WordNet

send a message from one computer to another to check whether it is reachable and active; "ping your machine in the office"
a sharp high-pitched resonant sound (as of a sonar echo or a bullet striking metal)
contact, usually in order to remind of something; "Ill ping my accountant--April 15 is nearing"
hit with a pinging noise; "The bugs pinged the lamp shade"
make a short high-pitched sound; "the bullet pinged when they struck the car"
the 16th letter of the Roman alphabet (同)p
the univalent hydrocarbon radical C2H5 derived from ethane by the removal of one hydrogen atom (同)ethyl_group, ethyl radical

PrepTutorEJDIC

(小銃弾などの)ピュー(ブーン)という音 / ピュー(ブーン)と音がする
parking
phosphorusの化学記号
エチル / エチルの

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/10/28 00:36:43」(JST)

wiki en

Benzocaine is a local anesthetic commonly used as a topical pain reliever or in cough drops. It is the active ingredient in many over-the-counter anesthetic ointments such as products for oral ulcers. It is also combined with antipyrine to form A/B otic drops to relieve ear pain and remove earwax.

Chemical properties

Benzocaine is the ethyl ester of p-aminobenzoic acid (PABA). It can be prepared from PABA and ethanol^[1] by Fischer esterification or via the reduction of ethyl p-nitrobenzoate. Benzocaine is sparingly soluble in water; it is more soluble in dilute acids and very soluble in ethanol, chloroform and ethyl ether. The melting point of benzocaine is 88–90 °C,^[2] and the boiling point is about 310 °C.^[3] The density of benzocaine is 1.17 g/cm³.

History

Benzocaine was first synthesized in 1890 by the German chemist Eduard Ritsert (1859–1946),^[4] in the town of Eberbach^[5] and introduced to the market in 1902 under the name "Anästhesin".^[6]^[7]

Mechanism of action

Pain is caused by the stimulation of free nerve endings. When the nerve endings are stimulated, sodium enters the neuron, causing depolarization of the nerve and subsequent initiation of an action potential. The action potential is propagated down the nerve toward the central nervous system, which interprets this as pain. Benzocaine acts to inhibit the voltage-dependent sodium channels (VDSCs) on the nerve membrane, stopping the propagation of the action potential.

Side effects

Over-application of oral anesthetics such as benzocaine can increase the risk of pulmonary aspiration by relaxing the gag-reflex and allowing regurgitated stomach contents or oral secretions to enter the airway. Applying an oral anesthetic and consuming beverages before going to bed can be particularly hazardous. The oral use of benzocaine products has been found to be a cause of methemoglobinemia, a disorder in which the amount of oxygen carried by the blood is greatly reduced. This side effect is most common in children under 2 years of age.^[8]

Benzocaine may cause allergic reactions.^[9]^[10]^[11]^[12]

Other uses

Jiffy Toothache Drops bottle (7.75% Benzocaine)

Benzocaine is used as a key ingredient in numerous pharmaceuticals:

Over the counter throat lozenges such as Cepacol.
Some glycerol-based ear medications for use in removing excess wax as well as relieving ear conditions such as otitis media and swimmers ear.
Some previous diet products such as Ayds.
Some condoms designed to prevent premature ejaculation. Benzocaine largely inhibits sensitivity on the penis, and can allow for an erection to be maintained longer (in a continuous act) by delaying ejaculation. Conversely, an erection will also fade faster if stimulus is interrupted.^[13]^[14]
Benzocaine mucoadhesive patches have been used in reducing orthodontic pain.^[15]
In Poland it is included, together with menthol and zinc oxide, in the liquid powder (not to be confused with the liquid face powder) used mainly after mosquito stings. Today's ready made Pudroderm^[16] was once used there as pharmaceutical compound.

Benzocaine is commonly found, particularly in Britain, as an impurity in street cocaine. Whilst giving a numbing effect similar to cocaine on users' gums it does not actually produce the effects of cocaine. But in terms of an orally based saliva drug test benzocaine can and has been mistaken for a false positive for cocaine.^[17]

References

^ Demare, Patricia; Regla, Ignacio (2012). "Synthesis of Two Local Anesthetics from Toluene: An Organic Multistep Synthesis in a Project-Oriented Laboratory Course". Journal of Chemical Education 89: 147. doi:10.1021/ed100838a.
^ "Monographs: Pharmaceutical substances: Benzocainum – Benzocaine". The International Pharmacopoeia. Retrieved September 29, 2009.
^ D'Ans-Lax, Taschenbuch für Chemiker und Physiker, 4. Auflage, Band 2, Springer Verlag 1982, ISBN 3-540-12263-X
^ Biography of Eduard Ritsert (in German): Deutsche Biographie: Ritsert, Eduard .
^ "100 years of Dr. Ritsert". Dr. Ritsert Pharma. Retrieved March 14, 2010.
^ Harry Auterhoff, Lehrbuch der pharmazeutischen Chemie (Stuttgart, Germany: Wissenschaftliche Verlagsgesellschaft, 1968).
^ Ritsert, E. (1925) "Über den Werdegang des Anästhesins" (On the development of Anästhesin), Pharmazeutische Zeitung, vol. 60, pages 1006–1008. See also: Christoph Friedrich and Magdalena Klimonow, "150. Geburtstag: Eduard Ritsert und das Anaesthesin" (150th birthday: Eduard Ritsert and Anästhetsin [Benzocaine]"), Pharmazeutische Zeitung online. First published clinical study demonstrating the efficacy of benzocaine: Noorden, C. v. (1902) "Ueber para-Aminobenzoesäure-Ester als locales Anästhetikum" (On [an] ester of para-aminobenzoic acid as a local anaesthetic), Klinische Wochenschrift, vol. 39, pages 373–375.
^ "Benzocaine Topical Products: Sprays, Gels and Liquids – Risk of Methemoglobinemia". Drugs.com. Retrieved March 20, 2014.
^ ".". Retrieved March 20, 2014.
^ "A 10-year retrospective study on benzoca... [Am J Contact Dermat. 1999". Ncbi.nlm.nih.gov. January 24, 2014. Retrieved March 20, 2014.
^ ".". Retrieved March 20, 2014.
^ By Leslie Goldman (February 5, 2008). "Go easy on medicated lotions, creams, gels". CNN. Retrieved March 20, 2014.
^ "'Longer-lasting' condom launched". BBC News. June 17, 2002.
^ Garner, Dwight (December 15, 2002). "Endurance Condoms". The New York Times.
^ Eslamian L, Borzabadi-Farahani A, Edini HZ, Badiee MR, Lynch E, Mortazavi A. (2013). "The analgesic effect of benzocaine mucoadhesive patches on orthodontic pain caused by elastomeric separators, a preliminary study.". Acta Odontol Scand. 71 (5): 1168–73. doi:10.3109/00016357.2012.757358. PMID 23301559.
^ "Produkty | PUDRODERM" (in Polish). Retrieved 9 May 2014.
^ "Drug prices: All cut up : Cocaine is cheaper, but weaker". The Economist. August 11, 2012.

External links

Public Health Advisory: Benzocaine Sprays by the Food and Drug Administration.

UpToDate Contents

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1. 小児における局所麻酔剤 topical anesthetics in children
2. 成人における急性咽頭炎の対症療法 symptomatic treatment of acute pharyngitis in adults
3. Oral lichen planus: Management and prognosis
4. メトヘモグロビン血症の臨床的特徴、診断、および治療 clinical features diagnosis and treatment of methemoglobinemia
5. 局所麻酔剤に対するアレルギー反応 allergic reactions to local anesthetics

English Journal

Comparison of NADH-dependent cytochrome b5 reductase activity and in vitro methemoglobin induction by sodium nitrite in Oncorhynchus mykiss, Salmo salar, and Salvelinus fontinalis.

McConkey S, Saunders J, Speare DJ.SourceDepartment of Biomedical Sciences, Atlantic Veterinary College, Charlottetown, PE, C1A 4P3, Canada, smcconkey@upei.ca.
Fish physiology and biochemistry.Fish Physiol Biochem.2013 Jun;39(3):713-9. doi: 10.1007/s10695-012-9734-x. Epub 2012 Oct 19.
Methemoglobin is hemoglobin containing ferric iron. Methemoglobin cannot bind to oxygen and at high concentrations causes tissue hypoxia. Brook trout (Salvelinus fontinalis) develop significantly greater methemoglobinemia than Atlantic salmon (Salmo salar) or rainbow trout (Oncorhynchus mykiss) foll
PMID 23079863

An evaluation of 10 percent and 20 percent benzocaine gels in patients with acute toothaches: Efficacy, tolerability and compliance with label dose administration directions.

Hersh EV, Ciancio SG, Kuperstein AS, Stoopler ET, Moore PA, Boynes SG, Levine SC, Casamassimo P, Leyva R, Mathew T, Shibly O, Creighton P, Jeffers GE, Corby PM, Turetzky SN, Papas A, Wallen J, Idzik-Starr C, Gordon SM.SourceDr. Hersh is a professor of pharmacology and the director, Division of Pharmacology and Therapeutics, Department of Oral Surgery and Pharmacology, School of Dental Medicine, University of Pennsylvania, 240 S. 40th St., Philadelphia, Pa. 19104-6030, evhersh@pobox.upenn.edu.
Journal of the American Dental Association (1939).J Am Dent Assoc.2013 May;144(5):517-26.
BACKGROUND: The authors evaluated the efficacy and tolerability of 10 percent and 20 percent benzocaine gels compared with those of a vehicle (placebo) gel for the temporary relief of toothache pain. They also assessed the compliance with the label dose administration directions on the part of parti
PMID 23633700

Japanese Journal

高エネルギーリン酸化代謝におけるドジョウに対する3種類の麻酔薬(MS222、ペントバルビタール、エチルパラアミノベンゾエイト)の比較

千葉惇,梶本禮義
医学と生物学 148(12), 24-31, 2004-12-10
NAID 40006546264

無水酢酸, 氷酢酸及びその混合溶液中における塩基及びその塩の過塩素酸滴定

朝日豊,田中正己,杉本真弓
分析化学 40(10), 557-562, 1991-10-05
日本薬局方収載の尿素(I), ピラジナミド(II), エテンザミド(III), アセトアミノフェン(IV), メチル硫酸ネオスチグミン(V), プリミドン(VI), 塩酸プロカイン(VII)及びアミノ安息香酸エチル(VIII)の非水滴定法を検討した.無水酢酸-氷酢酸溶液中0.1M過塩素酸-氷酢酸液で電位差滴定し, データ処理で数値の平滑化, 一次微分, 二次微分を行った, I, II, III, …
NAID 110002906203

「アミノ安息香酸エチル」

Benzocaine
Systematic (IUPAC) name
	Ethyl 4-aminobenzoate
Clinical data
Trade names	Anbesol, Cepacol, Lanacane
AHFS/Drugs.com	monograph
Pregnancy cat.	US: C;
Legal status	US: OTC;
Routes	Topical
Identifiers
CAS number	94-09-7
ATC code	C05AD03 D04AB04, QN01AX92, N01BA05, R02AD01
PubChem	CID 2337
DrugBank	DB01086
ChemSpider	13854242
UNII	U3RSY48JW5
KEGG	D00552
ChEBI	CHEBI:116735
ChEMBL	CHEMBL278172
Chemical data
Formula	C9H11NO2
Mol. mass	165.189 g/mol
	SMILES O=C(OCC)c1ccc(N)cc1;
	InChI InChI=1S/C9H11NO2/c1-2-12-9(11)7-3-5-8(10)6-4-7/h3-6H,2,10H2,1H3 ; Key:BLFLLBZGZJTVJG-UHFFFAOYSA-N ;
(what is this?) (verify)

　　[★]

英: ethylaminobenzoate
ラ: ethylis aminobenzoas
同: ベンゾカイン benzocaine、パラアミノ安息香酸エチル ethyl p-aminobenzoate
商: アネスタミン anestamine、ベンゾカイン benzocaine、ジンジカイン、スルカイン、ニチカイン、ネオザロカインパスタ、ハリケイン、ヒノポロン、ビーゾカイン、プロネスパスタ、ヘルミチンS

「パラアミノ安息香酸エチル」

　　[★]

英: ethyl p-aminobenzoate
関: アミノ安息香酸エチル

「aminobenzoate」

　　[★]

アミノ安息香酸、(化合物)ミノ安息香酸エステル

関: aminobenzoic acid

aminobenzoic acid

「P」

　　[★]

「ps」

　　[★]

ピコ秒

時間単位

関: picosecond、psec

「p」

　　[★]

ピコ

10の-12乗

関: pico

「ethyl」

　　[★]

エチル

関: Et

[1] Demare, Patricia; Regla, Ignacio (2012). "Synthesis of Two Local Anesthetics from Toluene: An Organic Multistep Synthesis in a Project-Oriented Laboratory Course". Journal of Chemical Education 89: 147. doi:10.1021/ed100838a.

[intpharm-2] "Monographs: Pharmaceutical substances: Benzocainum – Benzocaine". The International Pharmacopoeia. Retrieved September 29, 2009.

[3] D'Ans-Lax, Taschenbuch für Chemiker und Physiker, 4. Auflage, Band 2, Springer Verlag 1982, ISBN 3-540-12263-X

[4] Biography of Eduard Ritsert (in German): Deutsche Biographie: Ritsert, Eduard .

[5] "100 years of Dr. Ritsert". Dr. Ritsert Pharma. Retrieved March 14, 2010.

[6] Harry Auterhoff, Lehrbuch der pharmazeutischen Chemie (Stuttgart, Germany: Wissenschaftliche Verlagsgesellschaft, 1968).

[7] Ritsert, E. (1925) "Über den Werdegang des Anästhesins" (On the development of Anästhesin), Pharmazeutische Zeitung, vol. 60, pages 1006–1008. See also: Christoph Friedrich and Magdalena Klimonow, "150. Geburtstag: Eduard Ritsert und das Anaesthesin" (150th birthday: Eduard Ritsert and Anästhetsin [Benzocaine]"), Pharmazeutische Zeitung online. First published clinical study demonstrating the efficacy of benzocaine: Noorden, C. v. (1902) "Ueber para-Aminobenzoesäure-Ester als locales Anästhetikum" (On [an] ester of para-aminobenzoic acid as a local anaesthetic), Klinische Wochenschrift, vol. 39, pages 373–375.

[8] "Benzocaine Topical Products: Sprays, Gels and Liquids – Risk of Methemoglobinemia". Drugs.com. Retrieved March 20, 2014.

[9] ".". Retrieved March 20, 2014.

[10] "A 10-year retrospective study on benzoca... [Am J Contact Dermat. 1999". Ncbi.nlm.nih.gov. January 24, 2014. Retrieved March 20, 2014.

[11] ".". Retrieved March 20, 2014.

[12] By Leslie Goldman (February 5, 2008). "Go easy on medicated lotions, creams, gels". CNN. Retrieved March 20, 2014.

[13] "'Longer-lasting' condom launched". BBC News. June 17, 2002.

[14] Garner, Dwight (December 15, 2002). "Endurance Condoms". The New York Times.

[15] Eslamian L, Borzabadi-Farahani A, Edini HZ, Badiee MR, Lynch E, Mortazavi A. (2013). "The analgesic effect of benzocaine mucoadhesive patches on orthodontic pain caused by elastomeric separators, a preliminary study.". Acta Odontol Scand. 71 (5): 1168–73. doi:10.3109/00016357.2012.757358. PMID 23301559.

[16] "Produkty | PUDRODERM" (in Polish). Retrieved 9 May 2014.

[17] "Drug prices: All cut up : Cocaine is cheaper, but weaker". The Economist. August 11, 2012.

リンク元	「アミノ安息香酸エチル」「パラアミノ安息香酸エチル」
関連記事	「aminobenzoate」「P」「ps」「p」「ethyl」

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案内

案内

ethyl p-aminobenzoate