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Lincomycin

Lincomycin  Structure
CAS No.
154-21-2
Chemical Name:
Lincomycin
Synonyms
Lincomycine;Lincomycin hydrochoride;methyl6,8-dideoxy-6-(1-methyl-4-propyl-2-pyrrolidinecarboxamido)-1-thio-d-eryt;D-erythro-alpha-D-galacto-Octopyranoside, methyl 6,8-dideoxy-6-[[(1-methyl-4-propyl-2-pyrrolidinyl)carbonyl]amino]-1-thio-, (2S-trans)-;U-10149;Myvicin;Albiotic;U-10149A;jiemycin;NSC-70731
CBNumber:
CB3492619
Molecular Formula:
C18H34N2O6S
Molecular Weight:
406.54
MOL File:
154-21-2.mol
Modify Date:
2024/7/25 20:04:51

Lincomycin 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

Risk and Safety Statements

Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H315-H335-H319
Precautionary statements  P264-P280-P302+P352-P321-P332+P313-P362-P264-P280-P305+P351+P338-P337+P313P
Toxicity LD50 oral in rat: 1gm/kg

Lincomycin Chemical Properties,Uses,Production

Description

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

Chemical Properties

White Crystalline Solid

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.

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).

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U-10149A LINCOMYCIN STANDARD LINCOMYCIN LYNCOMYCIN Lincomycin HCL Bp98 USP24 EPIII CP2000 Lincomycin(baseand/orunspecifiedsalt) Albiotic Cillimycin NSC-70731 trans-alpha trans-alpha-opyl-2-pyrrolidinyl)carbonyl)amino)-1-thio trans-alpha--pyrrolidinecarboxamido)-1-thio U-10149 (2S-trans)-Methyl 6,8-dideoxy-6-[[(1-methyl-4-propyl-2-pyrrolidinyl)carbonyl]amino]-1-thio-D-threo-a-D-galacto-octopyranoside D-erythro-a-D-galacto-Octopyranoside, methyl 6,8-dideoxy-6-[[(1-methyl-4-propyl-2-pyrrolidinyl)carbonyl]amino]-1-thio-, (2S-trans)- D-erythro-a-D-galacto-Octopyranoside, methyl 6,8-dideoxy-6-[[[(2S,4R)-1-methyl-4-propyl-2-pyrrolidinyl]carbonyl]amino]-1-thio- (9CI) D-erythro-D-galacto-Octopyranoside, methyl 6,8-dideoxy-6-(1-methyl-4-propyl-L-2-pyrrolidinecarboxamido)-1-thio-, trans-a- (8CI) Lincomycin (base and/or unspecified salts) Methyl 6,8-dideoxy-6-[[[(2S,4R)-1-methyl-4-propyl-2-pyrrolidinyl]carbonyl]amino]-1-thio-D-erythro-alpha-D-gluco-octopyranoside (2S-trans)-Methyl 6,8-dideoxy-6-[[(1-methyl-4-propyl-2-pyrrolidinyl)carbonyl]amino]-1-thio-D-threo-α-D-galacto-octopyranoside Hydrochloride (2S-trans)-Methyl 6,8-dideoxy-6-[[(1-methyl-4-propyl-2-pyrrolidinyl)carbonyl]amino]-1-thio-D-threo-a-D-galacto-octopyranoside Hydrochloride d-erythro-alpha-d-galacto-octopyranoside,methyl6,8-dideoxy-6-(((1-methyl-4-pr D-erythro-D-galacto-Octopyranoside, methyl 6,8-dideoxy-6-(1-methyl-4-propyl-L-2-pyrrolidinecarboxamido)-1-thio-, trans- alpha- d-erythro-d-galacto-octopyranoside,methyl-6,8-dideoxy-6-(1-methyl-4-propyl-l-2 d-erythro-d-galacto-octopyranoside,methyl6,8-dideoxy-6-(1-methyl-4-propyl-l-2 hro-d-galacto-octopyranoside(alpha-form) jiemycin Lincocine Lincolcina Lincolnensin lincomycina Lincomyocin Methyl 6,8-dideoxy-6-([(1-methyl-4-propyl-2-pyrrolidinyl)carbonyl]amino)-1-thiooctopyranoside Methyl 6,8-dideoxy-6-trans-(1-methyl-4-propyl-L-2-pyrrolidinecarboxamido)-1-thio-D-erythro-alpha-D-galacto-octopyranoside (2S,4R)-N-[(1R,2R)-2-hydroxy-1-[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-methylsulfanyl-oxan-2-yl]propyl]-1-methyl-4-propyl-pyrrolidine-2-carboxamide Methyl-D-erythro-a-D-galacto-octopyranoside Myvicin Linocin, Lincolnensin, U 10149, JieMycin Clindamycin Phosphate EP Impurity A (Clindamycin HCl EP Impurity A) Clindamycin Phosphate EP Impurit A methyl 6,8-dideoxy-6-[[[(2S,4R)-1-methyl-4-propylpyrrolidin-2yl]carbonyl]amino]-1-thio-D-erythro-α-D-galacto-octopyranoside Clindamycin Impurity 10(Clindamycin Phosphate) Clindamycin HCl EP Impurity A ) Clindamycin Phosphate EP Impurity A/Lincomycin/(2S,4R)-N-((1R,2R)-2-hydroxy-1-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(methylthio)tetrahydro-2H-pyran-2-yl)propyl)-1-methyl-4-propylpyrrolidine-2-carboxamide Methyl 6,8-dideoxy-6-(1-methyl-4-propyl-2-pyrrolidinecarboxamido)-1-thio-D-erythro-a-D-galactooctopyranoside hydrochloride Clindamycin EP Impurity A Clindamycin Phosphate EP Impurity A Clindamycin Phosphate EP Impurities Clindamycin Impurity 10(Clindamycin Phosphate EP Impurity A (2S-trans)-Methyl 6,8-Dideoxy-6-[[(1-methyl-4-propyl-2-pyrrolidinyl)carbonyl ]amino]-1-thio-D-erythro-α-D-galacto-octopyranoside D-erythro-α-D-galacto-Octopyranoside, methyl 6,8-dideoxy-6-[[[(2S,4R)-1-methyl-4-propyl-2-pyrrolidinyl]carbonyl]amino]-1-thio- Clindamycin EP Impurity A (Lincomycine) Lincomycin USP/EP/BP Clindamycin Impurity 10(Clindamycin Phosphate EP Impurity A,Clindamycin HCl EP Impurity A ) Lincomycin(base) Clindamycin Hydrochloride EP Impurity A Clindamycin Phosphate Impurity A Clindamycin Phosphate Impurity A(EP)