A lincosamide antibiotic
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Lincomycin

Item No. 21526

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
methyl 6,8-dideoxy-6-[[[(2S,4R)-1-methyl-4-propyl-2-pyrrolidinyl]carbonyl]amino]-1-thio-D-erythro-α-D-galacto-octopyranoside
CAS Number
154-21-2
Synonyms
  • U-10149
Molecular Formula
C18H34N2O6S
Formula Weight
406.5
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Slightly SolubleMethanol: Slightly Soluble
SMILES
C[C@@H](O)[C@](NC([C@@H]1C[C@@H](CCC)CN1C)=O)([H])[C@@]2([H])O[C@H](SC)[C@H](O)[C@@H](O)[C@H]2O
InChi Code
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
InChi Key
OJMMVQQUTAEWLP-KIDUDLJLSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    5 mg

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    Product Description

    Lincomycin is a lincosamide antibiotic originally isolated from S. lincolnensis.1,2 It is active against Gram-positive bacteria, including various strains of S. aureus, S. epidermidis, S. pneumoniae, and S. pyogenes (MICs = 0.2-3.2, 0.4-1.8, 0.01-0.8, and 0.04-0.8 µg/ml, respectively).2 Lincomycin selectively inhibits protein synthesis in purified ribosomes from S. aureus over E. coli (IC50s = 0.03 and 1.7 µg/ml, respectively, in cell-free assays).3 It is protective against development of mastitis in a mouse model of acute mastitis induced by S. aureus with a 50% protective dose (PD50) value of 3.5 mg/kg.4 Formulations containing lincomycin have been used in the treatment of Gram-positive bacterial infections.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Wilson, D.N. The A-Z of bacterial translation inhibitors. Crit. Rev. Biochem. Mol. Biol. 44(6), 393-433 (2009).

    2. Spížek, J., and Řezanka, T. Lincomycin, clindamycin and their applications. Appl. Microbiol. Biotechnol. 64(4), 455-464 (2004).

    3. Matzov, D., Eyal, Z., Benhamou, R., et al. Structural insights of lincosamides targeting the ribosome of Staphylococcus aureus. Nucleic Acids Res. 45(17), 10284-10292 (2017).

    4. Yancey, R.J., Jr., Kinney, M.L., and Ford, C.W. Efficacy of lincosaminide antibiotics in the treatment of experimental staphylococcal mastitis in lactating mice. J. Antimicrob. Chemother. 15(2), 219-232 (1985).