Dinoprostone
(dye'' noe pros' tone).
Click to View Image

C20H32O5 352.47
Prosta-5,13-dien-1-oic acid, 11,15-dihydroxy-9-oxo-, (5Z,11,13E,15S)-;    
(E,Z)-(1R,2R,3R)-7-[3-Hydroxy-2-[(3S)-(3-hydroxy-1-octenyl)]-5-oxocyclopentyl]-5-heptenoic acid;    
Prostaglandin E2     [363-24-6].
DEFINITION
Dinoprostone contains NLT 97.0% and NMT 103.0% of C20H32O5.
[Note—Prepare all solutions in all tests immediately before use. ]
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
Mobile phase:  Methanol and 0.2% acetic acid (29:21)
Standard solution:  2.5 mg/mL of USP Dinoprostone RS in Mobile phase
Sample solution:  2.5 mg/mL of Dinoprostone in Mobile phase
Chromatographic system  
Mode:  LC
Detector:  UV 210 nm
Column:  4.6-mm × 25-cm; packing L1
Temperature:  30
Flow rate:  1 mL/min
Injection size:  20 µL
System suitability 
Sample:  Standard solution
Suitability requirements 
Resolution:  NLT 1.0 between dinoprostone and any other adjacent peak
Relative standard deviation:  NMT 2.0%
Analysis 
Samples:  Standard solution and Sample solution
Calculate the percentage of C20H32O5 in the portion of Dinoprostone 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 Dinoprostone RS in the Standard solution (mg/mL)
CU== concentration of Dinoprostone in the Sample solution (mg/mL)
Acceptance criteria:  97.0%–103.0%
IMPURITIES
Inorganic Impurities 
•  Residue on Ignition 281: NMT 0.5%
Organic Impurities 
•  Procedure
Mobile phase:  Proceed as directed in the Assay.
Standard stock solution:  Prepare as directed for the Standard solution in the Assay.
Standard solution:  Transfer 0.5 mL of the Standard stock solution to a 50-mL volumetric flask, and dilute with Mobile phase to volume.
Sample solution:  Prepare as directed in the Assay.
Chromatographic system 
Mode:  LC
Detector:  UV 210 nm
Column:  4.6-mm × 25-cm; packing L1
Temperature:  30
Flow rate:  1 mL/min
Injection size:  20 µL
System suitability 
Samples:  Standard stock solution and Sample solution
Suitability requirements 
Column efficiency:  NLT 6000 theoretical plates, Standard stock solution
Relative standard deviation:  NMT 2.0%, Standard stock solution
Resolution:  NLT 1.0 between dinoprostone and any other adjacent peak, Sample solution
Analysis 
Samples:  Standard solution and Sample solution
Calculate the percentage of each impurity in the portion of Dinoprostone taken:
Result = (rU/rS) × (CS/CU) × (1/F) × 100
rU== peak response of each impurity from the Sample solution
rS== peak response of dinoprostone from the Standard solution
CS== concentration of USP Dinoprostone RS in the Standard solution (mg/mL)
CU== concentration of Dinoprostone in the Sample solution (mg/mL)
F== relative response factor (see Impurity Table 1)
Acceptance criteria:  See Impurity Table 1.
Impurity Table 1
Name Relative
Retention
Time
Relative
Response
Factor
Acceptance
Criteria,
NMT (%)
15-Oxo-dinoprostone 0.79 5 *
15-Epi-dinoprostone 0.85 1.1 *
8-Isodinoprostone 0.90 1.0 *
5,6-trans-Dinoprostone 1.15 1.0 2.0
(5Z,13E,15S)-15-Hydroxy-9-oxoprosta-5, 10,13-triene-1-oic acid 1.80 5 1.0
(5Z,13E,15S)-15-Hydroxy-9-oxoprosta-5, 8(12),13-trien-1-oic
acid
1.90 1.43 1.0
Any individual unspecified impurity 1.0 0.10
*  The sum of these three impurities is NMT 1.0%.
SPECIFIC TESTS
•  Optical Rotation, Specific Rotation 781S: 82.0 to 90.0, at 20
Sample solution:  5 mg/mL, in alcohol
ADDITIONAL REQUIREMENTS
•  Packaging and Storage: Preserve in well-closed, light-resistant containers.
•  USP Reference Standards 11
USP Dinoprostone RS Click to View Structure
Auxiliary Information— Please check for your question in the FAQs before contacting USP.
Topic/Question Contact Expert Committee
Monograph Domenick Vicchio, Ph.D.
Senior Scientific Liaison
1-301-998-6828
(SM42010) Monographs - Small Molecules 4
Reference Standards RS Technical Services
1-301-816-8129
rstech@usp.org
USP35–NF30 Page 2929
Pharmacopeial Forum: Volume No. 35(5) Page 1132