Lincomycin Chemical Properties

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

Hazardous Substances Data

154-21-2(Hazardous Substances Data)

Toxicity

LD50 oral in rat: 1gm/kg

MSDS

• Language:English Provider:Methyl 6,8-dideoxy-6-[[[(2S,4R)-1-methyl-4-propyl-2-pyrrolidinyl]carbonyl]amino]-1-thio-D-erythro-alpha-D-gluco-octopyranoside

Lincomycin Usage And Synthesis

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.

Description

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

Chemical Properties

White Crystalline Solid

Originator

Lincocin,Upjohn,UK,1964

Uses

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).

Uses

An antibiotic produced by Streptomyces lincolnensis. Antibacterial

Uses

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.

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

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.

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