Carboprost Tromethamine

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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C₂₁H₃₆O₅ . C₄H₁₁NO₃   489.65 (ERR 1-May-2021)

Prosta-5,13-dien-1-oic acid, 9,11,15-trihydroxy-15-methyl-, (5Z, 9α,11α, 13E,15S)-, compound with 2-amino-2-(hydroxymethyl)-1,3-propanediol (1:1);

(Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(E)-(3S)-3-hydroxy-3-methyloct-1-enyl (ERR 1-May-2021) Icyclopentyl]-5-heptenoic acid compound with 2- amino-2-(hydroxymethyl)-1,3-propanediol (1:1); (15S)-15-Methylprostaglandin F tromethamine CAS RN: 58551-69-2; UNII: U4526F86FJ. 2α

1 DEFINITION

Carboprost Tromethamine contains NLT 95.0% and NMT 105.0% of carboprost tromethamine (C₂₁H₃₆O₅ . C₄H₁₁NO₃), calculated on the dried basis.

[CAUTION-Great care should be taken to prevent inhaling particles of Carboprost Tromethamine and exposing the skin to it.]

2 IDENTIFICATION

A. SPECTROSCOPIC IDENTIFICATION TESTS (197), Infrared Spectroscopy: 197M

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

PROCEDURE

Buffer: 0.02 M monobasic potassium phosphate

Mobile phase: Acetonitrile, methanol, and Buffer (20:30:50). Adjust with phosphoric acid to an apparent pH of 3.0.

Diluent: Acetonitrile, methanol, and water (20:30:50)

Standard solution: 1.0 mg/mL of USP Carboprost Tromethamine RS in Diluent

Sample solution: 1.0 mg/mL of Carboprost Tromethamine in Diluent

Chromatographic system

(See Chromatography (621), System Suitability.)

Mode: LC

Detector: UV 200 nm

Column: 4-mm x 15-cm; 3-µm packing L1

Column temperature: 30 ± 2°

Flow rate: 0.8 mL/min

Injection volume: 10 µL

System suitability

Sample: Standard solution

[NOTE-See Table 1 for the relative retention times of trans-carboprost and carboprost.]

Suitability requirements

Resolution: NLT 1.2 between trans-carboprost and carboprost

Tailing factor: NMT 2.0

Relative standard deviation: NMT 0.73%

Analysis

Samples: Standard solution and Sample solution

Calculate the percentage of carboprost tromethamine (C₂₁H₃₆O₅ . C₄H₁₁NO₃) in the portion of Carboprost Tromethamine taken:

Result = (r_U/r_S) x (C_S/C_U) × 100

r_U = peak response from the Sample solution

r_S = peak response from the Standard solution

C_S = concentration of USP Carboprost Tromethamine RS in the Standard solution (mg/mL)

C_U = concentration of Carboprost Tromethamine in the Sample solution (mg/mL)

Acceptance criteria: 95.0%–105.0% on the dried basis

4 IMPURITIES

Residue on Ignition 〈281〉: NMT 0.5%

Organic Impurities

Buffer, Mobile phase, and Diluent: Prepare as directed in the Assay.

Standard stock solution: 1.0 mg/mL of USP Carboprost Tromethamine RS in Diluent

System suitability solution: 0.1 mg/mL of 15-epicarboprost in the Standard stock solution

Standard solution: 0.025 mg/mL of USP Carboprost Tromethamine RS in Diluent from the Standard stock solution

Sensitivity solution: 0.001 mg/mL of USP Carboprost Tromethamine RS in Diluent from the Standard stock solution

Sample solution: 1 mg/mL of Carboprost Tromethamine in Diluent

Chromatographic system: Proceed as directed in the Assay, except use an Injection volume of 20 μL.

System suitability

Samples: System suitability solution, Standard solution, and Sensitivity solution

[Note—See Table 1 for the relative retention times.]

Suitability requirements

Resolution: NLT 1.0 between 15-epicarboprost and trans-carboprost; NLT 1.2 between trans-carboprost and carboprost, System suitability solution

Relative standard deviation: NMT 5.0% for carboprost, Standard solution

Signal-to-noise ratio: NLT 10 for carboprost, Sensitivity solution

Analysis

Samples: Standard solution and Sample solution

Calculate the percentage of each impurity in the portion of Carboprost Tromethamine taken:

Result = (r_U/r_S) x (C_S/C_U) × 100

r_U = peak response of each impurity from the Sample solution

r_S = peak response of carboprost tromethamine from the Standard solution

C_S = concentration of USP Carboprost Tromethamine RS in the Standard solution (mg/mL)

C_U = concentration of Carboprost Tromethamine in the Sample solution (mg/mL)

Acceptance criteria: See Table 1.

^a (Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(E)-(3R)-3-hydroxy-3-methyloct-1-enyl]cyclopentyl]-5-heptenoic acid.

^b (E)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(E)-(3S)-3-hydroxy-3-methyloct-1-enyl]cyclopentyl]-5-heptenoic acid.

5 SPECIFIC TESTS

Optical Rotation, Specific Rotation 〈781S〉

Sample solution: 10 mg/mL of Carboprost Tromethamine in alcohol

Acceptance criteria: +18° to +24°

Loss on Drying 〈731〉

Analysis: Dry under vacuum at a pressure not exceeding 5 mm of mercury at 50° for 16 h.

Acceptance criteria: NMT 1.0%

6 ADDITIONAL REQUIREMENTS

Packaging and Storage: Preserve in well-closed containers, and store in a freezer.

USP Reference Standards 〈11〉

USP Carboprost Tromethamine RS