| Size | Price | Stock | Qty |
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| 1mg |
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| 5mg | |||
| Other Sizes |
| Targets |
Target: Voltage-gated Sodium Channels (Nav channels). Ropivacaine is a potent sodium channel blocker, reversibly inhibiting sodium ion influx through voltage-gated sodium channels (primarily Nav1.7, Nav1.8) in nerve fibers. This prevents the generation and propagation of action potentials, leading to nerve impulse conduction blockade. It also inhibits the K2P (two-pore domain potassium channel) TREK-1 with an IC50 of 402.7 microM in COS-7 cell membranes. The labeled version is an analytical standard.
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| ln Vitro |
Drug compounds have included stable heavy isotopes of carbon, hydrogen, and other elements, mostly as quantitative tracers while the drugs were being developed. Because deuteration may have an effect on a drug's pharmacokinetics and metabolic properties, it is a cause for concern [1].
In vitro, the labeled standard has no direct biological activity. The unlabeled ropivacaine (10-1000 uM) causes concentration-dependent blockade of sodium channels in isolated nerve preparations (e.g., frog sciatic nerve, rat vagus nerve) and in cultured dorsal root ganglion (DRG) neurons, as measured by voltage clamp electrophysiology. It also shows use-dependent block, meaning it binds more effectively to channels in the active/inactivated state. The S-enantiomer (ropivacaine is a pure S-(-)-enantiomer) has lower cardiotoxicity than racemic bupivacaine and similar anesthetic potency. |
| ln Vivo |
In vivo, the unlabeled ropivacaine is used clinically as a local anesthetic for epidural, spinal, and peripheral nerve blocks, as well as for surgical anesthesia and postoperative pain management. It produces reversible loss of sensation (analgesia) and motor function (muscle relaxation) in the innervated region. Compared to bupivacaine, ropivacaine has a faster onset, similar duration, and reduced cardiotoxicity and neurotoxicity. The labeled standard is not administered in vivo but is used as an internal standard for PK studies of ropivacaine.
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| Enzyme Assay |
For cell-free assays (LC-MS/MS): plasma, serum, or urine samples are spiked with Ropivacaine-d7 internal standard. After protein precipitation with acetonitrile or methanol, and centrifugation, the supernatant is injected into an LC-MS/MS system. A C18 reverse-phase column and positive ion mode ESI-MS/MS are typically used. Quantitation is based on the analyte/internal standard peak area ratio. Isotope dilution mass spectrometry is used to correct for matrix effects and ensure accurate quantification of ropivacaine and its metabolites (e.g., 3-OH-ropivacaine). The deuterated standard co-elutes with the unlabeled analyte, providing an internal standard with identical extraction recovery and ionization efficiency.
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| Cell Assay |
No cell-based assays are performed with the deuterated standard. The unlabeled ropivacaine is tested in sodium channel-expressing cell lines (e.g., HEK293 cells transfected with Nav1.7 or Nav1.8 channels) for electrophysiology studies. Whole-cell patch-clamp recordings are performed to measure sodium currents. Ropivacaine (0.1-1000 uM) is applied to the cells, and inhibition of sodium current is recorded. IC50 values and use-dependent block are determined. The labeled standard is not used in these assays.
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| Animal Protocol |
No animal studies are conducted with the labeled internal standard itself. For PK studies of ropivacaine, animals (rats, rabbits, dogs) are administered the drug intravenously, epidurally, or by peripheral nerve block. Serial blood samples are collected, plasma is processed, and the deuterated internal standard is used in LC-MS/MS bioanalysis to determine ropivacaine concentrations. PK parameters (Cmax, Tmax, t1/2, AUC, volume of distribution, clearance) are calculated. The standard is also used in tissue distribution and metabolism studies to measure ropivacaine and its metabolites in cerebrospinal fluid (CSF), liver, kidney, and other tissues.
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| ADME/Pharmacokinetics |
PK properties of ropivacaine: After IV administration, it has a plasma half-life of approximately 2-3 h. After epidural administration, peak plasma concentrations occur at 30-60 min (Tmax). Plasma protein binding is high (>90%, primarily to alpha1-acid glycoprotein). It is extensively metabolized in the liver by CYP1A2 and CYP3A4 to its major metabolite, 3-hydroxy-ropivacaine, which has less than 10% of the parent‘s anesthetic activity. Approximately 10-15% of the dose is excreted unchanged in urine. The clearance is reduced in patients with hepatic impairment or low alpha1-acid glycoprotein levels (e.g., neonates). The deuterated standard co-elutes with the analyte, ensuring accurate PK parameter determination.
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| Toxicity/Toxicokinetics |
No toxicity data are reported for the deuterated standard. The unlabeled ropivacaine has a well-characterized safety profile: common adverse effects include hypotension, nausea, vomiting, bradycardia, and paresthesia. High doses can cause CNS toxicity (dizziness, tinnitus, seizures, respiratory depression) and cardiotoxicity (prolonged PR interval, QT prolongation, arrhythmias, cardiac arrest). However, ropivacaine has lower CNS and cardiotoxicity than bupivacaine due to its S-enantiomer configuration. The labeled compound is for research use only and is not intended for human therapeutic administration. It is non-hazardous for transport under normal laboratory conditions.
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| References |
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| Additional Infomation |
Ropivacaine-d7 is a research standard and not an active drug substance. The unlabeled ropivacaine (Naropin, Ropivan) is FDA-approved for the induction and maintenance of local anesthesia for surgical procedures, including epidural anesthesia for labor and delivery, spinal anesthesia, peripheral nerve blocks, and local infiltration. It is also used for postoperative pain management. The deuterated standard is used for analytical method development, method validation (AMV), quality control (QC), and abbreviated new drug application (ANDA) submissions for ropivacaine-containing pharmaceutical products. It is essential for therapeutic drug monitoring (TDM) in patients receiving regional anesthesia and for clinical PK studies.
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| Molecular Formula |
C17H26N2O
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|---|---|
| Molecular Weight |
274.401144504547
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| Exact Mass |
281.248
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| CAS # |
684647-62-9
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| Related CAS # |
Ropivacaine;84057-95-4;Ropivacaine hydrochloride monohydrate;132112-35-7;Ropivacaine hydrochloride;98717-15-8;Ropivacaine-d7 hydrochloride;1217667-10-1;Ropivacaine mesylate;854056-07-8;(Rac)-Ropivacaine-d7;1392208-04-6
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| PubChem CID |
46782900
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| Appearance |
White to off-white solid powder
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| LogP |
4.093
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
20
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| Complexity |
308
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| Defined Atom Stereocenter Count |
1
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| SMILES |
[2H]C([2H])([2H])C([2H])([2H])C([2H])([2H])N1CCCC[C@H]1C(=O)NC2=C(C=CC=C2C)C
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| InChi Key |
ZKMNUMMKYBVTFN-YMXBPWPKSA-N
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| InChi Code |
InChI=1S/C17H26N2O/c1-4-11-19-12-6-5-10-15(19)17(20)18-16-13(2)8-7-9-14(16)3/h7-9,15H,4-6,10-12H2,1-3H3,(H,18,20)/t15-/m0/s1/i1D3,4D2,11D2
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| Chemical Name |
(2S)-N-(2,6-dimethylphenyl)-1-(1,1,2,2,3,3,3-heptadeuteriopropyl)piperidine-2-carboxamide
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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) |
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 | 3.6443 mL | 18.2216 mL | 36.4431 mL | |
| 5 mM | 0.7289 mL | 3.6443 mL | 7.2886 mL | |
| 10 mM | 0.3644 mL | 1.8222 mL | 3.6443 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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