Cinchocaine: Difference between revisions

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{{drugbox
{{Drugbox
| IUPAC_name = 2-butoxy-''N''-(2-diethylaminoethyl) quinoline-4-carboxamide
| Watchedfields = changed
| image =
| verifiedrevid = 460037677
| IUPAC_name = 2-butoxy-''N''-[2-(diethylamino)ethyl]quinoline-4-carboxamide
| image = Cinchocaine.svg
| image2 = Cinchocaine 3D ball-and-stick.png
 
<!--Clinical data-->
| tradename = 
| Drugs.com = {{drugs.com|international|cinchocaine}}
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category = 
| legal_AU = <!-- Unscheduled / S2 / S4 / S8 -->
| legal_UK = <!-- GSL / P / POM / CD -->
| legal_US = OTC
| legal_status = 
| routes_of_administration = topical, intravenous (equine euthanasia)
 
<!--Pharmacokinetic data-->
| bioavailability = 
| protein_bound = 
| metabolism = 
| elimination_half-life = 
| excretion = 
 
<!--Identifiers-->
| 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 = APRD00915
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| C = 20 | H = 29 | N = 3 | O = 2
| DrugBank = DB00527
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2917
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = L6JW2TJG99
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00733
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 247956
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1086
 
<!--Chemical data-->
| C=20 | H=29 | N=3 | O=2
| molecular_weight = 343.463 g/mol
| molecular_weight = 343.463 g/mol
| bioavailability =  
| smiles = O=C(c1c2ccccc2nc(OCCCC)c1)NCCN(CC)CC
| protein_bound =  
| 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)
| metabolism =  
| InChIKey = PUFQVTATUTYEAL-UHFFFAOYAU
| elimination_half-life =  
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| excretion =
| 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)
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| pregnancy_US = <!-- A / B / C / D / X -->
| StdInChIKey = PUFQVTATUTYEAL-UHFFFAOYSA-N
| pregnancy_category =
| legal_AU = <!-- Unscheduled / S2 / S4 / S8 -->
| legal_UK = <!-- GSL / P / POM / CD -->
| legal_US = <!-- OTC / Rx-only -->
| legal_status =  
| routes_of_administration =  
}}
}}
'''Cinchocaine''' ([[International Nonproprietary Name|INN]]/[[British Approved Name|BAN]]) or '''dibucaine''' ([[United States Adopted Name|USAN]]) is an [[amide]] [[local anesthetic]]. 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>[http://www.nlm.nih.gov/cgi/mesh/2009/MB_cgi?mode=&term=Dibucaine Dibucaine]</ref> It is sold under the brand names '''Cincain''', '''Nupercainal''', '''Nupercaine''' and '''Sovcaine'''.
==Medical use==
Cinchocaine is the active ingredient in some topical hemorrhoid creams such as [[Proctosedyl]]. It is also a component of the [[veterinary]] drug '''Somulose''', used for [[animal euthanasia|euthanasia]] of [[horse]]s and [[cattle]].
==Physical properties==
Cinchocaine is relatively [[insoluble]] in [[alkaline]] aquatic solutions.


==Overview==
==See also==
'''Cinchocaine''' (or '''Dibucaine''') is an [[amide]] [[local anesthetic]].  It is the active ingredient in some topical hemorrhoid creams.
* [[Dibucaine number]]


It is also a component of the [[veterinary]] drug '''Somulose''', used for [[animal euthanasia|euthanasia]] of horses and cattle.
==References==
{{reflist}}


==External links==
==Further reading==
* {{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 | id = PMID 15910814}}
* {{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 = | issue = | pages = | year = 2006 | id = PMID 16612626}}
* {{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 = 317–20| 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 = | id = PMID 16459486}}
* {{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 =  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}}


{{Vasoprotectives}}
{{Vasoprotectives}}
{{Antipruritics}}
{{Antipruritics}}
{{local anesthetics}}
{{local anesthetics}}
{{dermatologic-drug-stub}}
{{nervous-system-drug-stub}}


[[Category:Local anesthetics]]
[[Category:Local anesthetics]]
 
[[Category:Quinolines]]
{{WikiDoc Help Menu}}
[[Category:Phenol ethers]]
 
[[Category:Amides]]
{{WS}}

Revision as of 12:43, 13 April 2015

Cinchocaine
File:Cinchocaine.svg
File:Cinchocaine 3D ball-and-stick.png
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration		topical, intravenous (equine euthanasia)
ATC code
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
DrugBank
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
FormulaC20H29N3O2
Molar mass343.463 g/mol
3D model (JSmol)
  (verify)

Cinchocaine (INN/BAN) or dibucaine (USAN) is an amide local anesthetic. Among the most potent and toxic of the long-acting local anesthetics, current use of cinchocaine is generally restricted to spinal and topical anesthesia.[1][2] It is sold under the brand names Cincain, Nupercainal, Nupercaine and Sovcaine.

Medical use

Cinchocaine is the active ingredient in some topical hemorrhoid creams such as Proctosedyl. It is also a component of the veterinary drug Somulose, used for euthanasia of horses and cattle.

Physical properties

Cinchocaine is relatively insoluble in alkaline aquatic solutions.

See also

References

  1. ↑ Martindale, The Extra Pharmacopoeia, 30th ed, p1006
  2. ↑ Dibucaine

Further reading

  • Abdel-Ghani N, Youssef A, Awady M (2005). "Cinchocaine hydrochloride determination by atomic absorption spectrometry and spectrophotometry". Farmaco. 60 (5): 419–24. doi:10.1016/j.farmac.2005.03.001. PMID 15910814.
  • Souto-Padron T, Lima AP, de Oliveira Ribeiro R. (2006). "Effects of dibucaine on the endocytic/exocytic pathways in Trypanosoma cruzi". Parasitol Res. 99 (4): 317–20. doi:10.1007/s00436-006-0192-1. PMID 16612626.
  • Nounou M, El-Khordagui L, Khalafallah N (2005). "Effect of various formulation variables on the encapsulation and stability of dibucaine base in multilamellar vesicles". Acta Pol Pharm. 62 (5): 369–79. PMID 16459486.
  • Aroti,A.;Leontidis, E. (2001). "Simultaneous Determination of the Ionization Constant and the Solubility of Sparingly Soluble Drug Substances. A Physical Chemistry Experiment". Journal of Chemical Education. 78 (6): 786–788. doi:10.1021/ed078p786.

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