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Lincomycin

Lincomycin is a lincosamide-class originally isolated from the soil bacterium Streptomyces lincolnensis in 1962, characterized by its molecular formula C18H34N2O6S and a molecular weight of 406.54 g/mol. It functions as a by binding to the 50S subunit of the bacterial , thereby inhibiting protein synthesis and preventing the growth of susceptible such as Staphylococcus aureus and Streptococcus pneumoniae. Approved by the U.S. on December 29, 1964, lincomycin was introduced for clinical use to treat serious infections, including skin and soft tissue infections, respiratory tract infections, , and bone and joint infections, particularly in patients allergic to penicillin or when other s are ineffective. Administered via intramuscular or intravenous routes, lincomycin achieves peak serum concentrations of approximately 11.6 μg/mL after a 600 mg intramuscular dose and 15.9 μg/mL after a 600 mg intravenous dose, with an elimination of about 5.4 hours in individuals with normal renal and hepatic function. Its spectrum of activity is primarily against Gram-positive organisms, including many strains resistant to other antibiotics, though it has limited efficacy against and anaerobes. While effective in early clinical studies for staphylococcal infections, such as , lincomycin has been largely supplanted in medicine by its more potent semi-synthetic , clindamycin, due to better and broader activity; however, it remains in use for veterinary applications and in specific cases where alternatives are unsuitable. Common adverse effects include gastrointestinal disturbances and potential pseudomembranous colitis, necessitating careful monitoring during therapy.

Medical Uses

Indications

Lincomycin is indicated for the treatment of serious infections caused by susceptible strains of , including streptococci, pneumococci, and staphylococci. It is particularly recommended for use in patients with or in scenarios where penicillin is deemed inappropriate by the prescribing physician. Common clinical applications include skin and soft tissue infections, respiratory tract infections, , and and infections in these patient populations. Due to its association with severe and increasing bacterial resistance patterns, current guidelines position lincomycin as a for such serious cases, rather than a first-line option. The U.S. approved lincomycin for human use on December 29, 1964. Lincomycin has a limited role in treating anaerobic infections, as its efficacy against anaerobes is narrower compared to its derivative clindamycin, which has largely replaced it for broader anaerobic coverage due to superior in vitro activity and pharmacological properties. In veterinary medicine, lincomycin is approved for treating bacterial infections in livestock, including swine dysentery (bloody scours) caused by susceptible organisms in pigs and necrotic enteritis due to Clostridium perfringens in broiler chickens. It is also indicated for infectious forms of arthritis in dogs and cats caused by sensitive bacteria, as well as respiratory and soft tissue infections in various species such as pigs and poultry.

Administration and Dosage

Lincomycin is available as a sterile injectable solution at a concentration of 300 mg/mL for intramuscular () or intravenous () administration. For adult patients, the standard IM administration is 600 mg every 24 hours for serious infections or every 12 hours for more severe infections, while IV administration involves 600 mg to 1 g every 8 to 12 hours, not exceeding 8 g per day. In patients with severe renal impairment (creatinine clearance <30 mL/min), the dosage should be reduced to 25-30% of the usual amount to account for prolonged half-life. For pediatric patients over 1 month of age, IM administration is 10 mg/kg every 20 to 24 hours for serious infections or every 12 hours for more severe infections; IV administration is 10 to 20 mg/kg per day divided into doses every 6 to 8 hours. In veterinary medicine, lincomycin is commonly used in swine, with a typical IM dosage of 11 mg/kg once daily for 3 to 7 days to treat conditions such as arthritis or . Intramuscular administration is preferred over IV for non-severe infections to minimize the risk of vein irritation or thrombophlebitis associated with IV use. Prolonged therapy with lincomycin requires monitoring for superinfections due to potential overgrowth of nonsusceptible organisms.

Safety and Adverse Effects

Contraindications

Lincomycin is contraindicated in patients with known hypersensitivity to lincomycin or clindamycin, as severe allergic reactions, including anaphylaxis, may occur. The U.S. Food and Drug Administration has issued a black box warning for lincomycin due to the risk of Clostridium difficile-associated diarrhea (CDAD), which can range from mild to fatal colitis; use with caution in patients with a history of gastrointestinal disease, particularly colitis. Relative contraindications include severe hepatic or renal impairment, where lincomycin should only be used with dose adjustments (typically 25-30% of the usual dose in severe renal impairment) and close monitoring to prevent accumulation and toxicity. Concurrent administration with neuromuscular blocking agents, such as or , is cautioned due to the potential for enhanced neuromuscular blockade leading to respiratory depression. Key drug interactions that contraindicate or caution lincomycin use include antagonism with erythromycin, resulting from competitive binding at the bacterial 50S ribosomal subunit and potential cross-resistance between lincosamides and macrolides. Additionally, co-administration with kaolin or cholestyramine should be avoided, as these agents bind lincomycin in the gastrointestinal tract, significantly reducing its absorption and efficacy.

Adverse Effects

Lincomycin is associated with a range of adverse effects, primarily affecting the gastrointestinal system, with less frequent but potentially severe reactions involving hypersensitivity, cardiovascular, and hematologic systems. Common adverse effects include gastrointestinal disturbances such as nausea, vomiting, and diarrhea, occurring in approximately 10-20% of patients based on clinical trial data where these symptoms were reported at a frequency of ≥1/10. Hypersensitivity reactions, manifesting as rash and pruritus, are also frequently observed, though exact incidence rates are not well-defined in post-marketing reports. Serious adverse effects encompass pseudomembranous colitis due to Clostridioides difficile overgrowth, which can range from mild diarrhea to life-threatening colitis and has been highlighted in post-marketing surveillance data up to 2023. Cardiovascular effects, such as hypotension, may occur with rapid intravenous infusion, while rare hematologic toxicities including neutropenia and thrombocytopenia have been documented. Long-term use of lincomycin carries risks of developing antibiotic resistance among bacterial populations and ototoxicity, particularly vertigo and tinnitus, which is more pronounced with high doses in patients with renal impairment. Management of serious effects like colitis typically involves immediate discontinuation of the drug and supportive care, including fluid and electrolyte replacement.

Pharmacology

Mechanism of Action

Lincomycin exerts its antibacterial effect by binding to the 50S subunit of the bacterial ribosome, specifically targeting the peptidyl transferase center (PTC) within the 23S ribosomal RNA (rRNA). This binding inhibits protein synthesis by sterically hindering the proper positioning of aminoacyl-tRNA or peptidyl-tRNA in the PTC, thereby preventing peptide bond formation and elongation of the nascent polypeptide chain. The drug is primarily bacteriostatic against most susceptible Gram-positive bacteria, as it reversibly blocks translation without causing immediate cell death; however, at higher concentrations, lincomycin can exhibit bactericidal activity against certain streptococci by more profoundly disrupting protein synthesis essential for bacterial survival. Lincomycin demonstrates high selectivity for bacterial ribosomes and lacks significant activity against mammalian eukaryotic ribosomes due to key structural differences in the rRNA sequences and ribosomal architecture, such as variations in the PTC region that prevent effective binding in host cells. Resistance to lincomycin commonly arises through mechanisms that alter the ribosomal target or expel the drug, including methylation of the 23S rRNA at adenine 2058 by erm genes, which sterically blocks antibiotic access to the PTC, or via active efflux pumps mediated by genes like lsa(E). Enzymatic inactivation by lincosamide nucleotidyltransferases, such as those encoded by lnu(A) or lnu(B), can also confer resistance by adding a nucleotide group to the antibiotic, reducing its affinity for the ribosome. Lincomycin's mechanism is closely related to that of its derivative clindamycin, which shares the same binding site but features enhanced ribosomal affinity due to a chlorine substitution that strengthens hydrogen bonding interactions within the PTC.

Pharmacokinetics

Lincomycin exhibits incomplete oral absorption, with bioavailability ranging from 20% to 50% in fasting individuals, though this is substantially reduced (to as low as 5%) when administered with food due to impaired gastrointestinal uptake. Peak plasma concentrations occur 2 to 4 hours following oral dosing, typically reaching 1.8 to 5.3 mcg/mL after a 500 mg dose. Intramuscular administration achieves higher peaks (9.3 to 18.5 mcg/mL after 600 mg) within 30 to 60 minutes, while intravenous infusion over 2 hours yields levels around 15.9 mcg/mL. The drug distributes widely throughout body tissues and fluids, achieving therapeutic concentrations in bone, lungs, bile, pleural and synovial spaces, and peritoneal fluid. Lincomycin readily crosses the placenta, potentially exposing the fetus, but demonstrates limited penetration into cerebrospinal fluid, even with inflamed meninges, making it unsuitable for central nervous system infections. Plasma protein binding is moderate, approximately 57% to 72%, varying with concentration and primarily involving alpha-1-acid glycoprotein. The volume of distribution at steady state approximates 0.8 to 1.2 L/kg, reflecting extensive tissue penetration. Lincomycin undergoes partial hepatic metabolism, primarily through N-demethylation and oxidation to form inactive metabolites such as N-desmethyl lincomycin and lincomycin sulfoxide, which contribute negligibly to overall antimicrobial activity. Excretion occurs mainly via biliary and fecal routes (up to 40%), with only 1.8% to 30.3% of the dose eliminated unchanged in urine following parenteral administration. The elimination half-life is 4 to 6.4 hours in individuals with normal renal function but can extend to 10 to 19 hours in severe renal impairment and twofold in hepatic dysfunction. Steady-state plasma levels are typically attained within 24 to 48 hours of repeated dosing. Hemodialysis and peritoneal dialysis remove negligible amounts of the drug, necessitating dose adjustments in renal impairment rather than reliance on dialysis for clearance.

Spectrum of Activity

Lincomycin exhibits strong bacteriostatic activity against many Gram-positive aerobic bacteria, particularly staphylococci, streptococci, and pneumococci. For susceptible strains of Staphylococcus aureus, minimum inhibitory concentrations (MICs) typically range from 0.2 to 3.2 μg/mL. Against Streptococcus pyogenes, MIC values are generally 0.04 to 0.8 μg/mL, while for Streptococcus pneumoniae, they fall between 0.05 and 0.4 μg/mL. This potency extends to toxin-producing strains such as S. pyogenes, where lincomycin inhibits growth effectively at low concentrations. The antibiotic shows moderate activity against certain anaerobic bacteria, including some Bacteroides and Clostridium species, with MICs ranging from 1 to 8 μg/mL. However, its efficacy against anaerobes is inferior to that of clindamycin, often requiring fourfold higher concentrations to achieve comparable inhibition. Lincomycin has limited or no activity against most Gram-negative bacteria, enterococci, and Mycoplasma species relevant to human infections. In veterinary medicine, however, it demonstrates activity against Mycoplasma hyopneumoniae in swine, supporting its use for mycoplasmal pneumonia in this context. Resistance to lincomycin is increasing among staphylococci, primarily mediated by erm(B) genes that encode ribosomal methylation, conferring cross-resistance to macrolides, lincosamides, and streptogramin B (MLSB phenotype). In the absence of formal EUCAST breakpoints for lincomycin as of 2025, susceptibility is often inferred from MIC distributions and clindamycin data, with strains considered susceptible at MIC ≤2 μg/mL and resistant at >4 μg/mL.
OrganismRepresentative MIC Range (μg/mL)Notes
Staphylococcus aureus (susceptible)0.2–3.2Strong activity; higher in resistant strains.
Streptococcus pyogenes0.04–0.8Effective against toxin producers.
Streptococcus pneumoniae0.05–0.4Good coverage for pneumococci.
Bacteroides spp. (selected)1–8Moderate; variable susceptibility.
Clostridium spp. (selected)1–8Inferior to clindamycin.

Chemistry and Production

Chemical Structure

Lincomycin is most commonly utilized in its hydrochloride monohydrate form, which has the empirical formula C_{18}H_{34}N_{2}O_{6}S \cdot HCl \cdot H_{2}O and a molecular weight of 461.01 g/mol. The core structure features a pyrrolidine ring as the amino acid moiety, connected through an amide bond to a modified octose sugar designated as methylthiolincosamide, incorporating a propylhygric acid side chain on the pyrrolidine. This architecture defines the lincosamide class, with the sulfur atom integrated into the sugar ring via a methylthio substituent at the 7-position, a hallmark that differentiates lincomycin within its antibiotic family. The hydrochloride salt enhances molecular stability, particularly for pharmaceutical formulations. Physically, lincomycin hydrochloride manifests as a white or practically white crystalline powder with a faint , freely soluble in water (approximately 50 mg/mL) and pKa of 7.6, reflecting the basic nature of its nitrogen-containing group. The complete structure, including absolute , was first elucidated in 1964 by researchers at The Company through chemical and spectroscopic analyses. Lincomycin contains seven chiral centers, contributing to its specific three-dimensional essential for .

Biosynthesis

Lincomycin is produced by the actinomycete Streptomyces lincolnensis through a bifurcated biosynthetic pathway that assembles the propylproline unit and the methylthiolincosaminide () sugar moiety, followed by their condensation and late-stage modifications. This pathway, fully elucidated by 2020 through integrated genomic sequencing, gene inactivation, and isotope labeling studies, relies on specialized enzymes rather than a classical type I (PKS)/non-ribosomal synthetase (NRPS) hybrid system, though it incorporates NRPS-like adenylation and condensation steps. The propylproline moiety, the component, originates from L-tyrosine as the primary precursor. The pathway begins with regioselective of L-tyrosine at the 3-position to form L-3,4-dihydroxyphenylalanine (), catalyzed by the unusual heme-dependent hydroxylase LmbB2 in the presence of as a cofactor. This is followed by extradiol ring cleavage of by the oxygenase LmbB1 to yield 5-alanyl-2-hydroxy-muconate 6-semialdehyde, which spontaneously cyclizes to a pyrrole-2-carboxylate intermediate. Subsequent steps include C-methylation at the 4-position using S-adenosylmethionine as the methyl donor, catalyzed by the radical SAM methyltransferase LmbW; oxidative C-C bond cleavage by the γ-glutamyltransferase-like LmbA; by LmbX; and finally, reduction by LmbY to produce (2S,4R)-4-propyl-L-proline. No direct incorporation of has been confirmed in modern studies; the propyl arises from rearrangement of the tyrosine-derived skeleton. The sugar moiety is biosynthesized from D-glucose as a key precursor, supplemented by and units from central (e.g., D-ribose 5-phosphate as the C5 acceptor and D-fructose 6-phosphate or sedoheptulose 7-phosphate as the C3 donor). The pathway constructs an unusual eight-carbon thio-octopyranose core through sequential C-methylation steps using S-adenosylmethionine-derived methyl groups and thiolation, with sulfur incorporated via mycothiol (MSH) and pathways involving LmbT and LmbV. Key transformations include GDP-activated octose formation, C6-epimerization and C4-epimerization by LmbM, 6,8-dehydration by LmbL/CcbZ, C6-transamination by CcbS to yield GDP-D-α-D-lincosamide, and N-methylation by LmbJ after MSH by LmbE. These steps highlight the pathway's reliance on atypical sugar nucleotide chemistry. The biosynthetic machinery is encoded by the lmb in the S. lincolnensis , spanning approximately 38 kb and comprising 27 core open reading frames dedicated to and , plus three genes (lmrAC). Notable genes include lmbB1 and lmbB2 for propylproline initiation, lmbW for , lmbA and lmbXY for maturation, lmbMS and ccb homologs for MTL processing, and lmbC encoding the unique lincosamide synthetase that catalyzes amide bond formation between the activated propylproline (as a thiol ) and the MTL . Late-stage tailoring involves N6-amidation (lmbN/D), S- (lmbG), and elimination of pyruvate/ammonium (lmbF), yielding mature lincomycin A. Regulatory genes like lmbU fine-tune expression. Industrial production of lincomycin exclusively employs microbial of optimized S. lincolnensis strains, with no commercial semisynthetic processes reported. Standard laboratory-scale under controlled conditions—pH 7.0, 28°C, and nutrient-rich supplemented with glucose and as primary carbon sources—yields 500–1000 mg/L for typical strains, though and medium optimization can elevate titers to over 4 g/L in shake flasks.

History

Discovery

Lincomycin was first isolated in 1961 by microbiologists at the Upjohn Company as part of a systematic screening program aimed at identifying new antibiotics to combat Gram-positive bacterial infections, particularly in the context of rising penicillin resistance among pathogens like Staphylococcus aureus. The compound was obtained from soil samples collected in Lincoln, Nebraska, which yielded a novel strain of the actinomycete Streptomyces lincolnensis var. lincolnensis (NRRL 2936). This strain was cultured in aqueous nutrient media under aerobic conditions, where it produced the antibiotic through fermentation. The discovery was credited to D. J. Mason, A. Dietz, and C. DeBoer, who identified its biological activity during initial screens. Initially termed "lincolnensin" in reference to its geographic origin, the antibiotic underwent preliminary characterization that revealed it as a basic substance with the empirical formula C₁₈H₃₄N₂O₆S and a pKa of approximately 7.6. Early biological assays, conducted by R. R. Herr and colleagues, demonstrated potent inhibitory effects against Gram-positive bacteria, including Staphylococcus aureus, Streptococcus species, and other pathogens resistant to existing therapies, while showing minimal activity against Gram-negative organisms. These tests highlighted its potential as a narrow-spectrum agent suitable for treating infections where penicillin had become ineffective. The initial findings were formally reported in 1962 in Antimicrobial Agents and Chemotherapy, marking the first public disclosure of lincomycin's and . By , further work by Herr and M. E. Bergy on and partial had confirmed its monobasic nature and provided insights into its chemical framework, laying the groundwork for subsequent full elucidation. This rapid progression from to basic characterization underscored the urgency of innovation during the era.

Development and Approval

Following the of lincomycin from samples, by The Upjohn Company focused on evaluating its safety profile through animal toxicity studies conducted between 1962 and 1963, which demonstrated low acute and in and other species at therapeutic doses, paving the way for human trials. These studies confirmed the antibiotic's tolerability, with no significant adverse effects observed at levels up to 2 g/kg orally in rats, supporting its progression to clinical evaluation. Subsequently, chemists at synthesized derivatives of lincomycin to enhance potency, resulting in clindamycin—a semisynthetic analog (7(S)-chloro-7-deoxylincomycin)—which exhibited improved activity against and better absorption. Clindamycin received FDA approval on February 22, 1970, for treating serious infections, largely supplanting lincomycin in clinical practice due to its superior efficacy and reduced gastrointestinal side effects. Clinical trials for lincomycin began in 1963 with Phase I pharmacological studies in healthy volunteers, confirming good tolerability and serum levels sufficient for antibacterial activity. Phase II and III trials from 1963 to 1964 involved patients with severe staphylococcal infections, demonstrating clinical success in approximately 80% of cases resistant to other antibiotics, with pivotal results published in 1964 highlighting its role in treating and infections. These trials, conducted primarily , underscored lincomycin's utility as an alternative to penicillin for gram-positive pathogens. The U.S. granted approval for lincomycin on December 29, 1964, under the trade name Lincocin for intramuscular and intravenous use in serious infections caused by susceptible streptococci, pneumococci, and staphylococci. Marketed by (later acquired by ), lincomycin saw global sales peak in the amid rising demand for antibiotics effective against resistant staphylococci, though usage declined thereafter with clindamycin's rise. Post-approval surveillance in the 1980s identified emerging resistance mechanisms, such as plasmid-mediated inactivation in staphylococci, prompting updates to prescribing guidelines to mitigate spread and preserve efficacy. In , lincomycin gained approvals across Europe in the 1970s for treating bacterial infections in and , often in combination formulations, though its use as a growth promoter was phased out in 1981 under EU Directive 74/180/EEC. By 2025, lincomycin's role has been de-emphasized in human medicine in favor of clindamycin, while veterinary applications continue under strict .

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