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HomeProduct name listLincomycin

Lincomycin

  • CAS NO.:154-21-2
  • Empirical Formula: C18H34N2O6S
  • Molecular Weight: 406.54
  • MDL number: MFCD00135816
  • EINECS: 205-824-6
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-10-30 18:52:02
Lincomycin  Structural

What is Lincomycin ?

Absorption

A 600 mg dose of lincomycin administered over two hours intravenously results in an average Cmax of 15.9 μg/mL while the same dose given by intramuscular injection produces an average Cmax of 11.6 μg/mL after 60 minutes. Lincomycin administered intramuscularly to healthy adult male volunteers in doses between 600 and 1500 mg had an AUC0-∞ between 92.22 and 159.91 μg*h/mL. A similar study using intravenous infusion of 600-2400 mg lincomycin found AUC0-∞ values between 72.5 and 212.8 μg*h/mL. Overall, the AUC increases disproportionally to dose.

Toxicity

Toxicity information regarding lincomycin is not readily available. Patients experiencing an overdose are at an increased risk of severe adverse effects such as gastrointestinal effects including colitis, secondary infections, and severe hypersensitivity reactions. Symptomatic and supportive measures are recommended. It is important to note that hemodialysis and peritoneal dialysis do not appreciably affect lincomycin serum concentrations.

Description

Lincomycin is an antibiotic active against grampositive bacteria. Occupational exposure occurs in poultry and pig breeders.

Description

Lincomycin was isolated from a strain of Streptomyces lincolnensis in the Upjohn Research Laboratories. Lincosamides are also produced by S. roseolus, S. caelestis, and Monomicrospora halophytica. They consist of an amino acid connected to a sugar by an amide bond. It is available for intravenous, intramuscular, oral, and rectal use. Absorption after oral administration is up to one-third of the dose and plasma protein binding is around 75%. Because of the superior activity and bioavailability of clindamycin, lincomycin is now infrequently used clinically, but it is still available in some countries, in particular for skin and skin structure infections. Thus, the information in this chapter will primarily apply to clindamycin. Many chemical modifications of the lincomycin molecule have been developed and, of these, clindamycin (7-chloro-7-deoxylincomycin) is the most promising and clinically superior to lincomycin.

Chemical properties

White Crystalline Solid

Originator

Lincocin,Upjohn,UK,1964

The Uses of Lincomycin

Lincomycin is a polar, water soluble, broad spectrum antibiotic first isolated from Streptomyces licolnensis by researchers at Upjohn in 1962. Lincomycin was the first of a unique structural class, the lincosamides, containing a rare amino acid, 4-propyl-N-methylproline, coupled to an equally rare aminomethylthio-octopyranoside sugar. Lincomycin and semi-synthetic analogues are often incorrectly considered to be aminoglycosides but share little or no structural similarity. Lincomycin is a broad spectrum antibiotic with activity against anaerobic bacteria and protozoans. Lincomycin acts by binding to the 23S ribosomal subunit, blocking protein synthesis. Lincomycin has been extensively studied with over 7,000 literature citations.

The Uses of Lincomycin

An antibiotic produced by Streptomyces lincolnensis. Antibacterial

The Uses of Lincomycin

Lincomycin (Clindamycin Phosphate EP Impurity A) is a lincosamide antibiotic that forms cross-links within the peptidyl transferase loop region of the 23S rRNA. Inhibits bacterial protein synthesis. Antibacterial.This compound is a contaminant of emerging concern (CECs).

Indications

Lincomycin is indicated for the treatment of serious bacterial infections by susceptible strains of streptococci, pneumococci, and staphylococci in patients who are allergic to penicillins or for situations in which a penicillin is deemed inappropriate. As with all antibacterial agents, lincomycin should only be used to treat infections proven or strongly suspected to be caused by susceptible bacteria.

Background

Lincomycin is a lincosamide antibiotic first isolated from the soil bacterium Streptomyces lincolnensis in Lincoln, Nebraska. Clinical use of lincomycin has largely been superseded by its semisynthetic derivative clindamycin due to its higher efficacy and a wider range of susceptible organisms, though lincomycin remains in use.
Lincomycin was approved by the FDA on December 29, 1964.

What are the applications of Application

Lincomycin is a water soluble, broad spectrum antibiotic with activity against anaerobic bacteria and protozoans

Definition

ChEBI: A carbohydrate-containing antibiotic produced by the actinomyces Streptomyces lincolnensis.

Manufacturing Process

As described in US Patent 3,086,912, the process comprises cultivating Streptomyces lincolnensis var. lincolnensis in an aqueous nutrient medium containing a source of assimilable carbohydrate and assimilable nitrogen under aerobic conditions until substantial activity is imparted to the medium by production of lincolnensin and isolating the lincolnensin so produced.

brand name

Lincocin (Pharmacia & Upjohn).

Therapeutic Function

Antibacterial

Antimicrobial activity

Lincomycin has an antibacterial effect with respect to Gram-positive microorganisms (staphylococci, streptococci, pneumococci, diphtheria bacillus, and clostridia). It is used for serious bacterial infections: sepsis, osteomyelitis, septic endocarditis, pneumonia, pulmonary abscess, infected wounds, and purulent meningitis. Lincomycin is a reserve drug for infections caused by strains of staphylococci and other Gram-positive microorganisms that are resistant to penicillin and other antibiotics. Synonyms of this drug are lincocin, mycivin, albiotic, and others.

General Description

Lincomycin was found in the culture broth of Streptomyces lincolnensis var. lincolnensis by the Upjohn Co. in 1962. It shows antibacterial activity similar to that of the macrolide antibiotics and also shows excellent activity against anaerobic bacteria. Lincomycin is used clinically in combination with other classes of antibiotics for postoperative, gynecological, urinary tract, ear and nose, and other infections.

Contact allergens

Lincomycin is an antibiotic of the lincosanide group,active against Gram-positive bacteria. Occupational exposure occurs in poultry and pig breeders

Pharmacokinetics

Lincomycin is a lincosamide antibiotic derived as a natural fermentation product from Streptomyces lincolnensis. Like clindamycin, lincomycin is active against Gram-positive cocci and bacilli as well as Gram-negative cocci and some other organisms such as Haemophilus spp. It is also effective against anaerobic bacteria, though in this regard clindamycin is generally more potent. Prescribing information highlights that the range of clinically confirmed effectiveness is largely limited to Staphylococcus spp. and Streptococcus spp., with additional activity noted in vitro.
Lincomycin should be used with caution due to its association with severe cutaneous hypersensitivity reactions such as Stevens-Johnson syndrome, toxic epidermal necrolysis, erythema multiforme, and acute generalized exanthematous pustulosis, and its potential to precipitate Clostridium difficile associated diarrhea (CDAD), which may lead to fatal colitis. Special care should therefore be exercised when used in elderly patients, individuals with a history of gastrointestinal disease, and those with a history of asthma or significant allergies. Lincomycin for injection may contain benzyl alcohol as a preservative, which has been associated with gasping syndrome in pediatric patients. The serum half-life is extended in patients with hepatic/renal impairment and may require dose adjustments and additional monitoring. Like all antibiotics, lincomycin use may cause overgrowth of non-susceptible organisms, which should be considered.

Clinical Use

Lincomycin is a natural product isolated from fermentations of Streptomyces lincolnensisvar. lincolnensis. It is active against Gram-positive organisms, including some anaerobes. It is indicated for the treatment of serious infections caused by sensitive strains of streptococci, pneumococci, and staphylococci. It generally is reserved for patients who are allergic to penicillin because of the increased risk of pseudomembranous colitis. It also serves as the starting material for the synthesis of clindamycin (by a SN-2 reaction that inverts the R stereochemistry of the C-7 hydroxyl to a C-7 S-chloride).

Synthesis

Lincomycin, 6,8-dideoxy-6-trans-(1-methyl-4-propyl-L-2-pyrrolidincarboxamido)-1-methylthio-D-erythro-α-D-galacto-octopyranoside (32.5.1), is the first lincosamide that has found use in clinical practice, and which was isolated in 1962 from the culture liquid of the activity of the actinomycete Streptomyces lincolnensis.

Veterinary Drugs and Treatments

Lincomycin has dosage forms approved for use in dogs, cats, swine, and in combination with other agents for chickens. Because clindamycin is generally better absorbed, more active, and probably less toxic, it has largely supplanted the use of lincomycin for oral and injectable therapy in small animals, but some clinicians believe that clindamycin does not offer enough clinically significant improvements over lincomycin to justify its higher cost. For further information, refer to the Pharmacology or Doses sections.

Metabolism

Lincomycin metabolism is poorly defined, though the primary product recovered following administration in humans is unchanged lincomycin.

Properties of Lincomycin

Melting point: 148-150°C
Boiling point: 646.8±55.0 °C(Predicted)
Density  1.1704 (rough estimate)
refractive index  1.6510 (estimate)
storage temp.  Hygroscopic, -20°C Freezer, Under inert atmosphere
solubility  Aqueous Acid (Slightly), DMSO (Slightly), Methanol (Slightly), Water
form  Solid
pka 7.6(at 25℃)
color  White to Off-White
Stability: Hygroscopic
NIST Chemistry Reference Lincomycin(154-21-2)
EPA Substance Registry System Lincomycin (154-21-2)

Safety information for Lincomycin

Computed Descriptors for Lincomycin

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