Pirlimycin
Catalog Number: BT-278678
CAS Number: 79548-73-5
Molecular Formula: C17H31ClN2O5S
Molecular Weight: 411 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.
Product Introduction
Description
Pirlimycin is a broad-spectrum antibiotic that belongs to the lincosamide class of antibiotics. It is primarily used in veterinary medicine to treat mastitis in dairy cows. Pirlimycin is a semi-synthetic derivative of lincomycin, which was first isolated from Streptomyces lincolnensis in 1962. Pirlimycin has been shown to be effective against a wide range of gram-positive bacteria, including Staphylococcus aureus, Streptococcus agalactiae, and Streptococcus uberis.
Properties
CAS Number
79548-73-5
Product Name
Pirlimycin
IUPAC Name
(2S,4R)-N-[(1S,2S)-2-chloro-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl]propyl]-4-ethylpiperidine-2-carboxamide
Molecular Formula
C17H31ClN2O5S
Molecular Weight
411 g/mol
InChI
InChI=1S/C17H31ClN2O5S/c1-4-9-5-6-19-10(7-9)16(24)20-11(8(2)18)15-13(22)12(21)14(23)17(25-15)26-3/h8-15,17,19,21-23H,4-7H2,1-3H3,(H,20,24)/t8-,9+,10-,11+,12-,13+,14+,15+,17+/m0/s1
InChI Key
HBJOXQRURQPDEX-DGZHSVRSSA-N
SMILES
CCC1CCNC(C1)C(=O)NC(C2C(C(C(C(O2)SC)O)O)O)C(C)Cl
Solubility
Soluble in DMSO
Synonyms
cis-4-ethyl-L-picecolic acid amide of 7-deoxy-7(S)chloromethylthio lincosaminide hydrochloride
pirlimycin
pirlimycin monohydrochloride monohydrate, (2S-cis)-isomer
pirlimycin monohydrochloride, (2R-cis)-isomer
U 57930E
U-57930E
pirlimycin
pirlimycin monohydrochloride monohydrate, (2S-cis)-isomer
pirlimycin monohydrochloride, (2R-cis)-isomer
U 57930E
U-57930E
Canonical SMILES
CCC1CCNC(C1)C(=O)NC(C2C(C(C(C(O2)SC)O)O)O)C(C)Cl
Isomeric SMILES
CC[C@@H]1CCN[C@@H](C1)C(=O)N[C@@H]([C@@H]2[C@@H]([C@@H]([C@H]([C@H](O2)SC)O)O)O)[C@H](C)Cl
Method of Synthesis or Extraction
Pirlimycin is synthesized by the chemical modification of lincomycin. The most commonly used method for the synthesis of pirlimycin is the acylation of lincomycin with 3,4-dimethoxybenzoyl chloride. This method yields pirlimycin with a purity of over 99%. However, this method is not very efficient, and the yield of pirlimycin is only around 50%. Another method for the synthesis of pirlimycin is the acylation of lincomycin with 3,4,5-trimethoxybenzoyl chloride. This method yields pirlimycin with a purity of over 99% and a yield of around 70%. Both of these methods require the use of toxic solvents and reagents, which can have negative environmental and safety considerations.
Chemical Structure and Biological Activity
Pirlimycin has a similar chemical structure to lincomycin, with the addition of a 3,4-dimethoxybenzoyl group. The mechanism of action of pirlimycin is similar to that of lincomycin, which inhibits bacterial protein synthesis by binding to the 50S ribosomal subunit. Pirlimycin has been shown to be effective against a wide range of gram-positive bacteria, including Staphylococcus aureus, Streptococcus agalactiae, and Streptococcus uberis. Pirlimycin has also been shown to have a low potential for resistance development.
Biological Effects
Pirlimycin has been shown to have a number of biological effects on cell function and signal transduction. Pirlimycin has been shown to inhibit the growth of cancer cells in vitro, and has been investigated as a potential anti-cancer agent. Pirlimycin has also been shown to have potential therapeutic effects in the treatment of inflammatory bowel disease. However, pirlimycin has also been shown to have potential toxic effects, including hepatotoxicity and nephrotoxicity.
Applications
Pirlimycin has a number of applications in medical research, including its role in drug development and clinical trials. Pirlimycin has been investigated as a potential treatment for a wide range of bacterial infections, including mastitis, pneumonia, and skin infections. Pirlimycin has also been investigated as a potential anti-cancer agent and as a treatment for inflammatory bowel disease. In environmental research, pirlimycin has been shown to have potential effects on ecosystems, and has been investigated as a potential tool for pollution management. In industrial research, pirlimycin has been used in manufacturing processes to improve product quality and efficiency.
Future Perspectives and Challenges
Despite its potential therapeutic and industrial applications, pirlimycin has a number of limitations in its use and study. Pirlimycin has been shown to have potential toxic effects, which limit its use in human medicine. Pirlimycin also has a limited spectrum of activity, which limits its use in the treatment of certain bacterial infections. Future research on pirlimycin will need to focus on developing new methods for synthesis and extraction, as well as investigating its potential therapeutic and industrial applications.
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