Prilocaine

log Kow= 2.11

2.1

2.11

Needles

WHITE

Crystals from ethanol + isopropyl ether; readily sol in water; mp 167-168 °C /Hydrochloride/

FREELY SOL IN ALC; SLIGHTLY SOL IN CHLOROFORM

VERY SLIGHTLY SOL IN ACETONE; PRACTICALLY INSOL IN ETHER

3.26e-01 g/L

Breast Feeding; Lactation; Anesthetics, Local

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Pharmaceuticals

159-162 °C at 1.00E-01 mm Hg

159-162 °C @ 1 mm Hg

37-38 °C

37-38 °C

37 - 38 °C

Warning

H302 (98.6%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P264+P265, P270, P273, P280, P301+P317, P302+P352, P305+P351+P338, P321, P330, P332+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 69 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

...MOUSE TRIALS INDICATE INCR TOXICITY WHEN COMBINED WITH TETRACAINE.

...PRILOCAINE...REPORTED TO INTERACT WITH SUCCINYLCHOLINE /RESULTING IN INCR IN INTENSITY & DURATION OF SUCCINYLCHOLINE-INDUCED NEUROMUSCULAR BLOCKADE & RESP DEPRESSION; OTHER DEPOLARIZING MUSCLE RELAXANTS (EG DECAMETHONIUM) & NONDEPOLARIZING MUSCLE RELAXANTS (EG GALLAMINE TRIETHIODIDE & PANCURONIUM) MAY BEHAVE SIMILARLY/.

.../PRILOCAINE/ PRODUCED A SLIGHT INCR IN INTENSITY OF NEUROMUSCULAR BLOCKADE /OF ALCURONIUM CHLORIDE/. ...MARKED DECR IN TIDAL VOL, INDICATING RESP DEPRESSION, WAS OBSERVED...

EPINEPHRINE PROLONGS THE EFFECT /OF PRILOCAINE/. /PRILOCAINE HCL/

For more Interactions (Complete) data for PRILOCAINE (15 total), please visit the HSDB record page.

◉ Summary of Use during Lactation

◈ What is prilocaine?

Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

N01BB04

N - Nervous system

QN - Nervous system

Prilocaine binds to the intracellular surface of sodium channels which blocks the subsequent influx of sodium into the cell. Action potential propagation and nerve function is, therefore, prevented. This block is reversible and when the drug diffuses away from the cell, sodium channel function is restored and nerve propagation returns.

Prilocaine acts on sodium channels on the neuronal cell membrane, limiting the spread of seizure activity and reducing seizure propagation. The antiarrhythmic actions are mediated through effects on sodium channels in Purkinje fibers.

... BLOCK CONDUCTION IN NERVE PERHAPS BY COMPETING WITH CA @ SOME SITE THAT CONTROLS PERMEABILITY OF MEMBRANE ... CA IS ALSO INVOLVED IN ACTION OF LOCAL ANESTHETICS ON SMOOTH MUSCLE ... & ON ADRENAL MEDULLA ... /LOCAL ANESTHETICS/

... PREVENT THE GENERATION & THE CONDUCTION OF THE NERVE IMPULSE. THEIR PRIMARY SITE OF ACTION IS THE CELL MEMBRANE. ... BLOCK CONDUCTION BY DECREASING OR PREVENTING THE LARGE TRANSIENT INCREASE IN THE PERMEABILITY OF EXCITABLE MEMBRANES TO NA+ THAT NORMALLY IS PRODUCED BY A SLIGHT DEPOLARIZATION OF THE MEMBRANE. /LOCAL ANESTHETICS/

AS ANESTHETIC ACTION PROGRESSIVELY DEVELOPS IN A NERVE, THRESHOLD FOR ELECTRICAL EXCITABILITY INCR & SAFETY FACTOR FOR CONDUCTION DECR; WHEN THIS ACTION IS SUFFICIENTLY WELL-DEVELOPED, BLOCK OF CONDUCTION IS PRODUCED. /LOCAL ANESTHETICS/

.../2 POSSIBILITIES:/ ACHIEVE BLOCK BY INCR SURFACE PRESSURE OF LIPID LAYER THAT CONSTITUTES NERVE MEMBRANE...CLOSING PORES THROUGH WHICH IONS MOVE. ... /OR:/ AFFECT PERMEABILITY BY INCR DEGREE OF DISORDER OF MEMBRANE. /LOCAL ANESTHETICS/

MEPIVACAINE-HCL (I-HCL) & PRILOCAINE-HCL (II-HCL) WERE INFUSED IV 250 MG INTO HEALTHY VOLUNTEERS. T/2 FOR I WAS GENERALLY LONGER THAN II; TOTAL BODY CLEARANCE II CONSISTENTLY GREATER THAN I. II CLEARANCE EXCEEDED NORMAL HEPATIC BLOOD FLOW: EXTRA-HEPATIC METAB SITE IS POSTULATED.

The amide-linked local anesthetics are, in general, degraded by the hepatic endoplasmic reticulum, the initial reactions involving N-dealkylation and subsequent hydrolysis. However, with prilocaine, the initial step is hydrolytic, forming o-toluidine metabolites that can cause methemoglobinemia.

BIOTRANSFORMATION OF PRILOCAINE...IN RATS GAVE O-TOLUIDINE & N-PROPYLALANINE.

046O35D44R

PRILOCAINE

Established Pharmacologic Class [EPC] - Amide Local Anesthetic

Chemical Structure [CS] - Amides

Physiologic Effects [PE] - Local Anesthesia

Prilocaine is an Amide Local Anesthetic. The physiologic effect of prilocaine is by means of Local Anesthesia.

Drugs that block nerve conduction when applied locally to nerve tissue in appropriate concentrations. They act on any part of the nervous system and on every type of nerve fiber. In contact with a nerve trunk, these anesthetics can cause both sensory and motor paralysis in the innervated area. Their action is completely reversible. (From Gilman AG, et. al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 8th ed) Nearly all local anesthetics act by reducing the tendency of voltage-dependent sodium channels to activate.

Prilocaine is metabolized in both the liver and the kidney and excreted via the kidney.

/CONCERNING/ HYDROLYSIS OF AMIDE BOND OF PRILOCAINE... PLASMA CONCN OF R-(-)-ENANTIOMER WERE FOUND TO BE LOWER THAN THOSE OF THE S-(+)-ENANTIOMER AFTER IV ADMIN TO CAT. IN VITRO STUDIES USING LIVER PREPN FROM VARIOUS MAMMALS CONFIRMED THE R-(-)-ISOMER TO BE HYDROLYZED @ MUCH HIGHER RATES THAN THE S-(+) FORM...

THERE IS...MORE RAPID PRODN OF METHEMOGLOBINEMIA BY D-(-) FORM, CAUSED PRESUMABLY BY HIGHER BLOOD LEVELS OF HYDROLYSIS PRODUCT, O-TOLUIDINE.

PRILOCAINE FETAL/MATERNAL CONCN RATIO: 1.0 /FROM TABLE/

PRILOCAINE DOSE 0.2 G IV GAVE BLOOD CONCN 0.26 MG% @ 0.3 HR & 0.14 MG% @ 0.17 HR; DOSE 0.4 G IV GAVE BLOOD CONCN 0.15 MG% @ 0.12 HR & 0.08 MG% @ 0.33 HR; DOSE 0.4 G EPIDURAL BLOCK GAVE BLOOD CONCN 0.26 MG% @ 0.25 HR (PEAK); DOSE 0.4 G INTERCOSTAL BLOCK GAVE BLOOD CONCN 0.40 MG% @ 0.25 HR. /FROM TABLE/

MEDICATION (VET)

MEDICATION

Local anesthetic

Use (kg; approx.) in Germany (2009): >1000

O-TOLUIDINE IS CONDENSED WITH 2-BROMOPROPIONYL BROMIDE & RESULTING 2-BROMO-O-PROPIONOTOLUIDIDE IS IN TURN CONDENSED WITH PROPYLAMINE TO YIELD PRILOCAINE (BASE). AN ACETONE SOLN OF BASE TREATED WITH HCL YIELDS THE OFFICIAL SALT. /PRILOCAINE HCL/

Prilocaine is synthesized by reacting 2-aminotoluene with 2-bromopropionyl chloride and then with n-propylamine. /Hydrochloride/