Ropivacaine Hydrochloride

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Cat Number

API0232524

CAS Number

98717-15-8

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Product Detail Description Scientific Support Advanced Innovations Customer Q&A

CAS Number

98717-15-8

EINECS

663-286-1

Synonyms

ROPIVACAINE HCl, Ropivacaine monohydrochloride, DTXSID2048379

Molecular Formula

C17H27ClN2O

Molecular Weight

310.86

Smiles

CCCN1CCCC[C@H]1C(=O)NC2=C(C=CC=C2C)C.Cl

Boiling Point

410.2ºC

General Description

Ropivacaine hydrochloride is the hydrochloride salt of ropivacaine, a long-acting amide-type local anesthetic approved by the FDA in 1996 for surgical anesthesia and acute pain management. It is chemically related to bupivacaine but is formulated as the pure S-enantiomer to enhance its safety profile.

Mechanism of Action

Ropivacaine reversibly blocks voltage-gated sodium channels in neuronal membranes, preventing sodium influx and inhibiting depolarization and impulse propagation. It exhibits preferential blockade of tetrodotoxin-resistant sodium channels predominantly found in small nociceptive neurons, which may explain its ability to produce differential sensory blockade with less profound motor impairment compared to other long-acting agents.

Application

Ropivacaine hydrochloride is indicated for epidural blocks including cesarean section, major nerve blocks, local infiltration, and continuous epidural infusion for postoperative or labor pain management. Lower concentrations (0.2%) provide analgesia with minimal motor block, while higher concentrations (0.5-1%) produce complete surgical anesthesia with motor blockade. Compared to bupivacaine, ropivacaine offers faster regression of sensory and motor blockade, potentially facilitating earlier mobilization, and is associated with reduced incidence of hypotension and cardiotoxicity.

Chen Y, et al. investigated the cellular toxicity of the local anesthetic ropivacaine using human neuronal SH-SY5Y cells. Exposure to clinically relevant concentrations (0.5% and 1%) induced fission-like mitochondrial morphological changes, selectively up-regulated the mitochondrial fission protein DRP1, increased reactive oxygen species generation, and caused mitochondrial dysfunction characterized by decreased membrane potential, reduced cytochrome C oxidase activity, and diminished ATP production. Critically, silencing DRP1 expression through genetic manipulation completely abolished these ropivacaine-induced effects, including mitochondrial fragmentation, dysfunction, cellular LDH release, apoptosis, and cell death. DRP1-deficient cells maintained normal cytochrome C oxidase activity and ATP production despite ropivacaine exposure.

Fig. 1 Ropivacaine induces fission-like changes in mitochondrial morphology. (Chen Y, et al., 2019)

References

Chen Y, et al. The role of DRP1 in ropivacaine-induced mitochondrial dysfunction and neurotoxicity. Artif Cells Nanomed Biotechnol. 2019;47(1):1788-1796.

Fu X, et al. developed and evaluated a thermosensitive hydrogel formulation for sustained delivery of ropivacaine hydrochloride to manage postoperative pain. The PLGA-PEG-PLGA copolymer solution remained liquid at room temperature but formed a gel at temperatures slightly below body temperature. In vitro release studies showed 37.5%, 51.3%, and 72.6% of ropivacaine released at 12, 24, and 48 hours, respectively, following Higuchi kinetics. In a rat incisional pain model, a single injection of ropivacaine-loaded gel at the surgical site provided analgesic effects lasting 48 hours, significantly longer than ropivacaine solution alone.

Fig. 2 Drug release rate (Fu X, et al, 2017)

References

Fu X, et al. A PLGA-PEG-PLGA Thermosensitive Gel Enabling Sustained Delivery of Ropivacaine Hydrochloride for Postoperative Pain Relief. Chem Pharm Bull (Tokyo). 2017;65(3):229-235.

Does Ropivacaine Hydrochloride require any special storage conditions to maintain its chiral purity?

Yes, as a single enantiomer drug, it must be stored under controlled conditions (15-25°C) to prevent racemization.

Is Ropivacaine Hydrochloride compatible with terminal sterilization processes?

The API itself is stable under typical steam sterilization conditions. However, we recommend validating the entire formulation, as excipients can influence stability.

What is the pH stability range for Ropivacaine Hydrochloride in solution?

It is most stable at slightly acidic pH (4-6).

How is the absence of 2,6-dimethylaniline (a genotoxic impurity) verified?

We use a highly sensitive LC-MS/MS method with a detection limit well below the TTC (Threshold of Toxicological Concern) to ensure this impurity is not present in the API.