154-21-2 Usage
Description
Different sources of media describe the Description of 154-21-2 differently. You can refer to the following data:
1. Lincomycin is an antibiotic active against grampositive
bacteria. Occupational exposure occurs in
poultry and pig breeders.
2. 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
Uses
Different sources of media describe the Uses of 154-21-2 differently. You can refer to the following data:
1. 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).
2. An antibiotic produced by Streptomyces lincolnensis. Antibacterial
3. 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.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 154-21-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,5 and 4 respectively; the second part has 2 digits, 2 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 154-21:
(5*1)+(4*5)+(3*4)+(2*2)+(1*1)=42
42 % 10 = 2
So 154-21-2 is a valid CAS Registry Number.
InChI:InChI=1/C18H34N2O6S.C15H16Cl3N3O2/c1-5-6-10-7-11(20(3)8-10)17(25)19-12(9(2)21)16-14(23)13(22)15(24)18(26-16)27-4;1-2-4-20(15(22)21-5-3-19-10-21)6-7-23-14-12(17)8-11(16)9-13(14)18/h9-16,18,21-24H,5-8H2,1-4H3,(H,19,25);3,5,8-10H,2,4,6-7H2,1H3/t9-,10-,11+,12-,13+,14-,15-,16-,18-;/m1./s1
154-21-2Relevant articles and documents
Differences in PLP-Dependent Cysteinyl Processing Lead to Diverse S-Functionalization of Lincosamide Antibiotics
Wang, Min,Zhao, Qunfei,Zhang, Qinglin,Liu, Wen
, p. 6348 - 6351 (2016)
Pyridoxal-5′-phosphate (PLP)-dependent proteins constitute one of the largest and most important families of enzymes in living organisms. These proteins participate in numerous biochemical processes, many of which have not been characterized, and transform substrates containing an amino group through various reactions that share aldimine as a common intermediate. Herein, we report that the PLP-dependent enzymes CcbF and LmbF, which are highly related in phylogenesis, process cysteine S-conjugated intermediates in different ways and associate with individual downstream enzyme(s) toward distinct S-functionalization of the lincosamide antibiotics celesticetin and lincomycin A. CcbF catalyzes an unusual conversion that involves decarboxylation-coupled oxidative deamination of the cysteinyl group during the formation of a two-carbon alcohol linker, whereas LmbF is responsible for β-elimination, followed by S-methylation to produce a methylmercapto group. The two tailoring routes are variable and exchangeable with each other, allowing for in vitro combinatorial biosynthesis of a number of hybrid lincosamide antibiotics, including the natural product Bu-2545. These findings demonstrate the wide diversity of PLP chemistry in enzymatic catalysis and its promising applicability in creation of new molecules.
Preparation method of clindamycin hydrochloride impurities
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Paragraph 0094; 0119; 0120; 0121; 0122; 0123, (2020/01/08)
The invention relates to a preparation method of clindamycin hydrochloride impurities, which belongs to the field of medicines. The technical problem to be solved by the invention is that a method forefficiently preparing clindamycin hydrochloride impurities 7-epilincomycin and 7-epilincomycin hydrochloride reference substances is lacked in the prior art. The invention provides a preparation method of a clindamycin hydrochloride impurity intermediate shown as a formula II, which comprises the following steps: by using a compound shown as a formula I and R1COOH as raw materials, carrying out aMitsunobu substitution reaction for preparation, and adding amine and/or a nitrogen-containing aromatic heterocyclic compound into a reaction solution. The invention further provides a complete synthesis method of the 7-epilincomycin and the 7-epilincomycin hydrochloride. The complete synthesis method comprises the following steps: by taking lincomycin as a raw material, carrying out silicon protection group coating, selective deprotection, Mitsunobu substitution reaction and hydrolysis reaction to obtain the 7-epilincomycin, and further carrying out a chlorination reaction to prepare the 7-epilincomycin hydrochloride.
Lincomycin. V. Amino acid fragment.
Magerlein,Birkenmeyer,Herr,Kagan
, p. 2459 - 2464 (2007/10/04)
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