Chloroprocaine

Identification

Summary

Chloroprocaine is a local anesthetic agent indicated for intrathecal injection in adults for the production of subarachnoid block, spinal anesthesia, or ocular surface anesthesia.

Brand Names
Clorotekal, Iheezo, Nesacaine
Generic Name
Chloroprocaine
DrugBank Accession Number
DB01161
Background

Chloroprocaine is an ester local anesthetic commonly available in its salt form, chloroprocaine hydrochloride. Similar to other local anesthetics, it increases the threshold for electrical excitation in nerves by slowing the propagation of the nerve impulse and reducing the rate of rise of the action potential.6 The pharmacological profile of chloroprocaine is characterized by a short latency and duration, similar to the one observed with lidocaine.1 Chloroprocaine can be given as an injection, and is available in formulations with and without methylparaben as a preservative. Both can be given as intrathecal injections for peripheral and central nerve block, but only the preservative-free formulation can be used for lumbar and caudal epidural blocks.1,4 Topical chloroprocaine for ophthalmic use was approved by the FDA in September 2022 for ocular surface anesthesia.5

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 270.755
Monoisotopic: 270.113505569
Chemical Formula
C13H19ClN2O2
Synonyms
  • 2-(Diethylamino)ethyl 4-amino-2-chlorobenzoate
  • 2-chloroprocaine
  • 4-amino-2-chlorobenzoic acid 2-(diethylamino)ethyl ester
  • Chloroprocain
  • Chloroprocaine
  • Chloroprocainum
  • Chlorprocaine
  • Cloroprocaina

Pharmacology

Indication

Chloroprocaine for intrathecal injection is indicated for the production of subarachnoid block (spinal anesthesia) in adults.3 It is also indicated for the production of local anesthesia by infiltration, peripheral and central nerve block, and a preservative-free form can also be used for lumbar and caudal epidural blocks.4 Topical chloroprocaine for ophthalmic use is indicated for ocular surface anesthesia.5

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Associated Therapies
Contraindications & Blackbox Warnings
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Pharmacodynamics

Chloroprocaine is an ester local anesthetic agent indicated for the production of local or regional anesthesia with effects on the cardiovascular and central nervous systems. Compared with lidocaine and bupivacaine, chloroprocaine has shorter ambulation and discharge times.2 Chloroprocaine has minimal effects on cardiac conduction, excitability, refractoriness, contractility, and peripheral vascular resistance at therapeutic doses.3,4 However, at toxic blood concentrations, chloroprocaine may cause atrioventricular block and cardiac arrest, as well as decreased cardiac output and arterial blood pressure. A high concentration of chloroprocaine in plasma can also lead to central nervous system stimulation, depression, or both. Some signs of central stimulation include restlessness, tremors and shivering, which may progress to convulsions. Depression, coma and respiratory arrest may also occur. As with other local anesthetics, patients may experience depression of the central nervous system without a prior stage of stimulation.3,4

Mechanism of action

Chloroprocaine acts mainly by binding to the alpha subunit on the cytoplasmic region of voltage-gated sodium channels and inhibiting sodium influx in neuronal cell membranes.6 This lowers the nerve membrane permeability to sodium and decreases the rate of rise of the action potential.3,4 Therefore, chloroprocaine inhibits signal conduction and leads to a reversible nerve conduction blockade.6 The progression of anesthesia depends on the diameter, myelination and conduction velocity of nerve fibers, and the order of loss of nerve function is the following: 1) pain, 2) temperature, 3) touch, 4) proprioception, and 5) skeletal muscle tone.3,4

TargetActionsOrganism
AVoltage-gated sodium channel alpha subunit
inhibitor
Humans
USodium-dependent dopamine transporter
inhibitor
Humans
Absorption

Thanks to its low risk for systemic toxicity, chloroprocaine has a rapid onset of action that usually ranges between 6 to 12 minutes.3,4,6 The duration of chloroprocaine-induced anesthesia may be up to 60 minutes. The absorption rate of local anesthetics depends on the total dose and concentration of chloroprocaine, as well as the route of administration, the vascularity of the administration site, and the presence or absence of epinephrine in the anesthetic injection. The presence of epinephrine reduces the rate of absorption and plasma concentration of local anesthetics.3,4 The systemic exposure to chloroprocaine following its topical ocular administration has not been evaluated.5

Volume of distribution

Not Available

Protein binding

Compared to the other clinically used local anesthetics, chloroprocaine has one of the lowest protein binding percentages.6

Metabolism

In plasma, chloroprocaine is quickly metabolized by pseudocholinesterases, a group of enzymes that perform the hydrolysis of the ester linkage. In ocular tissues, chloroprocaine is metabolized by nonspecific esterases.5 The hydrolysis of chloroprocaine leads to the production of ß-diethylaminoethanol and 2-chloro-4-aminobenzoic acid, which inhibits the action of the sulfonamides.3,4,5

Hover over products below to view reaction partners

Route of elimination

Like most local anesthetics and their metabolites, chloroprocaine is mainly excreted by the kidneys. The urinary excretion of chloroprocaine may be affected by urinary perfusion and factors that have an effect on urinary pH.3,4,5

Half-life

In adults, the average in vitro plasma half-life of chloroprocaine is 21 seconds for males and 25 seconds for females. In neonates, the average in vitro plasma half-life is 43 seconds.4 Following intrapartum epidural anesthesia, the apparent in vivo half-life of chloroprocaine detected in maternal plasma was 3.1 minutes (range from 1.5 to 6.4 minutes).3

Clearance

Not Available

Adverse Effects
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Toxicity

Most chloroprocaine overdose cases are related to high plasma levels during its therapeutic use or to the unintended administration of a subarachnoid injection. In mice, the intravenous LD50 of chloroprocaine HCl is 97 mg/kg and the subcutaneous LD50 of chloroprocaine HCl is 950 mg/kg. The first consideration in the management of local anesthetic emergencies is prevention, which can be achieved by carefully monitoring patients’ cardiovascular and respiratory vital signs, as well as their state of consciousness. If there are any changes, oxygen should be administered.3,4

In patients with chloroprocaine overdose with convulsions, underventilation or apnea, the drug label recommends giving immediate attention to maintaining a patent airway, assisted or controlled ventilation with oxygen and a delivery system capable of permitting immediate positive airway pressure by mask. If convulsions persist, provide small increments of an ultra-short acting barbiturate or a benzodiazepine intravenously. Refer to the chloroprocaine drug label for a complete description of the procedures recommended in case of overdose.3,4

Pathways
PathwayCategory
Chloroprocaine Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when Chloroprocaine is combined with 1,2-Benzodiazepine.
AbemaciclibThe risk or severity of methemoglobinemia can be increased when Abemaciclib is combined with Chloroprocaine.
AbirateroneThe risk or severity of methemoglobinemia can be increased when Abiraterone is combined with Chloroprocaine.
AcetaminophenThe risk or severity of methemoglobinemia can be increased when Acetaminophen is combined with Chloroprocaine.
AcetazolamideThe therapeutic efficacy of Acetazolamide can be decreased when used in combination with Chloroprocaine.
Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Chloroprocaine hydrochlorideLT7Z1YW11H3858-89-7SZKQYDBPUCZLRX-UHFFFAOYSA-N
International/Other Brands
Iheezo (Harrow Eye, LLC) / Nesacaine-CE (AstraZeneca) / Piocaine
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
(chloroprocaine HciInjection, solution10 mg/1mLInfiltration; PerineuralHF Acquisition Co LLC, DBA HealthFirst2019-10-13Not applicableUS flag
Chloroprocaine HciInjection, solution20 mg/1mLEpidural; Infiltration; Intracaudal; PerineuralHF Acquisition Co LLC, DBA HealthFirst2019-10-29Not applicableUS flag
Chloroprocaine HciInjection, solution20 mg/1mLInfiltration; PerineuralHF Acquisition Co LLC, DBA HealthFirst2019-10-13Not applicableUS flag
ClorotekalInjection, solution10 mg/1mLIntrathecalSintetica Sa2017-10-042018-05-09US flag
ClorotekalInjection, solution10 mg/1mLIntrathecalB. Braun Medical Inc.2018-05-01Not applicableUS flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Chloroprocaine HydrochlorideInjection, solution20 mg/1mLEpidural; InfiltrationBedford Pharmaceuticals1998-11-012012-06-30US flag
Chloroprocaine HydrochlorideInjection, solution20 mg/1mLEpidural; Infiltration; IntracaudalHospira, Inc.2005-07-082013-01-01US flag
Chloroprocaine HydrochlorideInjection, solution20 mg/1mLEpidural; Infiltration; Intracaudal; PerineuralHikma Pharmaceuticals USA Inc.1998-11-01Not applicableUS flag
Chloroprocaine HydrochlorideInjection, solution30 mg/1mLEpidural; Infiltration; Intracaudal; PerineuralHikma Pharmaceuticals USA Inc.1998-11-01Not applicableUS flag
Chloroprocaine HydrochlorideInjection, solution30 mg/1mLEpidural; InfiltrationBedford Pharmaceuticals1998-11-012012-06-30US flag

Categories

ATC Codes
N01BA04 — Chloroprocaine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzoic acids and derivatives
Direct Parent
Benzoic acid esters
Alternative Parents
2-halobenzoic acids and derivatives / Aminobenzoic acids and derivatives / Aniline and substituted anilines / Benzoyl derivatives / Chlorobenzenes / Aryl chlorides / Vinylogous halides / Trialkylamines / Amino acids and derivatives / Carboxylic acid esters
show 7 more
Substituents
2-halobenzoic acid or derivatives / Amine / Amino acid or derivatives / Aminobenzoic acid or derivatives / Aniline or substituted anilines / Aromatic homomonocyclic compound / Aryl chloride / Aryl halide / Benzoate ester / Benzoyl
show 19 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
monochlorobenzenes, benzoate ester (CHEBI:3636)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
5YVB0POT2H
CAS number
133-16-4
InChI Key
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

References

Synthesis Reference

Marks, HC and Rubin, MI (1949). Alkamine esters of 2-chloro-4-amino benzoic acid. US. Patent 2,460,139 Assigned to Wallace & Tiernan Products, Inc. https://patentimages.storage.googleapis.com/6c/19/84/5af4fc6dc359a3/US2460139.pdf

General References
  1. Camponovo C, Wulf H, Ghisi D, Fanelli A, Riva T, Cristina D, Vassiliou T, Leschka K, Fanelli G: Intrathecal 1% 2-chloroprocaine vs. 0.5% bupivacaine in ambulatory surgery: a prospective, observer-blinded, randomised, controlled trial. Acta Anaesthesiol Scand. 2014 May;58(5):560-6. doi: 10.1111/aas.12291. Epub 2014 Mar 6. [Article]
  2. Wulf H, Hampl K, Steinfeldt T: Speed spinal anesthesia revisited: new drugs and their clinical effects. Curr Opin Anaesthesiol. 2013 Oct;26(5):613-20. doi: 10.1097/ACO.0b013e3283606b71. [Article]
  3. FDA Approved Drug Products: CLOROTEKAL (chloroprocaine hydrochloride) injection for intrathecal use [Link]
  4. FDA Approved Drug Products: Nesacaine and Nesacaine-MPF (chloroprocaine HCl) injection, USP [Link]
  5. FDA Approved Drug Products: IHEEZOTM (chloroprocaine hydrochloride) gel for topical ophthalmic use [Link]
  6. NIH StatPearls: Chloroprocaine [Link]
Human Metabolome Database
HMDB0015292
KEGG Drug
D07678
KEGG Compound
C07877
PubChem Compound
8612
PubChem Substance
46508245
ChemSpider
8293
BindingDB
50239963
RxNav
20859
ChEBI
3636
ChEMBL
CHEMBL1179047
ZINC
ZINC000001530938
Therapeutic Targets Database
DAP000131
PharmGKB
PA448946
RxList
RxList Drug Page
Wikipedia
Chloroprocaine

Clinical Trials

Clinical Trials

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • APP Pharmaceuticals
  • Bedford Labs
  • Ben Venue Laboratories Inc.
  • Hospira Inc.
Dosage Forms
FormRouteStrength
Injection, solutionParenteral10 mg/ml
Injection, solutionParenteral20 mg/ml
Injection, solutionEpidural; Infiltration20 mg/1mL
Injection, solutionEpidural; Infiltration30 mg/1mL
Injection, solutionEpidural; Infiltration; Intracaudal20 mg/1mL
Injection, solutionEpidural; Infiltration; Intracaudal30 mg/1mL
Injection, solutionEpidural; Infiltration; Intracaudal; Perineural20 mg/1mL
Injection, solutionEpidural; Infiltration; Intracaudal; Perineural30 mg/1mL
Injection, solutionIntrathecal10 mg/1mL
Injection, solution
GelOphthalmic24 mg/800mg
InjectionIntravenous10 mg/1mL
InjectionIntravenous20 mg/1mL
InjectionIntravenous30 mg/1mL
Injection, solutionInfiltration; Perineural10 mg/1mL
Injection, solutionInfiltration; Perineural20 mg/1mL
SolutionEpidural; Intracaudal20 mg / mL
SolutionEpidural; Intracaudal30 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.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US8969412No2015-03-032026-09-05US flag
US9504666No2016-11-292033-12-11US flag
US10792271No2020-10-062038-09-15US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)173-174ºCMarks, HC and Rubin, MI (1949) US. Patent 2,460,139.
water solubility0.665 mg/mLNot Available
logP2.86HANSCH,C ET AL. (1995)
pKa9.1Cousins, M. J. (2012). Cousins and Bridenbaugh's Neural Blockade in Clinical Anesthesia and Pain Medicine: Wolters Kluwer Health.
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 RuleNoChemaxon
MDDR-like RuleNoChemaxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0k9i-9400000000-c227313b7fa92099b2dc
Mass Spectrum (Electron Ionization)MSsplash10-000i-9100000000-5a6841e384b0dfbd1238
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0uk9-0980000000-71991cf6242c53e5a701
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-9210000000-746dccad5f9fc1690a4b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-3910000000-1faab488ad1d6b94f0f0
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00wa-8920000000-10061d840a4d85455b2a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0f89-3900000000-bb56180d631ca79449c8
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-4900000000-f65eaf80ed5d18520ee6
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-162.7244124
predicted
DarkChem Lite v0.1.0
[M-H]-163.19975
predicted
DeepCCS 1.0 (2019)
[M+H]+164.3205124
predicted
DarkChem Lite v0.1.0
[M+H]+165.55775
predicted
DeepCCS 1.0 (2019)
[M+Na]+163.4102124
predicted
DarkChem Lite v0.1.0
[M+Na]+171.6509
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Kind
Protein group
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Voltage-gated sodium channel activity
Specific Function
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...

Components:
References
  1. Becker DE, Reed KL: Essentials of local anesthetic pharmacology. Anesth Prog. 2006 Fall;53(3):98-108; quiz 109-10. doi: 10.2344/0003-3006(2006)53[98:EOLAP]2.0.CO;2. [Article]
  2. NIH StatPearls: Chloroprocaine [Link]
Kind
Protein
Organism
Humans
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
Uniprot Name
Sodium-dependent dopamine transporter
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]

Enzymes

Kind
Protein
Organism
Humans
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
Uniprot Name
Cholinesterase
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. [Article]
  2. Tucker GT, Mather LE: Clinical pharmacokinetics of local anaesthetics. Clin Pharmacokinet. 1979 Jul-Aug;4(4):241-78. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  6. FDA Approved Drug Products: CLOROTEKAL (chloroprocaine hydrochloride) injection for intrathecal use [Link]
  7. FDA Approved Drug Products: Nesacaine and Nesacaine-MPF (chloroprocaine HCl) injection, USP [Link]
  8. FDA Approved Drug Products: IHEEZOTM (chloroprocaine hydrochloride) gel for topical ophthalmic use [Link]

Drug created at June 13, 2005 13:24 / Updated at March 03, 2024 02:34