Ormetoprim |
![]() Last updated: 16/09/2025 |
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(Also known as: ormethoprim) |
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A drug used in potentiated sulfonamide mixtures used as coccidiostats | |
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Numerous veterinary uses including the treatment of protozoal diseases such as leishmaniasis and toxoplasmosis | |
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Poultry; Fish; Sheep; Dogs |
Approval status |
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Not approved | |
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Not approved |
Chemical structure |
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None | |
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C₁₄H₁₈N₄O₂ | |
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CC1=CC(=C(C=C1CC2=CN=C(N=C2N)N)OC)OC | |
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No data | |
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KEEYRKYKLYARHO-UHFFFAOYSA-N | |
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InChI=1S/C14H18N4O2/c1-8-4-11(19-2)12(20-3)6-9(8)5-10-7-17-14(16)18-13(10)15/h4,6-7H,5H2,1-3H3,(H4,15,16,17,18) | |
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Yes |
General status |
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Antimicrobial, Antibiotic, Medicinal drug | |
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Diaminopyrimidine | |
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Synthetic | |
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Interferes with folic acid production by inhibition of dihydrofolate reductase | |
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[Dihydrofolate reductase, Inhibitor] | |
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6981-18-6 | |
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230-246-6 | |
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Antiinfectives for Systemic use: Combinations of sulfonamides and trimethoprim, incl. derivatives | |
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QJ01EW19 | |
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No | |
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274.32 | |
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5-(4,5-dimethoxy-2-methylbenzyl)-2,4-diaminopyrimidine | |
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2,4-diamino-5-(6-methylveratryl)pyrimidine | |
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Commercial |
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1970s, first synthesis & characterisation; 1993, first approvals USA | |||
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Often formulated as tables for orally administration, typically in combination with sulfadimethoxine | |||
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The synthesis of ormetoprim involves a multi-step chemical process designed to construct its diaminopyrimidine structure with precision. It begins with p-cresol, which undergoes methylation using dimethyl carbonate to form a methoxy-substituted intermediate. This compound is then subjected to bromination in an acetic anhydride–nitric acid system to introduce a bromine atom. The resulting product undergoes methoxylation using stannous chloride and sodium methoxide in methanol, followed by a formylation reaction with Vilsmeier–Haack reagents. The next step involves reacting the formylated compound with acrylonitrile and sodium methoxide, forming a key intermediate that is then isomerised under alkaline conditions to yield an alkene ether structure. This intermediate is treated with methanol and finally undergoes condensation and cyclisation with guanidine, producing the final compound, ormetoprim. | |||
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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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1540 | R4 R = Peer reviewed scientific publications 4 = Verified data |
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1.70 X 1001 | Calculated | - | |||||||
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1.23 | R4 R = Peer reviewed scientific publications 4 = Verified data |
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Weak base | |||||||||||
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3.03 X 10-03 | R4 R = Peer reviewed scientific publications 4 = Verified data |
Low volatility | ||||||||
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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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Soil adsorption and mobility |
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Slightly mobile | |||||||
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3687 | ||||||||||
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Koc 2517 mL g⁻¹ soil with 81.5% sand, 4856 mL g⁻¹ soil with 52% sand | ||||||||||
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Fate indices |
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Known metabolites |
None
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Terrestrial ecotoxicology |
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665 | E3 E = Manufacturers safety data sheets Rat3 = Unverified data of known source |
Moderate | ||||||||
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Aquatic ecotoxicology |
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400 | F3 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment ) Salmo gairdneri3 = Unverified data of known source |
Low | ||||||||
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33 | F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment ) Daphnia magna4 = Verified data |
Moderate | ||||||||
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90 | F3 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment ) Raphidocelis subcapitata3 = Unverified data of known source |
Low | ||||||||
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General |
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High (class III) | - | - | ||||||||
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665 | E3 E = Manufacturers safety data sheets Rat3 = Unverified data of known source |
Moderate | ||||||||
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Primarily eliminated, rapidly, through renal excretion | Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source |
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Health issues |
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No further information available |
Handling issues |
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No information available | |||
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Not listed (Not listed) | |||
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ormetoprim | ||
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ormetoprime | ||
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ormetoprima | ||
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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 |