CAS 79548-73-5

Pirlimycin

Description:

Pirlimycin is an antibiotic belonging to the lincosamide class, primarily used in veterinary medicine for the treatment of infections in cattle, particularly mastitis. It is effective against a range of Gram-positive bacteria, including certain strains of Staphylococcus and Streptococcus. The chemical structure of pirlimycin features a unique bicyclic core that is characteristic of lincosamides, which contributes to its mechanism of action by inhibiting bacterial protein synthesis. This inhibition occurs through binding to the 50S ribosomal subunit, effectively blocking peptide bond formation. Pirlimycin is typically administered via intramammary infusion or injection, and its pharmacokinetics allow for effective tissue penetration, making it suitable for treating localized infections. While it is generally well-tolerated, potential side effects may include gastrointestinal disturbances or allergic reactions in some animals. As with all antibiotics, responsible use is crucial to mitigate the risk of developing antibiotic resistance.

Formula: C₁₇H₃₁ClN₂O₅S

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: InChIKey=HBJOXQRURQPDEX-MHXMMLMNSA-N

SMILES: [C@@H](NC(=O)[C@@H]1C[C@H](CC)CCN1)([C@H](C)Cl)[C@]2(O[C@H](SC)[C@H](O)[C@@H](O)[C@H]2O)[H]

Synonyms:

• <span class="text-smallcaps">L</smallcap>-threo-α-<smallcap>D</span>-galacto-Octopyranoside, methyl 7-chloro-6,7,8-trideoxy-6-[[(4-ethyl-2-piperidinyl)carbonyl]amino]-1-thio-, (2S-cis)-
• <span class="text-smallcaps">L</smallcap>-threo-α-<smallcap>D</span>-galacto-Octopyranoside, methyl 7-chloro-6,7,8-trideoxy-6-[[[(2S,4R)-4-ethyl-2-piperidinyl]carbonyl]amino]-1-thio-
• L-threo-alpha-galacto-Octopyranoside, methyl 7-chloro-6,7,8-trideoxy-6-((((2S,4R)-4-ethyl-2-piperidinyl)carbonyl)amino)-1-thio-
• L-threo-alpha-galacto-Octopyranoside, methyl 7-chloro-6,7,8-trideoxy-6-(((4-ethyl-2-piperidinyl)carbonyl)amino)-1-thio-, (2S-cis)-
• Methyl 7-chloro-6,7,8-trideoxy-6-[[[(2S,4R)-4-ethyl-2-piperidinyl]carbonyl]amino]-1-thio-<span class="text-smallcaps">L</smallcap>-threo-α-<smallcap>D</span>-galacto-octopyranoside
• Methyl 7-chloro-6,7,8-trideoxy-6-[[[(2S,4R)-4-ethyl-2-piperidinyl]carbonyl]amino]-1-thio-L-threo-α-D-galacto-octopyranoside
• Pirlimycina
• Pirlimycina [INN-Spanish]
• Pirlimycine
• Pirlimycine [INN-French]
• Pirlimycinum
• Pirlimycinum [INN-Latin]
• Unii-Lm19Jt6G5K
• methyl 7-chloro-6,7,8-trideoxy-6-({[(2S,4R)-4-ethylpiperidin-2-yl]carbonyl}amino)-1-thio-L-threo-alpha-D-galacto-octopyranoside
• L-threo-α-D-galacto-Octopyranoside, methyl 7-chloro-6,7,8-trideoxy-6-[[[(2S,4R)-4-ethyl-2-piperidinyl]carbonyl]amino]-1-thio-
• L-threo-α-D-galacto-Octopyranoside, methyl 7-chloro-6,7,8-trideoxy-6-[[(4-ethyl-2-piperidinyl)carbonyl]amino]-1-thio-, (2S-cis)-

Pirlimycin Hydrochloride (Mixture of Diastereomers)

Controlled Product

CAS: 78822-40-9, 79548-73-5

Stability Hygroscopic
Applications Pirlimycin Hydrochloride (Mixture of Diastereomers) is a semi-synthetic lincosaminide antibiotic; structural analog of Clindamycin. Antibacterial.
References Ahonkhai, V.I., et al.: Antimicrob. Agents Chemother., 21, 902 (1982); Qadri, S.M.H., et al.: J. Antibiot., 36, 42 (1983); Birkenmeyer, R.D., et al.: J. Med. Chem., 27, 216 (1984);

Formula: C₁₇H₃₁ClN₂O₅S·ClH

Color and Shape: White To Off-White

Molecular weight: 447.42

Ref: TR-P509300

Pirlimycin

CAS: 79548-73-5

Pirlimycin is a glycol ester, glycol ether and a member of the antimicrobial agents that inhibits bacterial growth. It has been shown to be effective against streptococcus species and viruses, as well as human serum and fat. Pirlimycin inhibits the synthesis of proteins by binding to the 50S ribosomal subunit in bacteria, leading to cell death. It is also active against Streptococcus pneumoniae and Streptococcus pyogenes (viridans group). The analytical method for pirlimycin is found to be sensitive, simple, accurate and precise. This assay can detect pirlimycin at levels as low as 0.1 ppm in biological samples such as human serum or fatty acid.

Formula: C₁₇H₃₁ClN₂O₅S

Purity: Min. 95%

Molecular weight: 411 g/mol

Ref: 3D-EDA54873