30 Page 2396
Pharmacopeial Forum: Volume No. 29(5) Page 1432