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ent-Ezetimibe

Alias: entEzetimibe ent Ezetimibe
Cat No.:V40059 Purity: ≥98%
ent-Ezetimibe is the RRS-enantiomer and impurity of Ezetimibe (SCH-58235), which is a selective inhibitor of cholesterol absorption in the gut used to lower cholesterol levels.
ent-Ezetimibe
ent-Ezetimibe Chemical Structure CAS No.: 1376614-99-1
Product category: Drug Metabolite
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
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25mg
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Product Description
ent-Ezetimibe is the RRS-enantiomer and impurity of Ezetimibe (SCH-58235), which is a selective inhibitor of cholesterol absorption in the gut used to lower cholesterol levels.
ent-Ezetimibe is the enantiomer of Ezetimibe, a selective inhibitor of cholesterol absorption in the gut. It has a molecular weight of 409.40 g/mol and a molecular formula of C24H21F2NO3. This compound is the opposite enantiomer of the active drug and is used as a reference standard for analytical method development and quality control.
Biological Activity I Assay Protocols (From Reference)
Targets
ent-Ezetimibe targets the same cholesterol absorption pathway as its parent drug, Ezetimibe. However, as the enantiomer, it is significantly less active as a cholesterol absorption inhibitor. Its primary use is as a reference standard for chiral purity analysis of Ezetimibe.
ln Vitro
In vitro, ent-Ezetimibe is characterized as the enantiomer of Ezetimibe. It is significantly less active as a cholesterol absorption inhibitor compared to the parent drug. Its activity makes it a valuable tool for studying the stereospecificity of cholesterol absorption inhibition.
ln Vivo
In vivo, ent-Ezetimibe is not used as a therapeutic agent. It is the enantiomer of Ezetimibe and is used as a reference standard for analytical method development and quality control. Its in vivo effects are not characterized, as it is not intended for human use.
Enzyme Assay
In vitro assays for ent-Ezetimibe typically involve analytical method development using chiral HPLC or LC-MS. The compound is used as a reference standard to identify and quantify the enantiomeric impurity in Ezetimibe samples. Its retention time and mass spectrum are characterized for method validation.
Cell Assay
For in vitro cell-based assays, ent-Ezetimibe is not typically used, as it is an enantiomeric impurity and not a pharmacological agent. It could be used to study its potential effects on cholesterol absorption if necessary, but its primary role is as an analytical reference standard.
Animal Protocol
In vivo animal studies with ent-Ezetimibe are not typically performed, as it is an enantiomeric impurity and not a therapeutic candidate. Its use is confined to analytical and quality control applications. The compound is not intended for in vivo pharmacological evaluation.
ADME/Pharmacokinetics
ent-Ezetimibe (CAS: 1376614-99-1) has a molecular weight of 409.40 g/mol and a molecular formula of C24H21F2NO3. Appearance: solid powder. Purity: ≥95%. Storage: -20°C. The compound is the enantiomer of Ezetimibe.
Toxicity/Toxicokinetics
ent-Ezetimibe is a research compound and is not approved for human therapeutic use. As an enantiomeric impurity standard, it is used in very small quantities and does not pose significant toxicity risks under normal handling. Standard laboratory safety precautions should be followed when handling the compound.
Additional Infomation
See also: Ezetimibe (note moved to).
ent-Ezetimibe is the enantiomer of Ezetimibe, a selective inhibitor of cholesterol absorption. It is used as a reference standard for analytical method development and quality control. It is not FDA-approved as a drug and is intended for research and analytical use only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C₂₄H₂₁F₂NO₃
Molecular Weight
409.43
Exact Mass
409.149
CAS #
1376614-99-1
PubChem CID
69281225
Appearance
White to off-white solid powder
LogP
4.953
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
6
Heavy Atom Count
30
Complexity
567
Defined Atom Stereocenter Count
3
SMILES
C1=CC(=CC=C1C2C(C(=O)N2C3=CC=C(C=C3)F)CCC(C4=CC=C(C=C4)F)O)O
InChi Key
OLNTVTPDXPETLC-ZRBLBEILSA-N
InChi Code
InChI=1S/C24H21F2NO3/c25-17-5-1-15(2-6-17)22(29)14-13-21-23(16-3-11-20(28)12-4-16)27(24(21)30)19-9-7-18(26)8-10-19/h1-12,21-23,28-29H,13-14H2/t21-,22+,23-/m0/s1
Chemical Name
(3S,4R)-1-(4-fluorophenyl)-3-[(3R)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)azetidin-2-one
Synonyms
entEzetimibe ent Ezetimibe
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

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)
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
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
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*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 : PEG300Tween 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).
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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)]
*Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL 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).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.4424 mL 12.2121 mL 24.4242 mL
5 mM 0.4885 mL 2.4424 mL 4.8848 mL
10 mM 0.2442 mL 1.2212 mL 2.4424 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.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
  • Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
  • Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume
An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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.
             (2) Be sure to add the solvent(s) in order.

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