Cinchocaine

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. It is sold under the brand names Cincain, Nupercainal, Nupercaine and Sovcaine.

Cinchocaine

Clinical data
AHFS/Drugs.com	International Drug Names
Routes of administration	topical, intravenous (for animal euthanasia)
ATC code	C05AD04 (WHO) D04AB02 (WHO) N01BB06 (WHO) S01HA06 (WHO) S02DA04 (WHO)
Legal status
Legal status	US: OTC
Identifiers
IUPAC name 2-butoxy-N-[2-(diethylamino)ethyl]quinoline-4-carboxamide
CAS Number	85-79-0 Y
PubChem CID	3025
IUPHAR/BPS	7159
DrugBank	DB00527 Y
ChemSpider	2917 Y
UNII	L6JW2TJG99
KEGG	D00733 Y
ChEBI	CHEBI:247956 Y
ChEMBL	ChEMBL1086 Y
CompTox Dashboard (EPA)	DTXSID3045271
ECHA InfoCard	100.001.484
Chemical and physical data
Formula	C20H29N3O2
Molar mass	343.471 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=C(c1c2ccccc2nc(OCCCC)c1)NCCN(CC)CC
InChI InChI=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) Y Key:PUFQVTATUTYEAL-UHFFFAOYSA-N Y
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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 aqueous solutions.

See also

• Dibucaine number

Further reading

• Abdel-Ghani NT, Youssef AF, Awady MA (May 2005). "Cinchocaine hydrochloride determination by atomic absorption spectrometry and spectrophotometry". Farmaco. 60 (5): 419–424. doi:10.1016/j.farmac.2005.03.001. PMID 15910814.
• Souto-Padrón T, Lima AP, Ribeiro Rd (September 2006). "Effects of dibucaine on the endocytic/exocytic pathways in Trypanosoma cruzi". Parasitology Research. 99 (4): 317–320. doi:10.1007/s00436-006-0192-1. PMID 16612626. S2CID 5933459.
• Nounou MM, El-Khordagui LK, Khalafallah N (2005). "Effect of various formulation variables on the encapsulation and stability of dibucaine base in multilamellar vesicles". Acta Poloniae Pharmaceutica. 62 (5): 369–379. 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. Bibcode:2001JChEd..78..786A. doi:10.1021/ed078p786.