Dinoprost tromethamine |
![]() Last updated: 16/09/2025 |
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(Also known as: prostaglandin F2alpha; dinoprost trometamol ; PGF2 alpha THAM; prostaglandin F2 alpha tromethamine ; amoglandin) |
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The tromethamine salt of the naturally occurring prostaglandin F2 alpa substance used in veterinary medicine | |
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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 supplied 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 tromethamine exhibits both geometric and stereoisomerism. Its structure includes conjugated double bonds that can exist in cis–trans configurations, with the (5Z,13E) form being the most active. Additionally, the molecule contains four chiral centres on its cyclopentane ring, contributing to its stereoisomerism. | |
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C₂₄H₄₅NO₈ | |
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CCCCCC(C=CC1C(CC(C1CC=CCCCC(=O)O)O)O)O.C(C(CO)(CO)N)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.C(C(CO)(CO)N)O | |
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IYGXEHDCSOYNKY-RZHHZEQLSA-N | |
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InChI=1S/C20H34O5.C4H11NO3/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;5-4(1-6,2-7)3-8/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25);6-8H,1-3,5H2/b7-4-,13-12+;/t15-,16+,17+,18-,19+;/m0./s1 | |
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Yes |
General status |
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Abortifacient agent, Reproduction control, Medicinal drug | |
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Unclassified substance | |
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Synthetic | |
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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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38562-01-5 | |
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254-002-3 | |
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5282415 | |
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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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475.6 | |
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2-amino-2-(hydroxymethyl)propane-1,3-diol;(Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]cyclopentyl]hept-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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1970s, first synthesised; 1980s, vet use expanded | |||
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Usually supplied as solution for injection | |||
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The commercial production of dinoprost tromethamine begins with the synthesis of prostaglandin F2alpha, typically through multi-step organic reactions involving Corey lactone intermediates and Wittig reactions to construct the essential cyclopentane ring and side chains. Once prostaglandin F2alpha is obtained, it is dissolved in acetonitrile and reacted with tromethamine (tris(hydroxymethyl)aminomethane) in a controlled aqueous-organic mixture at elevated temperatures (around 53–57 DegC) to form the tromethamine salt. | |||
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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 |
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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 tromethamine | ||
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dinoprosta | ||
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Record last updated: | 16/09/2025 |
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 |