79548-73-5 Usage
Description
Pirlimycin is a semi-synthetic lincosamide antibiotic derived from clindamycin. It is more hydrophobic than clindamycin and exhibits increased potency against various significant pathogens. As a member of the lincosamide family, Pirlimycin possesses broad-spectrum antibiotic properties, demonstrating effectiveness against anaerobic bacteria and protozoans. Its mechanism of action involves binding to the 23S ribosomal subunit, thereby inhibiting protein synthesis. Although Pirlimycin has not been as extensively researched as older lincosamides, it holds promise in the field of antibiotic therapy.
Uses
Used in Pharmaceutical Industry:
Pirlimycin is used as a broad-spectrum antibiotic for treating various bacterial infections. Its increased potency against a range of pathogens, compared to clindamycin, makes it a valuable addition to the arsenal of antibiotics available for combating resistant bacteria.
Used in Veterinary Medicine:
In the veterinary field, Pirlimycin is utilized as an antibiotic to treat bacterial infections in animals. Its effectiveness against anaerobic bacteria and protozoans makes it suitable for a wide range of veterinary applications, contributing to the overall health and well-being of animals under treatment.
Used in Research and Development:
Pirlimycin serves as a subject of interest in the research and development of new antibiotics. Its unique properties and mechanism of action provide insights into the development of novel compounds with enhanced potency and broader spectrum coverage, potentially leading to the creation of more effective treatments for bacterial infections.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 79548-73-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,9,5,4 and 8 respectively; the second part has 2 digits, 7 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 79548-73:
(7*7)+(6*9)+(5*5)+(4*4)+(3*8)+(2*7)+(1*3)=185
185 % 10 = 5
So 79548-73-5 is a valid CAS Registry Number.
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
79548-73-5Relevant articles and documents
Synthesis and antimicrobial actvity of clindamycin analogues: Pirlimycin, a potent antibacterial agent
Birkenmeyer,Kroll,Lewis,et al.
, p. 216 - 223 (2007/10/02)
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.
