Procaine

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Overview

Procaine

Clinical data
Pregnancy category	AU: B2 US: C (Risk not ruled out)
Routes of administration	Parenteral
ATC code	N01BA02 (WHO) C05AD05 (WHO) S01HA05 (WHO)
Legal status
Legal status	AU: S4 (Prescription only)
Pharmacokinetic data
Bioavailability	n/a
Metabolism	Hydrolysis by plasma esterases
Elimination half-life	40–84 seconds
Excretion	Renal
Identifiers
IUPAC name 2-(diethylamino)ethyl 4-aminobenzoate
CAS Number	59-46-1
PubChem CID	4914
DrugBank	APRD00650
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Formula	C13H20N2O2
Molar mass	236.31 g/mol

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List of terms related to Procaine

Procaine is a local anesthetic drug of the amino ester group. It is used primarily to reduce the pain of intramuscular injection of penicillin, and is also used in dentistry. Owing to the ubiquity of the trade name Novocain, procaine is sometimes referred to generically as novocaine or novacaine.

Procaine was first synthesized in 1905, and was the first injectable man-made local anesthetic used. It was created by the German chemist Alfred Einhorn (1857–1917) who gave the chemical the trade name Novocaine, from the Latin Novus (meaning New) and caine, a common ending for alkaloids used as anesthetics. It was introduced into medical use by surgeon Heinrich Braun (1862–1934).

Procaine is used less frequently today since more effective (and hypoallergenic) alternatives such as lidocaine (xylocaine) exist. Prior to the discovery of procaine, cocaine was the most commonly used local anesthetic. Procaine (like cocaine) has the advantage of constricting blood vessels, which reduces bleeding, unlike other local anesthetics like lidocaine, and without the euphoric and addictive qualities of cocaine.

Procaine, an ester anesthetic, is metabolized in the plasma by the enzyme pseudocholinesterase through hydrolysis into para-amino benzoic acid (PABA), which is then excreted by the kidneys into the urine. Allergic reactions to procaine are usually not in response to procaine itself, but to PABA. About 1 in 3000 people have an atypical form of pseudocholinesterase, which doesn't hydrolyze ester anesthetics such as procaine, resulting in a prolonged period of high levels of the anesthetic in the blood and increased toxicity.

Procaine is the primary ingredient in the controversial preparation Gerovital H3, which is claimed by its advocates to remedy many effects of aging. The mainstream medical view is that these claims were seriously studied and discredited in the 1960s.

See also

• Procaine blockade