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Lincomycin

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
MDL Number:
MFCD00135816
MOL File:
154-21-2.mol
Last updated:2024-04-26 21:57:37

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
FDA 21 CFR 556.360; 558.325; 558.4
FDA UNII BOD072YW0F
ATC code J01FF02
NIST Chemistry Reference Lincomycin(154-21-2)
EPA Substance Registry System Lincomycin (154-21-2)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
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 price More Price(12)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Cayman Chemical 21526 Lincomycin ≥98% 154-21-2 5mg $130 2024-03-01 Buy
Cayman Chemical 21526 Lincomycin ≥98% 154-21-2 25mg $479 2024-03-01 Buy
Usbiological 471018 Lincomycin 154-21-2 1mg $595 2021-12-16 Buy
TRC L466230 Lincomycin 154-21-2 100mg $140 2021-12-16 Buy
TRC L466230 Lincomycin 154-21-2 1g $1070 2021-12-16 Buy
Product number Packaging Price Buy
21526 5mg $130 Buy
21526 25mg $479 Buy
471018 1mg $595 Buy
L466230 100mg $140 Buy
L466230 1g $1070 Buy

Lincomycin Chemical Properties,Uses,Production

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

An antibiotic produced by Streptomyces lincolnensis. Antibacterial

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

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.

859-18-7
154-21-2
Synthesis of Lincomycin from Lincomycin hydrochloride
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View Lastest Price from Lincomycin manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Lincomycin pictures 2024-04-26 Lincomycin
154-21-2
US $15.00 / kg 1kg 99.912% 10ton Ouhuang Engineering Materials (Hubei) Co., Ltd
Lincomycin pictures 2024-04-26 Lincomycin
154-21-2
US $21.00 / Grams 1000Grams 99.99% 100Tons Hebei Dangtong Import and export Co LTD
Lincomycin pictures 2024-04-10 Lincomycin
154-21-2
US $0.00-0.00 / mg 10mg 90%+ 10g Guangzhou PI PI BIOTECH INC
  • Lincomycin pictures
  • Lincomycin
    154-21-2
  • US $15.00 / kg
  • 99.912%
  • Ouhuang Engineering Materials (Hubei) Co., Ltd
  • Lincomycin pictures
  • Lincomycin
    154-21-2
  • US $21.00 / Grams
  • 99.99%
  • Hebei Dangtong Import and export Co LTD
  • Lincomycin pictures
  • Lincomycin
    154-21-2
  • US $0.00-0.00 / mg
  • 90%+
  • Guangzhou PI PI BIOTECH INC
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)