| Size | Price | Stock | Qty |
|---|---|---|---|
| 500μg |
|
||
| 1mg | |||
| 2mg | |||
| 5mg | |||
| 10mg | |||
| Other Sizes |
| Targets |
As an impurity, this compound does not have a specific pharmacological target; its presence is monitored for quality control purposes. The parent drug, atorvastatin, targets HMG-CoA reductase, the rate-limiting enzyme in cholesterol biosynthesis. This epoxy tetrahydrofuran impurity may have significantly reduced or no HMG-CoA reductase inhibitory activity compared to atorvastatin. Its structure suggests potential reactivity due to the epoxide ring, but it is not intended for therapeutic or mechanistic studies. It is strictly an analytical standard.
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|---|---|
| ln Vitro |
Endoplasmic reticulum (ER) stress is brought on by heart failure and angiotensin II (Ang II), and atorvastatin therapy decreases cardiomyocyte apoptosis by downregulating the expression of GRP78, caspase-12, and CHOP in cardiomyocytes following myocardial infarction. driven to action by stimuli.
No specific in vitro pharmacological activity is reported for this impurity. In the context of atorvastatin synthesis, this compound may form as a byproduct under acidic or oxidative conditions. It is used as a marker to assess the purity of atorvastatin batches and to study the degradation pathways of atorvastatin. Typically, it does not exhibit significant cytotoxicity or off-target effects at the trace levels found in pharmaceutical preparations. In vitro studies would involve analytical chemistry rather than biological assays. |
| ln Vivo |
No in vivo activity is reported for this impurity. As a process-related impurity, it is not intended for in vivo administration. At the low levels typically present in atorvastatin drug products (below ICH qualification thresholds, usually <0.1-0.5%), it is not expected to contribute to the therapeutic effect or to cause adverse effects. Preclinical toxicology studies for atorvastatin impurities are generally not performed unless the impurity exceeds a certain threshold. The compound is for analytical use only.
|
| Enzyme Assay |
For analytical characterization and quantification, use reversed-phase high-performance liquid chromatography (RP-HPLC) or ultra-high-performance liquid chromatography (UHPLC) coupled with UV or MS detection. A typical method: column C18 (2.1x100 mm, 1.7 um), mobile phase A: 0.05% formic acid in water, mobile phase B: 0.05% formic acid in acetonitrile. Gradient: 0-2 min 30% B, 2-10 min 30-70% B, 10-12 min 70% B, 12-12.1 min 70-30% B, 12.1-15 min 30% B. Flow rate 0.3 mL/min, injection volume 2-5 uL, column temperature 40degC. UV detection at 245 nm (typical for atorvastatin). MS detection in positive electrospray ionization (ESI+) mode, monitoring m/z for the impurity (exact mass to be confirmed from literature or calculated from formula). For identification, use high-resolution mass spectrometry (HRMS) and nuclear magnetic resonance (NMR) spectroscopy (¹H, ¹3C, COSY, HMQC, HMBC) to confirm the epoxy tetrahydrofuran structure. Purity determination: area normalization with correction for response factors if known.
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| Cell Assay |
This compound is not used in cell-based assays; it is an analytical standard. However, for forced degradation studies, dissolve atorvastatin drug substance in appropriate buffer or solvent, subject to stress conditions (e.g., 0.1 M HCl at 60degC for 2 h, 0.1 M NaOH at 60degC for 1 h, 3% H2O2 at 25degC for 1 h, UV light at 254 nm for 48 h, or 60degC heat for 10 days). Analyze stressed samples by HPLC to detect the formation of the epoxy tetrahydrofuran impurity. For quantitative purposes, prepare calibration solutions of the impurity reference standard in acetonitrile or methanol at concentrations ranging from 0.05-10 ug/mL. Spike the impurity into a placebo matrix (blank formulation) to assess recovery and method accuracy. The impurity may also be used in forced degradation studies to confirm that the HPLC method can separate it from the main peak and other degradation products.
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| Animal Protocol |
Not applicable for in vivo studies. The impurity is not administered to animals for research purposes. For validation of analytical methods, no animal experiments are needed. If one wishes to assess the toxicity of the impurity at high concentrations, such studies would require a separate protocol, but this is rarely done for impurities that are controlled at low levels. Typically, the impurity is used only for analytical method development and stability-indicating assays. For research use, follow standard chemical handling procedures.
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| ADME/Pharmacokinetics |
Molecular formula and weight depend on the specific structure of the epoxy tetrahydrofuran impurity of atorvastatin. Atorvastatin itself is C33H3₅FN2O₅ (MW 558.64). The impurity likely has an additional oxygen (epoxide) and altered ring structure, e.g., C33H3₅FN2O₆ (MW 574.64) or similar. Exact formula should be confirmed by mass spec. The compound is a solid powder. Solubility: soluble in DMSO, methanol, acetonitrile; poorly soluble in water. For HPLC, prepare stock solutions in acetonitrile or methanol at 0.5-1.0 mg/mL. Storage: store as powder at -20degC, protected from light and moisture. Solutions in organic solvents can be stored at -20degC for short-term (1 month); avoid repeated freeze-thaw. The compound is stable under recommended storage conditions for at least 2 years.
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| Toxicity/Toxicokinetics |
As an analytical reference standard, the toxicity of this impurity is not well-characterized, but it is expected to be low at the microgram-to-milligram quantities used in analytical work. Standard laboratory precautions: use personal protective equipment (gloves, lab coat, safety glasses). Avoid inhalation of dust. The compound is for research use only, not for human consumption. Consult the safety data sheet if available. Dispose of waste according to local regulations for chemical waste. Given that it is a related substance of a pharmaceutical, it should be handled with care as potential genotoxic impurities may be present; however, the epoxy group suggests potential reactivity, so treat as potentially hazardous.
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| References | |
| Additional Infomation |
This product is an impurity reference standard for atorvastatin, a blockbuster statin drug used to lower LDL cholesterol and prevent cardiovascular events. Impurities are monitored during drug manufacturing to ensure product quality and patient safety. The epoxy tetrahydrofuran impurity may arise from the degradation of atorvastatin under acidic or oxidative conditions. It serves as a marker for stability-indicating methods. No clinical or therapeutic use is associated with this impurity. It is not an active pharmaceutical ingredient and is not approved for any medical indication. This compound is strictly for research and quality control purposes in pharmaceutical analysis.
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| Molecular Formula |
C26H24NO5F
|
|---|---|
| Molecular Weight |
449.47086
|
| Exact Mass |
449.164
|
| CAS # |
873950-19-7
|
| PubChem CID |
11554184
|
| Appearance |
Typically exists as solid at room temperature
|
| LogP |
4.298
|
| Hydrogen Bond Donor Count |
3
|
| Hydrogen Bond Acceptor Count |
6
|
| Rotatable Bond Count |
5
|
| Heavy Atom Count |
33
|
| Complexity |
745
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
O=C(C12C(C(C3C=CC(F)=CC=3)(OC1(C(C)C)O)O)(C1C=CC=CC=1)O2)NC1C=CC=CC=1
|
| InChi Key |
NNEBPPHOMFPLDK-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C26H24FNO5/c1-17(2)25(30)24(22(29)28-21-11-7-4-8-12-21)23(32-24,18-9-5-3-6-10-18)26(31,33-25)19-13-15-20(27)16-14-19/h3-17,30-31H,1-2H3,(H,28,29)
|
| Chemical Name |
4-(4-fluorophenyl)-2,4-dihydroxy-N,5-diphenyl-2-propan-2-yl-3,6-dioxabicyclo[3.1.0]hexane-1-carboxamide
|
| 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)
|
| 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 | 2.2248 mL | 11.1242 mL | 22.2484 mL | |
| 5 mM | 0.4450 mL | 2.2248 mL | 4.4497 mL | |
| 10 mM | 0.2225 mL | 1.1124 mL | 2.2248 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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