Chloroprocaine

Common Name

Chloroprocaine 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 implises, presumably by increasing the threshold for electrical excitation in the nerve, by slowing the propagation of the nerve implise and by reducing the rate of rise of the action potential. Structure

Synonyms

Value Source 2-ChloroprocaineChEBI 4-amino-2-Chlorobenzoic acid 2-(diethylamino)ethyl esterChEBI ChloroprocainChEBI ChloroprocainumChEBI CloroprocainaChEBI 4-amino-2-Chlorobenzoate 2-(diethylamino)ethyl esterGenerator ChlorprocaineHMDB Nesacaine MPFMeSH Chlor-procaineMeSH NesacaineMeSH Chloroprocaine hydrochlorideMeSH

Chemical Formlia

C₁₃H₁₉ClN₂O₂ Average Molecliar Weight

270.755 Monoisotopic Molecliar Weight

270.113505569 IUPAC Name

2-(diethylamino)ethyl 4-amino-2-chlorobenzoate Traditional Name

chloroprocaine CAS Registry Number

133-16-4 SMILES

InChI Identifier

InChI Key

VDANGULDQQJODZ-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as benzoic acid esters. These are ester derivatives of benzoic acid. Kingdom

Chemical entities Super Class

Organic compounds Class

Benzenoids Sub Class

Benzene and substituted derivatives Direct Parent

Benzoic acid esters Alternative Parents

2-halobenzoic acids and derivatives

Aminobenzoic acids and derivatives

Aniline and substituted anilines

Benzoyl derivatives

Chlorobenzenes

Primary aromatic amines

Aryl chlorides

Vinylogous halides

Trialkylamines

Amino acids and derivatives

Carboxylic acid esters

Monocarboxylic acids and derivatives

Hydrocarbon derivatives

Organic oxides

Organochlorides

Organooxygen compounds

Organopnictogen compounds

Substituents

Aminobenzoic acid or derivatives

Benzoate ester

2-halobenzoic acid or derivatives

Halobenzoic acid or derivatives

Benzoyl

Aniline or substituted anilines

Chlorobenzene

Halobenzene

Aryl chloride

Primary aromatic amine

Aryl halide

Vinylogous halide

Amino acid or derivatives

Tertiary aliphatic amine

Tertiary amine

Carboxylic acid ester

Carboxylic acid derivative

Monocarboxylic acid or derivatives

Organochloride

Organonitrogen compound

Organooxygen compound

Hydrocarbon derivative

Amine

Organic oxygen compound

Primary amine

Organopnictogen compound

Organic nitrogen compound

Organic oxide

Organohalogen compound

Aromatic homomonocyclic compound

Molecliar Framework

Aromatic homomonocyclic compounds External Descriptors

monochlorobenzenes (CHEBI:3636 )

benzoate ester (CHEBI:3636 )

Ontology Status

Expected but not Quantified Origin

Drug

Biofunction

Anesthetics, Local

Application

Pharmaceutical

Cellliar locations

Cytoplasm

Extracellliar

Membrane

Physical Properties State

Solid Experimental Properties

Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water Solubility1.30e+00 g/LNot Available LogP2.5Not Available

Predicted Properties

Property Value Source 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 ŲChemAxon Rotatable Bond Count7ChemAxon Refractivity75.1 m³·mol^-1ChemAxon Polarizability28.74 ųChemAxon Number of Rings1ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

Spectra Spectra

Spectrum Type Description Splash Key Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available MS

Mass Spectrum (Electron Ionization)splash10-000i-9100000000-5a6841e384b0dfbd1238View in MoNA

Biological Properties Cellliar Locations

Cytoplasm

Extracellliar

Membrane

Biofluid Locations

Blood

Urine

Tissue Location

Not Available Pathways

Name SMPDB Link KEGG Link Chloroprocaine PathwaySMP00394Not Available

Normal Concentrations

Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01161

21059682

details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01161

21059682

details

Abnormal Concentrations

Not Available Predicted Concentrations

Biofluid Value Original age Original sex Original condition Comments Blood0-4 uMAdlit (>18 years old)BothNormalPredicted based on drug qualities Blood0-2 umol/mmol creatinineAdlit (>18 years old)BothNormalPredicted based on drug qualities

Associated Disorders and Diseases Disease References

None Associated OMIM IDs

None External Links DrugBank ID

DB01161 DrugBank Metabolite ID

Not Available Phenol Explorer Compound ID

Not Available Phenol Explorer Metabolite ID

Not Available FoodDB ID

Not Available KNApSAcK ID

Not Available Chemspider ID

8293 KEGG Compound ID

C07877 BioCyc ID

Not Available BiGG ID

Not Available Wikipedia Link

Chloroprocaine NuGOwiki Link

HMDB15292 Metagene Link

HMDB15292 METLIN ID

Not Available PubChem Compound

8612 PDB ID

Not Available ChEBI ID

3636

Product: BIBF 1203

References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References Not Available

Enzymes

General function:

Involved in carboxylesterase activity

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

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 ]

General function:

Involved in neurotransmitter:sodium symporter 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

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 ]

General function:

Involved in extracellular ligand-gated ion 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:

55279.8

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 ]

General function:

Involved in extracellular ligand-gated ion channel activity

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:

49704.3

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 ]

General function:

Involved in ionotropic glutamate receptor activity

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

Gene Name:

GRIN3A

Uniprot ID:

Q8TCU5

Molecular weight:

125464.1

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 ]

General function:

Involved in ion channel activity

Specific function:

This protein 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. It is a tetrodotoxin-resistant sodium channel isoform. Its electrophysiological properties vary depending on the type of the associated beta subunits (in vitro). Plays a role in neuropathic pain mechanisms

Gene Name:

SCN10A

Uniprot ID:

Q9Y5Y9

Molecular weight:

220623.6

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 ]

PMID: 24388993

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