Dinoprostone

This article is compiled based on the United States Pharmacopeia (USP) – 2025 Edition

Issued and maintained by the United States Pharmacopeial Convention (USP)

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C₂₀H₃₂O₅ 352.47

Prosta-5,13-dien-1-oic acid, 11,15-dihydroxy-9-oxo-, (5Z,11α,13E,15S)-;

(E,Z)-(1R,2R,3R)-7-[3-Hydroxy-2-[(3S)-(3-hydroxy-1-octenyl)]-5-oxocyclopentyl]-5-heptenoic acid;

Prostaglandin E₂    CAS RN®: 363-24-6; UNII: K7Q1JQR04M.

1 DEFINITION

Dinoprostone contains NLT 97.0% and NMT 103.0% of dinoprostone (C₂₀H₃₂O₅).

[Note-Prepare all solutions in all tests immediately before use.]

2 IDENTIFICATION

Change to read:

A. Spectroscopic Identification Tests 〈197〉, Infrared Spectroscopy: 197K

B. The retention time of the major peak of the Sample solution corresponds to that of the Standard solution, as obtained in the Assay.

3 ASSAY

3.1 Procedure

Solution A: 0.2% (v/v) of 5 N acetic acid in water

Mobile phase: Methanol and Solution A (29:21)

System suitability solution: 0.04 mg/mL each of USP Dinoprostone RS and USP Dinoprostone Related Compound C RS in Mobile phase

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

• (See Chromatography 〈621〉, System Suitability.)
• Mode: LC
• Detector: UV 210 nm
• Column: 4.6-mm × 25-cm; packing L1
• Column temperature: 30°
• Flow rate: 1 mL/min
• Injection volume: 20 µL

System suitability

• Samples: System suitability solution and Standard solution
• Suitability requirements
• Resolution: NLT 3.8 between dinoprostone and dinoprostone related compound C, System suitability solution
• Relative standard deviation: NMT 2.0%, Standard solution

Analysis

Samples: Standard solution and Sample solution

Calculate the percentage of dinoprostone (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%

4 IMPURITIES

4.1 Residue on Ignition 〈281〉: NMT 0.5%

4.2 Organic Impurities

Mobile phase, System suitability solution, and Sample solution: Prepare 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.

Chromatographic system

• (See Chromatography 〈621〉, System Suitability.)
• Mode: LC
• Detector: UV 210 nm
• Column: 4.6-mm × 25-cm; packing L1
• Column temperature: 30°
• Flow rate: 1 mL/min
• Injection volume: 20 µL

System suitability

• Samples: System suitability solution and Standard solution
• Suitability requirements
• Resolution: NLT 3.8 between dinoprostone and dinoprostone related compound C, System suitability solution
• Column efficiency: NLT 6000 theoretical plates, Standard solution
• Relative standard deviation: NMT 10.0%, Standard 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 Table 1)

Acceptance criteria: See Table 1.

Table 1

* The sum of these three impurities is NMT 1.0%.

5 SPECIFIC TESTS

5.1 Optical Rotation, Specific Rotation 〈781S〉

Sample solution: 5 mg/mL in alcohol

Acceptance criteria: −82.0° to −90.0°, at 20°

5.2 Water Determination, Method I 〈921〉: NMT 0.5%

6 ADDITIONAL REQUIREMENTS

Packaging and Storage: Preserve in well-closed, light-resistant containers.

USP Reference Standards 〈11〉

USP Dinoprostone RS

USP Dinoprostone Related Compound C RS

(E)-7-{(1R,2R,3R)-3-Hydroxy-2-[(S,E)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl}hept-5-enoic acid.

C₂₀H₃₂O₅ 352.47