ChemicalBook--->CAS DataBase List--->154-21-2

154-21-2

154-21-2 Structure

154-21-2 Structure
IdentificationBack Directory
[Name]

Lincomycin
[CAS]

154-21-2
[Synonyms]

U-10149
Myvicin
U-10149A
Albiotic
jiemycin
Lincocine
NSC-70731
Lincolcina
Cillimycin
LINCOMYCIN
LYNCOMYCIN
lincomycina
Lincomycine
Lincomyocin
trans-alpha
Lincolnensin
LINCOMYCIN STANDARD
Lincomycin hydrochoride
Lincomycin(baseand/orunspecifiedsalt)
Lincomycin HCL Bp98 USP24 EPIII CP2000
hro-d-galacto-octopyranoside(alpha-form)
Linocin, Lincolnensin, U 10149, JieMycin
Lincomycin (base and/or unspecified salts)
trans-alpha--pyrrolidinecarboxamido)-1-thio
Methyl-D-erythro-a-D-galacto-octopyranoside
trans-alpha-opyl-2-pyrrolidinyl)carbonyl)amino)-1-thio
d-erythro-d-galacto-octopyranoside,methyl6,8-dideoxy-6-(1-methyl-4-propyl-l-2
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
methyl6,8-dideoxy-6-(1-methyl-4-propyl-2-pyrrolidinecarboxamido)-1-thio-d-eryt
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-trans)-Methyl 6,8-dideoxy-6-[[(1-methyl-4-propyl-2-pyrrolidinyl)carbonyl]amino]-1-thio-D-threo-a-D-galacto-octopyranoside
Methyl 6,8-dideoxy-6-[[[(2S,4R)-1-methyl-4-propyl-2-pyrrolidinyl]carbonyl]amino]-1-thio-D-erythro-alpha-D-gluco-octopyranoside
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-pyrrolidinecarboxamido)-1-thio-, trans-a-(8CI)
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-alpha-D-galacto-Octopyranoside, methyl 6,8-dideoxy-6-[[(1-methyl-4-propyl-2-pyrrolidinyl)carbonyl]amino]-1-thio-, (2S-trans)-
(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
(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
[EINECS(EC#)]

205-824-6
[Molecular Formula]

C18H34N2O6S
[MDL Number]

MFCD00135816
[MOL File]

154-21-2.mol
[Molecular Weight]

406.54
Chemical PropertiesBack Directory
[Appearance]

White Crystalline Solid
[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
[Henry's Law Constant]

3.3×1017 mol/(m3Pa) at 25℃, HSDB (2015)
[Stability:]

Hygroscopic
[Contact allergens]

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

POUMFISTNHIPTI-KADGABRTNA-N
[SMILES]

[C@H]1([C@H](O)[C@@H]([C@@H](O)[C@@H](SC)O1)O)[C@@H]([C@H](O)C)NC(=O)[C@H]1N(C)C[C@H](CCC)C1.Cl |&1:0,1,3,4,6,11,12,18,22,r|
[NIST Chemistry Reference]

Lincomycin(154-21-2)
[EPA Substance Registry System]

D-erythro-.alpha.-D-galacto-Octopyranoside, methyl 6,8-dideoxy-6-[[[(2S,4R)-1-methyl-4-propyl-2-pyrrolidinyl] carbonyl]amino]-1-thio-(154-21-2)
Hazard InformationBack Directory
[Chemical Properties]

White Crystalline Solid
[Usage]

An antibiotic produced by Streptomyces lincolnensis. Antibacterial
[Usage]

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.
[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.
[Description]

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

Lincocin,Upjohn,UK,1964
[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.
[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.
[storage]

Store at -20°C
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
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
[Hazardous Substances Data]

154-21-2(Hazardous Substances Data)
[Toxicity]

LD50 oral in rat: 1gm/kg
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Lindane-->Methyl 6,8-Dideoxy-6-[[[(2S,4R)-1-Methyl-4-propyl-2-pyrrolidinyl]carbonyl]aMino]-1-thio-2,3,4-tris-O-(triMethylsilyl)-D-erythro-α-D-galacto-octopyranoside-->Lincomycin hydrochloride
[Preparation Products]

Clindamycin hydrochloride
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

Lincomycin (154-21-2).msds
Spectrum DetailBack Directory
[Spectrum Detail]

Lincomycin(154-21-2)1HNMR
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