79548-73-5

Basic information

• Product Name: Pirlimycin
• Synonyms: Pirlimycin;Methyl 7-chloro-6,7,8-trideoxy-6-[[[(2S,4R)-4-ethyl-2-piperidinyl]carbonyl]amino]-1-thio-L-threo-α-D-galacto-octopyranoside;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)-;Pirlimycina;Pirlimycina [inn-spanish];Pirlimycine;Pirlimycine [inn-french]
• CAS NO: 79548-73-5
• Molecular Formula: C17H31ClN2O5S
• Molecular Weight: 410.96
• Mol File: 79548-73-5.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 643.9 °C at 760 mmHg
• Flash Point: 343.2 °C
• Appearance: /
• Density: 1.31
• Vapor Pressure: 2.68E-19mmHg at 25°C
• Refractive Index: 1.574
• Solubility: Soluble in ethanol;Soluble in methanol;Soluble in DMSO;Soluble in dimethyl formamide
• PKA: 12.88±0.70(Predicted)
• CAS DataBase Reference: Pirlimycin(CAS DataBase Reference)
• NIST Chemistry Reference: Pirlimycin(79548-73-5)
• EPA Substance Registry System: Pirlimycin(79548-73-5)

Safety Data

• Hazardous Substances Data: 79548-73-5(Hazardous Substances Data)

Usage

Uses

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.

Biological Activity

pirlimycin, a lincosamide antibiotic, is effective against gram-positive bacteria, including staphylococcus, bacteroides, streptococcus, and plasmodium. it functions via inhibiting protein synthesis in bacteria by inducing premature dissociation of the peptidyl-trna from the ribosome.

Veterinary Drugs and Treatments

Pirlimycin mastitis tubes are indicated for the treatment of clinical and subclinical mastitis caused by susceptible organisms in lactating dairy cattle.

in vitro

pirlimycin showed activity against helicobacter pylori with a minimal inhibitory concentration [mic] 50 of 4 μg/ml and an mic90 of 64 μg/ml [1].

in vivo

cows were treated with 50 mg of pirlimycin via two intramammary infusions per quarter at a 24-hour interval (2-day) for 2, 5, or 8 days. pirlimycin showed antibiotic therapy against environmental streptococcus spp and staphylococcus aureus intramammary individual and combined infections [1]. specifically, pirlimycin cured environmental streptococcus spp infections in 66.7% (14/21), 85% (17/20), 100% (14/14) in the 2-day group, 5-day group and 8-day group, respectively. s. aureus infections were cured by the treatment of pirlimycin in 13.3% (2/15), 31.3% (5/16), 83.3% (5/6) in the 2-day group, 5-day group and 8-day group, respectively. furthermore, s. aureus, s. dysgalactiae subsp dysgalactiae, and enterococcus spp intramammary infections were eliminated by the extended treatment of pirlimycin in 8-day group [2].

references

[1]. westblom, t., midkiff, b., & czinn, s. in vitro susceptibility ofhelicobacter pylori to trospectomycin, pirlimycin (u-57930e), mirincamycin (u-24729a) and n-demethyl clindamycin (u-26767a). european journal of clinical microbiology & infectious diseases. 1993; 12(7): 560-562. [2]. b. e. gillespie, h. moorehead, p. lunn, h. h. dowlen, d. l. johnson, k. c. lamar, m. j. lewis, s. j. ivey, j. w. hallberg, s. t. chester, and s. p. oliver. efficacy of extended pirlimycin hydrochloride therapy for treatment of environmental streptococcus spp and staphylococcus aureus intramammary infections in lactating dairy cows. veterinary therapeutics. 2002; 3(4): 373-80.

InChI:InChI=1/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

Upstream product

• 88015-20-7 4-ethyl-2-pyridinecarboxylic 3-methylbutanoic anhydride 
• 22965-79-3 methyl 6-amino-7(S)-chloro-6,7,8-trideoxy-1-thio-L-threo-α-D-galacto-octopyranoside 
• 78788-60-0 4-ethyl-2-pyridinecarboxamide of methyl (7S)-7-chloro-7-deoxythiolincosamide 

Relevant articles and documents

Synthesis and antimicrobial actvity of clindamycin analogues: Pirlimycin, a potent antibacterial agent

The preparation of a series of analogues of clindamycin is described in which the naturally occurring five-membered cyclic amino acid amide portion of the molecule is replaced by a four-, six-, or seven-membered cyclic amino acid amide. The most interesting compounds is pirlimycin (U-57,930E), in which the (2S-trans)-4n-propylhygramide portion of clindamycin is replaced by (2S-cis)-4-ethylpipecolamide. This structural modification results in significantly favorable changes in toxicity, metabolism, and antibacterial potency. Although the in vitro antibacterial activity of clindamycin and pirlimycin are nearly identical, the latter compounds is 2-20 times more active than clindamycin when administered to mice experimentally infected with strains of Staphylococcus aureus, Streptococcus pyogenes, Streptococcus pneumoniae, Bacteroides fragilis, and Plasmodium berghei. Pirlimycin is absorbed in rats and mice and is sequestered within these abscesses. A drug concentration of at least 60 times the required inhibitory concentration is maintained for 6 h following a single subcutaneous dose of 200 mg/kg. Urinary excretion of total bioactivity consists only of intact pirlimycin with no other antibacterially active metabolites being detected. Pirlimycin is tolerated well in rats and mice at the administered levels.