Vecuronium Bromide
C34H57BrN2O4 637.73
Piperidinium, 1-[(2
,3
,5,16,17)-3,17-bis(acetyloxy)-2-(1-piperidinyl) androstan-16-yl]-1-methyl-, bromide;
1-(3,17-Dihydroxy-2-piperidino-5-androstan-16,5-yl)-1-methylpiperidinium bromide, diacetate
[50700-72-6].
(vek'' ue roe' nee um broe' mide; vek' ure oh'' nee um broe' mide).
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C34H57BrN2O4 637.73
Piperidinium, 1-[(2
,3,5,16,17)-3,17-bis(acetyloxy)-2-(1-piperidinyl) androstan-16-yl]-1-methyl-, bromide;
1-(3
,17-Dihydroxy-2-piperidino-5-androstan-16,5-yl)-1-methylpiperidinium bromide, diacetate
[50700-72-6].DEFINITION
Vecuronium Bromide contains NLT 98.0% and NMT 102.0% of C34H57BrN2O4, calculated on the dried basis.
IDENTIFICATION
• A. Infrared Absorption 
197K
:
Meets the requirements
197K:
Meets the requirements
• 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
Diluent:
Pipet 1.0 mL of 1 N hydrochloric acid into a 1000-mL volumetric flask, and dilute with acetonitrile to volume.
Solution A:
Dissolve 8.0 g of sodium perchlorate in 6.0 mL of water, and dilute with acetonitrile to 1 L.
Solution B:
Dissolve 1.6 g of ammonium chloride in 8 mL of ammonium hydroxide, and dilute with methanol to 1 L.[Note—Avoid excessive degassing to prevent the loss of ammonium hydroxide. ]
Mobile phase:
Solution A and Solution B (60:40)
Standard solution:
0.5 mg/mL of USP Vecuronium Bromide RS in Diluent
Sample solution:
0.5 mg/mL of Vecuronium Bromide in Diluent
Chromatographic system
Mode:
LC
Detector:
UV 215 nm
Column:
4.6-mm × 25-cm; 5-µm packing L3
Column temperature:
40
Flow rate:
0.5 mL/min
Injection size:
20 µL
System suitability
Sample:
Standard solution
Suitability requirements
Column efficiency:
NLT 5000 theoretical plates
Relative standard deviation:
NMT 2.0%
Analysis
Samples:
Standard solution and Sample solution
Calculate the percentage of vecuronium bromide (C34H57BrN2O4) in the portion of Vecuronium Bromide taken:
Result = (rU/rS) × (CS/CU) × 100
| rU | = | = peak response from the Sample solution |
| rS | = | = peak response from the Standard solution |
| CS | = | = concentration of USP Vecuronium Bromide RS in the Standard solution (mg/mL) |
| CU | = | = concentration of Vecuronium Bromide in the Sample solution (mg/mL) |
Acceptance criteria:
98.0%–102.0% on the dried basis
IMPURITIES
• Organic Impurities
Cation suppressor regeneration solution:
0.02 M tetrabutylammonium hydroxide
Mobile phase
[Note—Filter components before combining. Avoid evaporation of tetrahydrofuran during degassing. ]
Combine methanol, water, and hydrochloric acid (250:1500:1). Leave at room temperature for a few min. Add 45 mL of tetrahydrofuran, and then dilute with water to 2 L.
[Note—This applies to all of the solution preparations. The addition, with sonication, of a small amount of acetonitrile (NMT 0.5 mL per 25 mg) to the weighed quantity of the samples may be used to aid in dissolution. Shaking and sonication may also be used after the addition of the required amount of 2.5 mM hydrochloric acid. ]
System suitability solution:
5 µg/mL each of USP Vecuronium Bromide RS, USP Pancuronium Bromide RS, USP Vecuronium Bromide Related Compound A RS, USP Vecuronium Bromide Related Compound B RS, USP Vecuronium Bromide Related Compound C RS, and USP Vecuronium Bromide Related Compound F RS in 2.5 mM hydrochloric acid
Standard solution:
0.005 mg/mL of USP Vecuronium Bromide RS in 2.5 mM hydrochloric acid
Sample solution:
1 mg/mL of Vecuronium Bromide prepared as follows. To 25 mg of Vecuronium Bromide in a 25-mL volumetric flask add 0.5 mL of acetonitrile, sonicate, and rapidly dilute with 2.5 mM hydrochloric acid.
Chromatographic system
Mode:
LC
Detector:
Conductivity with 4-mm cation suppressor
Column:
4.6-mm × 25-cm; 5-µm packing L1
Flow rate:
1.5 mL/min
Flow rate (for cation suppressor):
2 mL/min
Injection size:
25 µL
System suitability
Samples:
System suitability solution and Standard solution
[Note—The system may need equilibration for 4 h. Rinse and store the column in acetonitrile and water (1:1). ]
Suitability requirements
Peak-to-valley ratio:
NLT 2.0 between the vecuronium bromide related compound F peak and the height of the trough between the vecuronium bromide related compound F and pancuronium peaks, System suitability solution
Relative standard deviation:
NMT 10.0% for three replicate injections, Standard solution
Analysis
Samples:
Standard solution and Sample solution
Calculate the percentage of each impurity in the portion of Vecuronium Bromide taken:
Result = (rU/rS) × (CS/CU) × (1/F) × 100
| rU | = | = peak area response for each impurity from the Sample solution |
| rS | = | = peak area response for USP Vecuronium Bromide RS from the Standard solution |
| CS | = | = concentration of the USP Vecuronium Bromide RS in the Standard solution (mg/mL) |
| CU | = | = concentration of Vecuronium Bromide in the Sample solution (mg/mL) |
| F | = | = relative response factor for the corresponding impurity (see Table 1) |
Acceptance criteria:
See Table 1.
Table 1
| Name | Relative Retention Time |
Relative Response Factor |
Acceptance Criteria, NMT (%) |
|
|---|---|---|---|---|
| Pancuronium bromide |
0.5 | 1.1 | 0.5 | |
| Vecuronium bromide related compound Fa |
0.6 | 1.3 | 0.5 | |
| Vecuronium bromide related compound Cb |
0.9 | 1.4 | 0.5 | |
| Vecuronium bromide |
1.0 | — | — | |
| Vecuronium bromide related compound Ac |
1.8 | 0.4 | 0.3 | |
| Vecuronium bromide related compound Bd |
2.2 | 1.0 | 0.5 | |
| Any other individual unidentified impurity |
— | 1.0 | 0.1 | |
| Total impurities | — | — | 1.0 | |
|
a
3-Deacetyl vecuronium bromide; piperidinium, 1-[(2
,3,5,16,17)-17-acetyloxy-3-hydroxy-2-(1-piperidinyl) androstan-16-yl]-1-methyl bromide.
b
3,17-bis Deacetyl vecuronium bromide; piperidinium, 1-[(2
,3,5,16,17)-3,17-dihydroxy-2-(1-piperidinyl) androstan-16-yl]-1-methyl bromide.
c
Dipiperidino diol diacetate; 3
,17-diacetyl-oxy-2,16-bispiperidinyl-5-androstan.
d
17-Deacetyl vecuronium bromide; piperidinium, 1-[(2
,3,5,16,17)-3-acetyloxy-17-hydroxy-2-(1-piperidinyl) androstan-16-yl]-1-methyl bromide.
|
||||
SPECIFIC TESTS
• Optical Rotation, Specific Rotation 781S
781S
Sample solution:
10 mg/mL, in dehydrated alcohol
Acceptance criteria:
16 to 20 at 20
16 to 20 at 20
• Bacterial Endotoxins Test 85:
NMT 10 USP Endotoxin Units/mg of vecuronium bromide
85:
NMT 10 USP Endotoxin Units/mg of vecuronium bromide
• Loss on Drying 731:
Dry a sample at 105 for 2 h: it loses NMT 2.5% of its weight.
731:
Dry a sample at 105 for 2 h: it loses NMT 2.5% of its weight.
ADDITIONAL REQUIREMENTS
• Packaging and Storage:
Preserve in tight containers, and store at room temperature.
• USP Reference Standards 11
11
USP Endotoxin RS
USP Pancuronium Bromide RS 
3,17-dihydroxy-2,16-dipiperidinyl-5-androstane, 3,17-diacetate, dimethobromide.
C35H60Br2N2O4 732.67
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3
,17-dihydroxy-2,16-dipiperidinyl-5-androstane, 3,17-diacetate, dimethobromide.
C35H60Br2N2O4 732.67
USP Vecuronium Bromide RS
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USP Vecuronium Bromide Related Compound A RS
3,17-diacetyl-oxy-2,16-bispiperidinyl-5-androstan.
C33H54N2O4 542.79
3
,17-diacetyl-oxy-2,16-bispiperidinyl-5-androstan.
C33H54N2O4 542.79
USP Vecuronium Bromide Related Compound B RS
Piperidinium, 1-[(2,3,5,16,17)-3-acetyloxy-17-hydroxy-2-(1-piperidinyl) androstan-16-yl]-1-methyl bromide.
C32H55BrN2O3 595.69
Piperidinium, 1-[(2
,3,5,16,17)-3-acetyloxy-17-hydroxy-2-(1-piperidinyl) androstan-16-yl]-1-methyl bromide.
C32H55BrN2O3 595.69
USP Vecuronium Bromide Related Compound C RS
Piperidinium, 1-[(2,3,5,16,17)-3,17-dihydroxy-2-(1-piperidinyl) androstan-16-yl]-1-methyl bromide.
C30H53BrN2O2 553.66
Piperidinium, 1-[(2
,3,5,16,17)-3,17-dihydroxy-2-(1-piperidinyl) androstan-16-yl]-1-methyl bromide.
C30H53BrN2O2 553.66
USP Vecuronium Bromide Related Compound F RS
Piperidinium, 1-[(2,3,5,16,17)-17-acetyloxy-3-hydroxy-2-(1-piperidinyl) androstan-16-yl]-1-methyl bromide.
C32H55BrN2O3 595.69
Piperidinium, 1-[(2
,3,5,16,17)-17-acetyloxy-3-hydroxy-2-(1-piperidinyl) androstan-16-yl]-1-methyl bromide.
C32H55BrN2O3 595.69
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 |
| 85 |
Radhakrishna S Tirumalai, Ph.D.
Principal Scientific Liaison 1-301-816-8339 |
(GCM2010) General Chapters - Microbiology |
| Reference Standards | RS Technical Services 1-301-816-8129 rstech@usp.org |
USP35–NF30 Page 5007
Pharmacopeial Forum: Volume No. 33(4) Page 682