関: chloroprocaine hydrochloride

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Chloroprocaine (trade name Nesacaine, Nesacaine-MPF) (often in the hydrochloride salt form as the aforementioned trade names) is a local anesthetic given by injection during surgical procedures and labor and delivery. Chloroprocaine vasodilates; this is in contrast to cocaine which vasoconstrics. Chloroprocaine is an ester anesthetic.^[1]

Sub-arachnoid block or SAB

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 without TNS.

These data are based upon a retrospective review of 672 patients suitable for spinal anaesthesia in surgical procedures of less than 60 minutes duration using 30–40 mg chloroprocaine. The results showed good surgical anaesthesia, a fast onset time and post-operative mobilization after 90 minutes without complications.^[2]

The use of chloroprocaine in the subarachnoid space has been questioned.^[3] In the early 1980s, there were several case reports of neurological deficits after inadvertent intrathecal injections intended for epidural delivery.^[4] These doses were an order of magnitude higher than is currently used for intrathecal delivery.^[5]^[6]^[7] It is also thought that these deficits were also related to the preservative sodium bisulfate,^[8]^[9] although this is also controversial.^[10]^[11]

In recent years, several studies have been published on the safe use of intrathecal chloroprocaine when appropriate dosage is used and with preservative-free preparations.^[12]^[13]

It is currently not FDA approved ^[14] in the United States for intrathecal use but is approved in Europe.^[15]

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, and therefore their net transfer across the placenta is increased. An ester-linked local anesthetic agent, 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.^[16]

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.^[17]^[18]

It is not used in intravenous regional anesthesia due to the risk of thrombophlebitis.^{[citation needed]}

Chemistry

Synthesis of this drug is accomplished by directly reacting the hydrochloride salt of 4-amino-2-chlorobenzoyl chloride with the hydrochloride salt of 2-diethylaminoethanol. The hydrochloride salt of 4-amino-2-chlorobenzoyl chloride is synthesized by reacting 2-chloro-4-aminobenzoic acid with thionyl chloride.

Chloroprocaine synthesis: H.C. Marks, H.I. Rubin, U.S. Patent 2,460,139 (1949).

References

^ Drug bank entry for Chloroprocaine
^ Ampres (chloroprocaine) Summary of Product Characteristics, Palas T, Cloroprocaina in chirurgia ambulatoriale: uno studio osservazionale, Perimed 2009, 3(2):31-34
^ Drasner K. Chloroprocaine spinal anesthesia: back to the future? Anes analg 2005; 100: 549-52.
^ Reisner, Laurence S., Bruce N. Hochman, and Michael H. Plumer. "Persistent neurologic deficit and adhesive arachnoiditis following intrathecal 2-chloroprocaine injection." Anesthesia & Analgesia 59.6 (1980): 452-454
^ Förster, J. G., et al. "Chloroprocaine vs. articaine as spinal anaesthetics for day‐case knee arthroscopy." Acta Anaesthesiologica Scandinavica 55.3 (2011): 273-281.
^ Förster, J. G., et al. "Chloroprocaine 40 mg produces shorter spinal block than articaine 40 mg in day‐case knee arthroscopy patients." Acta Anaesthesiologica Scandinavica (2013).
^ Lacasse, Marie-Andrée, et al. "Comparison of bupivacaine and 2-chloroprocaine for spinal anesthesia for outpatient surgery: a double-blind randomized trial." Canadian Journal of Anesthesia/Journal canadien d'anesthésie 58.4 (2011): 384-391.
^ Gissen, Aaron J., Sanjay Datta, and Donald Lambert. "The Chloroprocaine Controversy: II. Is Chloroprocaine Neurotoxic?." Regional Anesthesia and Pain Medicine 9.3 (1984): 135-145.
^ Wang, B. C., et al. "Lumbar Subarachnoid Ethylenediaminetetraacetate Induces Hindlimb Tetanic Contractions in Rats Prevention by CaCl2 Pretreatment; Observation of Spinal Nerve Root Degeneration." Anesthesia & Analgesia 75.6 (1992): 895-899.
^ Taniguchi, Masahiko, Andrew W. Bollen, and Kenneth Drasner. "Sodium bisulfite: scapegoat for chloroprocaine neurotoxicity?." Anesthesiology 100.1 (2004): 85-91.
^ Cabré, Francesc, et al. "Occurrence and comparison of sulfite oxidase activity in mammalian tissues." Biochemical medicine and metabolic biology 43.2 (1990): 159-162.
^ Goldblum, E., and A. Atchabahian. "The use of 2‐chloroprocaine for spinal anaesthesia." Acta Anaesthesiologica Scandinavica (2013).
^ Förster, J. G., et al. "Chloroprocaine 40 mg produces shorter spinal block than articaine 40 mg in day‐case knee arthroscopy patients." Acta Anaesthesiologica Scandinavica (2013).
^ Pollock, Julia E. "Intrathecal Chloroprocaine—Not yet “Safe” by US FDA Parameters." International Anesthesiology Clinics 50.1 (2012): 93-100.
^ http://www.anesthesiologynews.com/ViewArticle.aspx?d=Clinical+Anesthesiology&d_id=1&i=June+2013&i_id=962&a_id=23319
^ Philipson EH, Kuhnert BR, Syracuse CD. Fetal acidosis, 2-chloroprocaine, and epidural anesthesia for cesarean section. Am J Obstet Gynecol. 1985 Feb 1;151(3):322-4.
^ Chestnut: Obstetric Anesthesia, 3rd ed, p333.
^ Hughes: Anesthesia for Obstetrics, 4th ed, p75.

UpToDate Contents

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1. 局所麻酔剤に対するアレルギー反応 allergic reactions to local anesthetics
2. 陣痛および分娩に対する硬膜外・脊椎麻酔：薬 neuraxial analgesia and anesthesia for labor and delivery drugs
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4. 末梢神経ブロックの概要 overview of peripheral nerve blocks
5. 陰部神経ブロックおよび傍子宮頸管ブロック pudendal and paracervical block

English Journal

Intrathecal 1% 2-chloroprocaine vs. 0.5% bupivacaine in ambulatory surgery: a prospective, observer-blinded, randomised, controlled trial.

Camponovo C1, Wulf H, Ghisi D, Fanelli A, Riva T, Cristina D, Vassiliou T, Leschka K, Fanelli G.Author information 1Department of Anaesthesiology, Regional Hospital, Lugano, Switzerland.AbstractBACKGROUND: This prospective, observer-blinded, randomised, multicentre study aimed at determining the non-inferiority of 50 mg of plain 1% 2-chloroprocaine vs. 10 mg of 0.5% plain bupivacaine in terms of sensory block onset time at T10 after spinal injection. The study hypothesis was that the difference in onset times of sensory block to T10 between the two drugs is ≤ 4 min.
Acta anaesthesiologica Scandinavica.Acta Anaesthesiol Scand.2014 Mar 6. doi: 10.1111/aas.12291. [Epub ahead of print]
BACKGROUND: This prospective, observer-blinded, randomised, multicentre study aimed at determining the non-inferiority of 50 mg of plain 1% 2-chloroprocaine vs. 10 mg of 0.5% plain bupivacaine in terms of sensory block onset time at T10 after spinal injection. The study hypothesis was that the d
PMID 24601887

Intrathecal chloroprocaine vs. lidocaine in day-case surgery: recovery, discharge and effect of pre-hydration on micturition.

Breebaart MB, Teune A, Sermeus LA, Vercauteren MP.AbstractBACKGROUND: This randomised, double blind prospective study compares intrathecal lidocaine with chloroprocaine in day-case surgery and the influence of a 500 ml pre-load intravenously. We tested the hypothesis that chloroprocaine provides faster recovery and discharge in day-case surgery. Secondary we studied the influence of a preload compared with fluid restriction on discharge time and micturition problems.
Acta anaesthesiologica Scandinavica.Acta Anaesthesiol Scand.2014 Feb;58(2):206-13. doi: 10.1111/aas.12247.
BACKGROUND: This randomised, double blind prospective study compares intrathecal lidocaine with chloroprocaine in day-case surgery and the influence of a 500 ml pre-load intravenously. We tested the hypothesis that chloroprocaine provides faster recovery and discharge in day-case surgery. Secondary
PMID 24563922

The effect of different doses of chloroprocaine on saddle anesthesia in perianal surgery.

Zhang Y, Bao Y, Li L, Shi D.Author information Shanghai Jiading Central Hospital, Department of Anesthesiology, Shanghai, China.AbstractPURPOSE: To investigate a saddle anesthesia with different doses of chloroprocaine in perianal surgery.
Acta cirúrgica brasileira / Sociedade Brasileira para Desenvolvimento Pesquisa em Cirurgia.Acta Cir Bras.2014 Jan;29(1):66-70. doi: 10.1590/S0102-86502014000100010.
PURPOSE: To investigate a saddle anesthesia with different doses of chloroprocaine in perianal surgery.METHODS: Total 60 Patients aged 18-75 years (Anesthesiologists grade I or II) scheduled to receive perianal surgery. Patients using saddle anesthesia were randomized to group A, group B and group C
PMID 24474180

Japanese Journal

Effects of concentration and volume of 2-chloroprocaine on epidural anesthesia in volunteers

LIU SS
Anesthesiology 86, 1288-1293, 1997
NAID 30009127683

Rapid determination of chloroprocaine and its major metabolite, 2-chloroaminobenzoic acid, in plasma by high-performance liquid chromatography

JANICKI P. K.,JOHNSON R.,KAMBAM J. R.
Journal of chromatography. B, Biomedical applications 675(2), 336-341, 1996-01-26
NAID 10024552573

Chloroprocaine antagonism of epidural opioid analgesia : a receptor-specific phenomenon?

CAMANN WR
Anesthesiology 73, 860-863, 1990
NAID 30009153146

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リンク元	「クロロプロカイン」
拡張検索	「chloroprocaine hydrochloride」

「クロロプロカイン」

Chloroprocaine
Systematic (IUPAC) name
	2-diethylaminoethyl-4-amino-2-chloro-benzoate
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Identifiers
CAS Registry Number	133-16-4
ATC code	N01BA04
PubChem	CID: 8612
DrugBank	DB01161
ChemSpider	8293
UNII	5YVB0POT2H
KEGG	D07678
ChEBI	CHEBI:3636
ChEMBL	CHEMBL1179047
Chemical data
Formula	C13H19ClN2O2
Molecular mass	270.755 g/mol
	SMILES O=C(OCCN(CC)CC)c1ccc(cc1Cl)N;
	InChI 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 ; Key:VDANGULDQQJODZ-UHFFFAOYSA-N ;
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英: chloroprocaine、chloroprocaine hydrochloride
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関: chloroprocaine

[1] Drug bank entry for Chloroprocaine

[2] Ampres (chloroprocaine) Summary of Product Characteristics, Palas T, Cloroprocaina in chirurgia ambulatoriale: uno studio osservazionale, Perimed 2009, 3(2):31-34

[3] Drasner K. Chloroprocaine spinal anesthesia: back to the future? Anes analg 2005; 100: 549-52.

[4] Reisner, Laurence S., Bruce N. Hochman, and Michael H. Plumer. "Persistent neurologic deficit and adhesive arachnoiditis following intrathecal 2-chloroprocaine injection." Anesthesia & Analgesia 59.6 (1980): 452-454

[5] Förster, J. G., et al. "Chloroprocaine vs. articaine as spinal anaesthetics for day‐case knee arthroscopy." Acta Anaesthesiologica Scandinavica 55.3 (2011): 273-281.

[6] Förster, J. G., et al. "Chloroprocaine 40 mg produces shorter spinal block than articaine 40 mg in day‐case knee arthroscopy patients." Acta Anaesthesiologica Scandinavica (2013).

[7] Lacasse, Marie-Andrée, et al. "Comparison of bupivacaine and 2-chloroprocaine for spinal anesthesia for outpatient surgery: a double-blind randomized trial." Canadian Journal of Anesthesia/Journal canadien d'anesthésie 58.4 (2011): 384-391.

[8] Gissen, Aaron J., Sanjay Datta, and Donald Lambert. "The Chloroprocaine Controversy: II. Is Chloroprocaine Neurotoxic?." Regional Anesthesia and Pain Medicine 9.3 (1984): 135-145.

[9] Wang, B. C., et al. "Lumbar Subarachnoid Ethylenediaminetetraacetate Induces Hindlimb Tetanic Contractions in Rats Prevention by CaCl2 Pretreatment; Observation of Spinal Nerve Root Degeneration." Anesthesia & Analgesia 75.6 (1992): 895-899.

[10] Taniguchi, Masahiko, Andrew W. Bollen, and Kenneth Drasner. "Sodium bisulfite: scapegoat for chloroprocaine neurotoxicity?." Anesthesiology 100.1 (2004): 85-91.

[11] Cabré, Francesc, et al. "Occurrence and comparison of sulfite oxidase activity in mammalian tissues." Biochemical medicine and metabolic biology 43.2 (1990): 159-162.

[12] Goldblum, E., and A. Atchabahian. "The use of 2‐chloroprocaine for spinal anaesthesia." Acta Anaesthesiologica Scandinavica (2013).

[13] Förster, J. G., et al. "Chloroprocaine 40 mg produces shorter spinal block than articaine 40 mg in day‐case knee arthroscopy patients." Acta Anaesthesiologica Scandinavica (2013).

[14] Pollock, Julia E. "Intrathecal Chloroprocaine—Not yet “Safe” by US FDA Parameters." International Anesthesiology Clinics 50.1 (2012): 93-100.

[15] ttp://www.anesthesiologynews.com/ViewArticle.aspx?d=Clinical+Anesthesiology&d_id=1&i=June+2013&i_id=962&a_id=23319

[16] Philipson EH, Kuhnert BR, Syracuse CD. Fetal acidosis, 2-chloroprocaine, and epidural anesthesia for cesarean section. Am J Obstet Gynecol. 1985 Feb 1;151(3):322-4.

[17] Chestnut: Obstetric Anesthesia, 3rd ed, p333.

[18] Hughes: Anesthesia for Obstetrics, 4th ed, p75.

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chloroprocaine