Lincomycin
Identification
- Name
- Lincomycin
- Accession Number
- DB01627
- Description
An antibiotic produced by Streptomyces lincolnensis var. lincolnensis. It has been used in the treatment of staphylococcal, streptococcal, and Bacteroides fragilis infections.
- Type
- Small Molecule
- Groups
- Approved, Vet approved
- Structure
Structure for Lincomycin (DB01627)
- Weight
- Average: 406.54
Monoisotopic: 406.213757997 - Chemical Formula
- C18H34N2O6S
- Synonyms
- Cillimycin
- LCM
- Lincomicina
- Lincomycin
- Lincomycine
- Lincomycinum
- External IDs
- U-10,149
- U-10149
Pharmacology
Accelerate your drug discovery research with the industry’s only fully connected ADMET dataset, ideal for:Accelerate your drug discovery research with our fully connected ADMET dataset- Indication
Lincomycin is an antibiotic used in the treatment of staphylococcal, streptococcal, and Bacteroides fragilis infections.
- Associated Conditions
- Contraindications & Blackbox Warnings
Contraindications & Blackbox WarningsWith our commercial data, access important information on dangerous risks, contraindications, and adverse effects.Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects- Pharmacodynamics
Lincomycin is a lincosamide antibiotic that produced by Streptomyces lincolnensis. Lincomycin has been shown to be active in vitro against the following microorganisms: Aerobic gram-positive cocci: Streptococcus pyogenes and Viridans group streptococci; Aerobic gram-positive bacilli: Corynebacterium diphtheriae; Anaerobic gram-positive non-sporeforming bacilli: Propionibacterium acnes; Anaerobic gram-positive sporeforming bacilli: Clostridium tetani and Clostridium perfringens.
- Mechanism of action
Lincomycin inhibits protein synthesis in susceptible bacteria by binding to the 50 S subunits of bacterial ribosomes and preventing peptide bond formation upon transcription. It is usually considered bacteriostatic, but may be bactericidal in high concentrations or when used against highly susceptible organisms.
Target Actions Organism A50S ribosomal protein L10 inhibitorShigella flexneri - Absorption
Rapidly absorbed from the gastrointestinal tract following oral administration. Approximately 20 to 30% absorbed orally in fasting state; absorption decreased when taken with food.
- Volume of distribution
- Not Available
- Protein binding
Protein binding decreases with increased plasma concentrations. Range, 28 to 86% (average, 70 to 75%). Albumin is not thought to be the primary binding component.
- Metabolism
Presumed hepatic, however metabolites have not been fully characterized.
- Route of elimination
Urinary excretion after this dose ranges from 1.8 to 24.8 percent (mean: 3 percent). Biliary excretion is also an important route of excretion.
- Half-life
The biological half-life after intramuscular or intravenous administration is 5.4 ± 1.0 hours. The serum half-life may be prolonged in patients with severe impairment of renal function. Half life may be extended up to 2-fold in patients with hepatic impairment.
- Clearance
- Not Available
- Adverse Effects
Reduce medical errorsand improve treatment outcomes with our comprehensive & structured data on drug adverse effects.Reduce medical errors & improve treatment outcomes with our adverse effects data- Toxicity
- Not Available
- Affected organisms
- Enteric bacteria and other eubacteria
- Pathways
Pathway Category Lincomycin Action Pathway Drug action - Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAcenocoumarol The risk or severity of bleeding can be increased when Lincomycin is combined with Acenocoumarol. Acetophenazine Acetophenazine may increase the neurotoxic activities of Lincomycin. Alimemazine Alimemazine may increase the neurotoxic activities of Lincomycin. Amisulpride Lincomycin may increase the neurotoxic activities of Amisulpride. Amitriptyline Amitriptyline may increase the neurotoxic activities of Lincomycin. Amitriptylinoxide Lincomycin may increase the neurotoxic activities of Amitriptylinoxide. Amoxapine Amoxapine may increase the neurotoxic activities of Lincomycin. Aripiprazole Aripiprazole may increase the neurotoxic activities of Lincomycin. Aripiprazole lauroxil Lincomycin may increase the neurotoxic activities of Aripiprazole lauroxil. Ascorbic acid The therapeutic efficacy of Lincomycin can be decreased when used in combination with Ascorbic acid. 
Improve patient outcomesBuild effective decision support tools with the industry’s most comprehensive drug-drug interaction checker.Learn more - Food Interactions
- Take on an empty stomach. Food decreases absorption.
Products
Comprehensive & structured drug product infoFrom application numbers to product codes, connect different identifiers through our commercial datasets.Easily connect various identifiers back to our datasets- Product Ingredients
Ingredient UNII CAS InChI Key Lincomycin hydrochloride GCW8Y9936L 859-18-7 POUMFISTNHIPTI-BOMBIWCESA-N Lincomycin hydrochloride monohydrate M6T05Z2B68 7179-49-9 LFZGYTBWUHCAKF-DCNJEFSFSA-N - International/Other Brands
- Lincobect / Lincorex
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Lincocin Capsule 500 mg Oral Pfizer Canada Ulc 1964-12-31 2006-08-02 Canada 
Lincocin Injection, solution 300 mg/1mL Intramuscular; Intravenous; Subconjunctival Pharmacia and Upjohn Company LLC 1964-12-29 Not applicable US 
Lincocin Solution 300 mg Intramuscular; Intravenous Pfizer Canada Ulc 1964-12-31 2016-05-06 Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Lincomycin Injection, solution 300 mg/1mL Intramuscular; Intravenous; Subconjunctival X-GEN Pharmaceuticals, Inc. 2015-07-05 Not applicable US Lincomycin Injection, solution 300 mg/1mL Intramuscular; Intravenous; Subconjunctival General Injectables and Vaccines, Inc. 2020-11-06 Not applicable US Lincomycin Injection, solution 300 mg/1mL Intramuscular; Intravenous; Subconjunctival A-S Medication Solutions 2015-07-05 Not applicable US Lincomycin Injection, solution 300 mg/1mL Intramuscular; Intravenous; Subconjunctival X-GEN Pharmaceuticals, Inc. 2015-07-05 Not applicable US
Categories
- ATC Codes
- J01FF02 — Lincomycin
- Drug Categories
- Agents that produce neuromuscular block (indirect)
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antibacterials for Systemic Use
- Antiinfectives for Systemic Use
- Carbohydrates
- Enzyme Inhibitors
- Glycosides
- Lincosamides
- Macrolides, Lincosamides and Streptogramins
- Neurotoxic agents
- Protein Synthesis Inhibitors
- Pyrrolidines
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as proline and derivatives. These are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- Proline and derivatives
- Alternative Parents
- Alpha amino acid amides / Thioglycosides / Pyrrolidinecarboxamides / Monosaccharides / N-alkylpyrrolidines / Oxanes / Monothioacetals / Trialkylamines / Secondary carboxylic acid amides / Secondary alcohols show 8 more
- Substituents
- Alcohol / Aliphatic heteromonocyclic compound / Alpha-amino acid amide / Amine / Azacycle / Carbonyl group / Carboxamide group / Glycosyl compound / Hydrocarbon derivative / Monosaccharide show 23 more
- Molecular Framework
- Aliphatic heteromonocyclic compounds
- External Descriptors
- monocarboxylic acid amide, pyrrolidinecarboxamide, L-proline derivative, carbohydrate-containing antibiotic, S-glycosyl compound (CHEBI:6472)
Chemical Identifiers
- UNII
- BOD072YW0F
- CAS number
- 154-21-2
- InChI Key
- OJMMVQQUTAEWLP-KIDUDLJLSA-N
- InChI
- InChI=1S/C18H34N2O6S/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)/t9-,10-,11+,12-,13+,14-,15-,16-,18-/m1/s1
- IUPAC Name
- (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
- SMILES
- [H][C@]1(C[C@@H](CCC)CN1C)C(=O)N[C@H]([C@@H](C)O)[C@H]1O[C@H](SC)[C@H](O)[C@@H](O)[C@H]1O
References
- Synthesis Reference
Alexander D. Argoudelis, David W. Stroman, "Process of producing lincomycin nucleotides." U.S. Patent US4464466, issued June, 1972.
US4464466- General References
- Not Available
- External Links
- KEGG Drug
- D00223
- KEGG Compound
- C06812
- PubChem Compound
- 3000540
- PubChem Substance
- 46506668
- ChemSpider
- 2272112
- BindingDB
- 50335522
- 6398
- ChEBI
- 6472
- ChEMBL
- CHEMBL1447
- ZINC
- ZINC000003982483
- Therapeutic Targets Database
- DAP000839
- PharmGKB
- PA164749212
- PDBe Ligand
- 3QB
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Lincomycin
- PDB Entries
- 4wh5 / 5hkv
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Unknown Status Treatment Cellulitis 1 1 Completed Not Available Bacterial Infections 1 0 Unknown Status Treatment Osteomyelitis 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Bimeda Inc.
- Carlisle Laboratories Inc.
- Clint Pharmaceutical Inc.
- Dispensing Solutions
- Keene Pharmaceuticals Inc.
- Llorens Pharmaceutical
- Martin Surgical Supply
- Medisca Inc.
- Nord Ost Corp.
- Pharmacia Inc.
- Preferred Pharmaceuticals Inc.
- Raz Co. Inc.
- Dosage Forms
Form Route Strength Solution Intramuscular 600 mg Solution Intramuscular; Intravenous 600 mg Capsule Oral 549.571 MG Powder 600 mg Injection, solution Intramuscular; Intravenous; Subconjunctival 300 mg/1mL Injection, solution Parenteral 300 MG Injection, solution Parenteral 600 MG Solution Intramuscular; Intravenous 300 mg Injection Intramuscular; Intravenous 600 mg/2ml Injection Intramuscular; Intravenous 600 mg Capsule Oral 250 mg Capsule Oral 565 MG Solution 600 mg/2ml Injection Intramuscular; Intravenous 300 mg/ml Capsule Oral 500 mg Injection, solution Intramuscular; Intravenous 600 mg/2ml Syrup Oral 250 MG/5ML Injection, solution Solution - Prices
Unit description Cost Unit Lincocin 300 mg/ml vial 7.79USD ml Lincomycin hcl powder 3.29USD g DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source logP 0.56 HANSCH,C ET AL. (1995) - Predicted Properties
Property Value Source Water Solubility 29.3 mg/mL ALOGPS logP 0.5 ALOGPS logP -0.32 ChemAxon logS -1.1 ALOGPS pKa (Strongest Acidic) 12.37 ChemAxon pKa (Strongest Basic) 7.97 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 7 ChemAxon Hydrogen Donor Count 5 ChemAxon Polar Surface Area 122.49 Å2 ChemAxon Rotatable Bond Count 7 ChemAxon Refractivity 102.67 m3·mol-1 ChemAxon Polarizability 43.65 Å3 ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.5937 Blood Brain Barrier - 0.9659 Caco-2 permeable - 0.8957 P-glycoprotein substrate Substrate 0.7945 P-glycoprotein inhibitor I Non-inhibitor 0.6755 P-glycoprotein inhibitor II Non-inhibitor 0.5633 Renal organic cation transporter Non-inhibitor 0.8868 CYP450 2C9 substrate Non-substrate 0.8417 CYP450 2D6 substrate Non-substrate 0.8837 CYP450 3A4 substrate Substrate 0.6389 CYP450 1A2 substrate Non-inhibitor 0.9222 CYP450 2C9 inhibitor Non-inhibitor 0.907 CYP450 2D6 inhibitor Non-inhibitor 0.9269 CYP450 2C19 inhibitor Non-inhibitor 0.9203 CYP450 3A4 inhibitor Non-inhibitor 0.9342 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9563 Ames test Non AMES toxic 0.7696 Carcinogenicity Non-carcinogens 0.9482 Biodegradation Not ready biodegradable 0.9622 Rat acute toxicity 2.5777 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9847 hERG inhibition (predictor II) Non-inhibitor 0.7163
Spectra
- Mass Spec (NIST)
- Download (7.07 KB)
- Spectra
Targets
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- Kind
- Protein
- Organism
- Shigella flexneri
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Structural constituent of ribosome
- Specific Function
- Protein L10 is also a translational repressor protein. It controls the translation of the rplJL-rpoBC operon by binding to its mRNA (By similarity).Forms part of the ribosomal stalk, playing a cent...
- Gene Name
- rplJ
- Uniprot ID
- P0A7J6
- Uniprot Name
- 50S ribosomal protein L10
- Molecular Weight
- 17711.38 Da
References
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
- Odom OW, Hardesty B: Use of 50 S-binding antibiotics to characterize the ribosomal site to which peptidyl-tRNA is bound. J Biol Chem. 1992 Sep 25;267(27):19117-22. [PubMed:1527036]
- Champney WS, Tober CL: Specific inhibition of 50S ribosomal subunit formation in Staphylococcus aureus cells by 16-membered macrolide, lincosamide, and streptogramin B antibiotics. Curr Microbiol. 2000 Aug;41(2):126-35. [PubMed:10856379]
Drug created on August 29, 2007 21:12 / Updated on February 21, 2021 18:51