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Clindamycin Palmitate HCl

Alias: U 25179E; U-25179-E U25179E; U21251F; U-21251-F; Clinsol EC; 244-398-6; EC2443986; U 21251 F; Clindamycin palmitate HCl; CLINDAMYCIN PALMITATE HYDROCHLORIDE; 25507-04-4; Cleocin Pediatric; Clindamycin 2-palmitate hydrochloride; U-21251; EC-244-398-6; U 21251; Clindamycin; Cleocin, Clinacin, Dalacin
Cat No.:V18486 Purity: ≥98%
Clindamycin palmitate HCl(EC 244-398-6;U-21251; U21251;Cleocin;Clinsol; EC2443986; Clinacin, Dalacin), the Palmitate ester form and hydrochloride salt ofClindamycin which is a semisyntheticlincomycinanalog,is a potent antibiotic acting as aprotein synthesis inhibitor.
Clindamycin Palmitate HCl
Clindamycin Palmitate HCl Chemical Structure CAS No.: 25507-04-4
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
50mg
100mg
250mg
500mg
Other Sizes

Other Forms of Clindamycin Palmitate HCl:

  • Clindamycin HCl
  • Clindamycin phosphate
  • Clindamycin
  • Clindamycin hydrochloride monohydrate
Official Supplier of:
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Product Description
Clindamycin palmitate HCl (EC 244-398-6; U-21251;U21251; Cleocin; Clinsol; EC2443986; Clinacin, Dalacin), the Palmitate ester form and hydrochloride salt of Clindamycin which is a semisynthetic lincomycin analog, is a potent antibiotic acting as a protein synthesis inhibitor. It can be used for treatment of many bacterial infections such as bone or joint infections, middle ear infections, strep throat, pneumonia, pelvic inflammatory disease, and endocarditis. It can also be used for treatment of acne, and some cases of methicillin-resistant Staphylococcus aureus
Clindamycin palmitate hydrochloride is a water-soluble hydrochloride salt of the ester of clindamycin and palmitic acid and a lincosamide antibiotic. It is a semisynthetic derivative of lincomycin. Clindamycin palmitate hydrochloride is a bacterial protein synthesis inhibitor by inhibiting ribosomal translocation, in a similar way to macrolides. It is inactive in vitro, but rapid in vivo hydrolysis converts this compound to the antibacterially active clindamycin. It has a molecular formula of C34H63ClN2O6S·HCl and a molecular weight of 699.85.
Biological Activity I Assay Protocols (From Reference)
Targets
Bacterial protein synthesis
Clindamycin palmitate hydrochloride is a prodrug that targets the bacterial ribosome after conversion to clindamycin. Clindamycin binds to the 50S ribosomal subunit and inhibits protein synthesis by preventing the translocation of the ribosome along the mRNA. This inhibits bacterial growth and replication.
ln Vitro
Clindamycin palmitate hydrochloride is a water-soluble hydrochloride salt formed by esterification of clindamycin with palmitic acid. This compound is inactive in vitro but undergoes rapid in vivo hydrolysis to release clindamycin, the antibacterially active moiety. A total of 12 impurities were detected using isocratic reverse-phase high-performance liquid chromatography with refractive index detection, ranging from 0.05% to 0.5% of the sample. The molecular weights of these impurities were determined by liquid chromatography-mass spectrometry analysis. Two impurities were identified as residual starting materials, while the remaining impurities were isolated from crude samples or enriched mother liquors using reverse-phase preparative HPLC. Based on comprehensive spectral data—including proton nuclear magnetic resonance, carbon-13 nuclear magnetic resonance, mass spectrometry, and infrared spectroscopy—the structures of these impurities were characterized as follows: clindamycin palmitate sulfoxides (alpha and beta isomers) (Impurity I), clindamycin laurate (Impurity II), lincomycin palmitate (Impurity III), clindamycin myristate (Impurity IV), epiclindamycin palmitate (Impurity V), clindamycin palmitate 3-isomer (Impurity VI), clindamycin pentadecanoate (Impurity VII), clindamycin B-palmitate (Impurity VIII), clindamycin heptadecanoate (Impurity IX), and clindamycin stearate (Impurity X). The structural elucidation of all impurities and the mechanisms underlying their formation are discussed in detail. [1]
In vitro, Clindamycin palmitate hydrochloride is inactive. It requires hydrolysis to clindamycin to exert its antibacterial effects. Its activity can be measured in cell-free ribosomal translation assays using purified ribosomes and mRNA templates.
ln Vivo
In vivo, Clindamycin palmitate hydrochloride is rapidly hydrolyzed to the active antibiotic clindamycin. It shows strong efficacy against Gram-positive cocci and certain anaerobic bacteria. It is used to treat respiratory, skin, and soft tissue infections. It is often administered in oral formulations, making it suitable for pediatric use due to its palmitate ester, which enhances its taste and palatability.
Enzyme Assay
Clindamycin palmitate hydrochloride is evaluated in cell-free assays to measure its hydrolysis to clindamycin. The compound is incubated with esterases, and the formation of clindamycin is measured using HPLC or other analytical techniques. Its antibacterial activity is assessed after hydrolysis.
Cell Assay
Clindamycin palmitate hydrochloride is assessed in cell-based antibacterial assays using bacterial cultures. The compound is tested against various bacterial strains, and minimum inhibitory concentrations are determined. Its activity is compared to that of clindamycin to confirm its prodrug nature.
Animal Protocol
Clindamycin palmitate hydrochloride is administered orally in animal models and in clinical settings. It is used to treat infections caused by susceptible bacteria, including respiratory, skin, and soft tissue infections. Efficacy is assessed by measuring bacterial clearance and symptom improvement.
ADME/Pharmacokinetics
Clindamycin palmitate hydrochloride has a molecular weight of 699.85 and a molecular formula of C34H63ClN2O6S·HCl. It has a CAS number of 25507-04-4. The compound is a water-soluble hydrochloride salt. It should be stored under recommended conditions.
Toxicity/Toxicokinetics
No detailed toxicity data is available for Clindamycin palmitate hydrochloride beyond its known use as an antibiotic. It is generally well-tolerated but can cause gastrointestinal side effects. The compound is a therapeutic agent and is available by prescription only.
References

[1]. Identification, isolation and characterization of impurities of clindamycin palmitate hydrochloride. J Pharm Biomed Anal. 2008 Dec 1;48(4):1211-8.

Additional Infomation
Clindamycin palmitate is an S-glycoside compound. Clindamycin palmitate is the palmitate hydrochloride form of clindamycin, a semi-synthetic chlorinated broad-spectrum antibiotic derived from lincomycin through chemical modification. Clindamycin palmitate is used in oral suspensions. See also: Clindamycin (containing the active ingredient).
Clindamycin palmitate hydrochloride is also known as Cleocin Pediatric. It is a prodrug of clindamycin. It is used in the treatment of infections with anaerobic bacteria and protozoal diseases. The compound is a therapeutic agent.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C34H64CL2N2O6S
Molecular Weight
699.854
Exact Mass
698.386
Elemental Analysis
C, 58.35; H, 9.22; Cl, 10.13; N, 4.00; O, 13.72; S, 4.58
CAS #
25507-04-4
Related CAS #
Clindamycin hydrochloride;21462-39-5;Clindamycin phosphate;24729-96-2; 25507-04-4 (palmitate HCl); 21462-39-5 (HCl); 18323-44-9 (free); 58207-19-5 (HCl monohydrate)
PubChem CID
16052038
Appearance
Typically exists as solid at room temperature
Boiling Point
767.4ºC at 760 mmHg
Melting Point
141-143ºC
Flash Point
417.9ºC
Vapour Pressure
3.44E-27mmHg at 25°C
LogP
7.552
Hydrogen Bond Donor Count
4
Hydrogen Bond Acceptor Count
8
Rotatable Bond Count
23
Heavy Atom Count
45
Complexity
810
Defined Atom Stereocenter Count
9
SMILES
CCCCCCCCCCCCCCCC(O[C@H]1[C@@H](SC)O[C@H]([C@H](NC([C@H]2N(C)C[C@H](CCC)C2)=O)[C@@H](Cl)C)[C@H](O)[C@@H]1O)=O.Cl
InChi Key
GTNDZRUWKHDICY-DJHAJVGHSA-N
InChi Code
InChI=1S/C34H63ClN2O6S.ClH/c1-6-8-9-10-11-12-13-14-15-16-17-18-19-21-27(38)42-32-30(40)29(39)31(43-34(32)44-5)28(24(3)35)36-33(41)26-22-25(20-7-2)23-37(26)4/h24-26,28-32,34,39-40H,6-23H2,1-5H3,(H,36,41)1H/t24-,25+,26-,28+,29+,30-,31+,32+,34+/m0./s1
Chemical Name
(2R,3R,4S,5R,6R)-6-((1S,2S)-2-chloro-1-((2S,4R)-1-methyl-4-propylpyrrolidine-2-carboxamido)propyl)-4,5-dihydroxy-2-(methylthio)tetrahydro-2H-pyran-3-yl palmitate hydrochloride
Synonyms
U 25179E; U-25179-E U25179E; U21251F; U-21251-F; Clinsol EC; 244-398-6; EC2443986; U 21251 F; Clindamycin palmitate HCl; CLINDAMYCIN PALMITATE HYDROCHLORIDE; 25507-04-4; Cleocin Pediatric; Clindamycin 2-palmitate hydrochloride; U-21251; EC-244-398-6; U 21251; Clindamycin; Cleocin, Clinacin, Dalacin
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

Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~125 mg/mL (~178.61 mM)
H2O : ~50 mg/mL (~71.44 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (2.97 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.4289 mL 7.1444 mL 14.2888 mL
5 mM 0.2858 mL 1.4289 mL 2.8578 mL
10 mM 0.1429 mL 0.7144 mL 1.4289 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.

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Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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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.
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Clinical Trial Information
A Phase 3, Multicenter, Open-Label, Randomized, Comparator Controlled Trial of the Safety and Efficacy of Dalbavancin versus Active Comparator in Pediatric Subjects with Acute Bacterial Skin and Skin Structure Infections
EudraCT: 2014-005281-30
Phase: Phase 3
Status: Prematurely Ended, Completed
Date: 2016-11-03
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