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Revision as of 22:14, 10 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'DrugBank').← Previous edit Latest revision as of 14:19, 25 December 2023 edit undoBoghog (talk | contribs)Autopatrolled, Extended confirmed users, IP block exemptions, New page reviewers, Pending changes reviewers, Rollbackers, Template editors137,738 edits consistent citation formatting 
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{{Short description|Local anaesthetic drug}}
{{merge|Dibucaine number|discuss=Talk:Cinchocaine#Merger proposal|date=November 2009}}
{{Drugbox {{Drugbox
| Watchedfields = changed
| verifiedrevid = 443524583 | verifiedrevid = 460037677
| IUPAC_name = 2-butoxy-''N''-quinoline-4-carboxamide | IUPAC_name = 2-butoxy-''N''-quinoline-4-carboxamide
| image = Cinchocaine.svg | image = Cinchocaine.svg
| image2 = Cinchocaine 3D ball-and-stick.png

<!--Clinical data--> <!--Clinical data-->
| tradename = | tradename =
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| legal_AU = <!-- Unscheduled / S2 / S4 / S8 --> | legal_AU = <!-- Unscheduled / S2 / S4 / S8 -->
| legal_UK = <!-- GSL / P / POM / CD --> | legal_UK = <!-- GSL / P / POM / CD -->
| legal_US = <!-- OTC / Rx-only --> | legal_US = OTC
| legal_status = | legal_status =
| routes_of_administration = topical, intravenous (equine euthanasia) | routes_of_administration = topical, intravenous (for ])

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

<!--Identifiers--> <!--Identifiers-->
| IUPHAR_ligand = 7159
| CASNo_Ref = {{cascite|correct|CAS}} | CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 85-79-0 | CAS_number = 85-79-0
| ATC_prefix = C05 | ATC_prefix = C05
| ATC_suffix = AD04 | ATC_suffix = AD04
| ATC_supplemental = {{ATC|D04|AB02}} {{ATC|N01|BB06}} {{ATC|S01|HA06}} | ATC_supplemental = {{ATC|D04|AB02}} {{ATC|N01|BB06}} {{ATC|S01|HA06}} {{ATC|S02|DA04}}
| PubChem = 3025 | PubChem = 3025
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
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| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1086 | ChEMBL = 1086

<!--Chemical data--> <!--Chemical data-->
| C=20 | H=29 | N=3 | O=2 | C=20 | H=29 | N=3 | O=2
| molecular_weight = 343.463 g/mol
| smiles = O=C(c1c2ccccc2nc(OCCCC)c1)NCCN(CC)CC | smiles = O=C(c1c2ccccc2nc(OCCCC)c1)NCCN(CC)CC
| InChI = 1/C20H29N3O2/c1-4-7-14-25-19-15-17(16-10-8-9-11-18(16)22-19)20(24)21-12-13-23(5-2)6-3/h8-11,15H,4-7,12-14H2,1-3H3,(H,21,24)
| InChIKey = PUFQVTATUTYEAL-UHFFFAOYAU
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C20H29N3O2/c1-4-7-14-25-19-15-17(16-10-8-9-11-18(16)22-19)20(24)21-12-13-23(5-2)6-3/h8-11,15H,4-7,12-14H2,1-3H3,(H,21,24) | StdInChI = 1S/C20H29N3O2/c1-4-7-14-25-19-15-17(16-10-8-9-11-18(16)22-19)20(24)21-12-13-23(5-2)6-3/h8-11,15H,4-7,12-14H2,1-3H3,(H,21,24)
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| StdInChIKey = PUFQVTATUTYEAL-UHFFFAOYSA-N | StdInChIKey = PUFQVTATUTYEAL-UHFFFAOYSA-N
}} }}
'''Cinchocaine''' (or '''Dibucaine''') is an ] ]. It is the active ingredient in some topical hemorrhoid creams such as ]. It is sold under the brand names '''Cincain''', '''Nupercainal''', '''Nupercaine''' and '''Sovcaine''' . '''Cinchocaine''' (]/]) or '''dibucaine''' (]) is an ] ]. Among the most potent and toxic of the long-acting local anesthetics, current use of cinchocaine is generally restricted to spinal and topical anesthesia.<ref>Martindale, The Extra Pharmacopoeia, 30th ed, p1006</ref><ref>{{cite web | url = https://meshb.nlm.nih.gov/record/ui?ui=D003992 | title = Dibucaine | work = MeSH Browser | publisher = U.S. National Library of Medicine }}</ref> It is sold under the brand names '''Cincain''', '''Nupercainal''', '''Nupercaine''' and '''Sovcaine'''.


==Medical use==
Dibucaine is insoluble in alkaline aquatic environments.
Cinchocaine is the active ingredient in some topical ] creams such as ].<ref name="Netdoctor">{{Cite web | vauthors = Henderson R | date = 29 November 2020 | url=https://www.netdoctor.co.uk/medicines/digestion/a7401/proctosedyl-ointment-suppositories-cinchocaine-hydrocortisone/ | title=Proctosedyl ointment/suppositories (cinchocaine, hydrocortisone) | publisher = Netdoctor | access-date=25 December 2019}}</ref> It is also a component of the ] drug Somulose, used for ] of ]s and ].


==Physical properties==
It is also a component of the ] drug '''Somulose''', used for ] of ] and ].
Cinchocaine is relatively ] in ] aqueous solutions.


==See also== == See also ==
* ] * ]


==External links== == References ==
{{reflist}}
⚫ * {{cite journal | author = Abdel-Ghani N, Youssef A, Awady M | title = Cinchocaine hydrochloride determination by atomic absorption spectrometry and spectrophotometry. | journal = Farmaco | volume = 60 | issue = 5 | pages = 419–24 | year = 2005 | pmid = 15910814 | doi = 10.1016/j.farmac.2005.03.001}}
⚫ * {{cite journal | author = Souto-Padron T, Lima AP, de Oliveira Ribeiro R. | title = Effects of dibucaine on the endocytic/exocytic pathways in Trypanosoma cruzi. | journal = Parasitol Res | volume = 99| issue = 4| pages = 317| year = 2006 | pmid = 16612626 | doi = 10.1007/s00436-006-0192-1}}
⚫ * {{cite journal | author = Nounou M, El-Khordagui L, Khalafallah N | title = Effect of various formulation variables on the encapsulation and stability of dibucaine base in multilamellar vesicles. | journal = Acta Pol Pharm | volume = 62 | issue = 5 | pages = 369–79 | year = 2005| pmid = 16459486}}
* {{cite journal | author = Aroti,A.;Leontidis, E. | title = | journal = Journal of Chemical Education| volume = 76 | issue = | pages = 786–788 | year = 2001 | unused_data = pmid }}


== Further reading ==
{{refbegin}}
⚫ * {{cite journal | vauthors = Abdel-Ghani NT, Youssef AF, Awady MA | title = Cinchocaine hydrochloride determination by atomic absorption spectrometry and spectrophotometry | journal = Farmaco | volume = 60 | issue = 5 | pages = 419–424 | date = May 2005 | pmid = 15910814 | doi = 10.1016/j.farmac.2005.03.001 }}
⚫ * {{cite journal | vauthors = Souto-Padrón T, Lima AP, ((Ribeiro Rd)) | title = Effects of dibucaine on the endocytic/exocytic pathways in Trypanosoma cruzi | journal = Parasitology Research | volume = 99 | issue = 4 | pages = 317–320 | date = September 2006 | pmid = 16612626 | doi = 10.1007/s00436-006-0192-1 | s2cid = 5933459 }}
⚫ * {{cite journal | vauthors = Nounou MM, El-Khordagui LK, Khalafallah N | title = Effect of various formulation variables on the encapsulation and stability of dibucaine base in multilamellar vesicles | journal = Acta Poloniae Pharmaceutica | volume = 62 | issue = 5 | pages = 369–379 | year = 2005 | pmid = 16459486 }}
* {{cite journal | vauthors = Aroti A, Leontidis E | title = Simultaneous Determination of the Ionization Constant and the Solubility of Sparingly Soluble Drug Substances. A Physical Chemistry Experiment. | journal = Journal of Chemical Education| volume = 78 | issue = 6 | pages = 786–788 | year = 2001 | doi = 10.1021/ed078p786 | bibcode = 2001JChEd..78..786A }}
{{refend}}


{{Vasoprotectives}} {{Vasoprotectives}}
{{Antipruritics}} {{Antipruritics}}
{{local anesthetics}} {{local anesthetics}}



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{{cardiovascular-drug-stub}}
{{dermatologic-drug-stub}} {{dermatologic-drug-stub}}
{{nervous-system-drug-stub}} {{nervous-system-drug-stub}}

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