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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
SynonymLanguageCode
ChloroprocainNot AvailableNot Available
ChlorprocaineNot AvailableNot Available
Salts
Name/CAS Structure Properties
Chloroprocaine hydrochloride
Thumb
  • InChI Key: SZKQYDBPUCZLRX-UHFFFAOYSA-N
  • Monoisotopic Mass: 306.090183308
  • Average Mass: 307.216
DBSALT000823
Brand names
NameCompany
NesacaineAstraZeneca
Nesacaine-CEAstraZeneca
PiocaineNot Available
Brand mixturesNot Available
Categories
CAS number133-16-4
WeightAverage: 270.755
Monoisotopic: 270.113505569
Chemical FormulaC13H19ClN2O2
InChI KeyVDANGULDQQJODZ-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
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; Chlorobenzenes; Anilines; Primary Aromatic Amines; Aryl Chlorides; Carboxylic Acid Esters; Tertiary Amines; Polyamines; Enolates; Dialkyl Ethers; Organochlorides
Substituentsbenzoyl; aniline; chlorobenzene; primary aromatic amine; aryl halide; aryl chloride; tertiary amine; carboxylic acid ester; carboxylic acid derivative; ether; dialkyl ether; enolate; polyamine; organohalogen; organochloride; amine; primary amine; organonitrogen compound
Classification descriptionThis compound belongs to the benzoic acid esters. These are ester derivatives of benzoic acid.
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.
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
Property Value Probability
Human Intestinal Absorption + 0.9772
Blood Brain Barrier + 0.954
Caco-2 permeable + 0.6107
P-glycoprotein substrate Substrate 0.5855
P-glycoprotein inhibitor I Non-inhibitor 0.8563
P-glycoprotein inhibitor II Non-inhibitor 0.9707
Renal organic cation transporter Non-inhibitor 0.6843
CYP450 2C9 substrate Non-substrate 0.8593
CYP450 2D6 substrate Non-substrate 0.6718
CYP450 3A4 substrate Non-substrate 0.5215
CYP450 1A2 substrate Inhibitor 0.7507
CYP450 2C9 substrate Non-inhibitor 0.8687
CYP450 2D6 substrate Inhibitor 0.7746
CYP450 2C19 substrate Non-inhibitor 0.8061
CYP450 3A4 substrate Non-inhibitor 0.8334
CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.6017
Ames test Non AMES toxic 0.6613
Carcinogenicity Non-carcinogens 0.6653
Biodegradation Not ready biodegradable 0.9938
Rat acute toxicity 2.7123 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.8353
hERG inhibition (predictor II) Inhibitor 0.5819
Pharmacoeconomics
Manufacturers
  • Bedford laboratories div ben venue laboratories inc
  • Hospira inc
  • App pharmaceuticals llc
Packagers
Dosage forms
FormRouteStrength
Injection, solutionIntravenous
Prices
Unit descriptionCostUnit
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
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 solubility1.30e+00 g/lALOGPS
logP2.72ALOGPS
logP2.48ChemAxon
logS-2.3ALOGPS
pKa (strongest basic)8.96ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count3ChemAxon
hydrogen donor count1ChemAxon
polar surface area55.56ChemAxon
rotatable bond count7ChemAxon
refractivity75.1ChemAxon
polarizability28.74ChemAxon
number of rings1ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
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 ReferenceNot Available
External Links
ResourceLink
KEGG DrugD00732
PubChem Compound8612
PubChem Substance46508245
ChemSpider8293
ChEBI3636
ChEMBL
Therapeutic Targets DatabaseDAP000131
PharmGKBPA448946
Drug Product Database613304
RxListhttp://www.rxlist.com/cgi/generic3/chloroprocaine.htm
WikipediaChloroprocaine
ATC CodesNot Available
AHFS Codes
  • 72:00.00
PDB EntriesNot Available
FDA labelshow(182 KB)
MSDSshow(51.5 KB)
Interactions
Drug InteractionsSearched, but no interactions found.
Food InteractionsNot Available

Targets

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. 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

2. Glutamate receptor ionotropic, NMDA 3A

Kind: protein

Organism: Human

Pharmacological action: unknown

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. Neuronal acetylcholine receptor subunit alpha-10

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: antagonist

Components

Name UniProt ID Details
Neuronal acetylcholine receptor subunit alpha-10 Q9GZZ6 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

4. 5-hydroxytryptamine receptor 3A

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: antagonist

Components

Name UniProt ID Details
5-hydroxytryptamine receptor 3A P46098 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

5. Sodium-dependent dopamine transporter

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Sodium-dependent dopamine transporter Q01959 Details

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
  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
  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
  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

Enzymes

1. Cholinesterase

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cholinesterase P06276 Details

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
  2. Tucker GT, Mather LE: Clinical pharmacokinetics of local anaesthetics. Clin Pharmacokinet. 1979 Jul-Aug;4(4):241-78. Pubmed
  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
  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
  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

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Drug created on June 13, 2005 07:24 / Updated on April 04, 2014 09:38