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=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
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 8297		208.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 614 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/009435s035s036lbl.pdf	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 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 111		CYP 76

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP 147	inducer 1573 Sources: https://web.archive.org/web/20210125205139/http://www.drugs-porphyria.org/monograph2.php?id=3443	no
CYP 147	inhibitor 3277 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
Persistent neurologic deficit and adhesive arachnoiditis following intrathecal 2-chloroprocaine injection.	1980 Jun	7189987
Prolonged neural blockade following regional analgesia with 2-chloroprocaine.	1980 Jun	7189986
Deaths from local anesthetic-induced convulsions in mice.	1980 Jun	7189975
Chloroprocaine neurotoxicity: four additional cases.	1982 Feb	7198876
Neurological toxicity of the subarachnoid infusion of bupivacaine, lignocaine or 2-chloroprocaine in the rat.	1985 Apr	3986072
Effects of cimetidine and ranitidine on local anesthetic central nervous system toxicity in mice.	1986 Aug	3729019
Recent advances in local anaesthesia.	1986 May	3521804
The role of 2-chloroprocaine and sodium bisulfite in rat sciatic nerve edema.	1986 Sep	3018175
Grand mal seizures after 2-chloroprocaine epidural anesthesia in a patient with plasma cholinesterase deficiency.	1987 Jul	3111302
Panic disorder following 2-chloroprocaine.	1989 Jul	2742022
Back pain following epidurally administered Nesacaine-MPF.	1989 Jul	2525887
Does chloroprocaine (Nesacaine MPF) for epidural anesthesia increase the incidence of backache?	1989 Sep	2528307
Treatment of nesacaine-MPF-induced back pain with calcium chloride.	1990 Apr	2138439
More on back pain after Nesacaine-MPF.	1990 Nov	2145784
Spinal anesthesia.	2005 Oct	16534288
Use of spinal anaesthesia in day surgery.	2006 Dec	17093364
Chloroprocaine may not affect epidural morphine for postcesarean delivery analgesia.	2006 Feb	16517329
Intrathecal 2-chloroprocaine for lower limb outpatient surgery: a prospective, randomized, double-blind, clinical evaluation.	2006 Jul	16790659
Spinal anesthesia with lidocaine or preservative-free 2-chlorprocaine for outpatient knee arthroscopy: a prospective, randomized, double-blind comparison.	2007 Apr	17377114
A study comparing chloroprocaine with lidocaine for skin infiltration before intravenous catheter insertion.	2007 Aug	17711155
Delayed-type hypersensitivity (type IV) reactions in dental anesthesia.	2007 Jul-Aug	17883918
Pain and efficacy of local anesthetics for central venous access.	2008	22915859
Postdischarge complications and rehabilitation after ambulatory surgery.	2008 Dec	18997524
Lower-body warming mimics the normal epidural-induced reduction in the shivering threshold.	2008 Jan	18165586
Combined spinal and epidural anaesthesia with chloroprocaine for hysterectomy.	2008 Jan	18047629
Recurrent headache due to MS plaque.	2008 Mar	18081822
Spinal 2-chloroprocaine: effective dose for ambulatory surgery.	2008 May	18419724
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	18931242
Coming to a head.	2008 Oct	18812976
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
Pseudocholinesterase enzyme deficiency: a case series and review of the literature.	2009 Dec 4	20062665
A controlled clinical interventional trial comparing 2% chloroprocaine-bupivicaine versus 2% lidocaine-bupivicaine for retrobulbar anesthesia in scleral buckling surgery.	2009 Feb	19169319
Ultrasound improves the success rate of a sural nerve block at the ankle.	2009 Jan-Feb	19258984
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	19535707
Cytotoxicity of local anesthetics in human neuronal cells.	2009 Mar	19224816
Ultrasound improves the success rate of a tibial nerve block at the ankle.	2009 May-Jun	19587626
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	19587615
Complications and controversies of regional anaesthesia: a review.	2009 Oct	20640104
Prolonged neuromuscular blockade following succinylcholine administration to a patient with a reduced butyrylcholinesterase activity.	2010	20589221
Selected Gamma Aminobutyric Acid (GABA) Esters may Provide Analgesia for Some Central Pain Conditions.	2010 Aug 3	20703328
Advances in labor analgesia.	2010 Aug 9	21072284
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	20119585
Acute pain management in children.	2010 Jul 15	21197314
[Spinal anaesthesia in day case surgery--Old technique--new trends].	2010 Mar	20232274
Vacuoles: a hollow threat?	2010 Mar	20054677
Ultrasound does not improve the success rate of a deep peroneal nerve block at the ankle.	2010 Mar-Apr	20301828
Sertraline-induced pseudocholinesterase enzyme deficiency.	2010 Nov 16	21189834
Diabetic parturient - Anaesthetic implications.	2010 Sep	21189875
Diagnosis and management of pre-eclampsia: an update.	2010 Sep 30	21151680

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.

Name

Type

Language

CHLOROPROCAINE

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