Lincomycin hydrochloride |
![]() Last updated: 15/09/2025 |
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(Also known as: lincomycine HCl) |
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A lincosamide antibacterial veterinary drug active against gram-positive cocci and anaerobic bacteria | |
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Used to treat various bacterial infections including those of the gums, teeth, skin and bone as well as wound infections and pneumonia | |
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Dogs; Cats; Pigs; Poultry; Cattle; Bees |
Approval status |
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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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Lincomycin hydrochloride exhibits stereoisomerism due to the presence of eight chiral centres in its complex molecular structure, which are located on its pyrrolidine ring and sugar moiety. These chiral centres define the molecule’s three-dimensional configuration, and the biologically active form of lincomycin is a single, well-defined stereoisomer with the configuration: (2S,4R)-N-[(1R,2R)-2-hydroxy-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(methylsulfanyl)oxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboxamide hydrochloride. | |
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C₁₈H₃₅ClN₂O₆S | |
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CCCC1CC(N(C1)C)C(=O)NC(C2C(C(C(C(O2)SC)O)O)O)C(C)O.Cl | |
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CCC[C@@H]1C[C@H](N(C1)C)C(=O)N[C@@H]([C@@H]2[C@@H]([C@@H]([C@H]([C@H](O2)SC)O)O)O)[C@@H](C)O.Cl | |
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POUMFISTNHIPTI-BOMBIWCESA-N | |
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InChI=1S/C18H34N2O6S.ClH/c1-5-6-10-7-11(20(3)8-10)17(25)19-12(9(2)21)16-14(23)13(22)15(24)18(26-16)27-4;/h9-16,18,21-24H,5-8H2,1-4H3,(H,19,25);1H/t9-,10-,11+,12-,13+,14-,15-,16-,18-;/m1./s1 | |
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Yes |
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Common Name | Relationship | Link |
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lincomycin hydrochloride monohydrate | Hydrate | ![]() |
lincomycin hydrochloride | - | ![]() |
General status |
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Medicinal drug, Antibiotic, Antibacterial, Antimicrobial, Medicated feed additive | |
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Lincosamide | |
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Natural | |
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It inhibits bacteria by suppressing protein synthesis and growth. | |
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[50S ribosomal protein L10, Antagonist] | |
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859-18-7 | |
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212-726-7 | |
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64710 | |
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Antiinfectants for system use: Antibacterials for systemic use | |
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QJ01FF02 | |
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No | |
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Allowed substance (Table 1: All food producing species) | |
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443.0 | |
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(2S,4R)-N-[(1R,2R)-2-hydroxy-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboxamide; hydrochloride | |
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White crystalline powder with a pungent odour | |
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Commercial |
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Current but mainly superceded by its semisynthetic derivative, clindamycin | |||
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1964, first approval USA | |||
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Available in a variety of formulations including medicated feeds, drinking water additives, intramammary solutions, solutions for injection and soluble powders | |||
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The production of lincomycin hydrochloride begins with the fermentation of Streptomyces lincolnensis, a soil-dwelling actinomycete that naturally synthesises lincomycin as a secondary metabolite. The fermentation is carried out under controlled conditions using nutrient-rich media to optimize yield. After fermentation, the broth is filtered to remove biomass, and lincomycin is extracted using solvent extraction techniques, typically involving organic solvents like butanol. The crude extract is then subjected to purification steps such as ion-exchange chromatography and crystallisation to isolate lincomycin base. To convert it into its hydrochloride salt, the purified lincomycin is reacted with hydrochloric acid, forming lincomycin hydrochloride. | |||
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As microbial-based products tend to use fermentation-based production processes rather than chemical synthesis, they typically have a lower fossil fuel input in formulation and active ingredient creation, and also have reduced downstream emissions due to biodegradability and minimal soil disruption, their life-cycle GHG emissions are expected to be low. Whilst hard and precise data is not available, broad estimates suggest that typically emissions are likely to be below 5 kg CO₂e/kg. |
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500000 | 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 ) 4 = Verified data |
High | ||||||||
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20000 | 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 ) Methanol3 = Unverified data of known source |
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80 | 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 ) Benzene3 = Unverified data of known source |
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30 | 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 ) Methyl ethyl ketone3 = Unverified data of known source |
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60 | 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 ) Chloroform3 = Unverified data of known source |
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148 | 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 ) 3 = Unverified data of known source |
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148 | 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 ) 3 = Unverified data of known source |
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2.55 X 1000 | Calculated | - | |||||||
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0.406 | 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 ) 4 = Verified data |
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12.9 | R4 R = Peer reviewed scientific publications 4 = Verified data |
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2.46 X 10-14 | R4 R = Peer reviewed scientific publications 4 = Verified data |
Low volatility | ||||||||
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Substance may enter the environment via the urine and faeces of treated animals or by leaching from spilt medicated feed. |
Degradation |
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20 | 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 ) Clay loam3 = Unverified data of known source |
Non-persistent | |||||||
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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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- | R4 R = Peer reviewed scientific publications 4 = Verified data |
Mobile | |||||||
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0.009 | 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 ) 4 = Verified data |
Very mobile | |||||||
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0.25 | ||||||||||
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0.87 | ||||||||||
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USEPA data Kd range 0.0033-0.187 mL g⁻¹, Kfoc range 0.12-0.41 mL g⁻¹, 1/n range 0.841-0.912, Soils=3 | ||||||||||
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Fate indices |
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5.99 | Calculated | High leachability | ||||||||||||||||||||||||||
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Known soil and groundwater metabolites |
None
Other known metabolites |
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lincomycin sulfoxide | - | Mammals | - | ||||
N-desmethyl-lincomycin sulfoxide | - | Mammals | - |
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Terrestrial ecotoxicology |
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> 4000 | Q3 Q = Miscellaneous data from online sources Rat3 = Unverified data of known source |
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> 1000 | R4 R = Peer reviewed scientific publications Eisenia foetida4 = Verified data |
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Aquatic ecotoxicology |
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> 980 | Q3 Q = Miscellaneous data from online sources Lepomis macrochirus3 = Unverified data of known source |
Low | ||||||||
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379.4 | R4 R = Peer reviewed scientific publications Daphnia magna4 = Verified data |
Low | ||||||||
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General |
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High (class III) | - | - | ||||||||
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> 4000 | Q3 Q = Miscellaneous data from online sources Rat3 = Unverified data of known source |
Low | ||||||||
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Subcutaneous LD₅₀ = 9778 mg kg⁻¹ | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) Rat3 = Unverified data of known source |
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Intramuscular LD₅₀ = 0.2 mg kg⁻¹ | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) Rabbit3 = Unverified data of known source |
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The parent drug and metabolites are excreted mainly in the urine, bile and faeces. Has been detected in milk products. | Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source |
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Health issues |
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May cause diarrhoea, vomiting and colitis May cause hypotension and, albeit rarely, cardiac arrest |
Handling issues |
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No information available | |||
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Not listed (Not listed) | |||
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lincomycin hydrochloride | ||
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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 |