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Pirlimycin

CAS No.
79548-73-5
Chemical Name:
Pirlimycin
Synonyms
pyrimycin;Pirlimycin;Pirlimycina;Pirlimycine;Pirlimycinum;Pirlimycinum [inn-latin];Pirlimycine [inn-french];Pirlimycina [inn-spanish];Dexamethasone-4,6α,21,21-d;Methyl 7-chloro-6,7,8-trideoxy-6-[[[(2S,4R)-4-ethyl-2-piperidinyl]carbonyl]amino]-1-thio-L-threo-α-D-galacto-octopyranoside
CBNumber:
CB7947410
Molecular Formula:
C17H31ClN2O5S
Molecular Weight:
410.96
MDL Number:
MFCD00864968
MOL File:
79548-73-5.mol
Last updated:2023-05-21 10:59:17

Pirlimycin Properties

Boiling point 643.9±55.0 °C(Predicted)
Density 1.31
storage temp. Store at -20°C
solubility Soluble in ethanol;Soluble in methanol;Soluble in DMSO;Soluble in dimethyl formamide
form solid
pka 12.88±0.70(Predicted)
Stability Hygroscopic
FDA 21 CFR 556.515
FDA UNII LM19JT6G5K

Pirlimycin price More Price(9)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Cayman Chemical 20138 Pirlimycin ≥99% 79548-73-5 1mg $194 2024-03-01 Buy
Cayman Chemical 20138 Pirlimycin ≥99% 79548-73-5 5mg $773 2024-03-01 Buy
Usbiological P4205-50 Pirlimycin 79548-73-5 500ul $393 2021-12-16 Buy
American Custom Chemicals Corporation API0003875 PIRLIMYCIN 95.00% 79548-73-5 12KG $7069.76 2021-12-16 Buy
ApexBio Technology C5005 Pirlimycin 79548-73-5 1mg $243 2021-12-16 Buy
Product number Packaging Price Buy
20138 1mg $194 Buy
20138 5mg $773 Buy
P4205-50 500ul $393 Buy
API0003875 12KG $7069.76 Buy
C5005 1mg $243 Buy

Pirlimycin Chemical Properties,Uses,Production

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.

22965-79-3
79548-73-5
Synthesis of Pirlimycin from Methyl 7-Chloro-7-deoxy-1-thiolincosaMinide
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Pirlimycin Methyl 7-chloro-6,7,8-trideoxy-6-[[[(2S,4R)-4-ethyl-2-piperidinyl]carbonyl]amino]-1-thio-L-threo-alpha-D-galactooctopyranoside 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] Pirlimycinum Pirlimycinum [inn-latin] (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 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-a-D-galacto-Octopyranoside, methyl7-chloro-6,7,8-trideoxy-6-[[[(2S,4R)-4-ethyl-2-piperidinyl]carbonyl]amino]-1-thio- pyrimycin Dexamethasone-4,6α,21,21-d 79548-73-5 C17H31ClN2O5S