| Size | Price | Stock | Qty |
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| 5mg |
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| 10mg |
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| Other Sizes |
| Targets |
(S)-Nimodipine targets L-type voltage-gated calcium channels (Caᵥ1.2, Caᵥ1.3) in vascular smooth muscle and neurons. It binds to the alpha1 subunit, blocking calcium influx. This causes vasodilation, particularly in cerebral arteries, and reduces contractility. It also has neuroprotective effects by limiting calcium overload. The (S)-enantiomer has higher affinity for the DHP binding site than the (R)-enantiomer.
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|---|---|
| ln Vitro |
In vitro, (S)-Nimodipine inhibits [3H]-nimodipine binding to rat brain membranes with an IC₅0 in the low nanomolar range (e.g., 1-10 nM). In a functional assay using KCl-contracted rat aorta, it relaxes the tissue with an IC₅0 of ~5 nM. It is a potent vasodilator. It shows no significant cytotoxicity in HepG2 cells up to 100 uM.
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| ln Vivo |
In vivo, (S)-Nimodipine is expected to have efficacy similar to the racemic mixture. In a rabbit model of subarachnoid hemorrhage, it prevents vasospasm and improves neurological outcome. It is administered by intravenous infusion (0.5-2 mg/kg/h) or orally (10-30 mg/kg). It reduces the diameter reduction of the basilar artery.
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| Enzyme Assay |
In vitro calcium channel binding assay: Prepare rat brain cortical membranes (200 ug protein). Incubate with 1 nM [3H]-nimodipine and varying concentrations of (S)-Nimodipine (0.01-1000 nM) in 50 mM Tris-HCl, pH 7.4, for 60 min at 25degC in the dark. Non-specific binding determined with 1 uM nifedipine. Filter and count. IC₅0 is calculated.
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| Cell Assay |
In vitro vascular relaxation assay: Isolate rat thoracic aorta rings and mount in organ bath. Pre-constrict with 60 mM KCl. Add (S)-Nimodipine cumulatively (0.1 nM-10 uM). Measure isometric tension. Calculate EC₅0 for relaxation (expected <10 nM). For cell viability, treat HepG2 cells with compound (1-100 uM) for 48 h, then MTT; IC₅0 >100 uM.
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| Animal Protocol |
In vivo cerebral vasospasm model: Male New Zealand white rabbits (n=8/group) are subjected to double SAH induction. (S)-Nimodipine (10 ug/kg/min, i.v. infusion) is started 30 min after first SAH and continued for 48 h. Then sacrifice, perfuse, and measure basilar artery diameter by angiography. The treated group shows larger diameter vs. vehicle.
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| ADME/Pharmacokinetics |
(S)-Nimodipine is highly lipophilic (logP ~3). It is rapidly absorbed after oral administration but undergoes extensive first-pass metabolism (bioavailability ~10-20%). The plasma half-life is short (1-2 h). It is >95% protein bound. It is metabolized by CYP3A4 to inactive derivatives. The (S)-enantiomer may have similar PK to the racemate.
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| Toxicity/Toxicokinetics |
The toxicity of (S)-Nimodipine is similar to that of the racemic drug. The most common adverse effects are hypotension, headache, flushing, and bradycardia. It is not genotoxic. For impurity qualification, the (S)-enantiomer is not an impurity; it is the active ingredient. In a drug product, the limit of the (R)-enantiomer is controlled (≤0.15%).
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| References | |
| Additional Infomation |
(S)-Nimodipine is a single enantiomer reference standard for chiral purity analysis. It is stored at 2-8degC, protected from light (dihydropyridines are light-sensitive). It is used in analytical method development to separate the two enantiomers by chiral HPLC (e.g., using Chiralpak AD-H column). It is a solid powder, soluble in DMSO and ethanol.
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| Molecular Formula |
C21H26N2O7
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|---|---|
| Molecular Weight |
418.44
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| Exact Mass |
418.174
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| CAS # |
77940-93-3
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| Related CAS # |
Nimodipine; (R)-Nimodipine; Nimodipine-d7; Nimodipine; 66085-59-4
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| PubChem CID |
157133
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| Appearance |
White to off-white solid powder
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| Hydrogen Bond Donor Count |
1
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| Rotatable Bond Count |
9
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| Heavy Atom Count |
30
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| Complexity |
736
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| Defined Atom Stereocenter Count |
1
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| SMILES |
CC1=C([C@@H](C(=C(N1)C)C(=O)OC(C)C)C2=CC(=CC=C2)[N+](=O)[O-])C(=O)OCCOC
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| InChi Key |
UIAGMCDKSXEBJQ-IBGZPJMESA-N
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| InChi Code |
InChI=1S/C21H26N2O7/c1-12(2)30-21(25)18-14(4)22-13(3)17(20(24)29-10-9-28-5)19(18)15-7-6-8-16(11-15)23(26)27/h6-8,11-12,19,22H,9-10H2,1-5H3/t19-/m0/s1
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| Chemical Name |
3-O-(2-methoxyethyl) 5-O-propan-2-yl (4S)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
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| Synonyms |
(S)-BAY-e 9736
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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 : ~100 mg/mL (~238.98 mM; with sonication)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 5 mg/mL (11.95 mM)(saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween-80 + 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 50.0 mg/mL clear DMSO stock solution to 400 μL of PEG300 and mix thoroughly. Then add 50 μL of Tween-80 to the above system and mix thoroughly. Finally, add 450 μL of physiological saline to bring the volume to 1 mL. Preparation of physiological saline: Dissolve 0.9 g of sodium chloride in ddH₂O and bring the volume to 100 mL to obtain a clear and transparent physiological saline solution. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 5 mg/mL (11.95 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 50.0 mg/mL clarified DMSO stock solution to 900 μL of corn oil and mix well. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.3898 mL | 11.9491 mL | 23.8983 mL | |
| 5 mM | 0.4780 mL | 2.3898 mL | 4.7797 mL | |
| 10 mM | 0.2390 mL | 1.1949 mL | 2.3898 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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