Prilocaine

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Cat Number

API0231616

CAS Number

721-50-6

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Product Detail Description Scientific Support Customer Q&A

CAS Number

721-50-6

EINECS

211-957-0

Storage

Store at room temperature

Synonyms

Propitocaine; prilocaine base; N-(2-Methylphenyl)-2-(propylamino)propanamide; Prilocaina; Prilocainum

Molecular Formula

C13H20N2O

Molecular Weight

220.31

Smiles

CCCNC(C)C(=O)NC1=CC=CC=C1C

Appearance

White crystalline powder

Melting Point

37-38℃

Boiling Point

361.6±25.0℃ at 760 mmHg

Relative Density

1.0±0.1

General Description

Prilocaine is an aminoamide local anesthetic with intermediate duration and potency, commonly used for infiltration and regional nerve blocks. It is available as a plain solution and in combination with lidocaine as a eutectic mixture (EMLA cream) for topical dermal anesthesia. The drug has a lower risk of systemic toxicity than lidocaine due to rapid metabolism.

Mechanism of Action

Prilocaine diffuses across the axonal membrane in its uncharged base form and then binds to voltage-gated sodium channels from the intracellular side. This binding prevents sodium influx, stabilizing the membrane and blocking action potential propagation. The effect is reversible and concentration-dependent. Prilocaine has a pKa of 7.9, providing a favorable onset profile similar to lidocaine.

Application

Prilocaine is used for infiltration anesthesia, peripheral nerve blocks, epidural anesthesia, and as a topical anesthetic (in EMLA cream) for skin procedures, venous cannulation, and superficial genital surgery.

Lidocaine and prilocaine were co‑encapsulated in solid lipid nanoparticles (SLNs) and nanostructured lipid carriers (NLCs) for topical anesthesia. Both systems showed good drug loading and stability. SLNs exhibited superior ex vivo skin permeation, whereas NLCs produced a stronger in vivo anesthetic effect. Combination delivery of both drugs was more effective than single‑drug systems. The authors conclude that SLNs and NLCs have complementary advantages: SLNs for penetration, NLCs for efficacy. Both are promising carriers for dual‑drug topical anesthesia.

Fig. 1 In vitro cellular viability of BALB/c-3T3 fibroblast cells incubated with free drugs and drug-loaded SLN and NLC systems. (You P, et al., 2017)

References

You P, et al. Design and evaluation of lidocaine- and prilocaine-coloaded nanoparticulate drug delivery systems for topical anesthetic analgesic therapy: a comparison between solid lipid nanoparticles and nanostructured lipid carriers. Drug Des Devel Ther. 2017;11:2743-2752.

Does Prilocaine require protection from light during storage?

Yes, it is moderately photosensitive. Prolonged light exposure can cause discoloration and degradation. Store in light-resistant, tightly sealed containers.

What is the recommended storage temperature for Prilocaine?

Store at controlled room temperature (15-25°C). Avoid excessive heat above 30°C, which can accelerate oxidative degradation of the amide linkage.

Is Prilocaine stable in solution for injectable formulations?

Yes, when formulated at acidic pH and protected from light, solutions are stable. We provide compatibility data for preservatives (e.g., methylparaben) and antioxidants.

How is the impurity o-toluidine (a potential genotoxic impurity) monitored?

We use a highly sensitive LC-MS/MS method to monitor o-toluidine levels, ensuring they remain below the threshold of toxicological concern (TTC).