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Inhibitor Report for: Dibucaine

Dibucaine is a local anesthetic of the amide type now generally used for surface anesthesia. Dibucaine reversibly binds to and inactivates sodium channels in the neuronal cell membrane. Inhibition of sodium channels prevents the depolarization of nerve cell membranes and inhibits subsequent propagation of impulses along the course of the nerve, thereby limiting the excitation of nerve endings. This results in loss of sensation. Dibucaine inhibits normal butyrylcholinesterase activity. The percentage of butyrylcholine that remains unchanged in the blood of individuals administered a standard dose of dibucaine was the dibucaine number. This number was used to differentiate the genetic variants. A dibucaine number of 80 and above for wild type homozygotes (normal), 40-60 for heterozygotes (atypical), and 20 or less for atypical homozygotes (D70G)


General
Type Local anesthetic, Quinoline, Drug, Not A/B H target, Carboxamide
Chemical_Nomenclature 2-Butoxy-N-[2-(diethylamino)ethyl]-4-quinolinecarboxamide
Canonical SMILES CCCCOC1=NC2=CC=CC=C2C(=C1)C(=O)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)
InChIKey PUFQVTATUTYEAL-UHFFFAOYSA-N
Other name(s) Nupercainal ; Benzolin ; Nupercaine ; Percaine ; Cincaine ; Sovcaine ; Cinchocaine ; Dermacaine ; Dibucain ; Dibucaine Base ; Dibucainum ; Cincainum
________________________________________________________________________________________________
MW|343.5
Formula|C20H29N3O2
CAS_number|85-79-0
PubChem|3025
UniChem|PUFQVTATUTYEAL-UHFFFAOYSA-N
IUPHAR|7159
Wikipedia|Cinchocaine

Target
Families | Dibucaine ligand of proteins in family: BCHE

References:
Search PubMed for references concerning: Dibucaine

7 more
    Title: Genetic variants of human serum cholinesterase influence metabolism of the muscle relaxant succinylcholine.
    Lockridge O
    Ref: Pharmacol Ther, 47:35, 1990 : PubMed

            

    Title: Differential inhibition of plasma cholinesterase variants using the dibutyrate analogue of pancuronium bromide
    Whittaker M, Britten JJ
    Ref: Hum Hered, 31:242, 1981 : PubMed

            

    Title: The activity of various esterase inhibitors towards atypical human serum cholinesterase
    Kalow W, Davies R0
    Ref: Biochemical Pharmacology, 1:183, 1958 : PubMed

            


human-ACHE
MutationKiKsiIc50SubstrateConditionPaper
WT 710 uM - - Acetylthiocholine 50mM NaPhosphate pH7.4 Loewenstein-Lichtenstein_1996_Mol.Pharmacol_50_1423

human-BCHE
MutationKiKsiIc50SubstrateConditionPaper
> Mutations for human-BCHE (24)

WT Kinetics
Kinetic parametersKiKsiIc50SubstrateConditionsPapers
human-ACHE710 uM--Acetylthiocholine 50mM NaPhosphate pH7.4 Loewenstein-Lichtenstein_1996_Mol.Pharmacol_50_1423
human-BCHE--2.7 uM  Lockridge_1990_Pharmacol.Ther_47_35
human-BCHE6.9 & 4.6 uM-- Butyrylthiocholine 50mM NaPhosphate pH7.4 Loewenstein-Lichtenstein_1996_Mol.Pharmacol_50_1423