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Identification
NameChloroprocaine
Accession NumberDB01161  (APRD00404)
TypeSmall Molecule
GroupsApproved
Description

Chloroprocaine hydrochloride is a local anesthetic given by injection during surgical procedures and labor and delivery. Chloroprocaine, like other local anesthetics, blocks the generation and the conduction of nerve impulses, presumably by increasing the threshold for electrical excitation in the nerve, by slowing the propagation of the nerve impulse and by reducing the rate of rise of the action potential.

Structure
Thumb
Synonyms
2-Chloroprocaine
4-amino-2-Chlorobenzoic acid 2-(diethylamino)ethyl ester
Chloroprocain
Chloroprocaine
Chloroprocainum
Chlorprocaine
Cloroprocaina
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Nesacaineinjection, solution10 mg/mLinfiltration; perineuralGeneral Injectables & Vaccines, Inc2011-10-03Not applicableUs
Nesacaineinjection, solution20 mg/mLinfiltration; perineuralFresenius Kabi USA, LLC2010-10-14Not applicableUs
Nesacaineinjection, solution10 mg/mLinfiltration; perineuralFresenius Kabi USA, LLC2010-10-14Not applicableUs
Nesacaineinjection, solution20 mg/mLinfiltration; perineuralGeneral Injectables & Vaccines, Inc2013-01-30Not applicableUs
Nesacaine Ce 2% Inj 20mg/mlsolution20 mgintracaudal; epiduralAstrazeneca Canada Inc1984-12-312012-05-31Canada
Nesacaine Ce 3% Inj 30mg/mlsolution30 mgintracaudal; epiduralAstrazeneca Canada Inc1984-12-312005-08-02Canada
Nesacaine Mpfinjection, solution30 mg/mLepidural; infiltration; intracaudal; perineuralFresenius Kabi USA, LLC2010-10-14Not applicableUs
Nesacaine Mpfinjection, solution20 mg/mLepidural; infiltration; intracaudal; perineuralFresenius Kabi USA, LLC2010-10-14Not applicableUs
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Chloroprocaine Hydrochlorideinjection, solution20 mg/mLepidural; infiltrationHospira, Inc.1982-04-16Not applicableUs
Chloroprocaine Hydrochlorideinjection, solution30 mg/mLepidural; infiltrationHospira, Inc.1982-04-16Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
Nesacaine-CEAstraZeneca
PiocaineNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Chloroprocaine hydrochloride
Thumb
  • InChI Key: SZKQYDBPUCZLRX-UHFFFAOYSA-N
  • Monoisotopic Mass: 306.090183308
  • Average Mass: 307.216
DBSALT000823
Categories
UNII5YVB0POT2H
CAS number133-16-4
WeightAverage: 270.755
Monoisotopic: 270.113505569
Chemical FormulaC13H19ClN2O2
InChI KeyInChIKey=VDANGULDQQJODZ-UHFFFAOYSA-N
InChI
InChI=1S/C13H19ClN2O2/c1-3-16(4-2)7-8-18-13(17)11-6-5-10(15)9-12(11)14/h5-6,9H,3-4,7-8,15H2,1-2H3
IUPAC Name
2-(diethylamino)ethyl 4-amino-2-chlorobenzoate
SMILES
CCN(CC)CCOC(=O)C1=C(Cl)C=C(N)C=C1
Taxonomy
DescriptionThis compound 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
  • Halobenzoic acid or derivatives
  • 2-halobenzoic acid or derivatives
  • Benzoate ester
  • Aminobenzoic acid or derivatives
  • Benzylether
  • Substituted aniline
  • Benzoyl
  • Halobenzene
  • Chlorobenzene
  • Aniline
  • Primary aromatic amine
  • Aryl halide
  • Aryl chloride
  • Vinylogous halide
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Pharmacology
IndicationFor the production of local anesthesia by infiltration and peripheral nerve block. They are not to be used for lumbar or caudal epidural anesthesia.
PharmacodynamicsChloroprocaine is an anesthetic agent indicated for production of local or regional anesthesia, particularly for oral surgery. Chloroprocaine (like cocaine) has the advantage of constricting blood vessels which reduces bleeding, unlike other local anesthetics like lidocaine. Chloroprocaine is an ester anesthetic.
Mechanism of actionChloroprocaine 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. It is hypothesized that Chloroprocaine binds or antagonizes the function of N-methyl-D-aspartate (NMDA) receptors as well as nicotinic acetylcholine receptors and the serotonin receptor-ion channel complex.
Related Articles
AbsorptionThe rate of systemic absorption of local anesthetic drugs is dependent upon the total dose and concentration of drug administered, the route of administration, the vascularity of the administration site, and the presence or absence of epinephrine in the anesthetic injection.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Chloroprocaine is rapidly metabolized in plasma by hydrolysis of the ester linkage by pseudocholinesterase.

Route of eliminationChloroprocaine is rapidly metabolized in plasma by hydrolysis of the ester linkage by pseudocholinesterase. Urinary excretion is affected by urinary perfusion and factors affecting urinary pH.
Half life21 +/- 2 seconds
ClearanceNot Available
ToxicityIn mice, the intravenous LD50 of chloroprocaine HCl is 97 mg/kg and the subcutaneous LD50 of chloroprocaine HCl is 950 mg/kg.
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Chloroprocaine Action PathwayDrug actionSMP00394
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9772
Blood Brain Barrier+0.954
Caco-2 permeable+0.6107
P-glycoprotein substrateSubstrate0.5855
P-glycoprotein inhibitor INon-inhibitor0.8563
P-glycoprotein inhibitor IINon-inhibitor0.9707
Renal organic cation transporterNon-inhibitor0.6843
CYP450 2C9 substrateNon-substrate0.8593
CYP450 2D6 substrateNon-substrate0.6718
CYP450 3A4 substrateNon-substrate0.5215
CYP450 1A2 substrateInhibitor0.7507
CYP450 2C9 inhibitorNon-inhibitor0.8687
CYP450 2D6 inhibitorInhibitor0.7746
CYP450 2C19 inhibitorNon-inhibitor0.8061
CYP450 3A4 inhibitorNon-inhibitor0.8334
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6017
Ames testNon AMES toxic0.6613
CarcinogenicityNon-carcinogens0.6653
BiodegradationNot ready biodegradable0.9938
Rat acute toxicity2.7123 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8353
hERG inhibition (predictor II)Inhibitor0.5819
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Injection, solutionepidural; infiltration20 mg/mL
Injection, solutionepidural; infiltration30 mg/mL
Injection, solutioninfiltration; perineural10 mg/mL
Injection, solutioninfiltration; perineural20 mg/mL
Solutionintracaudal; epidural20 mg
Solutionintracaudal; epidural30 mg
Injection, solutionepidural; infiltration; intracaudal; perineural20 mg/mL
Injection, solutionepidural; infiltration; intracaudal; perineural30 mg/mL
Prices
Unit descriptionCostUnit
Nesacaine-mpf 3% vial1.34USD ml
Nesacaine-mpf 2% vial1.28USD ml
Nesacaine 2% vial0.74USD ml
Nesacaine 1% vial0.72USD ml
Chloroprocaine 3% vial0.33USD ml
Chloroprocaine 2% vial0.26USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point173-174Marks, H.C. and Rubin, M.I.; US. Patent 2,460,139; January 25,1949; assigned to Wallace & Tiernan Products, Inc.
water solubility0.665 mg/mLNot Available
logP2.86HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility1.3 mg/mLALOGPS
logP2.72ALOGPS
logP2.48ChemAxon
logS-2.3ALOGPS
pKa (Strongest Basic)8.96ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.56 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity75.1 m3·mol-1ChemAxon
Polarizability28.74 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
MSMass Spectrum (Electron Ionization)splash10-000i-9100000000-5a6841e384b0dfbd1238View in MoNA
References
Synthesis Reference

Marks, H.C. and Rubin, M.I.; US. Patent 2,460,139; January 25,1949; assigned to Wallace
& Tiernan Products, Inc.

General ReferencesNot Available
External Links
ATC CodesN01BA04
AHFS Codes
  • 72:00.00
PDB EntriesNot Available
FDA labelDownload (182 KB)
MSDSDownload (51.5 KB)
Interactions
Drug Interactions
Drug
HyaluronidaseThe risk or severity of adverse effects can be increased when Hyaluronidase is combined with Chloroprocaine.
Technetium Tc-99m tilmanoceptChloroprocaine may decrease effectiveness of Technetium Tc-99m tilmanocept as a diagnostic agent.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
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. [PubMed: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. [PubMed:17016423 ]
  3. Wong K, Strichartz GR, Raymond SA: On the mechanisms of potentiation of local anesthetics by bicarbonate buffer: drug structure-activity studies on isolated peripheral nerve. Anesth Analg. 1993 Jan;76(1):131-43. [PubMed:8418714 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
antagonist
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. [PubMed: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. [PubMed:17016423 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
antagonist
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 t...
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. [PubMed: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. [PubMed:17016423 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
antagonist
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. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed: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. [PubMed:17016423 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
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. Wilcox KM, Paul IA, Ordway GA, Woolverton WL: Role of the dopamine transporter and the sodium channel in the cocaine-like discriminative stimulus effects of local anesthetics in rats. Psychopharmacology (Berl). 2001 Sep;157(3):260-8. [PubMed:11605081 ]
  2. Mansbach RS, Jortani SA, Balster RL: Discriminative stimulus effects of esteratic local anesthetics in squirrel monkeys. Eur J Pharmacol. 1995 Feb 14;274(1-3):167-73. [PubMed:7768269 ]
  3. Wilcox KM, Paul IA, Woolverton WL: Comparison between dopamine transporter affinity and self-administration potency of local anesthetics in rhesus monkeys. Eur J Pharmacol. 1999 Feb 19;367(2-3):175-81. [PubMed:10078990 ]
  4. Wilcox KM, Rowlett JK, Paul IA, Ordway GA, Woolverton WL: On the relationship between the dopamine transporter and the reinforcing effects of local anesthetics in rhesus monkeys: practical and theoretical concerns. Psychopharmacology (Berl). 2000 Dec;153(1):139-47. [PubMed:11255924 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Identical protein binding
Specific Function:
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:
BCHE
Uniprot ID:
P06276
Molecular Weight:
68417.575 Da
References
  1. Kuhnert BR, Philipson EH, Pimental R, Kuhnert PM: A prolonged chloroprocaine epidural block in a postpartum patient with abnormal pseudocholinesterase. Anesthesiology. 1982 Jun;56(6):477-8. [PubMed:7081736 ]
  2. Tucker GT, Mather LE: Clinical pharmacokinetics of local anaesthetics. Clin Pharmacokinet. 1979 Jul-Aug;4(4):241-78. [PubMed:385208 ]
  3. Monedero P, Hess P: High epidural block with chloroprocaine in a parturient with low pseudocholinesterase activity. Can J Anaesth. 2001 Mar;48(3):318-9. [PubMed:11305839 ]
  4. Smith AR, Hur D, Resano F: Grand mal seizures after 2-chloroprocaine epidural anesthesia in a patient with plasma cholinesterase deficiency. Anesth Analg. 1987 Jul;66(7):677-8. [PubMed:3111302 ]
  5. Raj PP, Ohlweiler D, Hitt BA, Denson DD: Kinetics of local anesthetic esters and the effects of adjuvant drugs on 2-chloroprocaine hydrolysis. Anesthesiology. 1980 Oct;53(4):307-14. [PubMed:7425357 ]
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Drug created on June 13, 2005 07:24 / Updated on April 04, 2014 09:38