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WordNet

a white crystalline powder (trade name Ethocaine) administered near nerves as a local anesthetic in dentistry and medicine (同)Ethocaine

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パロカイン(局所麻酔な用いる薬品)

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/01/20 17:42:18」(JST)

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"Novocaine" redirects here. For other uses, see Novocaine (disambiguation).

"Allocaine" redirects here. It should not be confused with Allococaine.

Procaine is a local anesthetic drug of the amino ester group. It was used primarily to reduce the pain of intramuscular injection of penicillin, and it was also used in dentistry. Owing to the ubiquity of the trade name Novocain, in some regions procaine is referred to generically as novocaine. It acts mainly by being a sodium channel blocker.^[1]

Procaine was first synthesized in 1905,^[2] shortly after amylocaine.^[3] It was created by the German chemist Alfred Einhorn who gave the chemical the trade name Novocaine, from the Latin nov- (meaning new) and -caine, a common ending for alkaloids used as anesthetics. It was introduced into medical use by surgeon Heinrich Braun. Prior to the discovery of Stovaine and Novocaine, cocaine was the most commonly used local anesthetic.^{[citation needed]}

Pharmacology

Procaine application before removal of a decayed tooth

The primary use for procaine is as a topical anaesthetic.

Procaine is used less frequently today since more effective (and hypoallergenic) alternatives such as lidocaine (Xylocaine) exist. It has been discontinued from US markets.^[4] Like other local anesthetics (such as mepivacaine, and prilocaine), procaine is a vasodilator, and is often coadministered with epinephrine for the purpose of vasoconstriction. Vasoconstriction helps to reduce bleeding and prevents the drug from reaching systemic circulation in large amounts. Unlike cocaine, a vasoconstrictor, procaine does not have the euphoric and addictive qualities that put it at risk for abuse.

Procaine, an ester anesthetic, is metabolized in the plasma by the enzyme pseudocholinesterase through hydrolysis into para-amino benzoic acid (PABA), which is then excreted by the kidneys into the urine.

Procaine is the primary ingredient in the controversial preparation Gerovital H3 by Ana Aslan (Romania), which is claimed by its advocates to remedy many effects of aging. The mainstream medical view is that these claims were seriously studied and discredited in the 1960s.

A 1% procaine injection has been recommended for the treatment of extravasation complications associated with venipuncture (along with moist heat, ASA, steroids, antibiotics). It has likewise been recommended for treatment of inadvertent intra-arterial injections (10 ml of 1% procaine), as it helps relieve pain and vascular spasm.

Procaine is occasionally added as an additive in illicit street drugs such as cocaine.

Adverse effects

Application of procaine leads to the depression of neuronal activity. The depression causes the nervous system to become hypersensitive producing restlessness and shaking, leading to minor to severe convulsions. Studies on animals have shown the use of procaine led to the increase of dopamine and serotonin levels in the brain.^[5] Other issues may occur because of varying individual tolerance to procaine dosage. Nervousness and dizziness can arise from the excitation of the central nervous system, which may lead to respiratory failure if overdosed. Procaine may also induce weakening of the myocardium leading to cardiac arrest.^[6]

Procaine can also cause allergic reactions causing the individuals to have problems with breathing, rashes, and swelling. Allergic reactions to procaine are usually not in response to procaine itself, but to its metabolite PABA. About one in 3000 people have an atypical form of pseudocholinesterase,^{[citation needed]} which does not hydrolyze ester anesthetics such as procaine, resulting in a prolonged period of high levels of the anesthetic in the blood and increased toxicity.

Chemistry

Procaine, the 2-diethylaminoethyl ester of 4-aminobenzoic acid, is synthesized in two ways. The first way consists of the direct reaction of the 4-aminobenzoic acid ethyl ester with 2-diethylaminoethanol in the presence of sodium ethoxide. The second way is by reacting 4-nitrobenzoic acid with thionyl chloride, the resulting acid chloride is then esterified with 2-diethylaminoethanol. Finally, the nitro group is reduced by hydrogenation over Raney nickel catalyst.

References

^ DrugBank - Showing drug card for Procaine (DB00721) Update Date 2009-06-23
^ Ritchie, J. Murdoch; Greene, Nicholas M. (1990). "Local Anesthetics". In Gilman, Alfred Goodman; Rall, Theodore W.; Nies, Alan S. et al.. Goodman and Gilman's The Pharmacological Basis of Therapeutics (8 ed.). New York: Pergamon Press. p. 311. ISBN 0-08-040296-8.
^ R. Minard, "The Preparation of the Local Anesthetic, Benzocaine, by an Esterification Reaction", Adapted from Introduction to Organic Laboratory Techniques: A Microscale Approach, Pavia, Lampman, Kriz & Engel, 1989. Revised 10/18/06
^ Medscape
^ Sawaki, K., and Kawaguchim, M. "Some Correlations between procaine-induced convulsions and monoamides in the spinal cord of rats". Japanese Journal of Pharmacology,51(3), 1989, p. 369-376.
^ http://www.drugs.com/pro/novocain.html - Novocain Official FDA information. Updated(08/2007)

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. 局所麻酔剤の浸潤 infiltration of local anesthetics
3. 眼の待機手術に対する麻酔 anesthesia for elective eye surgery
4. 指神経ブロック digital nerve block
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English Journal

Gene expression of TWIST1 and ZBTB16 is regulated by methylation modifications during the osteoblastic differentiation of mesenchymal stem cells.

Marofi F, Vahedi G, Solali S, Alivand M, Salarinasab S, Zadi Heydarabad M, Farshdousti Hagh M.
Journal of cellular physiology. 2019 May;234(5)6230-6243.
Osteoblastic differentiation of mesenchymal stem cells (MSCs) is the principal stage during the restoration and regeneration of bone tissue. Epigenetic modifications such as DNA methylation play a key role in the differentiation process of stem cells. In this study, the methylation status of the pro
PMID 30246336

Antimicrobial dosing for common equine drugs: a content review and practical advice for veterinarians in Australia.

Hardefeldt LY, Crabb HK, Bailey KE, Gilkerson JR, Billman-Jacobe H, Browning GF.
Australian veterinary journal. 2019 Apr;97(4)103-107.
Appropriate dosing with antimicrobial agents is critical for effective treatment and to prevent the development of antimicrobial resistance. A review was undertaken of equine journal articles (Equine Veterinary Journal, Equine Veterinary Education, Australian Veterinary Journal, Australian Equine Ve
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Interpenetrated polymer network with modified chitosan in composition and self-healing properties.

Rusu AG, Chiriac AP, Nita LE, Bercea M, Tudorachi N, Ghilan A, Pamfil D, Rusu D, Cojocaru FD.
International journal of biological macromolecules. 2019 Mar;132()374-384.
Smart hydrogels endowed with self-healing performance, enhanced stability and unique environmental responsiveness were prepared by interpenetrating the crosslinked poly(2-dimethylaminoethyl methacrylate) between the chains of the water-soluble maleoyl-chitosan. The influence of the ratio between the
PMID 30914372

Japanese Journal

fMLPで誘導されるラット好中球の機能発現に及ぼす局所麻酔薬の影響

家始聡介,東幸雄,智原栄一,柏俣正典
岐阜歯科学会雑誌 = The Journal of Gifu Dental Society 45(1), 9-20, 2018-07
… All three local anesthetics (lidocaine, bupivacaine, and procaine) suppressed superoxide production and chemotaxis in fMLP-stimulated neutrophils, in a concentration-dependent manner. …
NAID 120006536711

Effect of diagnosis and treatment of clinical endometritis based on vaginal discharge score grading system in postpartum Holstein cows

OKAWA Hiroaki,FUJIKURA Atsushi,WIJAYAGUNAWARDANE Missaka M.P.,VOS Peter L.A.M.,TANIGUCHI Masayasu,TAKAGI Mitsuhiro
Ｔｈｅ　Ｊｏｕｒｎａｌ　ｏｆ　Ｖｅｔｅｒｉｎａｒｙ　Ｍｅｄｉｃａｌ　Ｓｃｉｅｎｃｅ 79(9), 1545-1551, 2017
… Cows treated with PGF2α that did not recover (VDS≥1, n=5) received intrauterine procaine penicillin and streptomycin. …
NAID 130006073251

Lipid peroxidation - inhibitory effects of perioperatively used drugs associated with their membrane interactions.

Tsuchiya Hironori,Department of Dental Basic Education Asahi University School of Dentistry Mizuho Japan.
Oxidants and antioxidants in medical science 3(2), 91-98, 2014-05-02
… The inhibition at 10 μM was greatest in propofol, followed by guaiacol, thiopental, thymol, phenol, midazolam, diazepam, lidocaine, eugenol, procaine, bupivacaine, ropivacaine, sevoflurane, ketamine, mepivacaine and prilocaine. …
NAID 120005603155

Related Pictures

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★リンクテーブル★

リンク元	「神経筋接合部」「プロカイン」
拡張検索	「chloroprocaine」「chloroprocaine hydrochloride」「procaine penicillin G」「oxybuprocaine」

「神経筋接合部」

Procaine
Systematic (IUPAC) name
	2-(diethylamino)ethyl 4-aminobenzoate
Clinical data
AHFS/Drugs.com	monograph
Pregnancy cat.	B2 (AU) C (US)
Legal status	Prescription Only (S4) (AU)
Routes	Parenteral
Pharmacokinetic data
Bioavailability	n/a
Metabolism	Hydrolysis by plasma esterases
Half-life	40–84 seconds
Excretion	Renal
Identifiers
CAS number	59-46-1
ATC code	N01BA02 C05AD05 S01HA05
PubChem	CID 4914
IUPHAR ligand	4291
DrugBank	DB00721
ChemSpider	4745
UNII	4Z8Y51M438
KEGG	D08422
ChEBI	CHEBI:8430
ChEMBL	CHEMBL569
NIAID ChemDB	019136
Chemical data
Formula	C13H20N2O2
Mol. mass	236.31 g/mol
	SMILES O=C(OCCN(CC)CC)c1ccc(N)cc1;
	InChI InChI=1S/C13H20N2O2/c1-3-15(4-2)9-10-17-13(16)11-5-7-12(14)8-6-11/h5-8H,3-4,9-10,14H2,1-2H3 ; Key:MFDFERRIHVXMIY-UHFFFAOYSA-N ;
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　　[★]

英: neuromuscular junction (K)
同: 神経筋シナプス neuromuscular synapse

神経筋接合部は軸索終末，シナプス間隙，筋細胞膜から構成される。

神経筋接合部に作用する薬物 (GPC.225)

	＋	－
神経活動電位発生		tetrodotoxin
神経活動電位発生		batrachotoxin
アセチルコリン放出	excess of Ca2+	hemicholinium
		botulinus toxin
		procaine
		Mg2+
		4-aminopyridine
		lack of Ca2+
終板電位発生	succinylcholine(suxamethonium)	curare alkaloids
終板電位発生	decamethonium	α-toxins
アセチルコリン加水分解	cholinesterase inhibitors
筋活動電位発生	veratridine	quinine
筋活動電位発生	veratridine	tetrodotoxin
筋収縮		procaine
筋収縮		dantrolene