ID 538

Prilocaine
Description:
Prilocaine is a local anesthetic of intermediate acting amino amide type and derivative of toluidine
used more often for infiltration anesthesia in dentistry. It is also used for induction anesthesia and
for surface anesthesia (in combination with lidocaine).
It is white needle-like odorless compound having initially acidic then bitter taste.
Clinical Data:
Accession number: DB00750 (APRD00180)
EC number: 211-957-0
CAS: 721-50-6
Kingdom: Organic compound
Molecular Formula: C13H20N2O
Molecular weight: 220.311 g/mol
Chirality: Racemic mixture
Boiling Point: 159-162 °C
Melting Point: 37-38 °C
Index of refraction: 1.5298
Dissociation Constant
 Pka acidic : 13.81
 Pka basic : 8.13
Iupac name: N-(2-methylphenyl)-2-(propylamino)propanamide
Elimination half-life: 10- 150 minutes, longer with impaired hepatic or renal function
Molecular framework: Aromatic homomonocyclic compounds
Solubility:
 Water solubility is 541 mg/L
 It is freely soluble in alcohol
 It is slightly soluble in chloroform
 It is very slightly soluble in acetone
 It is partially insoluble in ether.
Preparation:
Prilocaine is synthesized by reacting 2-aminotoluene with 2-bromopropionyl chloride and
then with n-propyl amine.
Uses of Prilocaine:
 It is a local anesthetic used in several dosage forms that include topic creams,
injection, patches, sprays etc.
 It is also used as anti-convulsant.
 If used topically, it is used on normal, unbroken skin or on the outer genital area to
prevent pain before certain procedures such as inserting a needle, skin grafts, or
skin laser surgery.
  It works by temporarily numbing the skin and surrounding area.
 It is used for Dental infiltration or nerve block.
Benefits:
Prilocaine has demonstrable benefit in reducing pain of procedures like lumbar puncture,
intramuscular injections and circumcision.
Eutectic mixture of prilocaine and lidocaine have shown effectiveness in reducing the pain or
distress of a number of common pediatric procedures including venous cannulation,
venipuncture, urethral meatotomy and adhesion release, immunizations, arterial cannulation
etc. with lowest side effects.
Contraindications:
Prilocaine may also be contraindicated in people with the following conditions due to
ortho-toluidine that causes methemoglobinemia;
 Sickle cell anemia
 Anemia
 Symptomatic hypoxia
It may be contraindicated in the following as well;
 Bacterial septicemia
 Sinus tachycardia
 Shock
 Parkinsonism
Side effects:
In topical creams, redness swelling, tingling/burning, or lightening of the skin may occur.
Storage:
 Store below 25ºC.
 Protect from direct sunlight.
 Keep the container tightly closed.