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Revision as of 12:33, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 460672620 of page Tetracaine for the Chem/Drugbox validation project (updated: '').  Latest revision as of 06:53, 5 August 2024 edit 173.47.14.190 (talk) grammatical smoothingTags: Visual edit Mobile edit Mobile web edit 
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{{Short description|Local anaesthetic drug}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
{{Drugbox {{Drugbox
⚫ | verifiedrevid = 470603479
| Verifiedfields = changed
⚫ | image = Tetracaine2DCSD.svg
⚫ | verifiedrevid = 417367726
⚫ | IUPAC_name = 2-(dimethylamino)ethyl 4-(butylamino)benzoate
⚫ | image = Tetracaine.svg


<!--Clinical data--> <!--Clinical data-->
| tradename = | tradename = Pontocaine, Ametop, Dicaine, others
| Drugs.com = {{drugs.com|monograph|tetracaine}} | Drugs.com = {{drugs.com|monograph|tetracaine}}
| MedlinePlus = a682640 | MedlinePlus = a682640
| DailyMedID = Tetracaine
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_AU = B2
| pregnancy_US = <!-- A / B / C / D / X --> | pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category = | pregnancy_category =
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> | legal_AU = S4
| legal_AU_comment = /&nbsp;S2
| legal_BR = C1
| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-16 |publisher=] |language=pt-BR |publication-date=2023-04-04}}</ref>
| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> | legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C --> | legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> | legal_US = Rx-only
| legal_status = Rx Only | legal_status = Rx-only
| routes_of_administration = Topical, Epidural, Spinal | routes_of_administration = ]
| ATC_prefix = C05
⚫ | ATC_suffix = AD02
⚫ | ATC_supplemental = {{ATC|D04|AB06}} {{ATC|N01|BA03}} {{ATC|S01|HA03}}


<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
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| metabolism = | metabolism =
| elimination_half-life = | elimination_half-life =
| excretion = | excretion =


<!--Identifiers--> <!--Identifiers-->
| index2_label = as HCl
⚫ | CASNo_Ref = {{cascite|correct|CAS}}
| CAS_number_Ref = {{cascite|correct|??}} | CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 94-24-6 | CAS_number = 94-24-6
⚫ | CAS_number2_Ref = {{cascite|correct|??}}
| CAS_supplemental = <br/>{{CAS|136-47-0}} (]) <!-- Also CAS verified -->
| ATC_prefix = C05 | CAS_number2 = 136-47-0
| CAS_supplemental =
⚫ | ATC_suffix = AD02
⚫ | ATC_supplemental = {{ATC|D04|AB06}} {{ATC|N01|BA03}} {{ATC|S01|HA03}}
| PubChem = 5411 | PubChem = 5411
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = | DrugBank = DB09085
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 5218 | ChemSpiderID = 5218
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 0619F35CGV | UNII = 0619F35CGV
| UNII2_Ref = {{fdacite|correct|FDA}}
| UNII2 = 5NF5D4OPCI
| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00551 | KEGG = D00551
| ChEBI_Ref = {{ebicite|changed|EBI}} | KEGG2_Ref = {{keggcite|correct|kegg}}
| KEGG2 = D00741
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 9468 | ChEBI = 9468
| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 698 | ChEMBL = 698
| PDB_ligand = TE4


<!--Chemical data--> <!--Chemical data-->
⚫ | IUPAC_name = 2-(Dimethylamino)ethyl 4-(butylamino)benzoate
| C=15 | H=24 | N=2 | O=2 | C=15 | H=24 | N=2 | O=2
| molecular_weight = 264.363 g/mol
| smiles = O=C(OCCN(C)C)c1ccc(NCCCC)cc1 | 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_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 | 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
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| StdInChIKey = GKCBAIGFKIBETG-UHFFFAOYSA-N | StdInChIKey = GKCBAIGFKIBETG-UHFFFAOYSA-N
}} }}
<!-- Definition and medical uses -->
'''Tetracaine''', also known as '''amethocaine''', is an ester ] used to numb the eyes, nose, or throat.<ref name=AHFS2016/> It may also be applied to the skin before starting ] therapy to decrease pain from the procedure.<ref name=BNF69>{{cite book|title=British national formulary : BNF 69|date=2015|publisher=British Medical Association|isbn=9780857111562|pages=769, 897|edition=69}}</ref> Typically it is applied as a liquid to the area.<ref name=AHFS2016/> Onset of effects when used in the eyes is within 30 seconds and last for less than 15 minutes.<ref name=AHFS2016>{{cite web|title=Tetracaine|url=https://www.drugs.com/monograph/tetracaine.html|publisher=The American Society of Health-System Pharmacists|access-date=8 December 2016|url-status=live|archive-url=https://web.archive.org/web/20161228195913/https://www.drugs.com/monograph/tetracaine.html|archive-date=28 December 2016}}</ref>

<!-- Side effects and mechanism -->
Common side effects include a brief period of burning at the site of use.<ref name=AHFS2016/> ] may uncommonly occur.<ref name=WHO2008/> Long-term use is generally not recommended as it may slow healing of the eye.<ref name=AHFS2016/> It is unclear if use during ] is safe for the baby.<ref name=AHFS2016/> Tetracaine is in the ] family of medications.<ref name=WHO2008>{{cite book | title = WHO Model Formulary 2008 | year = 2009 | isbn = 9789241547659 | vauthors = ((World Health Organization)) | veditors = Stuart MC, Kouimtzi M, Hill SR | hdl = 10665/44053 | author-link = World Health Organization | publisher = World Health Organization |page=437 }}</ref> It works by blocking the sending of ].<ref name=AHFS2016/>

<!-- History and culture -->
Tetracaine was patented in 1930 and came into medical use in 1941.<ref name=Fis2006>{{cite book| vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery|date=2006|publisher=John Wiley & Sons |isbn=9783527607495 |page=475 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA475|language=en|url-status=live|archive-url=https://web.archive.org/web/20161229100237/https://books.google.ca/books?id=FjKfqkaKkAAC&pg=PA475|archive-date=2016-12-29}}</ref> It is on the ]<ref name="WHO21st">{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 21st list 2019 | year = 2019 | hdl = 10665/325771 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO | hdl-access=free }}</ref>

==Medical uses==
A ] investigated tetracaine for use in emergency departments, especially for starting intravenous lines in children, in view of its analgesic and cost-saving properties. However, it did not find an improvement in first-attempt cannulations.<ref>{{cite journal | vauthors = Pywell A, Xyrichis A | title = Does topical Amethocaine cream increase first-time successful cannulation in children compared with a eutectic mixture of local anaesthetics (EMLA) cream? A systematic review and meta-analysis of randomised controlled trials | journal = Emergency Medicine Journal | volume = 32 | issue = 9 | pages = 733–737 | date = September 2015 | pmid = 25351196 | doi = 10.1136/emermed-2014-204066 | publisher = Emerg Med J | s2cid = 21769195 }}</ref>

Tetracaine is the T in ], a mixture of 5 to 12% tetracaine, 0.05% ], and 4 or 10% ] hydrochloride used in ear, nose, and throat surgery and in the emergency department where numbing of the surface is needed rapidly, especially when children have been injured in the eye, ear, or other sensitive locations.<ref>Appleton's Nursing Manual - "Cocaine"</ref>

==Mechanism==
In ], tetracaine is used to alter the function of calcium release channels (]s) that control the release of calcium from intracellular stores. Tetracaine is an ] 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 | vauthors = Györke S, Lukyanenko V, Györke I | title = Dual effects of tetracaine on spontaneous calcium release in rat ventricular myocytes | journal = The Journal of Physiology | volume = 500 | issue = Pt 2 | pages = 297–309 | date = April 1997 | pmid = 9147318 | pmc = 1159384 | doi = 10.1113/jphysiol.1997.sp022021 }}</ref>

== References ==
{{Reflist}}

== External links ==
* {{cite web | url = https://druginfo.nlm.nih.gov/drugportal/name/tetracaine | publisher = U.S. National Library of Medicine | work = Drug Information Portal | title = Tetracaine }}
* {{cite web | url = https://druginfo.nlm.nih.gov/drugportal/name/tetracaine%20hydrochloride | publisher = U.S. National Library of Medicine | work = Drug Information Portal | title = Tetracaine hydrochloride }}

{{Vasoprotectives}}
{{Local anesthetics}}
{{Ion channel modulators}}
{{Portal bar|Medicine}}

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