Canmetcon
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Record Information
Version2.0
Creation Date2009-07-21 20:27:29 UTC
Update Date2014-12-24 20:25:52 UTC
Accession NumberT3D2869
Identification
Common NameProcaine
ClassSmall Molecule
DescriptionProcaine is only found in individuals that have used or taken this drug. It is 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]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.
Compound Type
  • Amine
  • Anesthetic
  • Anesthetic, Local
  • Drug
  • Ester
  • Ether
  • Food Toxin
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
2-Diethylaminoethyl p-aminobenzoate
4-Aminobenzoic acid 2-diethylaminoethyl ester
beta-(Diethylamino)ethyl 4-aminobenzoate
beta-(Diethylamino)ethyl P-aminobenzoate
Novocain
Novocaine
p-Aminobenzoic acid 2-diethylaminoethyl ester
Procaina
Procaine HCl
Procainum
Vitamin H3
β-(diethylamino)ethyl 4-aminobenzoate
β-(diethylamino)ethyl p-aminobenzoate
Chemical FormulaC13H20N2O2
Average Molecular Mass236.310 g/mol
Monoisotopic Mass236.152 g/mol
CAS Registry Number59-46-1
IUPAC Name2-(diethylamino)ethyl 4-aminobenzoate
Traditional Nameprocaine
SMILESCCN(CC)CCOC(=O)C1=CC=C(N)C=C1
InChI IdentifierInChI=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
InChI KeyInChIKey=MFDFERRIHVXMIY-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentBenzoic acid esters
Alternative Parents
Substituents
  • Aminobenzoic acid or derivatives
  • Benzoate ester
  • Benzoyl
  • Aniline or substituted anilines
  • Amino acid or derivatives
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Amine
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
Procaine PathwayNot AvailableNot Available
Applications
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point61°C
Boiling PointNot Available
Solubility9450 mg/L (at 30°C)
LogP2.14
Predicted Properties
PropertyValueSource
Water Solubility6.81 g/LALOGPS
logP2.1ALOGPS
logP1.88ChemAxon
logS-1.5ALOGPS
pKa (Strongest Basic)8.96ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.56 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity70.3 m³·mol⁻¹ChemAxon
Polarizability26.81 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dr-9400000000-a3ea7ca30e23e0b5e656View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-0090000000-7c7d7173da9393c2d059View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-0910000000-279febfbe258e2ce2807View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0uk9-0900000000-997e743a0702a7a5b54fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-2900000000-39c6b968e8d17c932e10View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00dl-9700000000-157dc94224e66c932ae8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-0w29-0900000000-050d794abd6d3a7e685dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-01w0-1940000000-d4d5195f000d2d633df7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fki-1690000000-87e7bf5ac9024bfe7cbbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-3930000000-18dd034bea68e84f34deView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9200000000-983abfba088dd28ad16cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-3490000000-1d66ef09f6cac135ebfdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-8980000000-640e85b33add1758148cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00r6-9300000000-1c06ec2e51e41c54d063View in MoNA
MSMass Spectrum (Electron Ionization)splash10-000i-9200000000-44eb49be9b2baedfebddView in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
Toxicity Profile
Route of ExposureOral, Infiltration, Intramuscular
Mechanism of ToxicityProcaine 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.
MetabolismHydrolysis 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
Toxicity ValuesLD50: 350 mg/kg (Oral, mouse).
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesIt is used primarily to reduce the pain of intramuscular injection of penicillin, and it is also used in dentistry. [Wikipedia]
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsAn allergic reaction (difficulty breathing; closing of the throat; swelling of the lips, tongue, or face; or hives); chest pain or slow or irregular heartbeats; dizziness or drowsiness; anxiety or restlessness; nausea or vomiting; trembling, shaking, or seizures (convulsions). Other less serious side effects such as numbness, tingling, or minor pain at or around the injection site are more likely to occur.(4)
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB00721
HMDB IDHMDB14859
PubChem Compound ID4914
ChEMBL IDCHEMBL569
ChemSpider ID4745
KEGG IDC07375
UniProt IDNot Available
OMIM ID
ChEBI ID8430
BioCyc IDNot Available
CTD IDNot Available
Stitch IDProcaine
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkProcaine
References
Synthesis Reference

DrugSyn.org

MSDSLink
General References
  1. Boureau F, Legallicier P, Kabir-Ahmadi M: Tramadol in post-herpetic neuralgia: a randomized, double-blind, placebo-controlled trial. Pain. 2003 Jul;104(1-2):323-31. [12855342 ]
  2. 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. [11714893 ]
  3. Martindale, The Extra Pharmacopoeia, 30th ed, p1016
  4. Drugs.com [Link]
Gene Regulation
Up-Regulated Genes
GeneGene SymbolGene IDInteractionChromosomeDetails
Down-Regulated GenesNot Available

Targets

General Function:
Monoamine transmembrane transporter activity
Specific Function:
Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:
SLC6A3
Uniprot ID:
Q01959
Molecular Weight:
68494.255 Da
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. [10685879 ]
  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. [16206183 ]
  3. Kiyatkin EA, Brown PL: 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. [16956595 ]
General Function:
Protein phosphatase 2a binding
Specific Function:
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 (By similarity).
Gene Name:
GRIN3A
Uniprot ID:
Q8TCU5
Molecular Weight:
125464.07 Da
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. [17139284 ]
  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. [17016423 ]
General Function:
Receptor binding
Specific Function:
Ionotropic receptor with a probable role in the modulation of auditory stimuli. Agonist binding may induce an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane. The channel is permeable to a range of divalent cations including calcium, the influx of which may activate a potassium current which hyperpolarizes the cell membrane. In the ear, this may lead to a reduction in basilar membrane motion, altering the activity of auditory nerve fibers and reducing the range of dynamic hearing. This may protect against acoustic trauma.
Gene Name:
CHRNA10
Uniprot ID:
Q9GZZ6
Molecular Weight:
49704.295 Da
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. [17139284 ]
  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. [17016423 ]
General Function:
Voltage-gated sodium channel activity
Specific Function:
Tetrodotoxin-resistant channel that 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. Plays a role in neuropathic pain mechanisms.
Gene Name:
SCN10A
Uniprot ID:
Q9Y5Y9
Molecular Weight:
220623.605 Da
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. [17139284 ]
  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. [17016423 ]
General Function:
Voltage-gated potassium channel activity
Specific Function:
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.
Gene Name:
HTR3A
Uniprot ID:
P46098
Molecular Weight:
55279.835 Da
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. [7539114 ]
General Function:
Voltage-gated potassium channel activity
Specific Function:
Potassium channel activated by both membrane depolarization or increase in cytosolic Ca(2+) that mediates export of K(+). It is also activated by the concentration of cytosolic Mg(2+). Its activation dampens the excitatory events that elevate the cytosolic Ca(2+) concentration and/or depolarize the cell membrane. It therefore contributes to repolarization of the membrane potential. Plays a key role in controlling excitability in a number of systems, such as regulation of the contraction of smooth muscle, the tuning of hair cells in the cochlea, regulation of transmitter release, and innate immunity. In smooth muscles, its activation by high level of Ca(2+), caused by ryanodine receptors in the sarcoplasmic reticulum, regulates the membrane potential. In cochlea cells, its number and kinetic properties partly determine the characteristic frequency of each hair cell and thereby helps to establish a tonotopic map. Kinetics of KCNMA1 channels are determined by alternative splicing, phosphorylation status and its combination with modulating beta subunits. Highly sensitive to both iberiotoxin (IbTx) and charybdotoxin (CTX).
Gene Name:
KCNMA1
Uniprot ID:
Q12791
Molecular Weight:
137558.115 Da
References
  1. Benham CD, Bolton TB, Lang RJ, Takewaki T: The mechanism of action of Ba2+ and TEA on single Ca2+-activated K+ -channels in arterial and intestinal smooth muscle cell membranes. Pflugers Arch. 1985 Feb;403(2):120-7. [2580269 ]
7. DNA
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
References
  1. Villar-Garea A, Fraga MF, Espada J, Esteller M: Procaine is a DNA-demethylating agent with growth-inhibitory effects in human cancer cells. Cancer Res. 2003 Aug 15;63(16):4984-9. [12941824 ]
8. Lysophospholipase
References
  1. Kawashima Y, Nakagawa M, Suzuki Y, Uchiyama M: The relationship between chain elongation of palmitoyl-CoA and phospholipid content in rat liver microsomes. Biochim Biophys Acta. 1976 Aug 23;441(2):173-80. [952986 ]
9. Monoamine oxidase (Protein Group)
General Function:
Serotonin binding
Specific Function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Included Proteins:
P21397 , P27338
References
  1. MacFarlane MD: Procaine HCl (Gerovital H3): a weak, reversible, fully competitive inhibitor of monoamine oxidase. Fed Proc. 1975 Jan;34(1):108-10. [1109354 ]
General Function:
Drug binding
Specific Function:
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.
Gene Name:
CHRNA2
Uniprot ID:
Q15822
Molecular Weight:
59764.82 Da
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. doi: 10.1016/j.ejphar.2009.12.028. Epub 2010 Jan 4. [20045405 ]
11. Phospholipase A2
References
  1. Kunze H, Nahas N, Traynor JR, Wurl M: Effects of local anaesthetics on phospholipases. Biochim Biophys Acta. 1976 Jul 20;441(1):93-102. [952985 ]