| Size | Price | |
|---|---|---|
| 500mg | ||
| 1g | ||
| Other Sizes |
| Targets |
As a tetracycline antibiotic, 4-epi-chlortetracycline primarily targets the 30S subunit of the bacterial ribosome. The compound competitively binds to the A-site of the bacterial ribosome, where it competes with aminoacyl-tRNA. This binding prevents the addition of new amino acids to the growing peptide chain, thereby inhibiting bacterial protein synthesis. In addition to its ribosomal action, 4-epi-chlortetracycline also acts as a matrix metalloproteinase (MMP) inhibitor, making it potentially useful in research on tissue-destructive diseases and cancer. Furthermore, the compound suppresses neutrophil activity and dampens innate immune responses.
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| ln Vitro |
In vitro studies demonstrate that 4-epi-chlortetracycline exhibits broad-spectrum bacteriostatic properties similar to other tetracyclines. It acts as an aminoacyl-tRNA analog to disrupt polypeptide synthesis, effectively reducing bacterial growth. Beyond its antimicrobial activity, 4-epi-chlortetracycline is utilized in cancer research as a selective agent to study antibiotic effects on cancer cell proliferation and survival. In inflammation studies, it helps researchers understand the role of inflammation in chronic diseases by dampening immune responses. The compound also suppresses neutrophil activity and modifies aspects of the innate immune response.
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| ln Vivo |
In vivo studies have confirmed that 4-epi-chlortetracycline is a major metabolite of chlortetracycline in animals. Research in rats and dogs using C14-labeled chlortetracycline demonstrated that the excreted radioactivity was associated with two major components—unchanged chlortetracycline and the microbiologically active 4-epichlortetracycline. Following intravenous administration of C14-labeled chlortetracycline or 4-epichlortetracycline, significant amounts of radioactivity were excreted via the feces, with 40-50% of the dose eliminated through this pathway. Studies in chickens have shown that 4-epi-chlortetracycline exhibits tissue-specific distribution patterns, with the highest concentrations detected in kidney (835.3 µg/kg), followed by liver (192.7 µg/kg) and muscle (126.3 µg/kg).
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| Enzyme Assay |
Methodology for Ribosome Binding Analysis: To assess the direct binding of 4-epi-chlortetracycline to bacterial ribosomes, a cell-free system can be employed. Purified 70S ribosomes from E. coli are isolated and suspended in binding buffer containing Tris-HCl (pH 7.4), MgCl₂ (10 mM), and NH₄Cl (100 mM). 4-epi-chlortetracycline is radiolabeled with ³H or ¹⁴C and incubated with the ribosome preparation at 37°C for 15-30 minutes. The reaction mixture is filtered through nitrocellulose membranes (0.45 µm pore size) to separate ribosome-bound antibiotic from unbound drug. Retained radioactivity on the filters is quantified by liquid scintillation counting. Competition binding assays using unlabeled tetracycline or chlortetracycline can determine specific binding affinity. The diss
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| Cell Assay |
Methodology for Antimicrobial Susceptibility Testing: Minimum inhibitory concentration (MIC) of 4-epi-chlortetracycline hydrochloride is determined using the broth microdilution method following CLSI guidelines. Bacterial strains (e.g., E. coli, S. aureus) are cultured overnight in Mueller-Hinton broth. The bacterial suspension is adjusted to 0.5 McFarland standard (~1.5 × 10⁸ CFU/mL) and diluted 1:100 to achieve ~5 × 10⁵ CFU/mL. Two-fold serial dilutions of the compound (0.03-64 μg/mL) are prepared in 96-well plates. Each well receives 100 μL of bacterial suspension and 100 μL of antibiotic dilution. Plates are incubated at 37°C for 18-24 hours. The MIC is defined as the lowest concentration with no visible bacterial growth. For cancer research applications, cells can be treated with 4-epi-chlortetracycline at varying concentrations (1-100 μM) for 24-72 hours, and cell viability is assessed using MTT or CellTiter-Glo assays.
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| Animal Protocol |
Methodology for Metabolic Fate Study in Rats: Male Sprague-Dawley rats (200-250 g) are administered C14-labeled chlortetracycline or 4-epichlortetracycline via intravenous injection (tail vein) or oral gavage. Following administration, animals are placed in metabolic cages for separate collection of urine and feces at 24-hour intervals for up to 72 hours. Blood samples are collected at predetermined time points (0, 1, 2, 4, 8, 12, 24, 48, 72 hours post-dose). Total radioactivity in urine, feces, and plasma is measured by liquid scintillation counting. For metabolite identification, samples undergo paper strip chromatography or HPLC-UV analysis. The recovery of administered radioactivity in urine and feces ranges from 76-97% of the dose after 48-72 hours. For tissue distribution studies in chickens, tissues (kidney, liver, muscle) are collected post-mortem, homogenized, and analyzed by HPLC-FLD for compound quantification.
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| ADME/Pharmacokinetics |
The pharmacokinetic profile of 4-epi-chlortetracycline shows similarities to other tetracyclines. Following oral administration in chickens, the compound demonstrates an absolute oral bioavailability of approximately 17.76%. The time to reach maximum plasma concentration (Tmax) is approximately 1.79 hours post-administration. Mean recovery rates from plasma are approximately 94% for the parent compound and 86% for 4-epi-chlortetracycline. The elimination half-life is estimated to be between 5.6 to 9 hours, with 60% excreted renally and more than 10% via biliary excretion. Following intravenous administration in rats and dogs, 40-50% of the dose is excreted via the fecal route. Tissue distribution studies show highest concentrations in kidney (835.3 µg/kg), followed by liver (192.7 µg/kg) and muscle (126.3 µg/kg). A recommended withdrawal time of 3 days has been suggested for poultry.
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| Toxicity/Toxicokinetics |
According to GHS classification, 4-epi-chlortetracycline hydrochloride is considered hazardous. Hazard statements include H319 (Causes serious eye irritation) and H361 (Suspected of damaging the unborn child). The precautionary signal word is "Warning". Teratogenic effects have been observed in experimental animals. The compound has not been listed as a carcinogen by IARC, NTP, ACGIH, or OSHA. Acute toxicity data are limited, as the substance has not been fully tested. For environmental safety, release into the environment should be avoided. The compound is intended for research use only and is not approved for human or veterinary therapeutic use. Standard laboratory safety precautions, including eye protection and appropriate personal protective equipment, are recommended when handling this compound.
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| References |
| Molecular Formula |
C22H24CL2N2O8
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|---|---|
| Molecular Weight |
515.34
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| Exact Mass |
514.091
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| CAS # |
101342-45-4
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| PubChem CID |
54710414
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| Appearance |
Typically exists as solids at room temperature
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| Melting Point |
>250ºC
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| LogP |
1.941
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| Hydrogen Bond Donor Count |
7
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| Hydrogen Bond Acceptor Count |
9
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
34
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| Complexity |
1010
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| Defined Atom Stereocenter Count |
5
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| SMILES |
C[C@]1(O)[C@H]2C[C@H]3[C@@H](N(C)C)C(O)=C(C(N)=O)C([C@@]3(O)C(O)=C2C(C4=C(O)C=CC(Cl)=C41)=O)=O.Cl
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| InChi Key |
QYAPHLRPFNSDNH-QNUQNERCSA-N
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| InChi Code |
InChI=1S/C22H23ClN2O8.ClH/c1-21(32)7-6-8-15(25(2)3)17(28)13(20(24)31)19(30)22(8,33)18(29)11(7)16(27)12-10(26)5-4-9(23)14(12)21;/h4-5,7-8,15,26-27,30,32-33H,6H2,1-3H3,(H2,24,31);1H/t7-,8-,15+,21-,22-;/m0./s1
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| Chemical Name |
(4R,4aS,5aS,6S,12aR)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide;hydrochloride
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| Synonyms |
Chlortetracycline hydrochloride; 4-Epichlortetracycline Hydrochloride; 101342-45-4; 4-epi-Chlortetracycline Hydrochloride; 4-epi-Chlortetracycline (hydrochloride); (4R,4aS,5aS,6S,12aR)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide;hydrochloride;
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| HS Tariff Code |
2934.99.9001
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| 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)
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| 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 | 1.9405 mL | 9.7023 mL | 19.4047 mL | |
| 5 mM | 0.3881 mL | 1.9405 mL | 3.8809 mL | |
| 10 mM | 0.1940 mL | 0.9702 mL | 1.9405 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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