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Revision as of 14:15, 5 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 456883970 of page Prilocaine for the Chem/Drugbox validation project (updated: 'DrugBank').  Latest revision as of 19:23, 20 December 2023 edit JJMC89 bot III (talk | contribs)Bots, Administrators3,656,711 editsm Moving Category:AstraZeneca brands to Category:Drugs developed by AstraZeneca per Misplaced Pages:Categories for discussion/Log/2023 December 9#Category:AstraZeneca brands 
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{{short description|Local anesthetic of the amino amide type}}
{{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 = 464214246
| Verifiedfields = changed
| image = Prilocaine.svg
| verifiedrevid = 418550175
| IUPAC_name = (''RS'')-''N''-(2-methylphenyl)-''N''<sup>2</sup>-propylalaninamide
| image = Prilocaine.png
| width = 200px | width = 200px
| imagename = 1 : 1 mixture (racemate) | chirality = ]
| drug_name = Prilocaine


<!--Clinical data--> <!--Clinical data-->
| tradename = | tradename = Citanest
| Drugs.com = {{drugs.com|monograph|prilocaine-hydrochloride}} | Drugs.com = {{drugs.com|monograph|prilocaine-hydrochloride}}
| MedlinePlus = a603026 | MedlinePlus = a603026
| licence_EU = yes
| pregnancy_category = B <small>(])</small>
| DailyMedID = Prilocaine
| legal_status =
| licence_US = <!-- FDA may use generic or brand name (generic name preferred) -->
| routes_of_administration =
| pregnancy_AU = A
| pregnancy_AU_comment =
| pregnancy_US = B
| pregnancy_US_comment =
| pregnancy_category=
| dependency_liability =
| addiction_liability =
| routes_of_administration = ]
| class =
| ATCvet =
| ATC_prefix = N01
| ATC_suffix = BB04
| ATC_supplemental =

<!-- Legal status -->
| legal_AU = S4
| legal_AU_comment =
| legal_BR = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F -->
| legal_BR_comment =
| legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_CA_comment =
| legal_DE = <!-- Anlage I, II, III or Unscheduled -->
| legal_DE_comment =
| legal_NZ = <!-- Class A, B, C -->
| legal_NZ_comment =
| legal_UK = <!-- GSL, P, POM, CD, CD Lic, CD POM, CD No Reg POM, CD (Benz) POM, CD (Anab) POM or CD Inv POM / Class A, B, C -->
| legal_UK_comment =
| legal_US = Rx-only
| legal_US_comment =
| legal_EU =
| legal_EU_comment =
| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV -->
| legal_UN_comment =
| legal_status = <!-- For countries not listed above -->


<!--Pharmacokinetic data--> <!-- Pharmacokinetic data -->
| bioavailability = | bioavailability =
| protein_bound = 55% | protein_bound = 55%
| metabolism = Hepatic and renal | metabolism = ] and ]
| elimination_half-life = 10-150 minutes, longer with impaired hepatic or renal function | elimination_half-life = 10-150 minutes, longer with impaired liver or kidney function


<!--Identifiers--> <!--Identifiers-->
| index2_label = as HCl
| CASNo_Ref = {{cascite|correct|CAS}}
| CAS_number_Ref = {{cascite|correct|??}} | CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 721-50-6 | CAS_number = 721-50-6
| ATC_prefix = N01
| ATC_suffix = BB04
| ATC_supplemental =
| PubChem = 4906 | PubChem = 4906
| IUPHAR_ligand = 7276
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00750 | DrugBank = DB00750
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| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00553 | KEGG = D00553
| ChEBI_Ref = {{ebicite|changed|EBI}} | KEGG2_Ref = {{keggcite|correct|kegg}}
| KEGG2 = D01243
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 8404 | ChEBI = 8404
| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
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<!--Chemical data--> <!--Chemical data-->
| IUPAC_name = (''RS'')-''N''-(2-methylphenyl)-''N''<sup>2</sup>-propylalaninamide
| C=13 | H=20 | N=2 | O=1
| C=13 | H=20 | N=2 | O=1
| molecular_weight = 220.311 g/mol
| smiles = O=C(Nc1ccccc1C)C(NCCC)C | smiles = O=C(Nc1ccccc1C)C(NCCC)C
| InChI = 1/C13H20N2O/c1-4-9-14-11(3)13(16)15-12-8-6-5-7-10(12)2/h5-8,11,14H,4,9H2,1-3H3,(H,15,16)
| InChIKey = MVFGUOIZUNYYSO-UHFFFAOYAP
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C13H20N2O/c1-4-9-14-11(3)13(16)15-12-8-6-5-7-10(12)2/h5-8,11,14H,4,9H2,1-3H3,(H,15,16) | StdInChI = 1S/C13H20N2O/c1-4-9-14-11(3)13(16)15-12-8-6-5-7-10(12)2/h5-8,11,14H,4,9H2,1-3H3,(H,15,16)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = MVFGUOIZUNYYSO-UHFFFAOYSA-N | StdInChIKey = MVFGUOIZUNYYSO-UHFFFAOYSA-N
| melting_point = 37
| melting_high = 38
}} }}

'''Prilocaine''' ({{IPAc-en|ˈ|p|r|aɪ|l|ə|ˌ|k|eɪ|n}}{{refn|{{MerriamWebsterDictionary|access-date=2016-01-21|Prilocaine}}}}) is a ] of the ] ] type first prepared by ] and ]. In its ] form (trade name '''Citanest'''), it is often used in ]. It is also often combined with lidocaine as a topical preparation for dermal anesthesia (] or ]), for treatment of conditions like ]. As it has low cardiac toxicity, it is commonly used for ] (IVRA).

== Contraindications ==
In some patients, ortho-toluidine, a metabolite of prilocaine, may cause ], which may be treated with ]. Prilocaine may also be contraindicated in people with ], ], or symptomatic ].<ref>{{Cite book|title = Practical and Professional Clinical Skills|url = https://books.google.com/books?id=_DY5PCOFH4EC&pg=PA267|publisher = Oxford University Press|date = 2011-09-15|isbn = 9780199585618 | vauthors = Patel V, Morrissey J |page = 267}}</ref>

== Combinations ==
It is given as a ] ] under the trade name ''Citanest Forte''. It is used as a ] mixture with ], 50% w/w, as ]. The mixture is an oil with a melting point of {{convert|18|C|F}}. A 5% ] preparation, containing 2.5% each of lidocaine/prilocaine, is marketed by ] under the ] EMLA (an abbreviation for eutectic mixture of local anesthetics).<ref>{{cite web|url=http://www.medscape.com/viewarticle/704761_2 |title=Topical Anesthesia Use in Children: Eutectic Mixture of Local Anesthetics |publisher=Medscape.com |access-date=2014-01-07}}</ref>

== Compendial status ==
* ] 31 <ref name=rblp>{{citation| last =The United States Pharmacopeial Convention| title =Revision Bulletin: Lidocaine and Prilocaine Cream–Revision to Related Compounds Test| url =http://www.usp.org/USPNF/notices/lidocaineAndPrilocaine.html| access-date =10 July 2009| url-status =dead| archive-url =https://web.archive.org/web/20100705213713/http://www.usp.org/USPNF/notices/lidocaineAndPrilocaine.html| archive-date =5 July 2010}}</ref>
==Synthesis==
]

The amidation between ] ('''1''') and 2-bromopropionyl bromide ('''2''') leads to 2-bromo-N-(2-methylphenyl)propanamide ('''3'''). Displacement of the remaining halide with ] ('''4''') completed the synthesis of prilocaine ('''5''').

== See also ==
* ]

== References ==
{{Reflist}}

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

{{Local anesthetics}}
{{Portal bar | Medicine}}

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