Chloroprocaine, sold under the brand nameNesacaine among others is alocal anesthetic given byinjection.[2] It is used as the hydrochloride salt.[4] Chloroprocaine is a local anesthetic.[2][4]
Chloroprocaine (Nesacaine) isindicated 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 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 thesubarachnoid 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 preservativesodium 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]
Amide-linked local anesthetic agents, such aslidocaine andbupivacaine, can become "trapped" in their ionized forms on the fetal side of theplacenta, 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 forepidural 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]
Thein vitrohalf-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]
The hydrochloride salt of 4-amino-2-chlorobenzoyl chloride is made by the reaction of 2-chloro-4-aminobenzoic acid withthionyl chloride.[24] Synthesis of this drug is then accomplished by directly reacting the product of the last step with the hydrochloride salt of2-diethylaminoethanol.[25]
^Palas T (2009). "Ampres (chloroprocaine) Summary of Product Characteristics".Perimed.3 (2):31–34.Cloroprocaina in chirurgia ambulatoriale: uno studio osservazionale
^Cabré F, Marín C, Cascante M, Canela EI (April 1990). "Occurrence and comparison of sulfite oxidase activity in mammalian tissues".Biochemical Medicine and Metabolic Biology.43 (2):159–62.doi:10.1016/0885-4505(90)90021-r.PMID2346671.
^Goldblum E, Atchabahian A (May 2013). "The use of 2-chloroprocaine for spinal anaesthesia".Acta Anaesthesiologica Scandinavica.57 (5):545–52.doi:10.1111/aas.12071.PMID23320599.S2CID525005.
^Philipson EH, Kuhnert BR, Syracuse CD (February 1985). "Fetal acidosis, 2-chloroprocaine, and epidural anesthesia for cesarean section".American Journal of Obstetrics and Gynecology.151 (3):322–4.doi:10.1016/0002-9378(85)90295-9.PMID3970100.
^Chestnut DH (2004).Obstetric Anesthesia: Principles and Practice (3rd ed.). Philadelphia: Elsevier Mosby. p. 333.ISBN978-0-323-02357-3.
^Hughes SC, Levinson G, Rosen MA, eds. (2002).Shnider and Levinson's Anesthesia for Obstetrics (4th ed.). Philadelphia: Lippincott Williams & Wilkins. p. 75.ISBN978-0-683-30665-1.
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