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Details

Stereochemistry ACHIRAL
Molecular Formula C20H29N3O2
Molecular Weight 343.4632
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIBUCAINE

SMILES

CCCCOC1=NC2=CC=CC=C2C(=C1)C(=O)NCCN(CC)CC

InChI

InChIKey=PUFQVTATUTYEAL-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C20H29N3O2
Molecular Weight 343.4632
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Dibucaine is used as a local anesthetic for surface anesthesia. It is one of the most potent and toxic of the long-acting local anesthetics and its parenteral use is restricted to spinal anesthesia. Dibucaine is used to temporarily relieve pain and itching due to: hemorrhoids or other anorectal disorders, sunburn, minor burns, minor cuts; scrapes, insect bites, minor skin irritation. This drug acts via blocking of nerve impulses by decreasing the neuronal membrane's permeability to sodium ions through sodium channel blocking. This reversibly stabilizes the membrane and inhibits depolarization, resulting in the failure of a propagated action potential and subsequent conduction blockade.

CNS Activity

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Nupercainal

Cmax

ValueDoseCo-administeredAnalytePopulation
23 ng/mL
5 mg single, oral
DIBUCAINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
208 ng × h/mL
5 mg single, oral
DIBUCAINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
11 h
5 mg single, oral
DIBUCAINE plasma
Homo sapiens

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
If possible clean the affected area with mild soap and warm water and rinse thoroughly. Gently dry by patting or blotting with toilet tissue or a soft cloth before applying. Adults and children 12 and over - apply externally to the affected area up to 3 to 4 times a day. Children under 2 - 12 years of age - ask a doctor
Route of Administration: Topical
In Vitro Use Guide
Exposure of spinal nerves to dibucaine reduces the quantity of 3H-proteins, which is transported to a ligature by 72% at 0.5 mM and by greater than 90% at a 1 mM concentration; since 1 mM tetracaine reduces it by 64%, dibucaine is approximately twice as potent as tetracaine at inhibiting transport.
Substance Class Chemical
Record UNII
L6JW2TJG99
Record Status Validated (UNII)
Record Version