Chloroprocaine
Identification
- Summary
Chloroprocaine is a local anesthetic agent indicated for intrathecal injection in adults for the production of subarachnoid block, or spinal anesthesia.
- Brand Names
- Clorotekal, Nesacaine
- Generic Name
- Chloroprocaine
- DrugBank Accession Number
- DB01161
- Background
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.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Chloroprocaine (DB01161)
- Weight
- Average: 270.755
Monoisotopic: 270.113505569 - Chemical Formula
- C13H19ClN2O2
- Synonyms
- 2-chloroprocaine
- 4-amino-2-chlorobenzoic acid 2-(diethylamino)ethyl ester
- Chloroprocain
- Chloroprocaine
- Chloroprocainum
- Chlorprocaine
- Cloroprocaina
Pharmacology
- Indication
For the production of local anesthesia by infiltration and peripheral nerve block. They are not to be used for lumbar or caudal epidural anesthesia.
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- Contraindications & Blackbox Warnings
Contraindications & Blackbox WarningsWith our commercial data, access important information on dangerous risks, contraindications, and adverse effects.Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects- Pharmacodynamics
Chloroprocaine is an ester type 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.
- Mechanism of action
Chloroprocaine 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.
Target Actions Organism ASodium channel protein type 10 subunit alpha inhibitorHumans USodium-dependent dopamine transporter inhibitorHumans - Absorption
The 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 distribution
Not Available
- Protein binding
Not Available
- Metabolism
Chloroprocaine is rapidly metabolized in plasma by hydrolysis of the ester linkage by pseudocholinesterase.
- Route of elimination
Chloroprocaine 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-life
21 +/- 2 seconds
- Clearance
Not Available
- Adverse Effects
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In mice, the intravenous LD50 of chloroprocaine HCl is 97 mg/kg and the subcutaneous LD50 of chloroprocaine HCl is 950 mg/kg.
- Pathways
Pathway Category Chloroprocaine Action Pathway Drug 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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of adverse effects can be increased when Chloroprocaine is combined with 1,2-Benzodiazepine. Acetazolamide The risk or severity of adverse effects can be increased when Acetazolamide is combined with Chloroprocaine. Acetophenazine The risk or severity of adverse effects can be increased when Acetophenazine is combined with Chloroprocaine. Aclidinium Chloroprocaine may increase the central nervous system depressant (CNS depressant) activities of Aclidinium. Agomelatine The risk or severity of adverse effects can be increased when Chloroprocaine is combined with Agomelatine. Alfentanil The risk or severity of adverse effects can be increased when Chloroprocaine is combined with Alfentanil. Alimemazine The risk or severity of adverse effects can be increased when Chloroprocaine is combined with Alimemazine. Alloin The therapeutic efficacy of Alloin can be decreased when used in combination with Chloroprocaine. Almotriptan The risk or severity of adverse effects can be increased when Almotriptan is combined with Chloroprocaine. Alosetron The risk or severity of adverse effects can be increased when Alosetron is combined with Chloroprocaine. 
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- No interactions found.
Products
Comprehensive & structured drug product infoFrom application numbers to product codes, connect different identifiers through our commercial datasets.Easily connect various identifiers back to our datasets- Product Ingredients
Ingredient UNII CAS InChI Key Chloroprocaine hydrochloride LT7Z1YW11H 3858-89-7 SZKQYDBPUCZLRX-UHFFFAOYSA-N - International/Other Brands
- Nesacaine-CE (AstraZeneca) / Piocaine
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image (chloroprocaine Hci Injection, solution 10 mg/1mL Infiltration; Perineural HF Acquisition Co LLC, DBA HealthFirst 2019-10-13 Not applicable US 
Chloroprocaine Hci Injection, solution 20 mg/1mL Infiltration; Perineural HF Acquisition Co LLC, DBA HealthFirst 2019-10-13 Not applicable US Chloroprocaine Hci Injection, solution 20 mg/1mL Epidural; Infiltration; Intracaudal; Perineural HF Acquisition Co LLC, DBA HealthFirst 2019-10-29 Not applicable US Clorotekal Injection, solution 10 mg/1mL Intrathecal Sintetica Sa 2017-10-04 2018-05-09 US Clorotekal Injection, solution 10 mg/1mL Intrathecal B. Braun Medical Inc. 2018-05-01 Not applicable US Nesacaine Injection, solution 10 mg/1mL Infiltration; Perineural Fresenius Kabi USA, LLC 2010-10-14 Not applicable US Nesacaine Injection 30 mg/1mL Intravenous Astra Zeneca Lp 1996-10-01 2010-03-31 US Nesacaine Injection 10 mg/1mL Intravenous Astra Zeneca Lp 1990-09-30 2011-08-31 US Nesacaine Injection, solution 20 mg/1mL Infiltration; Perineural General Injectables & Vaccines, Inc 2013-01-30 Not applicable US Nesacaine Injection, solution 20 mg/1mL Infiltration; Perineural Fresenius Kabi USA, LLC 2010-10-14 Not applicable US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Chloroprocaine Hydrochloride Injection, solution 30 mg/1mL Epidural; Infiltration; Intracaudal; Perineural West-Ward Pharmaceuticals Corp 1998-11-01 Not applicable US Chloroprocaine Hydrochloride Injection, solution 20 mg/1mL Epidural; Infiltration Bedford Pharmaceuticals 1998-11-01 2012-06-30 US Chloroprocaine Hydrochloride Injection, solution 30 mg/1mL Epidural; Infiltration; Intracaudal Hospira, Inc. 2005-05-02 2013-07-01 US Chloroprocaine Hydrochloride Injection, solution 20 mg/1mL Epidural; Infiltration; Intracaudal; Perineural West-Ward Pharmaceuticals Corp 1998-11-01 Not applicable US Chloroprocaine Hydrochloride Injection, solution 20 mg/1mL Epidural; Infiltration; Intracaudal Hospira, Inc. 2005-07-08 2013-01-01 US Chloroprocaine Hydrochloride Injection, solution 30 mg/1mL Epidural; Infiltration Bedford Pharmaceuticals 1998-11-01 2012-06-30 US
Categories
- ATC Codes
- N01BA04 — Chloroprocaine
- Drug Categories
- Acids, Carbocyclic
- Aminobenzoates
- Anesthetics
- Anesthetics, Local
- Anticholinergic Agents
- Benzene Derivatives
- Benzoates
- Central Nervous System Agents
- Central Nervous System Depressants
- Cholinesterase substrates
- Esters of Aminobenzoic Acid
- Local Anesthesia
- Local Anesthetics (Ester)
- Nervous System
- Nicotinic Antagonists
- NMDA Receptor Antagonists
- para-Aminobenzoates
- Peripheral Nervous System Agents
- Sensory System Agents
- 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, H.C. and Rubin, M.I.; US. Patent 2,460,139; January 25,1949; assigned to Wallace & Tiernan Products, Inc.
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015292
- KEGG Drug
- D07678
- KEGG Compound
- C07877
- PubChem Compound
- 8612
- PubChem Substance
- 46508245
- ChemSpider
- 8293
- BindingDB
- 50239963
- 20859
- ChEBI
- 3636
- ChEMBL
- CHEMBL1179047
- ZINC
- ZINC000001530938
- Therapeutic Targets Database
- DAP000131
- PharmGKB
- PA448946
- RxList
- RxList Drug Page
- Wikipedia
- Chloroprocaine
- FDA label
- Download (182 KB)
- MSDS
- Download (51.5 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Not Available Anaesthesia therapy 1 4 Completed Diagnostic Cerclage, Cervical 1 4 Completed Other Adverse Reaction to Spinal Anesthetic / Maternal Care for Cervical Incompetence 1 4 Completed Treatment Cervical incompetence 1 4 Completed Treatment Knee Arthroscopy / Spinal Anaesthesia 1 4 Completed Treatment Pain 2 4 Completed Treatment Spinal Anaesthesia 1 4 Recruiting Treatment Analgesics / Analgesics, Opioid / Central Nervous System Depressants / Morphine / Narcotics / Physiological Effect of Drugs 1 4 Recruiting Treatment Spinal Anaesthesia 1 4 Unknown Status Treatment Pain Relief During Labour 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- APP Pharmaceuticals
- Bedford Labs
- Ben Venue Laboratories Inc.
- Hospira Inc.
- Dosage Forms
Form Route Strength Injection, solution Parenteral Injection, solution Epidural; Infiltration 20 mg/1mL Injection, solution Epidural; Infiltration 30 mg/1mL Injection, solution Epidural; Infiltration; Intracaudal 20 mg/1mL Injection, solution Epidural; Infiltration; Intracaudal 30 mg/1mL Injection, solution Epidural; Infiltration; Intracaudal; Perineural 20 mg/1mL Injection, solution Epidural; Infiltration; Intracaudal; Perineural 30 mg/1mL Injection, solution Intrathecal 10 mg/1mL Injection, solution Injection Intravenous 10 mg/1mL Injection Intravenous 20 mg/1mL Injection Intravenous 30 mg/1mL Injection, solution Infiltration; Perineural 10 mg/1mL Injection, solution Infiltration; Perineural 20 mg/1mL Solution Epidural; Intracaudal 20 mg / mL Solution Epidural; Intracaudal 30 mg / mL - Prices
Unit description Cost Unit Nesacaine-mpf 3% vial 1.34USD ml Nesacaine-mpf 2% vial 1.28USD ml Nesacaine 2% vial 0.74USD ml Nesacaine 1% vial 0.72USD ml Chloroprocaine 3% vial 0.33USD ml Chloroprocaine 2% vial 0.26USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US8969412 No 2015-03-03 2026-09-05 US US9504666 No 2016-11-29 2033-12-11 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 173-174 Marks, H.C. and Rubin, M.I.; US. Patent 2,460,139; January 25,1949; assigned to Wallace & Tiernan Products, Inc. water solubility 0.665 mg/mL Not Available logP 2.86 HANSCH,C ET AL. (1995) - Predicted Properties
Property Value Source Water Solubility 1.3 mg/mL ALOGPS logP 2.72 ALOGPS logP 2.48 ChemAxon logS -2.3 ALOGPS pKa (Strongest Basic) 8.96 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 3 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 55.56 Å2 ChemAxon Rotatable Bond Count 7 ChemAxon Refractivity 75.1 m3·mol-1 ChemAxon Polarizability 28.74 Å3 ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - 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 inhibitor Non-inhibitor 0.8687 CYP450 2D6 inhibitor Inhibitor 0.7746 CYP450 2C19 inhibitor Non-inhibitor 0.8061 CYP450 3A4 inhibitor 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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Mass Spectrum (Electron Ionization) MS splash10-000i-9100000000-5a6841e384b0dfbd1238 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- Kind
- Protein
- Organism
- Humans
- 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 acro...
- Gene Name
- SCN10A
- Uniprot ID
- Q9Y5Y9
- Uniprot Name
- Sodium channel protein type 10 subunit alpha
- Molecular Weight
- 220623.605 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- 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. [Article]
- 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
- 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]
- 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]
- 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]
- 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
- 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]
- Tucker GT, Mather LE: Clinical pharmacokinetics of local anaesthetics. Clin Pharmacokinet. 1979 Jul-Aug;4(4):241-78. [Article]
- 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]
- 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]
- 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]
Drug created on June 13, 2005 13:24 / Updated on May 07, 2021 21:25