Pirlimycin Hydrochloride
Catalog Number: BT-278679
CAS Number: 78822-40-9
Molecular Formula: C17H32Cl2N2O5S
Molecular Weight: 447.4 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.
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Product Introduction
Description
Pirlimycin Hydrochloride is a broad-spectrum antibiotic that belongs to the lincosamide class of antibiotics. It is commonly used in veterinary medicine to treat mastitis in dairy cows. Pirlimycin Hydrochloride is a semi-synthetic derivative of lincomycin, which was first isolated from Streptomyces lincolnensis in 1962.
Properties
CAS Number
78822-40-9
Product Name
Pirlimycin Hydrochloride
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;hydrochloride
Molecular Formula
C17H32Cl2N2O5S
Molecular Weight
447.4 g/mol
InChI
InChI=1S/C17H31ClN2O5S.ClH/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);1H/t8-,9+,10-,11+,12-,13+,14+,15+,17+;/m0./s1
InChI Key
DPVJWUUBZWFDPG-XEDDUELXSA-N
SMILES
CCC1CCNC(C1)C(=O)NC(C2C(C(C(C(O2)SC)O)O)O)C(C)Cl.Cl
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.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.Cl
Method of Synthesis or Extraction
Pirlimycin Hydrochloride can be synthesized by the semi-synthesis of lincomycin. The synthesis involves the acylation of lincomycin with pivaloyl chloride, followed by the reduction of the resulting pivaloyl derivative with sodium borohydride. The yield of this method is around 50%, and the process is time-consuming and expensive. Another method of synthesis involves the reaction of lincomycin with hydrochloric acid in the presence of a reducing agent. This method yields Pirlimycin Hydrochloride with a higher purity and yield of around 80%. However, this method is not commonly used due to environmental and safety considerations.
Chemical Structure and Biological Activity
Pirlimycin Hydrochloride has a chemical formula of C18H35ClN2O6S and a molecular weight of 450.01 g/mol. The chemical structure of Pirlimycin Hydrochloride consists of a lincosamide ring, a pivaloyl group, and a hydroxyl group. The mechanism of action of Pirlimycin Hydrochloride involves the inhibition of bacterial protein synthesis by binding to the 50S ribosomal subunit. Pirlimycin Hydrochloride has a broad-spectrum of activity against Gram-positive bacteria, including Staphylococcus aureus, Streptococcus agalactiae, and Streptococcus uberis.
Biological Effects
Pirlimycin Hydrochloride has been shown to have potential therapeutic effects on cell function and signal transduction. It has been found to inhibit the growth of cancer cells in vitro and in vivo. However, Pirlimycin Hydrochloride also has potential toxic effects, including hepatotoxicity and nephrotoxicity. In addition, Pirlimycin Hydrochloride has been found to have adverse effects on the gastrointestinal tract, including diarrhea and colitis.
Applications
Pirlimycin Hydrochloride has various applications in medical research, environmental research, and industrial research. In medical research, Pirlimycin Hydrochloride has been used in drug development and clinical trials. It has been found to be effective in the treatment of mastitis in dairy cows. However, Pirlimycin Hydrochloride has potential side effects, including the development of antibiotic-resistant bacteria. In environmental research, Pirlimycin Hydrochloride has been found to have effects on ecosystems and pollution management. It has been found to be persistent in soil and water, and its use in agriculture may contribute to the development of antibiotic-resistant bacteria. In industrial research, Pirlimycin Hydrochloride has been used in manufacturing processes to improve product quality and efficiency. However, health and safety considerations must be taken into account when using Pirlimycin Hydrochloride in industrial settings.
Future Perspectives and Challenges
The use of Pirlimycin Hydrochloride in scientific research is limited by its potential toxic effects and the development of antibiotic-resistant bacteria. Possible solutions and improvements include the development of new antibiotics with fewer side effects and the use of alternative methods for the treatment of mastitis in dairy cows. Future trends and prospects in the application of Pirlimycin Hydrochloride in scientific research include the development of new methods for the synthesis or extraction of Pirlimycin Hydrochloride and the investigation of its potential therapeutic effects on cancer cells.
Conclusion:
In conclusion, Pirlimycin Hydrochloride is a broad-spectrum antibiotic that has various applications in medical research, environmental research, and industrial research. The method of synthesis or extraction, chemical structure and biological activity, biological effects, applications, future perspectives, and challenges of Pirlimycin Hydrochloride have been discussed in this paper. The use of Pirlimycin Hydrochloride in scientific research is limited by its potential toxic effects and the development of antibiotic-resistant bacteria. Possible solutions and improvements include the development of new antibiotics with fewer side effects and the use of alternative methods for the treatment of mastitis in dairy cows.
Conclusion:
In conclusion, Pirlimycin Hydrochloride is a broad-spectrum antibiotic that has various applications in medical research, environmental research, and industrial research. The method of synthesis or extraction, chemical structure and biological activity, biological effects, applications, future perspectives, and challenges of Pirlimycin Hydrochloride have been discussed in this paper. The use of Pirlimycin Hydrochloride in scientific research is limited by its potential toxic effects and the development of antibiotic-resistant bacteria. Possible solutions and improvements include the development of new antibiotics with fewer side effects and the use of alternative methods for the treatment of mastitis in dairy cows.
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