Pirlimycin
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| Category | Antibiotics |
| Catalog number | BBF-03947 |
| CAS | 79548-73-5 |
| Molecular Weight | 410.96 |
| Molecular Formula | C17H31ClN2O5S |
| Purity | 95% |
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Description
A semi-synthetic lincosamide prepared from clindamycin by hydrolysing the propyl N-methylproline and re-annealing a 4-ethylpipecolic acid. It is a broad spectrum antibiotic with activity against anaerobic bacteria and protozoans by binding to the 23S ribosomal subunit, blocking protein synthesis.
Specification
| Synonyms | U-57930E; methyl 7-chloro-6,7,8-trideoxy-6-[[[(2S,4R)-4-ethyl-2-piperidinyl]carbonyl]amino]-1-thio-L-threo-α-D-galacto-octopyranoside |
| Storage | Store at -20°C |
| IUPAC Name | (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 |
| Canonical SMILES | CCC1CCNC(C1)C(=O)NC(C2C(C(C(C(O2)SC)O)O)O)C(C)Cl |
| 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 | HBJOXQRURQPDEX-MHXMMLMNSA-N |
| Source | Semi-synthetic |
Properties
| Appearance | White Solid |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Boiling Point | 643.9°C at 760 mmHg |
| Density | 1.31 g/cm3 |
| Solubility | Soluble in ethanol, methanol, DMF, DMSO; Good water solubility. |
Reference Reading
1.Performance characterization of a quantitative liquid chromatography-tandem mass spectrometric method for 12 macrolide and lincosamide antibiotics in salmon, shrimp and tilapia.
Dickson LC1. J Chromatogr B Analyt Technol Biomed Life Sci. 2014 Sep 15;967:203-10. doi: 10.1016/j.jchromb.2014.07.031. Epub 2014 Jul 27.
This paper describes an extension and performance characterization of a quantitative confirmatory multi-residue liquid chromatography-tandem mass spectrometric method for residues of macrolide and lincosamide antibiotics, originally validated for application to bovine kidney tissues, to tissues of salmon, shrimp and tilapia. The 12 analytes include clindamycin, erythromycin A, gamithromycin, josamycin, lincomycin, neospiramycin 1, oleandomycin, pirlimycin, spiramycin 1, tildipirosin, tilmicosin and tylosin A. The limit of detection was 0.5 μg/kg. Within-laboratory precision evaluated over the analytical range of 5.0-50.0 μg/kg ranged from 4 to 17%. The accuracy of the method ranged from 80 to 112%. Recoveries ranged from 47 to 99% with all but one recovery above 60%. This is the first report of a quantitative confirmatory method for gamithromycin, pirlimycin and tildipirosin in fish and shrimp.
2.Analysis of Pirlimycin Residues in Beef Muscle, Milk, and Honey by a Biotin-Streptavidin-Amplified Enzyme-Linked Immunosorbent Assay.
Jiang W1, Beier RC2, Luo P3, Zhai P1, Wu N3, Lin G1, Wang X1, Xu G4. J Agric Food Chem. 2016 Jan 13;64(1):364-70. doi: 10.1021/acs.jafc.5b05711. Epub 2015 Dec 31.
Food contamination by veterinary drug residues is a worldwide public health concern and requires continuous monitoring. In this study, we developed a biotin-streptavidin-amplified ELISA (BA-ELISA) using a produced monoclonal antibody for detecting pirlimycin residues in beef muscle, milk, and honey. The IC50 value of the BA-ELISA was 1.6 ng/mL for pirlimycin in buffer, and the sensitivity was improved 3 times compared to traditional ELISAs. The optimized BA-ELISA can be used to quantitate trace amounts of pirlimycin residues in beef muscle, milk, and honey. This method had limits of detection (LODs) of 4.45 μg/kg in beef muscle, 1.65 μg/L in milk, and 2.75 μg/kg in honey. The average recovery of the BA-ELISA ranged from 78 to 97%, and the coefficient of variation ranged from 5.3 to 13.5%. The developed BA-ELISA method was validated using LC-MS/MS, and the BA-ELISA can be used for routine screening analysis of pirlimycin residues.
3.Characterization of methicillin-resistant Staphylococcus spp. isolated from dogs in Korea.
Jang Y1, Bae Dh, Cho JK, Bahk GJ, Lim SK, Lee YJ. Jpn J Vet Res. 2014 Nov;62(4):163-70.
Staphylococci were isolated from dogs in animal hospitals, animal shelters, and the Daegu PET EXPO to investigate the characteristics of circulating methicillin-resistant Staphylococcal (MRS) strains in companion animals in Korea. A total of 36/157 isolates were classified as MRS, and subdivided as follows: 1 methicillin-resistant Staphylococcus aureus (MRSA), 4 methicillin-resistant Staphylococcus epidermidis, 2 methicillin-resistant Staphylococcus haemolyticus, and 29 MRS spp. Among the 36 MRS isolates tested, 100% were resistant to oxacillin and penicillin, and at least 50% were resistant to sulfamethoxazole/trimethoprim (69.4%), erythromycin (63.9%), tetracycline (58.3%), cefoxitin (55.6%), clindamycin (50.0%) or pirlimycin (50.0%). Additionally, 34/36 MRS isolates (94.4%) were mecA positive, 15 of which were further classified as SCCmec type V, 6 isolates as type I, 4 isolates as type IIIb, 1 isolate as type IVa, 1 isolate as type IV, with 7 isolates being non-classifiable.
4.Treatments of clinical mastitis occurring in cows on 51 large dairy herds in Wisconsin.
Oliveira L1, Ruegg PL2. J Dairy Sci. 2014 Sep;97(9):5426-36. doi: 10.3168/jds.2013-7756. Epub 2014 Jul 3.
Antimicrobials are frequently used for treatment of bovine mastitis and few studies have examined modern treatment strategies on large US dairy farms. The objective of this study was to describe treatment practices for clinical mastitis occurring in cows on large dairy herds in Wisconsin. Treatments performed on 747 cows experiencing cases of mild, moderate, or severe symptoms of clinical mastitis were recorded on 51 Wisconsin dairy farms. Duplicate milk samples were collected from the affected quarter for microbiological analysis at the onset of clinical mastitis and 14 to 21 d after treatment ended. Cows were treated according to individual farm protocol. Drugs and doses used for treatments were recorded for each case. Among all herds, 5 intramammary (IMM) antimicrobials (amoxicillin, hetacillin, pirlimycin, ceftiofur, and cephapirin) were used to treat cows for clinical mastitis. Of 712 cows with complete treatment data, 71.6% were treated with IMM ceftiofur either solely or combined with other antimicrobials (administered either IMM or systemically).
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
