| Size | Price | |
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| 500mg | ||
| 1g | ||
| Other Sizes |
Chlortetracycline, formerly known as Aureomycin, is a potent and broad-spectrum antibiotic used as a veterinary medicine for pulmonary or digestive infections. Chlortetracycline and its metal complexes are toxic to bacteria when they are biologically available. Chlortetracycline and copper plus Chlortetracycline supplementation increased both the prevalence and gene copy numbers of tetA, while decreasing both the prevalence and gene copies of tetB.
Chlortetracycline (also known as Aureomycin) is a first-generation, broad-spectrum tetracycline antibiotic discovered in the 1940s. Chemically identified as 7-Chlorotetracycline with the molecular formula C₂₂H₂₃ClN₂O₈ and a molecular weight of 478.88 g/mol. It is the first discovered member of the tetracycline class and exhibits potent antibacterial activity against a wide range of Gram-positive and Gram-negative bacteria, spirochetes, rickettsiae, certain protozoa, mycoplasmas, and chlamydia. Chlorotetracycline also possesses calcium ionophore activity, enabling it to act as a fluorescent probe for studying calcium-related cellular processes, particularly in sperm capacitation studies.| Targets |
Chlortetracycline inhibits bacterial protein synthesis by binding to the 30S subunit of the bacterial ribosome. This binding prevents the aminoacyl-tRNA from binding to the ribosome, thereby blocking the addition of amino acids to the growing peptide chain. This mechanism effectively halts bacterial protein synthesis, leading to growth inhibition or bacterial death. Additionally, chlortetracycline acts as a calcium ionophore, interacting with divalent cations such as Ca²⁺ and Mg²⁺, which contributes to its fluorescence properties and enables its use as a probe for monitoring calcium-dependent cellular processes. The compound also shows affinity for bacterial efflux pumps, which represent a major mechanism of tetracycline resistance.
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| ln Vitro |
In vitro, chlortetracycline demonstrates broad-spectrum antibacterial activity against both Gram-positive and Gram-negative bacteria. It inhibits protein synthesis by binding to the 30S ribosomal subunit, effectively blocking the addition of amino acids to the growing peptide chain. Additionally, chlortetracycline enhances estradiol (E2) production in H295R human adrenocortical carcinoma cells, an effect consistent with increased aromatase activity and enhanced expression of CYP17, CYP19, and 3βHSD2 mRNA. It also increases aromatase enzyme activity in this cell system. The compound's fluorescence properties enable visualization of calcium-dependent changes, as demonstrated by its ability to stain human spermatozoa with three distinct patterns (F, B, AR) corresponding to different capacitation states.
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| ln Vivo |
In vivo, chlortetracycline exhibits antimicrobial efficacy against various pathogens in animal models. It enhances estradiol (E2) production in male medaka fish (Oryzias latipes), demonstrating its endocrine-modulating effects in living organisms. Studies in broiler chickens have shown that chlortetracycline bioavailability is influenced by efflux pump activity, with co-administration of cyclosporine A (a non-specific efflux-pump blocker) significantly increasing plasma concentrations and oral bioavailability. Additionally, bound chlortetracycline residues in bone can be released under acidic conditions (simulating gastric digestion), and hens fed contaminated bone meal were able to release these bound residues and absorb the antibiotic from the intestine. Low-dose exposure in humans (33 µg/kg bw/day) showed no adverse effects, with induction of resistant Enterobacteriaceae as the most sensitive endpoint.
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| Enzyme Assay |
Methodology for Ribosome Binding Assay: To assess direct binding of chlortetracycline to bacterial ribosomes, cell-free translation systems can be employed. Purified 70S ribosomes from E. coli are incubated with radiolabeled or fluorescently labeled chlortetracycline in binding buffer containing appropriate concentrations of Mg²⁺ and monovalent cations. After incubation at 37°C, the reaction mixture is filtered through nitrocellulose membranes to separate bound antibiotic from unbound. The retained radioactivity or fluorescence on the filters is quantified to calculate binding affinity. Alternatively, competition binding assays can be performed using known tetracycline-binding site ligands to determine binding specificity. Surface plasmon resonance (SPR) can also be employed with immobilized ribosomes to measure real-time binding kinetics and calculate association/dissociation constants.
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| Cell Assay |
Methodology for Chlortetracycline Fluorescence Assay (Sperm Capacitation): Human or mouse spermatozoa are washed and resuspended in capacitation medium. Chlortetracycline (CTC) is prepared fresh as a stock solution (e.g., 500 µM) in a buffer containing NaCl and Tris-HCl, protected from light. The working solution typically contains 50-100 µM CTC. For staining, an equal volume of CTC working solution is mixed with the sperm suspension and incubated for 30-60 seconds at room temperature. Glutaraldehyde (e.g., 0.5% final concentration) is added to fix the cells. The stained spermatozoa are then examined under a fluorescence microscope (excitation ~400 nm, emission ~520 nm). Three distinct fluorescence patterns are observed: 'F' pattern (uniform fluorescence over the whole head, characteristic of uncapacitated, acrosome-intact cells), 'B' pattern (fluorescence-free band in the post-acrosomal region, characteristic of capacitated, acrosome-intact cells), and 'AR' pattern (only the equatorial segment fluoresces, characteristic of acrosome-reacted cells). The percentage of each pattern is calculated by counting at least 200 cells per sample.
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| Animal Protocol |
Methodology for Pharmacokinetic Study in Broiler Chickens: Broiler chickens (typically 6-8 weeks old) are used as the animal model. The study design includes three groups: intravenous (IV) group, oral (PO) group, and oral + cyclosporine A (CsA) group. For the PO group, chlortetracycline is administered via gavage at a dose of 10 mg/kg body weight. For the combination group, CsA (50 mg/kg BW) is administered either orally or intravenously prior to chlortetracycline administration. Blood samples are collected at predetermined time points (e.g., 0, 0.25, 0.5, 1, 2, 4, 6, 8, 12, 24 hours post-dose) via the wing vein. Plasma is separated by centrifugation. Chlortetracycline concentrations are measured using high-performance liquid chromatography coupled with tandem mass spectrometry (HPLC-MS/MS). Pharmacokinetic parameters including Cmax, Tmax, AUC, bioavailability (F), and elimination half-life (t½) are calculated using compartmental or non-compartmental analysis.
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| ADME/Pharmacokinetics |
Chlortetracycline exhibits relatively poor oral bioavailability due to limited absorption from the gastrointestinal tract, primarily because of active efflux by intestinal efflux pumps. Studies in broiler chickens demonstrate that co-administration of cyclosporine A (a non-specific efflux-pump blocker) significantly increases plasma concentrations, with bioavailability increasing up to two-fold compared to oral administration alone. The compound is poorly absorbed from the GI tract, leading to high concentrations readily achieved in the intestine. It has a tendency to accumulate in bone tissue by forming chlortetracycline-calcium-orthophosphate chelates, where residues can persist as covalently bound forms that may be released under acidic conditions (e.g., during gastric digestion). The WHO Joint Expert Committee on Food Additives (JECFA) has established an Acceptable Daily Intake (ADI) of 0-30 µg/kg body weight per day for tetracyclines including chlortetracycline.
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| Toxicity/Toxicokinetics |
Chlortetracycline exhibits a low degree of acute toxicity. In humans, no toxic effects were reported from treatment of premature infants, children, adults, or elderly with chlortetracycline, with effects after short- and long-term exposure including increased body-weight gain and prophylactic activity against infections. A 52-week study in rats fed a diet containing 1% chlortetracycline (equivalent to 1000 mg/kg bw/day) showed no significant difference in body weight and no evidence of toxicity. The most sensitive endpoint for risk assessment is the selection of resistant bacterial strains, particularly resistant Enterobacteriaceae, with a NOEL of 2 mg/day (equivalent to 33 µg/kg bw/day) established from human studies. GHS classification indicates: H315 (Causes skin irritation), H319 (Causes serious eye irritation), H335 (May cause respiratory irritation), and H411 (Toxic to aquatic life with long-lasting effects). Bound residues in bones are microbiologically inactive but can be released under acidic conditions, raising concerns for human consumption of mechanically deboned meat.
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| References |
[1]. https://pubchem.ncbi.nlm.nih.gov/compound/54703985
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| Additional Infomation |
Chlorotetracycline is a tetracycline compound with the molecular formula C22H23ClN2O8, isolated from Streptomyces aureofaciens. It can be used as an antimicrobial agent, fluorescent probe, calcium ion carrier, and antibacterial agent. It belongs to the monochlorobenzene class, tertiary amine class, tertiary alcohol class, monocarboxylic acid amide class, tertiary α-hydroxy ketone class, and tetracycline class. It is the conjugate acid of chlorotetracycline (1-). A 7-chlorinated tetracycline. See also: Chlorotetracycline (note moved to).
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| Molecular Formula |
C22H23CLN2O8
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|---|---|
| Molecular Weight |
478.88
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| Exact Mass |
478.114
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| Elemental Analysis |
C, 55.18; H, 4.84; Cl, 7.40; N, 5.85; O, 26.73
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| CAS # |
57-62-5
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| Related CAS # |
Chlortetracycline hydrochloride;64-72-2； 57-62-5 (free); 27823-62-7 (bisulfate)
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| PubChem CID |
54675777
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| Appearance |
Light yellow to yellow solid at room temperature
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| Density |
1.7±0.1 g/cm3
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| Boiling Point |
821.1±65.0 °C at 760 mmHg
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| Melting Point |
168.5ºC
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| Flash Point |
450.4±34.3 °C
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| Vapour Pressure |
0.0±3.1 mmHg at 25°C
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| Index of Refraction |
1.745
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| LogP |
-0.53
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| Hydrogen Bond Donor Count |
6
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| Hydrogen Bond Acceptor Count |
9
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
33
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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
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| InChi Key |
DHPRQBPJLMKORJ-XRNKAMNCSA-N
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| InChi Code |
InChI=1S/C22H23ClN2O8/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)/t7-,8-,15-,21-,22-/m0/s1
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| Chemical Name |
(4S,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
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| Synonyms |
6945-20-6; NSC44180; Component CAS registry number(s): 57-62-5; DTXSID70716045; NSC-44180;
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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 | 2.0882 mL | 10.4410 mL | 20.8821 mL | |
| 5 mM | 0.4176 mL | 2.0882 mL | 4.1764 mL | |
| 10 mM | 0.2088 mL | 1.0441 mL | 2.0882 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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