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Identification
NameProcaine
Accession NumberDB00721  (APRD00650)
Typesmall molecule
Groupsapproved, investigational
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
Synonyms
SynonymLanguageCode
2-Diethylaminoethyl p-aminobenzoateNot AvailableNot Available
NovocaineNot AvailableNot Available
p-Aminobenzoic acid 2-diethylaminoethyl esterNot AvailableNot Available
Vitamin H3Not AvailableNot Available
β-(diethylamino)ethyl 4-aminobenzoateNot AvailableNot Available
β-(diethylamino)ethyl p-aminobenzoateNot AvailableNot Available
Salts
Name/CAS Structure Properties
Procaine Hydrochloride
Thumb
  • InChI Key: HCBIBCJNVBAKAB-UHFFFAOYSA-N
  • Monoisotopic Mass: 272.129155633
  • Average Mass: 272.771
DBSALT000551
Brand names
NameCompany
NovocainNot Available
Brand mixturesNot Available
Categories
CAS number59-46-1
WeightAverage: 236.3101
Monoisotopic: 236.152477894
Chemical FormulaC13H20N2O2
InChI KeyInChIKey=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
IUPAC Name
2-(diethylamino)ethyl 4-aminobenzoate
SMILES
CCN(CC)CCOC(=O)C1=CC=C(N)C=C1
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassBenzoic Acid and Derivatives
Direct parentBenzoic Acid Esters
Alternative parentsAminobenzoic Acid Derivatives; Benzylethers; Benzoyl Derivatives; Anilines; Primary Aromatic Amines; Tertiary Amines; Carboxylic Acid Esters; Enolates; Polyamines; Dialkyl Ethers
Substituentsbenzoyl; aniline; primary aromatic amine; tertiary amine; carboxylic acid ester; polyamine; enolate; ether; dialkyl ether; carboxylic acid derivative; primary amine; amine; organonitrogen compound
Classification descriptionThis compound belongs to the benzoic acid esters. These are ester derivatives of benzoic acid.
Pharmacology
IndicationUsed as a local anesthetic primarily in oral surgery
PharmacodynamicsProcaine 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 actionProcaine 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.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hydrolysis by plasma esterases to PABA

Route of eliminationWith normal kidney function, the drug is excreted rapidly by tubular excretion.
Half life7.7 minutes
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Procaine Action PathwayDrug actionSMP00402
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9747
Blood Brain Barrier + 0.9533
Caco-2 permeable + 0.6291
P-glycoprotein substrate Substrate 0.587
P-glycoprotein inhibitor I Non-inhibitor 0.9492
P-glycoprotein inhibitor II Non-inhibitor 0.9884
Renal organic cation transporter Non-inhibitor 0.684
CYP450 2C9 substrate Non-substrate 0.8646
CYP450 2D6 substrate Non-substrate 0.6643
CYP450 3A4 substrate Non-substrate 0.6456
CYP450 1A2 substrate Non-inhibitor 0.6308
CYP450 2C9 substrate Non-inhibitor 0.9312
CYP450 2D6 substrate Inhibitor 0.8932
CYP450 2C19 substrate Non-inhibitor 0.9294
CYP450 3A4 substrate Non-inhibitor 0.8308
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7918
Ames test Non AMES toxic 0.6165
Carcinogenicity Non-carcinogens 0.6462
Biodegradation Not ready biodegradable 0.9449
Rat acute toxicity 2.5160 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.8728
hERG inhibition (predictor II) Non-inhibitor 0.6234
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
FormRouteStrength
CapsuleOral
SolutionInfiltration
SolutionIntramuscular
Tablet, extended releaseOral
Prices
Unit descriptionCostUnit
Novocain 10% ampul2.4USDml
Novocain 1% ampul1.79USDml
Procaine hcl crystals1.76USDg
Nesacaine-mpf 3% vial1.34USDml
Nesacaine-mpf 2% vial1.28USDml
Nesacaine 2% vial0.74USDml
Nesacaine 1% vial0.72USDml
Chloroprocaine 3% vial0.33USDml
Chloroprocaine 2% vial0.26USDml
Procaine hcl 2% vial0.15USDml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point61 °CPhysProp
water solubility9450 mg/L (at 30 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP2.14AVDEEF,A (1997)
logS-1.4ADME Research, USCD
pKa8.05 (at 15 °C)PERRIN,DD (1965)
Predicted Properties
PropertyValueSource
water solubility6.81e+00 g/lALOGPS
logP2.1ALOGPS
logP1.88ChemAxon
logS-1.5ALOGPS
pKa (strongest basic)8.96ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count3ChemAxon
hydrogen donor count1ChemAxon
polar surface area55.56ChemAxon
rotatable bond count7ChemAxon
refractivity70.3ChemAxon
polarizability26.81ChemAxon
number of rings1ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

DrugSyn.org

US812554
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
ResourceLink
KEGG CompoundC07375
PubChem Compound4914
PubChem Substance46507724
ChemSpider4745
ChEBI8430
ChEMBLCHEMBL569
Therapeutic Targets DatabaseDAP000296
PharmGKBPA451110
IUPHAR4291
Guide to Pharmacology4291
Drug Product Database2241979
Drugs.comhttp://www.drugs.com/mtm/procaine.html
WikipediaProcaine
ATC CodesC05AD05D04AB03J01CE09N01BA02N01BA04S01HA02S01HA05C01BA02
AHFS Codes
  • 72:00.00
  • 24:04.04.04
PDB EntriesNot Available
FDA labelNot Available
MSDSshow(73.1 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

1. Sodium channel protein type 10 subunit alpha

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Sodium channel protein type 10 subunit alpha Q9Y5Y9 Details

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 receptor ionotropic, NMDA 3A

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Glutamate receptor ionotropic, NMDA 3A Q8TCU5 Details

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 receptor 3A

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
5-hydroxytryptamine receptor 3A P46098 Details

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

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Sodium-dependent dopamine transporter Q01959 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: antagonist

Components

Name UniProt ID Details
Neuronal acetylcholine receptor subunit alpha-2 Q15822 Details

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

1. Cholinesterase

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cholinesterase P06276 Details

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 October 08, 2013 14:25