Pirlimycin
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Pirlimycin
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CAS No:
79548-73-5
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Formula:
C17H31ClN2O5S
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Chemical Name:
Pirlimycin
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Synonyms:
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)-;Methyl 7-chloro-6,7,8-trideoxy-6-[[[(2S,4R)-4-ethyl-2-piperidinyl]carbonyl]amino]-1-thio-L-threo-α-D-galacto-octopyranoside;Pirlimycin
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CAS No:
Description
Pirlimycin hydrochloride is an antibiotic belonging to the lincosamide class. Often marketed as Pirsue, this drug is used to treat mastitis in cattle.|Pirlimycin is a derivative of clindamycin with a 6-membered ring replacing clindamycin's 5-membered ring. Compared to clindimycin, pirlimycin has increased activity against gram-positive bacteria, including Staphylococcus aureus and coagulase negative species of Staphylococcus and Streptococcus. This agent is primarily used in the treatment of mastitis in cattle.
Drug Information
For the treatment of subclinical mastitis in lactating cows due to Gram-positive cocci susceptible to pirlimycin including staphylococcal organisms such as Staphylococcus aureus, both penicillinase-positive and penicillinase-negative, and coagulase-negative staphylococci; streptococcal organisms including Streptococcus agalactiae, Streptococcus dysgalactiae and Streptococcus uberis.
cis-4-ethyl-L-picecolic acid amide of 7-deoxy-7(S)chloromethylthio lincosaminide hydrochloride
Pirlimycin Use and Manufacturing
Pirlimycin is a semi-synthetic lincosamide prepared from clindamycin by hydrolysing the propyl N-methylproline and re-annealing a 4-ethylpipecolic acid. Pirlimycin is more hydrophobic than clindamycin and is more potent against a number of important pathogens. Like other members of the lincosamide family, pirlimycin is a broad spectrum antibiotic with activity against anaerobic bacteria and protozoans. Pirlimycin acts by binding to the 23S ribosomal subunit, blocking protein synthesis. Pirlimycin has been less extensively researched than the older lincosamides.
Veterinary drugs -> Pirsue -> EMA Drug Category|Antibacterials for intramammary use -> Veterinary pharmacotherapeutic group|Pharmaceuticals
Veterinary Drug -> ANTIMICROBIAL_AGENT;
Computed Properties
Molecular Weight:411.0
XLogP3:1.7
Hydrogen Bond Donor Count:5
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:6
Exact Mass:410.1642210
Monoisotopic Mass:410.1642210
Topological Polar Surface Area:136
Heavy Atom Count:26
Complexity:474
Defined Atom Stereocenter Count:9
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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