| Size | Price | |
|---|---|---|
| 500mg | ||
| 1g | ||
| Other Sizes |
| Targets |
The primary target of vincanol is the voltage-gated sodium channel (VGSC), through which it exerts its pharmacological effects via channel blockade. Studies have shown that vincanol inhibits [³H]batrachotoxin binding to sodium channels with an IC₅₀ of 10.7 μM and blocks sodium currents in rat cortical neurons with an IC₅₀ of 40 μM. Additionally, computational prediction analysis suggests that vincanol may interact with multiple proteins including the cannabinoid CB2 receptor, NF-κB subunit p105, histone deacetylase 8, and cyclooxygenase-1/2, though these predicted targets require experimental validation.
|
|---|---|
| ln Vitro |
In vitro studies demonstrate that vincanol exerts multiple biological activities by blocking voltage-gated sodium channels. In sodium channel binding assays, vincanol inhibits [³H]batrachotoxin binding to sodium channels in rat cortical synaptosomes with an IC₅₀ of 10.7 μM. In whole-cell patch-clamp experiments, vincanol concentration-dependently blocks sodium currents in rat cortical neurons with an IC₅₀ of 40 μM. In neuroprotection assays, vincanol protects cortical neurons from veratridine-induced cell death with an IC₅₀ of 33 μM.
|
| ln Vivo |
In vivo studies demonstrate that vincanol exhibits anticonvulsant activity in the maximal electroshock seizure model. Following intraperitoneal administration, vincanol dose-dependently attenuates maximal electroshock-induced convulsions in mice with an ED₅₀ of 14.6 mg/kg, demonstrating comparable or slightly superior potency to vinpocetine (27 mg/kg) and vincamine (15.4 mg/kg). This effect is directly related to its sodium channel blocking mechanism, suggesting its potential application as an anticonvulsant agent.
|
| Enzyme Assay |
Synaptosome Preparation: Isolate rat cerebral cortex, homogenize in buffer, and prepare crude synaptosomal fractions by differential centrifugation.
[³H]Batrachotoxin Binding Assay: Incubate synaptosomes with varying concentrations of vincanol (0.1-100 μM) and [³H]batrachotoxin at 37°C for 60 minutes.
Separation and Detection: Terminate the reaction by rapid filtration and detect filter-bound radioactivity using a scintillation counter. Vincanol inhibits binding with an IC₅₀ of 10.7 μM.
Data Analysis: Calculate inhibition rates at each concentration and fit IC₅₀ values by non-linear regression.
|
| Cell Assay |
Cell Culture: Culture neonatal rat cortical neurons in Neurobasal medium containing B27 supplements at 37°C in a 5% CO₂ incubator for 7-10 days.
Drug Treatment: Dissolve vincanol in DMSO to prepare stock solution, dilute to working concentrations (e.g., 1-100 μM) with culture medium, and pre-incubate with cells for appropriate duration.
Veratridine-Induced Toxicity: Add veratridine (e.g., 3-10 μM) to induce sodium channel-dependent cell death and co-incubate for 24 hours.
Viability Assay: Measure cell viability using MTT or LDH release assays. Vincanol protects neurons with an IC₅₀ of 33 μM.
Data Analysis: Compare cell survival rates between treatment and control groups to calculate EC₅₀ for neuroprotection.
|
| Animal Protocol |
Animal Model: Use adult male mice (e.g., NMRI or Swiss strains) weighing 20-30 g to establish the maximal electroshock seizure model.
Dosing Regimen: Administer vincanol via intraperitoneal injection at doses ranging from 3-30 mg/kg, typically formulated in saline or buffer with appropriate co-solvents.
Electroshock Treatment: Thirty minutes after administration, apply electrical stimulation (e.g., 50 mA, 0.2 seconds) via ear clip electrodes to induce convulsions.
Efficacy Assessment: Record hindlimb tonic extension duration following seizure induction, using the abolition of tonic extension as an indicator of anticonvulsant effect. Vincanol exhibits an ED₅₀ of 14.6 mg/kg.
Data Analysis: Calculate protection rates for each dose group and determine ED₅₀ by Probit analysis.
|
| ADME/Pharmacokinetics |
Predicted pharmacokinetic parameters for vincanol indicate favorable intestinal absorption and blood-brain barrier penetration: human intestinal absorption probability is 99.18%, Caco-2 permeability prediction is 93.55%, and blood-brain barrier penetration prediction is 87.50%. The compound has an XLogP of 3.0, a predicted LogP of 3.63, and a topological polar surface area of 28.40 Ų, showing no violations of Lipinski's rule of five. Vincanol is not a P-glycoprotein substrate (probability 90.74%). Regarding solubility, the compound is soluble in DMSO, with powder stable for 3 years at -20°C protected from light and solutions stable for 1 year at -80°C.
|
| Toxicity/Toxicokinetics |
mouse LD50 oral 370 mg/kg French Demande Patent Document., #2319362
Acute toxicity data for vincanol are relatively limited. The oral LD₅₀ in mice is 370 mg/kg. Predicted toxicological assessments indicate no Ames mutagenicity (probability 56.00%), no carcinogenicity (probability 97.00%), and no skin or eye irritation. Potential toxicological effects include: hERG channel inhibition (probability 83.21%), suggesting a potential risk for QT interval prolongation; respiratory toxicity (probability 88.89%); reproductive toxicity (probability 92.22%); mitochondrial toxicity (probability 98.75%); and hepatotoxicity (probability 53.67%). |
| References | |
| Additional Infomation |
It has been reported that Vincanol is present in both Kopsia officinalis and Kopsia arborea, and relevant data is available for reference.
|
| Molecular Formula |
C19H24N2O
|
|---|---|
| Molecular Weight |
296.41
|
| Exact Mass |
296.189
|
| Elemental Analysis |
C, 76.99; H, 8.16; N, 9.45; O, 5.40
|
| CAS # |
19877-89-5
|
| PubChem CID |
10017481
|
| Appearance |
Typically exists as solid at room temperature
|
| Density |
1.35 g/cm3
|
| Boiling Point |
484.4ºC at 760 mmHg
|
| Flash Point |
246.8ºC
|
| Vapour Pressure |
0mmHg at 25°C
|
| Index of Refraction |
1.719
|
| LogP |
3.563
|
| Hydrogen Bond Donor Count |
1
|
| Hydrogen Bond Acceptor Count |
2
|
| Rotatable Bond Count |
1
|
| Heavy Atom Count |
22
|
| Complexity |
455
|
| Defined Atom Stereocenter Count |
3
|
| SMILES |
CC[C@@]12CCCN3[C@@H]1C1=C(CC3)C3=CC=CC=C3N1[C@H](C2)O
|
| InChi Key |
HONLKDDLTAZVQV-UHOSZYNNSA-N
|
| InChi Code |
InChI=1S/C19H24N2O/c1-2-19-9-5-10-20-11-8-14-13-6-3-4-7-15(13)21(16(22)12-19)17(14)18(19)20/h3-4,6-7,16,18,22H,2,5,8-12H2,1H3/t16-,18+,19-/m0/s1
|
| Chemical Name |
(15S,17S,19S)-15-ethyl-1,11-diazapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2,4,6,8(18)-tetraen-17-ol
|
| Synonyms |
Vincanolum; 19877-89-5; Vincanol [INN]; Vincanolum; Vincanolum [INN-Latin]; Vincanol
|
| 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 (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
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 | 3.3737 mL | 16.8685 mL | 33.7371 mL | |
| 5 mM | 0.6747 mL | 3.3737 mL | 6.7474 mL | |
| 10 mM | 0.3374 mL | 1.6869 mL | 3.3737 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.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
