CHLOROPROCAINE

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 Search

SMILES

CCN(CC)CCOC(=O)C1=CC=C(N)C=C1Cl

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

Molecular Formula	C13H19ClN2O2
Molecular Weight	270.755
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/009435s035s036lbl.pdf
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Sodium channel alpha subunits; brain (Types I, II, III) 28 Target ID: CHEMBL2096682 Sources: https://www.drugbank.ca/drugs/DB01161	Inhibitor 8504		208.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 619 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/009435s035s036lbl.pdf	Primary		Approved 8583	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 1955

T_1/2

Value	Dose	Co-administered	Analyte	Population
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

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP 110		CYP 74

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP 150	inducer 1966 Sources: https://web.archive.org/web/20210125205139/http://www.drugs-porphyria.org/monograph2.php?id=3443	no
CYP 150	inhibitor 4027 Sources: https://web.archive.org/web/20210125205139/http://www.drugs-porphyria.org/monograph2.php?id=3443	no

Sourcing

Vendor/Aggregator	ID	URL
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

Title	Date	PubMed
Sertraline-induced pseudocholinesterase enzyme deficiency.	2010-11-16	21189834
Diagnosis and management of pre-eclampsia: an update.	2010-09-30	21151680
Diabetic parturient - Anaesthetic implications.	2010-09	21189875
Advances in labor analgesia.	2010-08-09	21072284
Selected Gamma Aminobutyric Acid (GABA) Esters may Provide Analgesia for Some Central Pain Conditions.	2010-08-03	20703328
Acute pain management in children.	2010-07-15	21197314
Ultrasound does not improve the success rate of a deep peroneal nerve block at the ankle.	2010-03-23	20301828
[Spinal anaesthesia in day case surgery--Old technique--new trends].	2010-03	20232274
[Vacuoles: a hollow threat?].	2010-03	20054677
Effects of epidural fentanyl on speed and quality of block for emergency cesarean section in extending continuous epidural labor analgesia using ropivacaine and fentanyl.	2010-02	20119585
Prolonged neuromuscular blockade following succinylcholine administration to a patient with a reduced butyrylcholinesterase activity.	2010	20589221
Pseudocholinesterase enzyme deficiency: a case series and review of the literature.	2009-12-04	20062665
Complications and controversies of regional anaesthesia: a review.	2009-10	20640104
A fully implanted drug delivery system for peripheral nerve blocks in behaving animals.	2009-09-15	19524613
Ultrasound improves the success rate of a tibial nerve block at the ankle.	2009-07-10	19587626
Bicarbonate plus epinephrine shortens the onset and prolongs the duration of sciatic block using chloroprocaine followed by bupivacaine in sprague-dawley rats.	2009-07-10	19587615
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.	2009-07	19535707
Transient neurologic symptoms (TNS) following spinal anaesthesia with lidocaine versus other local anaesthetics.	2009-04-15	19370578
Ultrasound improves the success rate of a sural nerve block at the ankle.	2009-03-05	19258984
Cytotoxicity of local anesthetics in human neuronal cells.	2009-03	19224816
A controlled clinical interventional trial comparing 2% chloroprocaine-bupivicaine versus 2% lidocaine-bupivicaine for retrobulbar anesthesia in scleral buckling surgery.	2009-02	19169319
A survey of perioperative and postoperative anesthetic practices for cesarean delivery.	2009	21217809
Corrected scoliosis, cholinesterase deficiency, and cesarean section: a case report.	2009	19718241
Comparison of the potency of lidocaine and chloroprocaine in sciatic nerve block in Sprague-Dawley rats.	2009	19420984
Postdischarge complications and rehabilitation after ambulatory surgery.	2008-12	18997524
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.	2008-11	18931242
Coming to a head.	2008-10	18812976
Spinal 2-chloroprocaine: effective dose for ambulatory surgery.	2008-05	18419724
Recurrent headache due to MS plaque.	2008-03	18081822
Lower-body warming mimics the normal epidural-induced reduction in the shivering threshold.	2008-01	18165586
Combined spinal and epidural anaesthesia with chloroprocaine for hysterectomy.	2008-01	18047629
Pain and efficacy of local anesthetics for central venous access.	2008	22915859
Delayed-type hypersensitivity (type IV) reactions in dental anesthesia.	2007-09-22	17883918
A study comparing chloroprocaine with lidocaine for skin infiltration before intravenous catheter insertion.	2007-08	17711155
Spinal anesthesia with lidocaine or preservative-free 2-chlorprocaine for outpatient knee arthroscopy: a prospective, randomized, double-blind comparison.	2007-04	17377114
Use of spinal anaesthesia in day surgery.	2006-12	17093364
More on back pain after Nesacaine-MPF.	1990-11	2145784
Treatment of nesacaine-MPF-induced back pain with calcium chloride.	1990-04	2138439
Does chloroprocaine (Nesacaine MPF) for epidural anesthesia increase the incidence of backache?	1989-09	2528307
Panic disorder following 2-chloroprocaine.	1989-07	2742022
Back pain following epidurally administered Nesacaine-MPF.	1989-07	2525887
Grand mal seizures after 2-chloroprocaine epidural anesthesia in a patient with plasma cholinesterase deficiency.	1987-07	3111302
The role of 2-chloroprocaine and sodium bisulfite in rat sciatic nerve edema.	1986-09	3018175
Effects of cimetidine and ranitidine on local anesthetic central nervous system toxicity in mice.	1986-08	3729019
Recent advances in local anaesthesia.	1986-05	3521804
Neurological toxicity of the subarachnoid infusion of bupivacaine, lignocaine or 2-chloroprocaine in the rat.	1985-04	3986072
Chloroprocaine neurotoxicity: four additional cases.	1982-02	7198876
Persistent neurologic deficit and adhesive arachnoiditis following intrathecal 2-chloroprocaine injection.	1980-06	7189987
Prolonged neural blockade following regional analgesia with 2-chloroprocaine.	1980-06	7189986
Deaths from local anesthetic-induced convulsions in mice.	1980-06	7189975

Patents

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:07:35 GMT 2025` Edited by `admin` on `Mon Mar 31 18:07:35 GMT 2025`
Record UNII	5YVB0POT2H
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CHLOROPROCAINE

Official Name

English

2-CHLOROPROCAINE

Preferred 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-(DIETHYLAMINO)ETHYL 4-AMINO-2-CHLOROBENZOATE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C245