WordNet

a crystalline compound used in the form of a hydrochloride as a local anesthetic

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/04/23 13:28:51」(JST)

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Tetracaine (INN, also known as amethocaine; trade name Pontocaine. Ametop and Dicaine) is a potent local anesthetic of the ester group. It is mainly used topically in ophthalmology and as an antipruritic, and it has been used in spinal anesthesia.

In biomedical research, tetracaine is used to alter the function of calcium release channels (ryanodine receptors) that control the release of calcium from intracellular stores. Tetracaine is an allosteric blocker of channel function. At low concentrations, tetracaine causes an initial inhibition of spontaneous calcium release events, while at high concentrations, tetracaine blocks release completely.^[1]

Chemistry

Tetracaine is synthesized from 4-butylaminobenzoic acid. The ethyl ester is formed through an acid-catalyzed esterification reaction. Base-catalyzed transesterification is achieved by boiling the ethyl ester of 4-butylaminobenzoic acid with excess 2-dimethylaminoethanol in the presence of a small amount of sodium ethoxide.^[2]

Tetracaine synthesis from Winthrop Chem. Co. Patent US1889645, 1932

References

^ Györke, S; Lukyanenko, V et al. (1997). Dual effects of tetracaine on spontaneous sodium release in rat ventricular myocytes 500 (2). J Physiol. pp. 297–309.
^ Winthrop Chemical Company, Inc. U.S. Patent 1,889,645, 1932.

UpToDate Contents

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English Journal

Benzonatate inhibition of voltage-gated sodium currents.

Evans MS1, Maglinger GB2, Fletcher AM3, Johnson SR4.
Neuropharmacology.Neuropharmacology.2016 Feb;101:179-87. doi: 10.1016/j.neuropharm.2015.09.020. Epub 2015 Sep 16.
Benzonatate was FDA-approved in 1958 as an antitussive. Its mechanism of action is thought to be anesthesia of vagal sensory nerve fibers that mediate cough. Vagal sensory neurons highly express the Nav1.7 subtype of voltage-gated sodium channels, and inhibition of this channel inhibits the cough re
PMID 26386152

Endotracheal Administration of Sufentanil and Tetracaine During Awake Fiberoptic Intubation.

Ji M1, Tao J, Cheng M, Wang Q.
American journal of therapeutics.Am J Ther.2016 Jan-Feb;23(1):e92-7. doi: 10.1097/MJT.0b013e31828fdb8c.
Combined use of local anesthetics and low-dose opioids enhances the effects of local anesthetics. This study aimed to evaluate the efficacy of combined administration of sufentanil and tetracaine through the cricothyroid membrane during awake nasal intubation using fiberoptic bronchoscopy in patient
PMID 23676347

Biphasic decay of the Ca transient results from increased sarcoplasmic reticulum Ca leak.

Sankaranarayanan R1, Li Y1, Greensmith DJ2, Eisner DA1, Venetucci L1,2,3.
The Journal of physiology.J Physiol.2015 Nov 5. doi: 10.1113/JP271473. [Epub ahead of print]
In heart failure reduction in Ca transient amplitude and contractile dysfunction can by caused by Ca leak through the sarcoplasmic reticulum (SR) Ca channel (Ryanodine Receptor, RyR) and/or decreased activity of the SR Ca ATPase (SERCA). We have characterized the effects of two forms of Ca leak (Ca-
PMID 26537441

Japanese Journal

Destabilization of phase-separated structures in local anesthetic-containing model biomembranes

Chemistry Letters advpub(0), 2015
NAID 130005092611

神経ブロックにより診断が遅れた症候性三叉神経痛の1例

日本ペインクリニック学会誌 22(2), 92-95, 2015
NAID 130005083680

神経ブロックにより診断が遅れた症候性三叉神経痛の1例

日本ペインクリニック学会誌 advpub(0), 2014
NAID 130005061961

★リンクテーブル★

リンク元	「テトラカイン」
拡張検索	「tetracaine hydrochloride」

「テトラカイン」

Tetracaine
Systematic (IUPAC) name
	2-(dimethylamino)ethyl 4-(butylamino)benzoate
Clinical data
AHFS/Drugs.com	monograph
MedlinePlus	a682640
Pregnancy cat.	?
Legal status	Rx Only
Routes	Topical, Epidural, Spinal
Pharmacokinetic data
Protein binding	75.6
Identifiers
CAS number	94-24-6 ; 136-47-0 (hydrochloride)
ATC code	C05AD02 D04AB06 N01BA03 S01HA03
PubChem	CID 5411
ChemSpider	5218
UNII	0619F35CGV
KEGG	D00551
ChEBI	CHEBI:9468
ChEMBL	CHEMBL698
Chemical data
Formula	C15H24N2O2
Mol. mass	264.363 g/mol
	SMILES O=C(OCCN(C)C)c1ccc(NCCCC)cc1;
	InChI InChI=1S/C15H24N2O2/c1-4-5-10-16-14-8-6-13(7-9-14)15(18)19-12-11-17(2)3/h6-9,16H,4-5,10-12H2,1-3H3 ; Key:GKCBAIGFKIBETG-UHFFFAOYSA-N ;
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