| Size | Price | Stock | Qty |
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| 10mg |
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| 25mg |
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| 50mg |
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| 100mg |
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| Other Sizes |
| Targets |
PDE5 (Inactive; IC50 > 10 μM)
ent-Tadalafil targets phosphodiesterase 5 (PDE5), the same enzyme as its active enantiomer Tadalafil. However, it serves as an inactive control as it does not effectively inhibit PDE5. While Tadalafil has an IC50 of approximately 0.090 μM (or 5 nM in some references), ent-Tadalafil shows no significant inhibitory activity at concentrations up to 10 µM. This lack of activity makes it a valuable negative control for research. |
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| ln Vitro |
In vitro, ent-Tadalafil is characterized by its lack of PDE5 inhibitory activity, with an IC50 greater than 10 μM. It is used as an inactive control in assays to validate the specificity of PDE5 inhibition by active compounds. Its primary role is analytical, serving as a reference standard for identifying and quantifying the cis-enantiomer impurity in Tadalafil samples, ensuring the purity and quality of the active pharmaceutical ingredient.
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| ln Vivo |
In vivo, ent-Tadalafil is not a therapeutic agent and lacks the pharmacological activity of its active enantiomer. Its use is confined to analytical and quality control applications. The active Tadalafil has profound and long-lasting blood pressure lowering activity, but ent-Tadalafil does not exhibit such effects. The compound is used in pharmacokinetic studies as a reference to distinguish the active drug from its inactive impurities.
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| Enzyme Assay |
In vitro enzyme assays for ent-Tadalafil typically involve measuring its inhibition of PDE5 activity. The enzyme is incubated with increasing concentrations of the compound (up to 10 µM) and a substrate in kinase assay buffer. Phosphorylation is measured using radioactive or luminescence-based assays. IC50 values are calculated, confirming its inactivity. This assay validates the specificity of PDE5 inhibition by active compounds.
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| Cell Assay |
For in vitro cell-based assays, ent-Tadalafil is used as a negative control. Cells are treated with the compound at various concentrations, and its effects on cell proliferation or signaling pathways are measured. Its lack of activity confirms that any observed effects are due to the active enantiomer. The compound's primary use is as a reference standard in analytical method development.
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| Animal Protocol |
In vivo animal studies are not typically performed with ent-Tadalafil, as it is an inactive impurity and not a therapeutic candidate. Its use is confined to analytical and quality control applications. The compound is used as a reference standard for the quantification of Tadalafil and its impurities in pharmaceutical formulations and biological samples.
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| ADME/Pharmacokinetics |
ent-Tadalafil (CAS: 629652-72-8) has a molecular weight of 389.40 g/mol and a molecular formula of C22H19N3O4. It is a white to off-white solid powder with a melting point of 302-304 ºC. The compound is soluble in DMSO. Storage recommendations: powder at -20°C for up to 3 years and in solvent at -80°C for up to 1 year.
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| Toxicity/Toxicokinetics |
ent-Tadalafil is a research compound and is not approved for human therapeutic use. As an 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. The compound is not intended for human therapeutic use.
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| References | |
| Additional Infomation |
Modification of the hydantoin ring in the previously described lead compound 2a led to the discovery of compound 12a, tadalafil, a highly potent and selective PDE5 inhibitor. Substituting the hydantoin ring in compound 2a with a piperazine dione ring yielded compound cis-11a, which exhibits similar PDE5 inhibitory activity to 2a. Introducing a 3,4-methylenedioxy group at the 6-position of the benzene ring resulted in cis-11c, a highly potent PDE5 inhibitor with enhanced cellular activity. Chain optimization on the piperazine dione ring identified the racemic cis-N-methyl derivative 11i. The piperazine dione series of compounds exhibits high diastereoselectivity for PDE5 inhibition, with the cis-(6R,12aR) enantiomer showing the highest PDE5 inhibitory activity. Piperazine dione compound 12a, namely tadalafil (GF196960), has been shown to be a highly potent PDE5 inhibitor (IC50 = 5 nM) with much higher selectivity for PDE5 than for PDE1-4 and PDE6. Compound 12a has 85 times higher selectivity for PDE6 than sildenafil. In a spontaneously hypertensive rat model, oral administration of 12a (5 mg/kg) resulted in a significant and sustained decrease in blood pressure (30 mmHg/>7 h). [1]
ent-Tadalafil (ent-IC-351) is the inactive cis-enantiomer of Tadalafil and a known impurity (Tadalafil impurity B). It has the CAS number 629652-72-8 and a molecular weight of 389.40 g/mol. It is used as a reference standard for analytical method development, method validation, and quality control applications to ensure the purity of Tadalafil. The compound is not intended for therapeutic use and is for research and analytical use only. |
| Molecular Formula |
C₂₂H₁₉N₃O₄
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|---|---|
| Molecular Weight |
389.40
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| Exact Mass |
389.138
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| CAS # |
629652-72-8
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| Related CAS # |
Nortadalafil;171596-36-4;Tadalafil;171596-29-5;cis-Tadalafil;171596-27-3;cis-ent-Tadalafil;171596-28-4
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| PubChem CID |
9908373
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| Appearance |
White to off-white solid powder
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| Density |
1.51±0.1 g/cm3 (20 ºC 760 Torr)
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| Melting Point |
302-304 ºC
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| LogP |
2.087
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
29
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| Complexity |
702
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| Defined Atom Stereocenter Count |
2
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| SMILES |
CN1CC(=O)N2[C@H](C1=O)CC3=C([C@@H]2C4=CC5=C(C=C4)OCO5)NC6=CC=CC=C36
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| InChi Key |
WOXKDUGGOYFFRN-KKSFZXQISA-N
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| InChi Code |
InChI=1S/C22H19N3O4/c1-24-10-19(26)25-16(22(24)27)9-14-13-4-2-3-5-15(13)23-20(14)21(25)12-6-7-17-18(8-12)29-11-28-17/h2-8,16,21,23H,9-11H2,1H3/t16-,21-/m0/s1
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| Chemical Name |
(2S,8S)-2-(1,3-benzodioxol-5-yl)-6-methyl-3,6,17-triazatetracyclo[8.7.0.03,8.011,16]heptadeca-1(10),11,13,15-tetraene-4,7-dione
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| Synonyms |
ent-IC-351; ent-IC351; ent-Tadalafil; 629652-72-8; Tadalafil, (6S,12AS)-; Tadalafil, (6S ,12aS)-; UNII-HZ6QJN0D4Z; HZ6QJN0D4Z; Tadalafil impurity B [EP]; Tadalafil 6S ,12as enantiomer; ent-Tadalafil; ent Tadalafil
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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) |
DMSO : ~250 mg/mL (~642.01 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (5.34 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (5.34 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.5681 mL | 12.8403 mL | 25.6805 mL | |
| 5 mM | 0.5136 mL | 2.5681 mL | 5.1361 mL | |
| 10 mM | 0.2568 mL | 1.2840 mL | 2.5681 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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