Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C13H19ClN2O2.ClH |
| Molecular Weight | 307.216 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CCN(CC)CCOC(=O)C1=C(Cl)C=C(N)C=C1
InChI
InChIKey=SZKQYDBPUCZLRX-UHFFFAOYSA-N
InChI=1S/C13H19ClN2O2.ClH/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;1H
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.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2096682 |
208.0 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| 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 Date1955 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Persistent neurologic deficit and adhesive arachnoiditis following intrathecal 2-chloroprocaine injection. | 1980 Jun |
|
| Prolonged neural blockade following regional analgesia with 2-chloroprocaine. | 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 |
|
| Grand mal seizures after 2-chloroprocaine epidural anesthesia in a patient with plasma cholinesterase deficiency. | 1987 Jul |
|
| Treatment of nesacaine-MPF-induced back pain with calcium chloride. | 1990 Apr |
|
| Inhibition of the Na,K-ATPase of canine renal medulla by several local anesthetics. | 2001 Apr |
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| From cocaine to ropivacaine: the history of local anesthetic drugs. | 2001 Aug |
|
| Comparison of paracervical block techniques during first trimester pregnancy termination. | 2001 Feb |
|
| Hospital discharge after ambulatory knee arthroscopy: A comparison of epidural 2-chloroprocaine versus lidocaine. | 2001 Jan-Feb |
|
| Santayana's prophecy fulfilled. | 2001 Nov-Dec |
|
| Role of the dopamine transporter and the sodium channel in the cocaine-like discriminative stimulus effects of local anesthetics in rats. | 2001 Sep |
|
| Evidence that spinal segmental nitric oxide mediates tachyphylaxis to peripheral local anesthetic nerve block. | 2001 Sep |
|
| Benefit and risks of local anesthetics in infants and children. | 2002 |
|
| Clinically significant concentrations of local anesthetics inhibit Staphylococcus aureus in vitro. | 2002 Apr |
|
| Chloroprocaine is less painful than lidocaine for skin infiltration anesthesia. | 2002 Feb |
|
| Short-acting peribulbar anesthesia with 2-chloroprocaine. | 2002 Jan |
|
| "Santayana's prophecy fulfilled" requires a critique. | 2002 Sep-Oct |
|
| A comparison of two regional anesthetic techniques for outpatient knee arthroscopy. | 2003 Aug |
|
| Toxicity of local anaesthetics. | 2003 Mar |
|
| Block-dependent sedation during epidural anaesthesia is associated with delayed brainstem conduction. | 2004 Aug |
|
| A new look at the hemolytic effect of local anesthetics, considering their real membrane/water partitioning at pH 7.4. | 2004 Aug 1 |
|
| Transient cardiovascular toxicity with unintentional intravascular injection of 3% 2-chloroprocaine in a 2-month-old infant. | 2004 Jan |
|
| Spinal 2-chloroprocaine: the effect of added dextrose. | 2004 Jan |
|
| Spinal chloroprocaine solutions: density at 37 degrees C and pH titration. | 2004 Jan |
|
| A comparison of infraclavicular nerve block versus general anesthesia for hand and wrist day-case surgeries. | 2004 Jul |
|
| Spinal 2-chloroprocaine: a comparison with small-dose bupivacaine in volunteers. | 2005 Feb |
|
| Spinal 2-chloroprocaine for surgery: an initial 10-month experience. | 2005 Feb |
|
| Spinal anesthesia. | 2005 Oct |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| A fully implanted drug delivery system for peripheral nerve blocks in behaving animals. | 2009 Sep 15 |
|
| 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
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
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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ACTIVE MOIETY
SUBSTANCE RECORD
