Chloroprocaine
Local anesthetic medication
title: "Chloroprocaine" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["local-anesthetics", "4-aminobenzoate-esters", "chlorobenzene-derivatives", "diethylamino-compounds"] description: "Local anesthetic medication" topic_path: "general/local-anesthetics" source: "https://en.wikipedia.org/wiki/Chloroprocaine" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0
::summary Local anesthetic medication ::
::data[format=table title="Infobox drug"]
| Field | Value |
|---|---|
| Verifiedfields | changed |
| verifiedrevid | 460032727 |
| image | Chloroprocaine.svg |
| image_class | skin-invert-image |
| width | 250 |
| tradename | Nesacaine, others |
| Drugs.com | {{ubl |
| DailyMedID | Chloroprocaine |
| pregnancy_AU | |
| routes_of_administration | Intrathecal, eye drop |
| class | Local anesthetic |
| ATC_prefix | N01 |
| ATC_suffix | BA04 |
| ATC_supplemental | |
| legal_AU | |
| legal_BR | |
| legal_CA | Rx-only |
| legal_CA_comment | |
| legal_DE | |
| legal_NZ | |
| legal_UK | |
| legal_US | Rx-only |
| legal_US_comment | |
| legal_UN | |
| legal_status | Rx-only |
| CAS_number_Ref | |
| CAS_number | 133-16-4 |
| CAS_number2 | 3858-89-7 |
| PubChem | 8612 |
| PubChem2 | 441348 |
| IUPHAR_ligand | 7145 |
| DrugBank_Ref | |
| DrugBank | DB01161 |
| DrugBank2 | DBSALT000823 |
| ChemSpiderID_Ref | |
| ChemSpiderID | 8293 |
| UNII_Ref | |
| UNII | 5YVB0POT2H |
| UNII2 | LT7Z1YW11H |
| KEGG_Ref | |
| KEGG | D07678 |
| KEGG2 | D00732 |
| ChEBI_Ref | |
| ChEBI | 3636 |
| ChEBI2 | 3637 |
| ChEMBL_Ref | |
| ChEMBL | 1179047 |
| ChEMBL2 | 944 |
| IUPAC_name | 2-diethylaminoethyl-4-amino-2-chloro-benzoate |
| C | 13 |
| SMILES | CCN(CC)CCOC(=O)C1=C(Cl)C=C(N)C=C1 |
| SMILES2 | Cl.CCN(CC)CCOC(=O)C1=C(Cl)C=C(N)C=C1 |
| StdInChI_Ref | |
| StdInChI | 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 |
| StdInChI2 | 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 |
| StdInChIKey_Ref | |
| StdInChIKey | VDANGULDQQJODZ-UHFFFAOYSA-N |
| StdInChIKey2 | SZKQYDBPUCZLRX-UHFFFAOYSA-N |
| :: |
| Verifiedfields = changed | verifiedrevid = 460032727 | image = Chloroprocaine.svg | image_class = skin-invert-image | width = 250 | alt = | caption =
| pronounce = | tradename = Nesacaine, others | Drugs.com = {{ubl | Hcl: | Ophthalmic: | MedlinePlus = | DailyMedID = Chloroprocaine | pregnancy_AU = | pregnancy_AU_comment = | pregnancy_category = | routes_of_administration = Intrathecal, eye drop | class = Local anesthetic | ATC_prefix = N01 | ATC_suffix = BA04 | ATC_supplemental =
| legal_AU = | legal_AU_comment = | legal_BR = | legal_BR_comment = | legal_CA = Rx-only | legal_CA_comment = | legal_DE = | legal_DE_comment = | legal_NZ = | legal_NZ_comment = | legal_UK = | legal_UK_comment = | legal_US = Rx-only | legal_US_comment = | legal_EU = | legal_EU_comment = | legal_UN = | legal_UN_comment = | legal_status = Rx-only
| bioavailability = | protein_bound = | metabolism = | metabolites = | onset = | elimination_half-life = | duration_of_action = | excretion =
| CAS_number_Ref = | CAS_number = 133-16-4 | CAS_number2 = 3858-89-7 | CAS_supplemental = | PubChem = 8612 | PubChem2 = 441348 | IUPHAR_ligand = 7145 | DrugBank_Ref = | DrugBank = DB01161 | DrugBank2 = DBSALT000823 | ChemSpiderID_Ref = | ChemSpiderID = 8293 | UNII_Ref = | UNII = 5YVB0POT2H | UNII2 = LT7Z1YW11H | KEGG_Ref = | KEGG = D07678 | KEGG2 = D00732 | ChEBI_Ref = | ChEBI = 3636 | ChEBI2 = 3637 | ChEMBL_Ref = | ChEMBL = 1179047 | ChEMBL2 = 944 | NIAID_ChemDB = | PDB_ligand = | synonyms =
| IUPAC_name = 2-diethylaminoethyl-4-amino-2-chloro-benzoate | C=13 | H=19 | Cl=1 | N=2 | O=2 | SMILES = CCN(CC)CCOC(=O)C1=C(Cl)C=C(N)C=C1 | SMILES2 = Cl.CCN(CC)CCOC(=O)C1=C(Cl)C=C(N)C=C1 | StdInChI_Ref = | StdInChI = 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 | StdInChI2 = 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 | StdInChI_comment = | StdInChIKey_Ref = | StdInChIKey = VDANGULDQQJODZ-UHFFFAOYSA-N | StdInChIKey2 = SZKQYDBPUCZLRX-UHFFFAOYSA-N | density = | density_notes = | melting_point = | melting_high = | melting_notes = | boiling_point = | boiling_notes = | solubility = | sol_units = | specific_rotation =
Chloroprocaine, sold under the brand name Nesacaine among others is a local anesthetic given by injection. It is used as the hydrochloride salt. Chloroprocaine is a local anesthetic.
Medical uses
Chloroprocaine (Nesacaine) is indicated for the production of local anesthesia by infiltration and peripheral nerve block; and for the production of local anesthesia by infiltration, peripheral and central nerve block, including lumbar and caudal epidural blocks.
Chloroprocaine (Clorotekal) is indicated for intrathecal injection in adults for the production of subarachnoid block (spinal anesthesia).
Chloroprocaine is used for regional anesthesia including spinal anesthesia, caudal anesthesia and epidural anesthesia.
It is also indicated for local anesthesia including brachial plexus block, cervical nerve block, occipital nerve block. mandibular nerve block or maxillary nerve block for dental anesthesia, ophthalmic anesthesia via infraorbital nerve block, ulnar nerve block, paravertebral block, intercostal nerve block, sciatic nerve block, stellate ganglion block, lumbar sympathetic block and interdigital block.
It is also used for obstetric anesthesia including pudendal nerve block and paracervical block.
Chloroprocaine (Iheezo) is indicated for ocular surface anesthesia.
Subarachnoid block
Chloroprocaine was developed to meet the need for a short-acting spinal anaesthetic that is reliable and has a favourable safety profile to support the growing need for day-case surgery. Licensed in Europe for surgical procedures up to 40 minutes, chloroprocaine is an ester-type local anaesthetic with the shortest duration of action of all the established local anaesthetics. It has a significantly shorter duration of action than lidocaine and is significantly less toxic. Chloroprocaine has a motor block lasting for 40 minutes, a rapid onset time of 3–5 minutes (9.6 min ± 7.3 min at 40 mg dose; 7.9 min ± 6.0 min at 50 mg dose) and a time to ambulation of 90 minutes without complications, especially lacking transient neurologic symptomatology.
These data are based upon a retrospective review of 672 patients suitable for spinal anesthesia in surgical procedures less than 60 minutes' duration using 30–40 mg chloroprocaine. The results showed good surgical anesthesia, a fast onset time, and postoperative mobilization after 90 minutes without complications.
The use of chloroprocaine in the subarachnoid space has been questioned. In the early 1980s, several cases were reported of neurological deficits after inadvertent intrathecal injections intended for epidural delivery. These doses were an order of magnitude higher than is currently used for intrathecal delivery. It is also thought that these deficits were also related to the preservative sodium bisulfite, although this is also controversial.
Some studies have been published on the safe use of intrathecal chloroprocaine when appropriate dosage is used and with preservative-free preparations.
It is approved for intrathecal use in the United States, Europe, and Canada.
Obstetrics
Amide-linked local anesthetic agents, such as lidocaine and bupivacaine, can become "trapped" in their ionized forms on the fetal side of the placenta, so their net transfer across the placenta is increased. An ester-linked local anesthetic agent, such as 2-chloroprocaine, is rapidly metabolized, and placental transfer is limited. Since the metabolism of 2-chloroprocaine by fetal plasma is slower than in maternal plasma, the potential for ion trapping exists. Fetal pH is slightly lower than maternal (7.32 to 7.38), thus most unionized drugs are "ion trapped" to a degree, even in a healthy fetus. Chloroprocaine (pKa 8.7) is the drug of choice for epidural analgesia and a decompensating fetus, because it does not participate in ion trapping. Placental transfer of 2-chloroprocaine is not influenced by fetal acidosis.
The in vitro half-life of chloroprocaine is 21 seconds for maternal and 43 seconds for fetal blood. In patients who are homozygous atypical for plasma cholinesterase, chloroprocaine typically exists for two minutes in circulation.
Synthesis
::figure[src="https://upload.wikimedia.org/wikipedia/commons/3/33/Chloroprocaine_synthesis.png" caption="2460139}} (1949 to Wallace & Tiernan Inc)."] ::
The hydrochloride salt of 4-amino-2-chlorobenzoyl chloride is made by the reaction of 2-chloro-4-aminobenzoic acid with thionyl chloride. Synthesis of this drug is then accomplished by directly reacting the product of the last step with the hydrochloride salt of 2-diethylaminoethanol.
References
References
- (22 August 2024). "Regulatory Decision Summary for Clorotekal".
- (1 September 2022). "Nesacaine- chloroprocaine hydrochloride injection, solution; Nesacaine MPF- chloroprocaine hydrochloride injection, solution".
- (4 December 2020). "Clorotekal- chloroprocaine hydrochloride injection, solution".
- (27 October 2022). "List of nationally authorised medicinal products Active substance(s): chloroprocaine hydrochloride". European Medicines Agency.
- Sintetica Limited. (9 March 2017). "Ampres 10 mg/ml solution for injection". EMC.
- Physicians' Desk Reference. "chloroprocaine hydrochloride". PDR.net.
- (27 September 2022). "Iheezo- chloroprocaine hydrochloride ophthalmic gel gel".
- (2009). "Ampres (chloroprocaine) Summary of Product Characteristics". Perimed.
- (February 2005). "Chloroprocaine spinal anesthesia: back to the future?". Anesthesia & Analgesia.
- (June 1980). "Persistent neurologic deficit and adhesive arachnoiditis following intrathecal 2-chloroprocaine injection". Anesthesia and Analgesia.
- (March 2011). "Chloroprocaine vs. articaine as spinal anaesthetics for day-case knee arthroscopy". Acta Anaesthesiologica Scandinavica.
- (August 2013). "Chloroprocaine 40 mg produces shorter spinal block than articaine 40 mg in day-case knee arthroscopy patients". Acta Anaesthesiologica Scandinavica.
- (April 2011). "Comparison of bupivacaine and 2-chloroprocaine for spinal anesthesia for outpatient surgery: a double-blind randomized trial". Canadian Journal of Anaesthesia.
- (July 1984). "The chloroprocaine controversy: II. Is chloroprocaine neurotoxic?". Regional Anesthesia and Pain Medicine.
- (December 1992). "Lumbar subarachnoid ethylenediaminetetraacetate induces hindlimb tetanic contractions in rats: prevention by CaCl2 pretreatment; observation of spinal nerve root degeneration". Anesthesia and Analgesia.
- (January 2004). "Sodium bisulfite: scapegoat for chloroprocaine neurotoxicity?". Anesthesiology.
- (April 1990). "Occurrence and comparison of sulfite oxidase activity in mammalian tissues". Biochemical Medicine and Metabolic Biology.
- (May 2013). "The use of 2-chloroprocaine for spinal anaesthesia". Acta Anaesthesiologica Scandinavica.
- (21 March 2018). "Drug Approval Package: Clorotekal (chloroprocaine HCl) Injection".
- (5 June 2013). "Rediscovered Local Holds Promise for Spinal Anesthesia". McMahon Publishing.
- (February 1985). "Fetal acidosis, 2-chloroprocaine, and epidural anesthesia for cesarean section". American Journal of Obstetrics and Gynecology.
- (2004). "Obstetric Anesthesia: Principles and Practice". Elsevier Mosby.
- (2002). "Shnider and Levinson's Anesthesia for Obstetrics". Lippincott Williams & Wilkins.
- (January 2006). "Synthesis of Essential Drugs". Elsevier.
- "Preparation method of chloroprocaine hydrochloride".
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