Procaine

"Novocaine" redirects here. For other uses, see Novocaine (disambiguation).

Procaine

File:Procaine.svg
File:Procainemodel.png
Systematic (IUPAC) name
2-(diethylamino)ethyl 4-aminobenzoate
Clinical data
Pregnancy category	AU: B2 US: C (Risk not ruled out)
Routes of administration	Parenteral
Legal status
Legal status	AU: S4 (Prescription only)
Pharmacokinetic data
Bioavailability	n/a
Metabolism	Hydrolysis by plasma esterases
Biological half-life	40–84 seconds
Excretion	Renal
Identifiers
CAS Number	59-46-1
ATC code	N01BA02 (WHO) C05AD05 S01HA05
PubChem	CID 4914
DrugBank	APRD00650
ChemSpider	4745
Chemical data
Formula	C13H20N2O2
Molar mass	236.31 g/mol[[]]
(verify)

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 it was also used in dentistry. Owing to the ubiquity of the trade name Novocain, procaine is usually referred to generically as novocaine. It acts mainly by being a sodium channel blocker.

Procaine was first synthesized in 1905, shortly after amylocaine, and is the oldest man-made local anesthetic still in clinical use. It was created by the German chemist Alfred Einhorn (1856–1917) who gave the chemical the trade name Novocaine, from the Latin nov- (meaning new) and -caine, a common ending for alkaloids used as anesthetics. It was introduced into medical use by surgeon Heinrich Braun (1862–1934).

File:US Navy 020623-M-7929S-040 Dental Officer participating in exercise Landing Force Cooperation Readiness and Training (LF CARAT).jpg

Novocain application before removal of a decayed tooth

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. Like other local anesthetics (with the exception of cocaine), mepivacaine, and prilocaine, procaine is a vasodilator, and is often coadministered with epinephrine for the purpose of vasoconstriction. Vasoconstriction helps to reduce bleeding and prevents the drug from reaching systemic circulation in large amounts. Also unlike cocaine, procaine does not have the euphoric and addictive qualities that put it at risk for abuse.

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 does not 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 by Ana Aslan (Romania), 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.

Procaine is occasionally added as an additive in illicit street drugs such as cocaine. It is also used by professional dominatrices to enhance BDSM play.

See also

• Procaine blockade

Further reading

• Hahn-Godeffroy, J.D.: Wirkungen und Nebenwirkungen von Procain: was ist gesichert?. Komplement. integr. Med. 02/2007, 32-34

cs:Prokain sv:Prokain