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
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
DescriptionCurator's Comment: description was created based on several sources, including
http://www.hmdb.ca/metabolites/HMDB15292 | https://www.drugbank.ca/drugs/DB01161
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.
Originator
Sources: https://www.google.com/patents/US2460139
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
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2096682 Sources: https://www.drugbank.ca/drugs/DB01161 |
208.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | NESACAINE Approved UseNesacaine 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 |
PubMed
Title | Date | PubMed |
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Deaths from local anesthetic-induced convulsions in mice. | 1980 Jun |
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Grand mal seizures after 2-chloroprocaine epidural anesthesia in a patient with plasma cholinesterase deficiency. | 1987 Jul |
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More on back pain after Nesacaine-MPF. | 1990 Nov |
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Complications of regional anaesthesia Incidence and prevention. | 2001 |
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From cocaine to ropivacaine: the history of local anesthetic drugs. | 2001 Aug |
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Hospital discharge after ambulatory knee arthroscopy: A comparison of epidural 2-chloroprocaine versus lidocaine. | 2001 Jan-Feb |
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High epidural block with chloroprocaine in a parturient with low pseudocholinesterase activity. | 2001 Mar |
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Role of the dopamine transporter and the sodium channel in the cocaine-like discriminative stimulus effects of local anesthetics in rats. | 2001 Sep |
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A comparison of two regional anesthetic techniques for outpatient knee arthroscopy. | 2003 Aug |
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Effects of repeated injection of local anesthetic on sciatic nerve blocks response. | 2004 |
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Block-dependent sedation during epidural anaesthesia is associated with delayed brainstem conduction. | 2004 Aug |
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Spinal 2-chloroprocaine: the effect of added fentanyl. | 2004 Jan |
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Spinal chloroprocaine solutions: density at 37 degrees C and pH titration. | 2004 Jan |
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Chloroprocaine or sulfite toxicity? | 2004 Nov |
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Spinal 2-chloroprocaine: the effect of added clonidine. | 2005 Feb |
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Spinal 2-chloroprocaine for surgery: an initial 10-month experience. | 2005 Feb |
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Spinal anesthesia. | 2005 Oct |
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Epidural chloroprocaine-standard of care for postpartum bilateral tubal ligation. | 2005 Oct |
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Interaction of botulinum toxin type A with local anesthetic agents: an experimental study with rabbits. | 2006 Jan-Feb |
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Delayed-type hypersensitivity (type IV) reactions in dental anesthesia. | 2007 Jul-Aug |
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Postdischarge complications and rehabilitation after ambulatory surgery. | 2008 Dec |
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Spinal 2-chloroprocaine: effective dose for ambulatory surgery. | 2008 May |
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Coming to a head. | 2008 Oct |
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Cytotoxicity of local anesthetics in human neuronal cells. | 2009 Mar |
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Complications and controversies of regional anaesthesia: a review. | 2009 Oct |
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Selected Gamma Aminobutyric Acid (GABA) Esters may Provide Analgesia for Some Central Pain Conditions. | 2010 Aug 3 |
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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 |
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[Spinal anaesthesia in day case surgery--Old technique--new trends]. | 2010 Mar |
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Vacuoles: a hollow threat? | 2010 Mar |
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Ultrasound does not improve the success rate of a deep peroneal nerve block at the ankle. | 2010 Mar-Apr |
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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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/4005099
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.
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NCI_THESAURUS |
C245
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NDF-RT |
N0000175976
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WHO-ATC |
N01BA04
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NDF-RT |
N0000166743
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N0000175683
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WHO-VATC |
QN01BA04
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Chloroprocaine
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8612
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SUB06193MIG
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m3430
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DB01161
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DTXSID8022799
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Chloroprocaine
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C004616
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100000081848
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5YVB0POT2H
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20859
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C72168
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CHEMBL1179047
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ACTIVE MOIETY
METABOLITE (PARENT)
METABOLITE (PARENT)
SALT/SOLVATE (PARENT)