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.[1][2] 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
PubChem CID	3025
IUPHAR/BPS	7159
DrugBank	DB00527
ChemSpider	2917
UNII	L6JW2TJG99
KEGG	D00733
ChEBI	CHEBI:247956
ChEMBL	ChEMBL1086
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) Key:PUFQVTATUTYEAL-UHFFFAOYSA-N
(verify)

Medical use

Cinchocaine is the active ingredient in some topical hemorrhoid creams such as Proctosedyl.[3] 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

References

1. Martindale, The Extra Pharmacopoeia, 30th ed, p1006
2. Dibucaine
3. "Proctosedyl ointment/suppositories (cinchocaine, hydrocortisone)". Netdoctor. June 2012. Retrieved 25 December 2019.

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. S2CID 5933459.
• 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.