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Identification
Name Procaine
Accession Number DB00721 (APRD00650)
Type small molecule
Groups approved
Description

A local anesthetic of the ester type that has a slow onset and a short duration of action. It is mainly used for infiltration anesthesia, peripheral nerve block, and spinal block. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1016). [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
procaine HCl
Salts Not Available
Brand names
Name Company
Allocaine
Anticort
Chloroprocaine Hcl
Diethylaminoethyl P-Aminobenzoate
Duracaine
Gerovital
Gerovital H-3
Jenacain
Jenacaine
Neocaine
Nesacaine
Nissocaine
Norocaine
Novocain
Novocaine
P-Aminobenzoyldiethylaminoethanol
Pfizerpen-As
Procain
Procaine Hcl
Procaine Hydrochloride
Procaine, Base
Scurocaine
Spinocaine
Vitamin H3
First Prev Next Last
Brand mixtures Not Available
Categories
  • Anesthetics
  • Local Anesthetics
  • Anesthetics, Local
CAS number 59-46-1
Weight Average: 236.3101
Monoisotopic: 236.152477894
Chemical Formula C13H20N2O2
InChI Key InChIKey=MFDFERRIHVXMIY-UHFFFAOYSA-N
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
Plain Text
IUPAC Name
2-(diethylamino)ethyl 4-aminobenzoate
SMILES
CCN(CC)CCOC(=O)C1=CC=C(N)C=C1
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Aminobenzoates
Substructures
  • Aminobenzoates
  • Carboxylic Acids and Derivatives
  • Benzyl Alcohols and Derivatives
  • Acetates
  • Benzoates
  • Aliphatic and Aryl Amines
  • Ethers
  • Benzene and Derivatives
  • Aromatic compounds
  • Benzoyl Derivatives
  • Anilines
Pharmacology
Indication Used as a local anesthetic primarily in oral surgery
Pharmacodynamics Procaine is an anesthetic agent indicated for production of local or regional anesthesia, particularly for oral surgery. Procaine (like cocaine) has the advantage of constricting blood vessels which reduces bleeding, unlike other local anesthetics like lidocaine. Procaine is an ester anesthetic. It is metabolized in the plasma by the enzyme pseudocholinesterase through hydrolysis into para-aminobenzoic acid (PABA), which is then excreted by the kidneys into the urine.
Mechanism of action Procaine acts mainly by inhibiting sodium influx through voltage gated sodium channels in the neuronal cell membrane of peripheral nerves. When the influx of sodium is interrupted, an action potential cannot arise and signal conduction is thus inhibited. The receptor site is thought to be located at the cytoplasmic (inner) portion of the sodium channel. Procaine has also been shown to bind or antagonize the function of N-methyl-D-aspartate (NMDA) receptors as well as nicotinic acetylcholine receptors and the serotonin receptor-ion channel complex.
Absorption Not Available
Volume of distribution Not Available
Protein binding Not Available
Metabolism Hydrolysis by plasma esterases to PABA
Route of elimination With normal kidney function, the drug is excreted rapidly by tubular excretion.
Half life 7.7 minutes
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Pathways
Pathway Name SMPDB ID
Smp00402 Procaine Pathway SMP00402
Pharmacoeconomics
Manufacturers
  • Eli lilly and co
  • Consolidated pharmaceutical group inc
  • King pharmaceuticals inc
  • Parke davis div warner lambert co
  • Pfizer laboratories div pfizer inc
  • Hospira inc
  • Abraxis pharmaceutical products
  • Bel mar laboratories inc
  • Elkins sinn div ah robins co inc
  • Gd searle llc
  • Miles laboratories inc
  • Watson laboratories inc
Packagers
Dosage forms
Form Route Strength
Capsule Oral
Solution Infiltration
Solution Intramuscular
Tablet, extended release Oral
Prices
Unit description Cost Unit
Novocain 10% ampul 2.4 USD ml
Novocain 1% ampul 1.79 USD ml
Procaine hcl crystals 1.76 USD g
Nesacaine-mpf 3% vial 1.34 USD ml
Nesacaine-mpf 2% vial 1.28 USD ml
Nesacaine 2% vial 0.74 USD ml
Nesacaine 1% vial 0.72 USD ml
Chloroprocaine 3% vial 0.33 USD ml
Chloroprocaine 2% vial 0.26 USD ml
Procaine hcl 2% vial 0.15 USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 61 °C PhysProp
water solubility 9450 mg/L (at 30 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP 2.14 AVDEEF,A (1997)
logS -1.4 ADME Research, USCD
pKa 8.05 (at 15 °C) PERRIN,DD (1965)
Predicted Properties
Property Value Source
water solubility 6.81e+00 g/l ALOGPS
logP 2.1 ALOGPS
logP 1.88 ChemAxon
logS -1.5 ALOGPS
pKa (strongest basic) 8.96 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 3 ChemAxon
hydrogen donor count 1 ChemAxon
polar surface area 55.56 ChemAxon
rotatable bond count 7 ChemAxon
refractivity 70.3 ChemAxon
polarizability 26.81 ChemAxon
References
Synthesis Reference Not Available
General Reference
  1. Gentry CL, Lukas RJ: Local anesthetics noncompetitively inhibit function of four distinct nicotinic acetylcholine receptor subtypes. J Pharmacol Exp Ther. 2001 Dec;299(3):1038-48. Pubmed
External Links
Resource Link
KEGG Compound C07375 Link_out
PubChem Compound 4914 Link_out
PubChem Substance 46507724 Link_out
ChemSpider 4745 Link_out
ChEBI 8430 Link_out
ChEMBL 8430 Link_out
Therapeutic Targets Database DAP000296 Link_out
PharmGKB PA451110 Link_out
IUPHAR 4291 Link_out
Guide to Pharmacology 4291 Link_out
Drug Product Database 2241979 Link_out
Drugs.com http://www.drugs.com/mtm/procaine.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Procaine Link_out
ATC Codes
  • C05AD05
  • D04AB03
  • J01CE09
  • N01BA02
  • N01BA04
  • S01HA02
  • S01HA05
  • C01BA02
AHFS Codes
  • 72:00.00
  • 24:04.04.04
PDB Entries Not Available
FDA label Not Available
MSDS show (73.1 KB)
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Sodium channel protein type 10 subunit alpha

Pharmacological action: yes
Actions: inhibitor

This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which sodium ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant sodium channel isoform. Its electrophysiological properties vary depending on the type of the associated beta subunits (in vitro). Plays a role in neuropathic pain mechanisms

Organism class: human
UniProt ID: Q9Y5Y9 Link_out
Gene: SCN10A Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Brau ME, Vogel W, Hempelmann G: Fundamental properties of local anesthetics: half-maximal blocking concentrations for tonic block of Na+ and K+ channels in peripheral nerve. Anesth Analg. 1998 Oct;87(4):885-9. Pubmed
  4. Katalymov LL: [The effect of inhibitors of sodium permeability (novocaine and tetrodotoxin) on the trace depolarization of myelinated nerve fibers] Fiziol Zh Im I M Sechenova. 1995 Sep;81(9):127-33. Pubmed
  5. Creveling CR, Bell ME, Burke TR Jr, Chang E, Lewandowski-Lovenberg GA, Kim CH, Rice KC, Daly JW: Procaine isothiocyanate: an irreversible inhibitor of the specific binding of [3H]batrachotoxinin-A benzoate to sodium channels. Neurochem Res. 1990 Apr;15(4):441-8. Pubmed

2. Glutamate [NMDA] receptor subunit 3A

Pharmacological action: yes
Actions: antagonist

NMDA receptor subtype of glutamate-gated ion channels with reduced single-channel conductance, low calcium permeability and low voltage-dependent sensitivity to magnesium. Mediated by glycine. May play a role in the development of dendritic spines. May play a role in PPP2CB-NMDAR mediated signaling mechanism

Organism class: human
UniProt ID: Q8TCU5 Link_out
Gene: GRIN3A Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Hahnenkamp K, Durieux ME, Hahnenkamp A, Schauerte SK, Hoenemann CW, Vegh V, Theilmeier G, Hollmann MW: Local anaesthetics inhibit signalling of human NMDA receptors recombinantly expressed in Xenopus laevis oocytes: role of protein kinase C. Br J Anaesth. 2006 Jan;96(1):77-87. Epub 2005 Nov 18. Pubmed
  4. Nishizawa N, Shirasaki T, Nakao S, Matsuda H, Shingu K: The inhibition of the N-methyl-D-aspartate receptor channel by local anesthetics in mouse CA1 pyramidal neurons. Anesth Analg. 2002 Feb;94(2):325-30, table of contents. Pubmed

3. 5-hydroxytryptamine 3 receptor

Pharmacological action: yes
Actions: antagonist

This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor is a ligand-gated ion channel, which when activated causes fast, depolarizing responses in neurons. It is a cation-specific, but otherwise relatively nonselective, ion channel

Organism class: human
UniProt ID: P46098 Link_out
Gene: HTR3A Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Fan P, Weight FF: Procaine impairs the function of 5-HT3 receptor-ion channel complex in rat sensory ganglion neurons. Neuropharmacology. 1994 Dec;33(12):1573-9. Pubmed
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

4. Sodium-dependent dopamine transporter

Pharmacological action: yes
Actions: inhibitor

Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals

Organism class: human
UniProt ID: Q01959 Link_out
Gene: SLC6A3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Sato T, Kitayama S, Mitsuhata C, Ikeda T, Morita K, Dohi T: Selective inhibition of monoamine neurotransmitter transporters by synthetic local anesthetics. Naunyn Schmiedebergs Arch Pharmacol. 2000 Feb;361(2):214-20. Pubmed
  2. Wilcox KM, Kimmel HL, Lindsey KP, Votaw JR, Goodman MM, Howell LL: In vivo comparison of the reinforcing and dopamine transporter effects of local anesthetics in rhesus monkeys. Synapse. 2005 Dec 15;58(4):220-8. Pubmed
  3. Kiyatkin EA, Leon Brown P: The role of peripheral and central sodium channels in mediating brain temperature fluctuations induced by intravenous cocaine. Brain Res. 2006 Oct 30;1117(1):38-53. Epub 2006 Sep 7. Pubmed

5. Neuronal acetylcholine receptor subunit alpha-2

Pharmacological action: unknown
Actions: antagonist

After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane

Organism class: human
UniProt ID: Q15822 Link_out
Gene: CHRNA2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Wang H, Zhang Y, Li ST: The effect of local anesthetics on the inhibition of adult muscle-type nicotinic acetylcholine receptors by nondepolarizing muscle relaxants. Eur J Pharmacol. 2010 Mar 25;630(1-3):29-33. Epub 2010 Jan 4. Pubmed
Enzymes

1. Cholinesterase

Actions: inhibitor

An acylcholine + H(2)O = choline + a carboxylate

UniProt ID: P06276 Link_out
Gene: BCHE Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Perez-Guillermo F, Delgado EM, Vidal CJ: Inhibition of human serum and rabbit muscle cholinesterase by local anesthetics. Biochem Pharmacol. 1987 Nov 1;36(21):3593-6. Pubmed
  2. Dorokhov KE, Grigorian GL: [Binding of reversible spin-labeled inhibitors with an butyrylcholinesterase active center]. Biofizika. 1986 Sep-Oct;31(5):746-51. Pubmed]
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19