Dinoprost |
![]() Last updated: 15/09/2025 |
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(Also known as: prostaglandin F2alpha; dinoprost trometamol ; PGF2 alpha THAM; prostaglandin F2 alpha tromethamine ; amoglandin) |
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A prostaglandin substance used in veterinary medicine usually formulated as the synthetic analogue dinoprost thromethamine | |
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Used for inducing abortion and at low-doses for medically indicated induction of labour at full term | |
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Horses; Cattle; Pigs |
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Approved - usually available as a prescription only medicine to be authorised by a veterinarian (POM-V) | |
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Approved |
Chemical structure |
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Dinoprost exhibits both geometric and optical isomerism due to its double bonds and multiple chiral centres. The molecule contains cis-configured double bonds and five stereocentres, which together define its three-dimensional shape and biological activity. The naturally occurring isomer, with specific (Z)-geometry and (15S)-configuration, is essential for its function in inducing uterine contractions and luteolysis in veterinary and reproductive medicine. | |
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C₂₀H₃₄O₅ | |
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CCCCCC(C=CC1C(CC(C1CC=CCCCC(=O)O)O)O)O | |
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CCCCC[C@@H](/C=C/[C@H]1[C@@H](C[C@@H]([C@@H]1C/C=C\CCCC(=O)O)O)O)O | |
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PXGPLTODNUVGFL-YNNPMVKQSA-N | |
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InChI=1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,18-,19+/m0/s1 | |
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Yes |
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Common Name | Relationship | Link |
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Prostaglandin E2 | - | ![]() |
General status |
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Abortifacient agent, Reproduction control, Medicinal drug | |
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Prostaglandin substance | |
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Natural | |
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Stimulates myometrial contractions in the gravid uterus that are similar to the contractions that occur in the term uterus during labor | |
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[Prostaglandin F2-alpha receptor, Agonist], [Prostacyclin receptor, Antagonist] | |
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551-11-1 | |
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Genito Urinary system & sex hormones: Other gynecologicals | |
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QG02AD | |
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No | |
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Allowed substance (Table 1: All mammalian food producing species) | |
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354.48 | |
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(Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)- 3-hydroxyoct-1-enyl]cyclopentylhept-5-enoic acid | |
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White to off-white, very hygroscopic, crystalline powder | |
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Commercial |
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Current | |||
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Circa 1975, introduced | |||
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Usually supplied as solution for injection | |||
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Dinoprost is produced through a semi-synthetic process that mimics its natural biosynthesis from arachidonic acid, a fatty acid found in cell membranes. In industrial settings, the synthesis begins with chemical modification of arachidonic acid or related precursors, using cyclooxygenase (COX) enzymes to convert it into prostaglandin H2 (PGH₂), an unstable intermediate. PGH2 is then selectively reduced by prostaglandin F synthase to yield dinoprost. The process requires precise control of stereochemistry to ensure the correct configuration at multiple chiral centres, as only the naturally occurring (15S)-isomer is biologically active. | |||
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Published GHG data is not available for most pharmaceuticals. However, according to industry, global averages suggest producing 1 kg of a typical active pharmaceutical ingredient can range from 10 to 100 kg CO₂e for small molecule drugs and potentially up to 1000 kg CO₂e for complex biologicals such as vaccines, depending on the drug type, its formulation, complexity of synthesis, solvent recovery, and energy sources used. |
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2.58 | v3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) 3 = Unverified data of known source |
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30 | Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source |
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2.45 X 1004 | Calculated | - | |||||||
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4.39 | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) 3 = Unverified data of known source |
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5.01 X 10-09 | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) 3 = Unverified data of known source |
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Degradation |
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As this parameter is not normally measured directly, a surrogate measure is used: ‘Photochemical oxidative DT₅₀’. Where data is available, this can be found in the Fate Indices section below. | ||||||||||
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Fate indices |
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Known metabolites |
None
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Terrestrial ecotoxicology |
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> 1170 | E3 E = Manufacturers safety data sheets Rat3 = Unverified data of known source |
Moderate | ||||||||
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Aquatic ecotoxicology |
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General |
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Low (class I) | - | - | ||||||||
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> 1170 | E3 E = Manufacturers safety data sheets Rat3 = Unverified data of known source |
Moderate | ||||||||
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Subcutaneous LD₅₀ = 95 mg kg⁻¹ | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) Rat3 = Unverified data of known source |
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Intramuscular LD₅₀ = 106 mg kg⁻¹ | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) Rat3 = Unverified data of known source |
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Mostly excreted in the urine, only around 5% lost via the faeces | Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source |
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Health issues |
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Large doses may cause nausea, vomiting, and diarrhoea |
Handling issues |
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No information available | |||
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Not listed (Not listed) | |||
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dinoprost | ||
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dinoprosta | ||
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Record last updated: | 15/09/2025 |
Contact: | aeru@herts.ac.uk |
Please cite as: | Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242 |