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Vancomycin Hydrochloride
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C66H75Cl2N9O24·HCl 1485.71

Vancomycin, monohydrochloride.
Vancomycin monohydrochloride.
(Sa)-(3S,6R,7R,22R,23S,26S,36R,38aR)-44-[[2-O-(3-Amino- 2,3,6-trideoxy-3-C-methyl--L-lyxo-hexopyranosyl)--D-glucopyranosyl]oxy]-3-(carbamoylmethyl)-10,19-dichloro-2,3,4,5,6,7,23,24,25,26,36,37,38,38a-tetradecahydro- 7,22,28,30,32-pentahydroxy-6-[(2R)-4-methyl-2-(methylamino)]valeramido]-2,5,24,38,39-pentaoxo-22H-8,11:18,21-dietheno-23,36-(iminomethano)-13,16:31,35-dimetheno-1H,16H-[1,6,9]oxadiazacyclohexadecino[4,5-m][10,2,16]benzoxadiazacyclotetracosine-26-carboxylic acid, monohydrochloride.
[3S-[3R*,6S*(S*),7S*,22S*,23R*,26R*,36S*,38aS*]]-3-(2-Amino-2-oxoethyl)-44-[[2-O-(3-amino-2,3,6-trideoxy-3-C-methyl--L-lyxo-hexopyranosyl)--D-glucopyranosyl]oxy]-10,19-dichloro-2,3,4,5,6,7,23,24,25,26,36,37,38,38a-tetradecahydro-7,22,28,30,32-pentahydroxy-6-[[4-methyl-2-(methylamino)-1-oxopentyl]amino]-2,5,24,38,39-pentaoxo-22H-8,11:18,21-dietheno-23,36-(iminomethano)-13,16:31,35-dimetheno-1H,16H-[1,6,9]oxadiazacyclohexadecino[4,5-m][10,2,16]-benzoxadiazacyclotetracosine-26-carboxylic acid, monohydrochloride [1404-93-9].
» Vancomycin Hydrochloride is the hydrochloride salt of a kind of vancomycin, a substance produced by the growth of Streptomyces orientalis (Fam. Streptomycetaceae), or a mixture of two or more such salts. It has a potency equivalent to not less than 900 µg of vancomycin per mg, calculated on the anhydrous basis.
Packaging and storage— Preserve in tight containers.
Identification, Infrared Absorption 197K: undried.
pH 791 : between 2.5 and 4.5, in a solution containing 50 mg per mL.
Water, Method I 921 : not more than 5.0%.
Chromatographic purity—
Triethylamine buffer— Mix 4 mL of triethylamine and 2000 mL of water, and adjust with phosphoric acid to a pH of 3.2.
Solution A— Prepare a mixture of Triethylamine buffer, acetonitrile, and tetrahydrofuran (92:7:1), and degas briefly.
Solution B— Prepare a suitable mixture of Triethylamine buffer, acetonitrile, and tetrahydrofuran (70:29:1), and degas briefly.
Mobile phase— Use variable mixtures of Solution A and Solution B as directed for Chromatographic system. Make adjustments if necessary (see System Suitability under Chromatography 621), changing the acetonitrile proportion in Solution A to obtain a retention time of 7.5 to 10.5 minutes for the main vancomycin peak.
Resolution solution— Prepare a solution ofUSP Vancomycin Hydrochloride RS in water containing 0.5 mg per mL, heat at 65 for 48 hours, and allow to cool.
Test preparation A— Prepare a solution of Vancomycin Hydrochloride in Solution A containing 10 mg per mL.
Test preparation B— Transfer 2.0 mL of Test preparation A to a 50-mL volumetric flask, dilute with Solution A to volume, and mix.
Chromatographic system (see Chromatography 621)— The liquid chromatograph is equipped with a 280-nm detector and a 4.6-mm × 25-cm column that contains 5-µm packing L1. The flow rate is about 2 mL per minute. The chromatograph is programmed as follows.
Solution A
Solution B
0–12 100 0 isocratic
12–20 100®0 0®100 linear gradient
20–22 0 100 isocratic
22–23 0®100 100®0 linear gradient
23–30 100 0 isocratic
Chromatograph the Resolution solution, and record the peak responses as directed for Procedure: the elution order is resolution compound 1, vancomycin B, and resolution compound 2. The resolution, R, between resolution compound 1 and vancomycin B is not less than 3.0; and the column efficiency, calculated from the vancomycin B peak, is not less than 1500 theoretical plates. Resolution compound 2 is eluted at between 3 and 6 minutes after the start of the period when the percentage of Solution B is increasing from 0% to 100%.
Procedure— [NOTE—Where baseline separation is not achieved, peak areas are defined by vertical lines extended from the valleys between peaks to the baseline. The main component peak may include a fronting shoulder, which is attributed to monodechlorovancomycin. This shoulder should not be integrated separately.] Separately inject equal volumes (about 20 µL) of Test preparation A and Test preparation B into the chromatograph, record the chromatograms, and measure the area responses for all of the peaks. [NOTE—Correct any peak observed in the chromatograms obtained from Test preparation A and Test preparation B by subtracting the area response of any peak observed in the chromatogram of Solution A at the corresponding elution time.] Calculate the percentage of vancomycin B in the specimen tested by the formula:
2500rB /(25rB + rA),
in which rB is the corrected area response of the main peak obtained in the chromatogram of Test preparation B; and rA is the sum of the corrected area responses of all the peaks, other than the main peak, in the chromatogram obtained from Test preparation A: not less than 80.0% of vancomycin B is found. Calculate the percentage of each other peak taken by the formula:
100rAi / (25rB + rA),
in which rAi is the corrected area response of any individual peak, other than the main peak, obtained in the chromatogram of Test preparation A: not more than 9.0% of any peak other than the main peak is found.
Residual solvents 467: meets the requirements.
(Official January 1, 2007)
Assay— Proceed with Vancomycin Hydrochloride as directed under Antibiotics—Microbial Assays 81.
Auxiliary Information— Staff Liaison : Brian D. Gilbert, Ph.D., Scientist
Expert Committee : (MDANT05) Monograph Development-Antibiotics
USP29–NF24 Page 2239
Pharmacopeial Forum : Volume No. 27(4) Page 2784
Phone Number : 1-301-816-8223