Procaine
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| Procaine
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| Systematic (IUPAC) name | |
| 2-(diethylamino)ethyl 4-aminobenzoate | |
| Identifiers | |
| CAS number | |
| ATC code | N01 C05AD05 S01HA05 |
| PubChem | |
| DrugBank | |
| Chemical data | |
| Formula | C13H20N2O2 |
| Mol. mass | 236.31 g/mol |
| Pharmacokinetic data | |
| Bioavailability | n/a |
| Metabolism | Hydrolysis by plasma esterases |
| Half life | 40–84 seconds |
| Excretion | Renal |
| Therapeutic considerations | |
| Pregnancy cat. | |
| Legal status | |
| Routes | Parenteral |
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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
Vasoprotectives (C05) | |
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| Antihemorrhoidals for topical use | corticosteroids (Hydrocortisone, Prednisolone, Betamethasone, Fluorometholone, Fluocortolone, Dexamethasone, Fluocinolone acetonide, Fluocinonide) - local anesthetics (Lidocaine, Tetracaine, Benzocaine, Cinchocaine, Procaine, Oxetacaine, Pramocaine) - other (Tribenoside) |
| Antivaricose therapy | heparins or heparinoids for topical use (Organo-heparinoid, Sodium apolate, Heparin, Pentosan polysulfate) - sclerosing agents for local injection (Monoethanolamine oleate, Polidocanol, Invert sugar, Sodium tetradecyl sulfate, Phenol) - Other (Calcium dobesilate) |
| Capillary stabilising agents | bioflavonoids (Rutoside, Monoxerutin, Diosmin, Troxerutin, Hidrosmin) - other (Tribenoside) |
fr:Procaïne it:Procaina nl:Novocaïne ja:プロカインsimple:Procaine sv:Prokain
Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
