| Size | Price | |
|---|---|---|
| 500mg | ||
| 1g | ||
| Other Sizes |
| Targets |
(Z)-Entacapone shares a similar chemical structure with entacapone and theoretically targets catechol-O-methyltransferase (COMT). However, the (Z)-isomer exhibits significantly lower pharmacological activity compared to (E)-entacapone and primarily exists as a metabolite. In human studies, (Z)-entacapone is the only phase I metabolite detected in human plasma.
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|---|---|
| ln Vitro |
In vitro erythrocyte incubation experiments demonstrate that (Z)-entacapone is the major phase I metabolite formed from entacapone in erythrocytes. During sample processing, approximately 1-2% of entacapone can convert to its Z-isomer. Specific IC₅₀ data for direct COMT inhibitory activity of this compound were not found in the available search results.
|
| ln Vivo |
In human pharmacokinetic studies, (Z)-entacapone is detected in human plasma as the only phase I metabolite besides unchanged entacapone. In urine, the glucuronide of the (Z)-isomer accounts for approximately 25% of urinary metabolites, while entacapone glucuronide accounts for about 70%. (Z)-Entacapone is also detected in both plasma and urine of rats.
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| Enzyme Assay |
(Z)-Entacapone is primarily used as an analytical reference standard rather than for enzyme activity studies. In LC method development, (Z)-entacapone is separated from entacapone and other impurities on a C18 stationary phase using a gradient mobile phase combination of buffer containing 0.1% orthophosphoric acid and acetonitrile, with ultraviolet detection at 220 nm. The resolution (Rs) between entacapone and its impurities is >2.0, and the method can detect impurities at a level of 0.003%.
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| ADME/Pharmacokinetics |
(Z)-Entacapone has a molecular weight of 305.29 g/mol. Predicted physicochemical properties include a logP of 2.38, polar surface area (PSA) of 130 Ų, 8 hydrogen bond acceptors, 2 hydrogen bond donors, and 6 freely rotatable bonds. Human pharmacokinetic studies indicate that (Z)-entacapone is the only phase I metabolite detected in human plasma and is primarily excreted in urine as glucuronide conjugates. Analytical methods can detect concentrations as low as 10 ng/mL in plasma and urine. Storage conditions: The European Directorate for the Quality of Medicines recommends long-term storage at +5°C±3°C.
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| Toxicity/Toxicokinetics |
As an impurity reference standard for entacapone, this compound is for research use only and is not intended for diagnostic or therapeutic purposes. According to the European Directorate for the Quality of Medicines classification, this compound is not classified as a hazardous substance (UN Code: Not classified).
|
| References | |
| Additional Infomation |
(Z)-Entacapone is a geometric isomer of entacapone, designated as Impurity A in the European Pharmacopoeia (EP) and as Related Compound A in the United States Pharmacopeia (USP). Isomerization primarily occurs under light exposure or during acidic extraction processes. Since the pharmacological activity of the (Z)-isomer is significantly lower than that of (E)-entacapone, and it is detected in human plasma, strict control of this impurity content is necessary in the quality control of entacapone drug substance and drug products. This compound serves as a pharmacopoeial reference standard and is primarily used for pharmaceutical quality control and analytical method validation.
|
| Molecular Formula |
C14H15N3O5
|
|---|---|
| Molecular Weight |
305.29
|
| Exact Mass |
305.1012
|
| Elemental Analysis |
C, 55.08; H, 4.95; N, 13.76; O, 26.20
|
| CAS # |
145195-63-7
|
| Related CAS # |
130929-57-6 (E isomer); 145195-63-7 (Z isomer)
|
| PubChem CID |
21864625
|
| Appearance |
Typically exists as solids at room temperature
|
| Melting Point |
142-144°C
|
| LogP |
2.305
|
| Hydrogen Bond Donor Count |
2
|
| Hydrogen Bond Acceptor Count |
6
|
| Rotatable Bond Count |
4
|
| Heavy Atom Count |
22
|
| Complexity |
500
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
CCN(C(/C(=C\C1C=C(O)C(O)=C([N+]([O-])=O)C=1)/C#N)=O)CC
|
| InChi Key |
JRURYQJSLYLRLN-YHYXMXQVSA-N
|
| InChi Code |
InChI=1S/C14H15N3O5/c1-3-16(4-2)14(20)10(8-15)5-9-6-11(17(21)22)13(19)12(18)7-9/h5-7,18-19H,3-4H2,1-2H3/b10-5-
|
| Chemical Name |
(Z)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethylprop-2-enamide
|
| Synonyms |
145195-63-7; (Z)-Entacapone; Entacapone, (Z)-; (2Z)-2-Cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethylprop-2-enamide; 4X96VV9HUQ;
|
| 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)
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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 | 3.2756 mL | 16.3779 mL | 32.7557 mL | |
| 5 mM | 0.6551 mL | 3.2756 mL | 6.5511 mL | |
| 10 mM | 0.3276 mL | 1.6378 mL | 3.2756 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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