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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

CNS Active
3913
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

Wallace & Tiernan Products
2
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

1955
116
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 208.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
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
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208791s000lbl.pdf
single, epidural
 CHLOROPROCAINE HYDROCHLORIDE plasma
Homo sapiens
population: PREGNANT
age: ADULT
sex: FEMALE
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP
111
CYP
76
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP
147
 no
CYP
147
 no
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:3636
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:3636
ChemicalBook
CB4183345
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB4183345
MolPort
MolPort-006-167-725
https://www.molport.com/shop/molecule-link/MolPort-006-167-725
ZINC
ZINC000001530938
http://zinc15.docking.org/substances/ZINC000001530938
PubMed

PubMed

TitleDatePubMed
Persistent neurologic deficit and adhesive arachnoiditis following intrathecal 2-chloroprocaine injection.
1980 Jun
Prolonged neural blockade following regional analgesia with 2-chloroprocaine.
1980 Jun
Deaths from local anesthetic-induced convulsions in mice.
1980 Jun
Chloroprocaine neurotoxicity: four additional cases.
1982 Feb
Neurological toxicity of the subarachnoid infusion of bupivacaine, lignocaine or 2-chloroprocaine in the rat.
1985 Apr
Effects of cimetidine and ranitidine on local anesthetic central nervous system toxicity in mice.
1986 Aug
Recent advances in local anaesthesia.
1986 May
The role of 2-chloroprocaine and sodium bisulfite in rat sciatic nerve edema.
1986 Sep
Grand mal seizures after 2-chloroprocaine epidural anesthesia in a patient with plasma cholinesterase deficiency.
1987 Jul
Panic disorder following 2-chloroprocaine.
1989 Jul
Back pain following epidurally administered Nesacaine-MPF.
1989 Jul
Does chloroprocaine (Nesacaine MPF) for epidural anesthesia increase the incidence of backache?
1989 Sep
Treatment of nesacaine-MPF-induced back pain with calcium chloride.
1990 Apr
More on back pain after Nesacaine-MPF.
1990 Nov
Use of spinal anaesthesia in day surgery.
2006 Dec
Spinal anesthesia with lidocaine or preservative-free 2-chlorprocaine for outpatient knee arthroscopy: a prospective, randomized, double-blind comparison.
2007 Apr
A study comparing chloroprocaine with lidocaine for skin infiltration before intravenous catheter insertion.
2007 Aug
Delayed-type hypersensitivity (type IV) reactions in dental anesthesia.
2007 Jul-Aug
Pain and efficacy of local anesthetics for central venous access.
2008
Postdischarge complications and rehabilitation after ambulatory surgery.
2008 Dec
Lower-body warming mimics the normal epidural-induced reduction in the shivering threshold.
2008 Jan
Combined spinal and epidural anaesthesia with chloroprocaine for hysterectomy.
2008 Jan
Recurrent headache due to MS plaque.
2008 Mar
Spinal 2-chloroprocaine: effective dose for ambulatory surgery.
2008 May
A randomized, prospective, double-blind trial comparing 3% chloroprocaine followed by 0.5% bupivacaine to 2% lidocaine followed by 0.5% bupivacaine for interscalene brachial plexus block.
2008 Nov
Coming to a head.
2008 Oct
A survey of perioperative and postoperative anesthetic practices for cesarean delivery.
2009
Corrected scoliosis, cholinesterase deficiency, and cesarean section: a case report.
2009
Comparison of the potency of lidocaine and chloroprocaine in sciatic nerve block in Sprague-Dawley rats.
2009
Transient neurologic symptoms (TNS) following spinal anaesthesia with lidocaine versus other local anaesthetics.
2009 Apr 15
Pseudocholinesterase enzyme deficiency: a case series and review of the literature.
2009 Dec 4
A controlled clinical interventional trial comparing 2% chloroprocaine-bupivicaine versus 2% lidocaine-bupivicaine for retrobulbar anesthesia in scleral buckling surgery.
2009 Feb
Ultrasound improves the success rate of a sural nerve block at the ankle.
2009 Jan-Feb
The interaction between epidural 2-chloroprocaine and morphine: a randomized controlled trial of the effect of drug administration timing on the efficacy of morphine analgesia.
2009 Jul
Cytotoxicity of local anesthetics in human neuronal cells.
2009 Mar
Ultrasound improves the success rate of a tibial nerve block at the ankle.
2009 May-Jun
Bicarbonate plus epinephrine shortens the onset and prolongs the duration of sciatic block using chloroprocaine followed by bupivacaine in sprague-dawley rats.
2009 May-Jun
Complications and controversies of regional anaesthesia: a review.
2009 Oct
A fully implanted drug delivery system for peripheral nerve blocks in behaving animals.
2009 Sep 15
Prolonged neuromuscular blockade following succinylcholine administration to a patient with a reduced butyrylcholinesterase activity.
2010
Selected Gamma Aminobutyric Acid (GABA) Esters may Provide Analgesia for Some Central Pain Conditions.
2010 Aug 3
Advances in labor analgesia.
2010 Aug 9
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
Acute pain management in children.
2010 Jul 15
[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
Sertraline-induced pseudocholinesterase enzyme deficiency.
2010 Nov 16
Diabetic parturient - Anaesthetic implications.
2010 Sep
Diagnosis and management of pre-eclampsia: an update.
2010 Sep 30
Patents

Patents

JPH04208229A
10
US2460139
2
US3000783
2

Sample Use Guides

In Vivo Use Guide
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
Created by admin on Fri Dec 15 15:45:27 UTC 2023 , Edited by admin on Fri Dec 15 15:45:27 UTC 2023
WHO-ATC N01BA04
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 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
Created by admin on Fri Dec 15 15:45:27 UTC 2023 , Edited by admin on Fri Dec 15 15:45:27 UTC 2023
WHO-VATC QN01BA04
Created by admin on Fri Dec 15 15:45:27 UTC 2023 , Edited by admin on Fri Dec 15 15:45:27 UTC 2023
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
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
HSDB
3301
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
INN
487
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
IUPHAR
7145
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
CAS
133-16-4
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
PUBCHEM
8612
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
EVMPD
SUB06193MIG
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
MERCK INDEX
m3430
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 Merck Index
DRUG BANK
DB01161
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
EPA CompTox
DTXSID8022799
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
LACTMED
Chloroprocaine
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
MESH
C004616
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
SMS_ID
100000081848
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
CHEBI
3636
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
FDA UNII
5YVB0POT2H
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
DAILYMED
5YVB0POT2H
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
RXCUI
20859
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 RxNorm
NCI_THESAURUS
C72168
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
ChEMBL
CHEMBL1179047
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
ACTIVE MOIETY
Structure of CHLOROPROCAINE
METABOLITE (PARENT)
Structure of 2-(DIETHYLAMINO)ETHANOL
NIH
NCATS
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ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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