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Procaine information


Procaine
Clinical data
AHFS/Drugs.comMonograph
Pregnancy
category
  • AU: B2
Routes of
administration
Parenteral
ATC code
  • N01BA02 (WHO) C05AD05 (WHO) S01HA05 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)
Pharmacokinetic data
BioavailabilityN/A
MetabolismHydrolysis by plasma esterases
Elimination half-life40–84 seconds
ExcretionRenal
Identifiers
IUPAC name
  • 2-(diethylamino)ethyl 4-aminobenzoate
CAS Number
  • 59-46-1 checkY
PubChem CID
  • 4914
IUPHAR/BPS
  • 4291
DrugBank
  • DB00721 ☒N
ChemSpider
  • 4745 checkY
UNII
  • 4Z8Y51M438
KEGG
  • D08422 checkY
ChEBI
  • CHEBI:8430 ☒N
ChEMBL
  • ChEMBL569 checkY
NIAID ChemDB
  • 019136
CompTox Dashboard (EPA)
  • DTXSID7045021 Edit this at Wikidata
ECHA InfoCard100.000.388 Edit this at Wikidata
Chemical and physical data
FormulaC13H20N2O2
Molar mass236.315 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • O=C(OCCN(CC)CC)c1ccc(N)cc1
InChI
  • InChI=1S/C13H20N2O2/c1-3-15(4-2)9-10-17-13(16)11-5-7-12(14)8-6-11/h5-8H,3-4,9-10,14H2,1-2H3 checkY
  • Key:MFDFERRIHVXMIY-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Procaine is a local anesthetic drug of the amino ester group. It is most commonly used in dental procedures to numb the area around a tooth[1] and is also used to reduce the pain of intramuscular injection of penicillin. Owing to the ubiquity of the trade name Novocain or Novocaine, in some regions, procaine is referred to generically as novocaine. It acts mainly as a sodium channel blocker.[2] Today, it is used therapeutically in some countries due to its sympatholytic, anti-inflammatory, perfusion-enhancing, and mood-enhancing effects.[3]

Procaine was first synthesized in 1905,[4] shortly after amylocaine.[5] It was created by the chemist Alfred Einhorn 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.

Prior to the discovery of amylocaine and procaine, cocaine was a commonly used local anesthetic.[6] Einhorn wished his new discovery to be used for amputations, but for this surgeons preferred general anesthesia. Dentists, however, found it very useful.[7]

  1. ^ "How long does numbness last after the dentist?". Medical News Today. May 22, 2018. Retrieved July 14, 2020.
  2. ^ "Procaine (DB00721)". DrugBank. 2009-06-23.
  3. ^ Hahn-Godeffroy JD (2011). "Procain-Reset: Ein Therapiekonzept zur Behandlung chronischer Erkrankungen" [Procaine reset: A therapy concept for the treatment of chronic diseases.]. Schweizerische Zeitschrift für Ganzheitsmedizin [Swiss Journal of Integrative Medicine] (in German). 23 (5): 291–6. doi:10.1159/000332021.
  4. ^ Ritchie JM, Greene NM (1990). "Local Anesthetics". In Gilman AG, Rall TW, Nies AS, Taylor P (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics (8th ed.). New York: Pergamon Press. p. 311. ISBN 0-08-040296-8.
  5. ^ Minard R (18 October 2006). "The Preparation of the Local Anesthetic, Benzocaine, by an Esterification Reaction" (PDF). Archived from the original (PDF) on 20 July 2011. Retrieved 10 March 2011. Adapted from Introduction to Organic Laboratory Techniques: A Microscale Approach, Pavia, Lampman, Kriz & Engel, 1989.
  6. ^ Ruetsch YA, Böni T, Borgeat A (August 2001). "From cocaine to ropivacaine: the history of local anesthetic drugs". Current Topics in Medicinal Chemistry. 1 (3): 175–82. doi:10.2174/1568026013395335. PMID 11895133.
  7. ^ Drucker P (May 1985). "The discipline of innovation". Harvard Business Review. 3 (3): 68. PMID 10272260.

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chemical formula C13-H21-N3-O. Procainamide is structurally similar to procaine, but in place of an ester group, procainamide contains an amide group....

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reasonably rapid onset (less rapid than that of procaine) and medium duration of action (longer than that of procaine) and is marketed under various trade names...

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Benzylpenicillin

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or procaine salt. Benzylpenicillin is given by injection into a vein or muscle. Two long-acting forms benzathine benzylpenicillin and procaine benzylpenicillin...

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Gerovital

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Gerovital H3 (or procaine hydrochloride and products known as GH3 and other variants which may or may not be identical to Gerovital H3) is a preparation...

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Demethylating agent

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approved by FDA for treating MDS and has been given orphan drug status. Procaine is a DNA-demethylating agent with growth-inhibitory effects in human cancer...

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Dimethocaine

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of dimethocaine, being a 4-aminobenzoic acid ester, resembles that of procaine. It is found as a white powder at room temperature. When a product sold...

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Diethylethanolamine

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production of a variety of chemical commodities such as the local anesthetic procaine. Diethylethanolamine is used as a corrosion inhibitor in steam and condensate...

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"cut" with talc, lactose, sucrose, glucose, mannitol, inositol, caffeine, procaine, phencyclidine, phenytoin, lignocaine, strychnine, levamisole, amphetamine...

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ATCvet code QJ51

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Ampicillin, combinations QJ51CE01 Benzylpenicillin QJ51CE09 Procaine penicillin QJ51CE59 Procaine penicillin, combinations QJ51CE90 Phenetamate QJ51CF01 Dicloxacillin...

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Peter DeMarco

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a medical practice in Pine Hill, New Jersey. He treated patients with procaine polyvinylpyrrolidone (PVP), but his medical license was suspended in New...

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Amino esters

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ester-type agents, as opposed to amide-type. Amino ester-type include: Cocaine Procaine (Novocain) Tetracaine (Pontocaine) Benzocaine Chloroprocaine University...

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Crack cocaine

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("paco") Structurally related chemicals: proparacaine, tetracaine, lidocaine, procaine, hexylcaine, bupivacaine, benoxinate, mepivacaine, prilocaine, etidocaine...

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agricultural pesticide Procaine, a local anaesthetic agent used before and during various surgical or dental procedures. Procaine causes loss of feeling...

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benzathine, penicillin G potassium, Penicillin G sodium, penicillin G procaine, and penicillin V) as well as a number of β-lactam antibiotics derived...

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