| Size | Price | |
|---|---|---|
| 2mg | ||
| Other Sizes |
Purity: ≥98%
| Targets |
Pirlimycin targets the bacterial ribosome, specifically the 50S subunit, where it binds and inhibits protein synthesis. By binding to the 23S ribosomal RNA, it blocks the peptidyl transferase reaction, preventing the elongation of the polypeptide chain. This results in the inhibition of bacterial protein synthesis and ultimately bacterial cell death. Pirlimycin is bacteriostatic rather than bactericidal.
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|---|---|
| ln Vitro |
In vitro, Pirlimycin demonstrates potent antibacterial activity against Gram-positive bacteria including Staphylococcus aureus, Streptococcus species, and anaerobic bacteria. It has no activity against Gram-negative bacteria due to the inability to penetrate the outer membrane. The compound shows activity against protozoa such as Plasmodium. Minimum inhibitory concentrations (MICs) for susceptible organisms are in the low microgram per milliliter range. Detailed in vitro susceptibility data are available from published studies.
|
| ln Vivo |
In vivo, Pirlimycin is used in veterinary medicine for the treatment of mastitis in dairy cattle. It is administered as an intramammary infusion (Pirsue® aqueous gel) for the treatment of bovine mastitis. The compound effectively eliminates susceptible Gram-positive bacteria from the mammary gland, resolving the infection and restoring milk quality. It is not used in human medicine.
|
| Enzyme Assay |
In vitro susceptibility testing for antibiotics typically uses broth microdilution or agar dilution methods according to CLSI guidelines. Bacterial cultures are prepared at a standardized inoculum (e.g., 5 × 10⁵ CFU/mL) and incubated with varying concentrations of Pirlimycin in 96-well plates or on agar plates. Minimum inhibitory concentrations (MICs) are determined as the lowest concentration that inhibits visible bacterial growth after 18-24 hours of incubation. Quality control strains are included to ensure assay validity.
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| Cell Assay |
Cellular assays for antibiotics typically involve bacterial cell culture rather than mammalian cell culture. Bacteria are grown in appropriate media and treated with varying concentrations of Pirlimycin. Bacterial growth is monitored by measuring optical density (OD600) over time to generate growth curves. The compound's effect on bacterial protein synthesis can be assessed by measuring incorporation of radiolabeled amino acids (e.g., [³H]leucine) into newly synthesized proteins. Time-kill assays are performed to determine whether the compound is bacteriostatic or bactericidal.
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| Animal Protocol |
In vivo animal studies for mastitis treatment typically use dairy cows with experimentally induced or naturally occurring mastitis. Pirlimycin is administered as an intramammary infusion according to the approved dosing regimen. Milk samples are collected before and after treatment for bacterial culture and somatic cell count. Clinical signs of mastitis (e.g., udder swelling, milk appearance) are monitored. The cure rate and time to resolution of infection are determined.
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| ADME/Pharmacokinetics |
Pirlimycin is administered as an intramammary infusion for the treatment of bovine mastitis. Systemic absorption following intramammary administration is minimal, resulting in low systemic exposure and favorable safety. The compound is primarily eliminated in milk. Following systemic administration (if used), it would be metabolized in the liver and excreted via the kidneys and bile. Detailed PK parameters in cattle are available from veterinary pharmacology studies.
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| Toxicity/Toxicokinetics |
Pirlimycin is generally well-tolerated in dairy cattle when administered as an intramammary infusion. Local reactions at the infusion site are rare. Systemic toxicity is minimal due to low absorption. The compound is not used in humans, so human toxicity data are limited. Withdrawal times are established to ensure that milk from treated cows does not contain antibiotic residues above regulatory limits.
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| References |
Kulesza SB, Maguire RO, Xia K, Cushman J, Knowlton K, Ray P. Manure Injection Affects the Fate of Pirlimycin in Surface Runoff and Soil. J Environ Qual. 2016 Mar;45(2):511-8. doi: 10.2134/jeq2015.06.0266. PubMed PMID: 27065398.
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| Additional Infomation |
Pirlimycin hydrochloride is the hydrochloride salt form of clindamycin, a derivative of clindamycin in which a six-membered ring replaces the five-membered ring of clindamycin. Compared to clindamycin, Pirlimycin has higher activity against Gram-positive bacteria, including Staphylococcus aureus, coagulase-negative staphylococci, and streptococci. This drug is primarily used to treat bovine mastitis.
See also: Pirlimycin hydrochloride (note moved here). Indications For the treatment of subclinical mastitis in lactating cows caused by Gram-positive cocci sensitive to Pirlimycin (including Staphylococcus aureus, whether penicillinase-positive or negative, and coagulase-negative staphylococci); streptococcal organisms include agalactiae, dysgalactiae, and mammary streptococci. Pirlimycin Hydrochloride is a lincosamide antibiotic active against Gram-positive bacteria. It inhibits bacterial protein synthesis by binding to the 50S ribosomal subunit. The compound is active against Staphylococcus, Streptococcus, and anaerobic bacteria, but not against Gram-negative organisms. It is used in veterinary medicine as Pirsue® for the treatment of mastitis in dairy cattle. Pirlimycin is available for research use only in human applications. |
| Molecular Formula |
C17H33CL3N2O5S
|
|---|---|
| Molecular Weight |
447.41738
|
| Exact Mass |
464.151
|
| CAS # |
78822-40-9
|
| Related CAS # |
Pirlimycin;79548-73-5
|
| PubChem CID |
115329
|
| Appearance |
White to off-white solid powder
|
| Melting Point |
>160 °C (dec.) (lit.)
|
| LogP |
1.569
|
| Hydrogen Bond Donor Count |
6
|
| Hydrogen Bond Acceptor Count |
7
|
| Rotatable Bond Count |
6
|
| Heavy Atom Count |
27
|
| Complexity |
474
|
| Defined Atom Stereocenter Count |
9
|
| SMILES |
CCC1CCNC(C1)C(=O)NC(C2C(C(C(C(O2)SC)O)O)O)C(C)Cl.Cl
|
| InChi Key |
WOOZGIRLEZDLSO-RWMVMHIMSA-N
|
| InChi Code |
InChI=1S/C17H31ClN2O5S.2ClH/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)2*1H/t8-,9+,10-,11+,12-,13+,14+,15+,17+/m0../s1
|
| Chemical Name |
(2S,4R)-N-((1S,2S)-2-chloro-1-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(methylthio)tetrahydro-2H-pyran-2-yl)propyl)-4-ethylpiperidine-2-carboxamide
dihydrochloride
|
| Synonyms |
Pirsue Pirlimycin hydrochloride Pirlimycin HCl U 57930E U-57930E U57930E
|
| HS Tariff Code |
2934.99.9001
|
| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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|---|---|
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.2350 mL | 11.1752 mL | 22.3504 mL | |
| 5 mM | 0.4470 mL | 2.2350 mL | 4.4701 mL | |
| 10 mM | 0.2235 mL | 1.1175 mL | 2.2350 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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