Tetracaine (ophthalmic): Difference between revisions
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{{Drugbox | |||
| verifiedrevid = 470603479 | |||
| IUPAC_name = 2-(dimethylamino)ethyl 4-(butylamino)benzoate | |||
| image = Tetracaine2DCSD.svg | |||
<!--Clinical data--> | |||
| tradename = | |||
| Drugs.com = {{drugs.com|monograph|tetracaine}} | |||
| MedlinePlus = a682640 | |||
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | |||
| pregnancy_US = <!-- A / B / C / D / X --> | |||
| pregnancy_category = | |||
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> | |||
| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> | |||
| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C --> | |||
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> | |||
| legal_status = Rx Only | |||
| routes_of_administration = Topical, Epidural, Spinal | |||
<!--Pharmacokinetic data--> | |||
| bioavailability = | |||
| protein_bound = 75.6 | |||
| metabolism = | |||
| elimination_half-life = | |||
| excretion = | |||
<!--Identifiers--> | |||
| CASNo_Ref = {{cascite|correct|CAS}} | |||
| CAS_number_Ref = {{cascite|correct|??}} | |||
| CAS_number = 94-24-6 | |||
| CAS_supplemental = <br/>{{CAS|136-47-0}} ([[hydrochloride]]) <!-- Also CAS verified --> | |||
| ATC_prefix = C05 | |||
| ATC_suffix = AD02 | |||
| ATC_supplemental = {{ATC|D04|AB06}} {{ATC|N01|BA03}} {{ATC|S01|HA03}} | |||
| PubChem = 5411 | |||
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | |||
| DrugBank = | |||
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | |||
| ChemSpiderID = 5218 | |||
| UNII_Ref = {{fdacite|correct|FDA}} | |||
| UNII = 0619F35CGV | |||
| KEGG_Ref = {{keggcite|correct|kegg}} | |||
| KEGG = D00551 | |||
| ChEBI_Ref = {{ebicite|correct|EBI}} | |||
| ChEBI = 9468 | |||
| ChEMBL_Ref = {{ebicite|correct|EBI}} | |||
| ChEMBL = 698 | |||
<!--Chemical data--> | |||
| C=15 | H=24 | N=2 | O=2 | |||
| molecular_weight = 264.363 g/mol | |||
| smiles = O=C(OCCN(C)C)c1ccc(NCCCC)cc1 | |||
| InChI = 1/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 | |||
| InChIKey = GKCBAIGFKIBETG-UHFFFAOYAR | |||
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | |||
| StdInChI = 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 | |||
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | |||
| StdInChIKey = GKCBAIGFKIBETG-UHFFFAOYSA-N | |||
}} | |||
__NOTOC__ | |||
{{SI}} | |||
{{CMG}} | |||
==Overview== | |||
'''Tetracaine''' ([[International Nonproprietary Name|INN]], also known as '''amethocaine'''; trade name '''Pontocaine'''. '''Ametop''' and '''Dicaine''') is a potent [[local anesthetic]] of the [[ester]] group. It is mainly used [[topical anesthetic|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 receptor]]s) that control the release of calcium from intracellular stores. Tetracaine is an [[allosteric regulation|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.<ref>{{cite journal|last=Györke|first=S|coauthors=Lukyanenko, V ''et al.''|title=Dual effects of tetracaine on spontaneous sodium release in rat ventricular myocytes|publisher=J Physiol|volume=500|issue=2|year=1997|pages=297–309}}</ref> | |||
<!-- Society and culture --> | |||
It is on the [[World Health Organization's List of Essential Medicines]], a list of the most important medication needed in a basic [[health system]].<ref>{{cite web|title=WHO Model List of EssentialMedicines|url=http://apps.who.int/iris/bitstream/10665/93142/1/EML_18_eng.pdf?ua=1|work=World Health Organization|accessdate=22 April 2014|date=October 2013}}</ref> | |||
==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]].<ref>Winthrop Chemical Company, Inc. U.S. Patent 1,889,645, 1932.</ref> | |||
[[File:Winthrop tetracaine synthesis.png|thumb|center|400px|Tetracaine synthesis from Winthrop Chem. Co. Patent US1889645, 1932]] | |||
==References== | |||
{{Reflist}} | |||
==Further reading== | |||
*O. Eisleb, {{US Patent|1889645}} (1932). | |||
{{Vasoprotectives}} | |||
[[Category:Local anesthetics]] | |||
[[Category:Drug]] | |||
Revision as of 20:04, 23 July 2014
| File:Tetracaine2DCSD.svg | |
| Clinical data | |
|---|---|
| AHFS/Drugs.com | Monograph |
| MedlinePlus | a682640 |
| Routes of administration | Topical, Epidural, Spinal |
| ATC code | |
| Legal status | |
| Legal status |
|
| Pharmacokinetic data | |
| Protein binding | 75.6 |
| Identifiers | |
| |
| CAS Number | |
| PubChem CID | |
| ChemSpider | |
| UNII | |
| KEGG | |
| ChEBI | |
| ChEMBL | |
| E number | {{#property:P628}} |
| ECHA InfoCard | {{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value). |
| Chemical and physical data | |
| Formula | C15H24N2O2 |
| Molar mass | 264.363 g/mol |
| 3D model (JSmol) | |
| |
| |
| (verify) | |
Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]
Overview
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]
It is on the World Health Organization's List of Essential Medicines, a list of the most important medication needed in a basic health system.[2]
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.[3]
References
- ↑ Györke, S (1997). "Dual effects of tetracaine on spontaneous sodium release in rat ventricular myocytes". 500 (2). J Physiol: 297&ndash, 309. Unknown parameter
|coauthors=ignored (help) - ↑ "WHO Model List of EssentialMedicines" (PDF). World Health Organization. October 2013. Retrieved 22 April 2014.
- ↑ Winthrop Chemical Company, Inc. U.S. Patent 1,889,645, 1932.
Further reading
- O. Eisleb, Template:US Patent (1932).
Categories:
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- Local anesthetics
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