Chloroprocaine

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Chloroprocaine
Chloroprocaine.svg
Clinical data
Trade names Nesacaine, others
AHFS/Drugs.com
License data
Routes of
administration
Intrathecal, eye drop
Drug class Local anesthetic
ATC code
Legal status
Legal status
Identifiers
  • 2-diethylaminoethyl-4-amino-2-chloro-benzoate
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C13H19ClN2O2
Molar mass 270.76 g·mol−1
3D model (JSmol)
  • CCN(CC)CCOC(=O)C1=C(Cl)C=C(N)C=C1

  • Cl.CCN(CC)CCOC(=O)C1=C(Cl)C=C(N)C=C1
  • 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 Yes check.svgY
  • Key:VDANGULDQQJODZ-UHFFFAOYSA-N Yes check.svgY

  • 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
  • Key:SZKQYDBPUCZLRX-UHFFFAOYSA-N
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Chloroprocaine, sold under the brand name Nesacaine among others is a local anesthetic given by injection. [2] It is used as the hydrochloride salt. [4] Chloroprocaine is a local anesthetic. [2] [4]

Contents

Medical uses

Chloroprocaine (Nesacaine) is indicated for the production of local anesthesia by infiltration and peripheral nerve block; [2] and for the production of local anesthesia by infiltration, peripheral and central nerve block, including lumbar and caudal epidural blocks. [2]

Chloroprocaine (Clorotekal) is indicated for intrathecal injection in adults for the production of subarachnoid block (spinal anesthesia). [4]

Chloroprocaine is used for regional anesthesia including spinal anesthesia, caudal anesthesia and epidural anesthesia. [6] [7]

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. [7]

It is also used for obstetric anesthesia including pudendal nerve block and paracervical block. [7]

Chloroprocaine (Iheezo) is indicated for ocular surface anesthesia. [3]

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. [8]

The use of chloroprocaine in the subarachnoid space has been questioned. [9] In the early 1980s, several cases were reported of neurological deficits after inadvertent intrathecal injections intended for epidural delivery. [10] These doses were an order of magnitude higher than is currently used for intrathecal delivery. [11] [12] [13] It is also thought that these deficits were also related to the preservative sodium bisulfite, [14] [15] although this is also controversial. [16] [17]

Some studies have been published on the safe use of intrathecal chloroprocaine when appropriate dosage is used and with preservative-free preparations. [18] [12]

It is approved for intrathecal use in the United States, [19] Europe, [20] and Canada. [1]

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. [21]

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. [22] [23]

Synthesis

Chloroprocaine synthesis: H.C. Marks, H.I. Rubin, U.S. patent 2,460,139 (1949 to Wallace & Tiernan Inc). Chloroprocaine synthesis.png
Chloroprocaine synthesis: H.C. Marks, H.I. Rubin, U.S. patent 2,460,139 (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. [24] Synthesis of this drug is then accomplished by directly reacting the product of the last step with the hydrochloride salt of 2-diethylaminoethanol.

Related Research Articles

<span class="mw-page-title-main">Anesthesia</span> State of medically-controlled temporary loss of sensation or awareness

Anesthesia or anaesthesia is a state of controlled, temporary loss of sensation or awareness that is induced for medical or veterinary purposes. It may include some or all of analgesia, paralysis, amnesia, and unconsciousness. An individual under the effects of anesthetic drugs is referred to as being anesthetized.

<span class="mw-page-title-main">Local anesthetic</span> Medications to reversibly block pain

A local anesthetic (LA) is a medication that causes absence of all sensation in a specific body part without loss of consciousness, providing local anesthesia, as opposed to a general anesthetic, which eliminates all sensation in the entire body and causes unconsciousness. Local anesthetics are most commonly used to eliminate pain during or after surgery. When it is used on specific nerve pathways, paralysis also can be induced.

<span class="mw-page-title-main">Lidocaine</span> Local anesthetic

Lidocaine, also known as lignocaine and sold under the brand name Xylocaine among others, is a local anesthetic of the amino amide type. It is also used to treat ventricular tachycardia and ventricular fibrillation. When used for local anaesthesia or in nerve blocks, lidocaine typically begins working within several minutes and lasts for half an hour to three hours. Lidocaine mixtures may also be applied directly to the skin or mucous membranes to numb the area. It is often used mixed with a small amount of adrenaline (epinephrine) to prolong its local effects and to decrease bleeding.

<span class="mw-page-title-main">General anaesthesia</span> Medically induced loss of consciousness

General anaesthesia (UK) or general anesthesia (US) is medically induced loss of consciousness that renders a patient unarousable even by painful stimuli. It is achieved through medications, which can be injected or inhaled, often with an analgesic and neuromuscular blocking agent.

<span class="mw-page-title-main">Spinal anaesthesia</span> Form of neuraxial regional anaesthesia

Spinal anaesthesia, also called spinal block, subarachnoid block, intradural block and intrathecal block, is a form of neuraxial regional anaesthesia involving the injection of a local anaesthetic or opioid into the subarachnoid space, generally through a fine needle, usually 9 cm (3.5 in) long. It is a safe and effective form of anesthesia usually performed by anesthesiologists that can be used as an alternative to general anesthesia commonly in surgeries involving the lower extremities and surgeries below the umbilicus. The local anesthetic with or without an opioid injected into the cerebrospinal fluid provides locoregional anaesthesia: true anaesthesia, motor, sensory and autonomic (sympathetic) blockade. Administering analgesics in the cerebrospinal fluid without a local anaesthetic produces locoregional analgesia: markedly reduced pain sensation, some autonomic blockade, but no sensory or motor block. Locoregional analgesia, due to mainly the absence of motor and sympathetic block may be preferred over locoregional anaesthesia in some postoperative care settings. The tip of the spinal needle has a point or small bevel. Recently, pencil point needles have been made available.

Combined spinal and epidural anaesthesia is a regional anaesthetic technique, which combines the benefits of both spinal anaesthesia and epidural anaesthesia and analgesia. The spinal component gives a rapid onset of a predictable block. The indwelling epidural catheter gives the ability to provide long lasting analgesia and to titrate the dose given to the desired effect.

<span class="mw-page-title-main">Epidural administration</span> Medication injected into the epidural space of the spine

Epidural administration is a method of medication administration in which a medicine is injected into the epidural space around the spinal cord. The epidural route is used by physicians and nurse anesthetists to administer local anesthetic agents, analgesics, diagnostic medicines such as radiocontrast agents, and other medicines such as glucocorticoids. Epidural administration involves the placement of a catheter into the epidural space, which may remain in place for the duration of the treatment. The technique of intentional epidural administration of medication was first described in 1921 by Catalan military surgeon Fidel Pagés.

<span class="mw-page-title-main">Intrathecal administration</span> Drug injected into the spinal canal

Intrathecal administration is a route of administration for drugs via an injection into the spinal canal, or into the subarachnoid space so that it reaches the cerebrospinal fluid (CSF). It is useful in several applications, such as for spinal anesthesia, chemotherapy, or pain management. This route is also used to introduce drugs that fight certain infections, particularly post-neurosurgical. Typically, the drug is given this way to avoid being stopped by the blood–brain barrier, as it may not be able to pass into the brain when given orally. Drugs given by the intrathecal route often have to be compounded specially by a pharmacist or technician because they cannot contain any preservative or other potentially harmful inactive ingredients that are sometimes found in standard injectable drug preparations.

<span class="mw-page-title-main">Bupivacaine</span> Local anaesthetic drug

Bupivacaine, marketed under the brand name Marcaine among others, is a medication used to decrease sensation in a specific small area. In nerve blocks, it is injected around a nerve that supplies the area, or into the spinal canal's epidural space. It is available mixed with a small amount of epinephrine to increase the duration of its action. It typically begins working within 15 minutes and lasts for 2 to 8 hours.

<span class="mw-page-title-main">Nerve block</span> Deliberate inhibition of nerve impulses

Nerve block or regional nerve blockade is any deliberate interruption of signals traveling along a nerve, often for the purpose of pain relief. Local anesthetic nerve block is a short-term block, usually lasting hours or days, involving the injection of an anesthetic, a corticosteroid, and other agents onto or near a nerve. Neurolytic block, the deliberate temporary degeneration of nerve fibers through the application of chemicals, heat, or freezing, produces a block that may persist for weeks, months, or indefinitely. Neurectomy, the cutting through or removal of a nerve or a section of a nerve, usually produces a permanent block. Because neurectomy of a sensory nerve is often followed, months later, by the emergence of new, more intense pain, sensory nerve neurectomy is rarely performed.

<span class="mw-page-title-main">Levobupivacaine</span> Chemical compound

Levobupivacaine (rINN) is a local anaesthetic drug indicated for minor and major surgical anaesthesia and pain management. It is a long-acting amide-type local anaesthetic that blocks nerve impulses by inhibiting sodium ion influx into the nerve cells. Levobupivacaine is the S-enantiomer of racemic bupivacaine and therefore similar in pharmacological effects. The drug typically starts taking effect within 15 minutes and can last up to 16 hours depending on factors such as site of administration and dosage.

Dental anesthesia is the application of anesthesia to dentistry. It includes local anesthetics, sedation, and general anesthesia.

<span class="mw-page-title-main">Post-dural-puncture headache</span> Common side effect of lumbar puncture or spinal anaesthesia

Post-dural-puncture headache (PDPH) is a complication of puncture of the dura mater. The headache is severe and described as "searing and spreading like hot metal", involving the back and front of the head and spreading to the neck and shoulders, sometimes involving neck stiffness. It is exacerbated by movement and sitting or standing and is relieved to some degree by lying down. Nausea, vomiting, pain in arms and legs, hearing loss, tinnitus, vertigo, dizziness and paraesthesia of the scalp are also common.

<span class="mw-page-title-main">Epidural blood patch</span> Blood injected epidurally to resolve a cerebrospinal fluid leak

An epidural blood patch (EBP) is a surgical procedure that uses autologous blood, meaning the patient's own blood, in order to close one or many holes in the dura mater of the spinal cord, which occurred as a complication of a lumbar puncture or epidural placement. The punctured dura causes cerebrospinal fluid leak. The procedure can be used to relieve orthostatic headaches, most commonly post dural puncture headache (PDPH).

<span class="mw-page-title-main">Thecal sac</span> Tubular sheath of dura mater that surrounds the spinal cord and cauda equina

The thecal sac or dural sac is the membranous sheath (theca) or tube of dura mater that surrounds the spinal cord and the cauda equina. The thecal sac contains the cerebrospinal fluid which provides nutrients and buoyancy to the spinal cord. From the skull the tube adheres to bone at the foramen magnum and extends down to the second sacral vertebra where it tapers to cover over the filum terminale. Along most of the spinal canal it is separated from the inner surface by the epidural space. The sac has projections that follow the spinal nerves along their paths out of the vertebral canal which become the dural root sheaths.

<span class="mw-page-title-main">Brachial plexus block</span> Medical intervention

Brachial plexus block is a regional anesthesia technique that is sometimes employed as an alternative or as an adjunct to general anesthesia for surgery of the upper extremity. This technique involves the injection of local anesthetic agents in close proximity to the brachial plexus, temporarily blocking the sensation and ability to move the upper extremity. The subject can remain awake during the ensuing surgical procedure, or they can be sedated or even fully anesthetized if necessary.

<span class="mw-page-title-main">History of neuraxial anesthesia</span>

The history of neuraxial anaesthesia dates back to the late 1800s and is closely intertwined with the development of anaesthesia in general. Neuraxial anaesthesia, in particular, is a form of regional analgesia placed in or around the Central Nervous System, used for pain management and anaesthesia for certain surgeries and procedures.

<span class="mw-page-title-main">James Leonard Corning</span> American physician

James Leonard Corning was an American neurologist, mainly known for his early experiments on neuraxial blockade in New York City.

Obstetric anesthesia or obstetric anesthesiology, also known as ob-gyn anesthesia or ob-gyn anesthesiology, is a sub-specialty of anesthesiology that provides peripartum pain relief (analgesia) for labor and anesthesia for cesarean deliveries ('C-sections').

<span class="mw-page-title-main">Caudal anaesthesia</span> Form of neuraxial regional anaesthesia

Caudal anaesthesia is a form of neuraxial regional anaesthesia conducted by accessing the epidural space via the sacral hiatus. It is typically used in paediatrics to provide peri- and post-operative analgesia for surgeries below the umbilicus. In adults, it can be used in the context of anorectal surgery or for chronic low back pain management.

References

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