U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C13H19ClN2O2
Molecular Weight 270.755
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CHLOROPROCAINE

SMILES

CCN(CC)CCOC(=O)C1=C(Cl)C=C(N)C=C1

InChI

InChIKey=VDANGULDQQJODZ-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including http://www.hmdb.ca/metabolites/HMDB15292 | https://www.drugbank.ca/drugs/DB01161

Chloroprocaine (Nesacaine®, Nesacaine®-MPF) is a non pyrogenic local anesthetic. Nesacaine® is indicated for the production of local anesthesia by infiltration and peripheral nerve block. It is not to be used for lumbar or caudal epidural anesthesia. Nesacaine®-MPF is indicated for the production of local anesthesia by infiltration, peripheral and central nerve block, including lumbar and caudal epidural blocks. Nesacaine® and Nesacaine®-MPF are not to be used for subarachnoid administration. Chloroprocaine (Nesacaine®, Nesacaine®-MPF), 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. It 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.

CNS Activity

Curator's Comment: Use of chloroprocaine declined rapidly after 1980 following reports of prolonged sensory and motor block resulting from unintentional subarachnoid administration of an intended epidural dose.

Originator

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

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
208.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
NESACAINE

Approved Use

Nesacaine 1% and 2% Injections, in multidose vials with methylparaben as preservative, are indicated for the production of local anesthesia by infiltration and peripheral nerve block. They are not to be used for lumbar or caudal epidural anesthesia. Nesacaine-MPF 2% and 3% Injections, in single dose vials without preservative and without EDTA, are indicated for the production of local anesthesia by infiltration, peripheral and central nerve block, including lumbar and caudal epidural blocks. Nesacaine and Nesacaine-MPF Injections are not to be used for subarachnoid administration.

Launch Date

-4.67423986E11
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
3.1 min
single, epidural
CHLOROPROCAINE HYDROCHLORIDE plasma
Homo sapiens
population: PREGNANT
age: ADULT
sex: FEMALE
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​
PubMed

PubMed

TitleDatePubMed
Deaths from local anesthetic-induced convulsions in mice.
1980 Jun
Grand mal seizures after 2-chloroprocaine epidural anesthesia in a patient with plasma cholinesterase deficiency.
1987 Jul
More on back pain after Nesacaine-MPF.
1990 Nov
Complications of regional anaesthesia Incidence and prevention.
2001
From cocaine to ropivacaine: the history of local anesthetic drugs.
2001 Aug
Hospital discharge after ambulatory knee arthroscopy: A comparison of epidural 2-chloroprocaine versus lidocaine.
2001 Jan-Feb
High epidural block with chloroprocaine in a parturient with low pseudocholinesterase activity.
2001 Mar
Role of the dopamine transporter and the sodium channel in the cocaine-like discriminative stimulus effects of local anesthetics in rats.
2001 Sep
A comparison of two regional anesthetic techniques for outpatient knee arthroscopy.
2003 Aug
Effects of repeated injection of local anesthetic on sciatic nerve blocks response.
2004
Block-dependent sedation during epidural anaesthesia is associated with delayed brainstem conduction.
2004 Aug
Spinal 2-chloroprocaine: the effect of added fentanyl.
2004 Jan
Spinal chloroprocaine solutions: density at 37 degrees C and pH titration.
2004 Jan
Chloroprocaine or sulfite toxicity?
2004 Nov
Spinal 2-chloroprocaine: the effect of added clonidine.
2005 Feb
Spinal 2-chloroprocaine for surgery: an initial 10-month experience.
2005 Feb
Spinal anesthesia.
2005 Oct
Epidural chloroprocaine-standard of care for postpartum bilateral tubal ligation.
2005 Oct
Interaction of botulinum toxin type A with local anesthetic agents: an experimental study with rabbits.
2006 Jan-Feb
Delayed-type hypersensitivity (type IV) reactions in dental anesthesia.
2007 Jul-Aug
Postdischarge complications and rehabilitation after ambulatory surgery.
2008 Dec
Spinal 2-chloroprocaine: effective dose for ambulatory surgery.
2008 May
Coming to a head.
2008 Oct
Cytotoxicity of local anesthetics in human neuronal cells.
2009 Mar
Complications and controversies of regional anaesthesia: a review.
2009 Oct
Selected Gamma Aminobutyric Acid (GABA) Esters may Provide Analgesia for Some Central Pain Conditions.
2010 Aug 3
Effects of epidural fentanyl on speed and quality of block for emergency cesarean section in extending continuous epidural labor analgesia using ropivacaine and fentanyl.
2010 Feb
[Spinal anaesthesia in day case surgery--Old technique--new trends].
2010 Mar
Vacuoles: a hollow threat?
2010 Mar
Ultrasound does not improve the success rate of a deep peroneal nerve block at the ankle.
2010 Mar-Apr
Diabetic parturient - Anaesthetic implications.
2010 Sep
Diagnosis and management of pre-eclampsia: an update.
2010 Sep 30
Patents

Sample Use Guides

Chloroprocaine may be administered as a single injection or continuously through an indwelling catheter. The smallest dose and concentration required to produce the desired result should be used. The maximum single recommended doses of chloroprocaine in adults are: without epinephrine, 11 mg/kg, not to exceed a maximum total dose of 800 mg; with epinephrine (1:200,000), 14 mg/kg, not to exceed a maximum total dose of 1000 mg.
Route of Administration: Intravenous
In Vitro Use Guide
The study was instituted to examine the differential blocking activity of a series of amino-ester agents using an in vitro rabbit vagus nerve preparation. The ED50 (50% depression of the action potential amplitude) of the chloroprocaine hydrochloride were 0.17 mM, 0.20 mM and 0.23 mM for A, B and C fibres, respectively.
Name Type Language
CHLOROPROCAINE
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
BENZOIC ACID, 4-AMINO-2-CHLORO-, 2-(DIETHYLAMINO)ETHYL ESTER
Common Name English
CHLOROPROCAINE [MI]
Common Name English
CHLOROPROCAINE [HSDB]
Common Name English
CHLOROPROCAINE [VANDF]
Common Name English
chloroprocaine [INN]
Common Name English
Chloroprocaine [WHO-DD]
Common Name English
2-CHLOROPROCAINE
Common Name English
2-(DIETHYLAMINO)ETHYL 4-AMINO-2-CHLOROBENZOATE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C245
Created by admin on Fri Dec 15 15:45:27 UTC 2023 , Edited by admin on Fri Dec 15 15:45:27 UTC 2023
NDF-RT N0000175976
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WHO-ATC N01BA04
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NDF-RT N0000166743
Created by admin on Fri Dec 15 15:45:27 UTC 2023 , Edited by admin on Fri Dec 15 15:45:27 UTC 2023
NDF-RT N0000175683
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WHO-VATC QN01BA04
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Code System Code Type Description
DRUG CENTRAL
605
Created by admin on Fri Dec 15 15:45:27 UTC 2023 , Edited by admin on Fri Dec 15 15:45:27 UTC 2023
PRIMARY
WIKIPEDIA
Chloroprocaine
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HSDB
3301
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INN
487
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IUPHAR
7145
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PRIMARY
CAS
133-16-4
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PUBCHEM
8612
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EVMPD
SUB06193MIG
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MERCK INDEX
m3430
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PRIMARY Merck Index
DRUG BANK
DB01161
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PRIMARY
EPA CompTox
DTXSID8022799
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LACTMED
Chloroprocaine
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MESH
C004616
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PRIMARY
SMS_ID
100000081848
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CHEBI
3636
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FDA UNII
5YVB0POT2H
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DAILYMED
5YVB0POT2H
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PRIMARY
RXCUI
20859
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PRIMARY RxNorm
NCI_THESAURUS
C72168
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PRIMARY
ChEMBL
CHEMBL1179047
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PRIMARY