| Size | Price | Stock | Qty |
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| 5mg |
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| Other Sizes |
4-Epitetracycline hydrochloride is an entiomer of tetracycline which is an antibiotic. 4-Epitetracycline is a degradation product from tetracycline. 4-Epitetracycline hydrochloride has decreased activity as an antibiotic or a Tet repressor effector but may have stronger toxic effects in animals.
| Targets |
Bacterial ribosome (30S subunit; decreased activity).
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|---|---|
| ln Vitro |
4-Epitetracycline is a degradation product of tetracycline, and its biological activity is significantly decreased compared to tetracycline. It has reduced antibiotic activity and lower affinity for the Tet repressor protein. However, it may have stronger toxic effects in animals, presumably due to its increased ability to form toxic complexes with calcium or other ions in tissues, leading to nephrotoxicity.
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| ln Vivo |
No specific in vivo activity reported; as a degradation product, 4-Epitetracycline is not used therapeutically. In animal models (e.g., rodents, fish), it is used as a positive control to study tetracycline-related toxicity or as a marker to trace the metabolic fate of tetracycline and its degradation products. Its primary utility is as a standard in analytical chemistry.
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| Enzyme Assay |
Assay: Competitive binding to the Tet repressor. Protocol: The Tet repressor protein is incubated with a fluorescently labeled tetracycline derivative (e.g., Tet-Fl) and increasing concentrations of 4-Epitetracycline. The decrease in fluorescence polarization or FRET signal is measured to calculate the binding affinity (IC50) of the epimer for the Tet repressor. Compare to tetracycline to determine relative affinity.
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| Cell Assay |
No specific cell-based assay; 4-Epitetracycline hydrochloride is not used to treat cells for functional assays. It is primarily used as an analytical standard. In cellular studies, it can be added to cultures to confirm its reduced antibiotic activity; MIC values are determined using standard broth microdilution methods, which are typically several-fold higher than tetracycline. Alternatively, it can be used to spike cell lysates for LC-MS method validation.
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| Animal Protocol |
No specific in vivo protocol; 4-Epitetracycline hydrochloride is not administered to animals as a therapeutic agent. It can be dosed to animals (e.g., rodents) to study the toxicokinetics of tetracycline degradation products. For standard pharmacokinetic studies, the compound is dissolved in water or saline and administered by oral gavage (PO) or intraperitoneal (IP) injection to rats or mice. Blood and tissue samples are collected over 24 hours and analyzed by HPLC or LC-MS/MS.
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| ADME/Pharmacokinetics |
No specific PK data for 4-Epitetracycline; as a tetracycline analog, it likely shares similar properties: poor oral bioavailability, high plasma protein binding, and tissue distribution. However, its PK may differ from tetracycline due to altered stereochemistry affecting metabolism and excretion. In toxicokinetic studies, 4-Epitetracycline may exhibit a longer terminal half-life in tissues such as kidney, which could explain its higher toxicity.
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| Toxicity/Toxicokinetics |
4-Epitetracycline hydrochloride is more toxic than tetracycline in animals, with a higher potential for causing Fanconi syndrome (nephrotoxicity) and other toxic effects. This increased toxicity is thought to be due to its stereochemistry, which may favor the formation of toxic complexes with calcium and other divalent cations in the kidneys.
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| Additional Infomation |
4-Epitetracycline is an analytical reference standard used to quantify the degradation of tetracycline in pharmaceutical products and environmental samples. It is not FDA-approved for human use. The compound is also known as 4-epi-Tetracycline hydrochloride and is classified as an impurity in tetracycline drug substance. Its use is strictly for research and quality control in forensic and pharmaceutical applications.
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| Molecular Formula |
C22H24N2O8.HCL
|
|---|---|
| Molecular Weight |
480.8955
|
| Exact Mass |
480.129
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| CAS # |
23313-80-6
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| PubChem CID |
54686189
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| Appearance |
Yellow to brown solid powder
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| Boiling Point |
682.8ºC at 760mmHg
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| Melting Point |
217ºC
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| Flash Point |
366.7ºC
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| Index of Refraction |
1.74
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| LogP |
1.287
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| Hydrogen Bond Donor Count |
7
|
| Hydrogen Bond Acceptor Count |
9
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| Rotatable Bond Count |
2
|
| Heavy Atom Count |
33
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| Complexity |
971
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| Defined Atom Stereocenter Count |
5
|
| SMILES |
C[C@@]1(O)C2=C(C(C3=C(O)[C@@]4(O)[C@H]([C@@H](N(C)C)C(O)=C(C(N)=O)C4=O)C[C@@H]31)=O)C(O)=CC=C2.Cl
|
| InChi Key |
YCIHPQHVWDULOY-DXDJYCPMSA-N
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| InChi Code |
InChI=1S/C22H24N2O8.ClH/c1-21(31)8-5-4-6-11(25)12(8)16(26)13-9(21)7-10-15(24(2)3)17(27)14(20(23)30)19(29)22(10,32)18(13)28;/h4-6,9-10,15,25-26,29,31-32H,7H2,1-3H3,(H2,23,30);1H/t9-,10-,15+,21+,22-;/m0./s1
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| Chemical Name |
(4R,4aS,5aS,6S,12aR)-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 | 2.0794 mL | 10.3972 mL | 20.7943 mL | |
| 5 mM | 0.4159 mL | 2.0794 mL | 4.1589 mL | |
| 10 mM | 0.2079 mL | 1.0397 mL | 2.0794 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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