Dibucaine

Summary

Dibucaine (CHEMBL1086) is an approved small-molecule topical anaesthetic (ATC S02DA04); indicated across 3 conditions including hemorrhoid and sunburn.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: S02DA04 (+4 more)
• Indications: 3 conditions
• Chemistry: 343.5 Da · C20H29N3O2

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL1086
Name	Dibucaine
Type	Small molecule
Max phase	4
FDA approved	yes
PubChem CID	3025
ChEBI	CHEBI:247956
ATC	S02DA04, S01HA06, D04AB02, N01BB06, C05AD04
Molecular formula	C20H29N3O2
Molecular weight	343.5
InChIKey	PUFQVTATUTYEAL-UHFFFAOYSA-N

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

IUPAC name: 2-butoxy-N-[2-(diethylamino)ethyl]quinoline-4-carboxamide

ChEBI definition: A monocarboxylic acid amide that is the 2-(diethylamino)ethyl amide of 2-butoxyquinoline-4-carboxylic acid. One of the most potent and toxic of the long-acting local anesthetics, its parenteral use was restricted to spinal anesthesia. It is now generally only used (usually as the hydrochloride) in creams and ointments and in suppositories for temporary relief of pain and itching associated with skin and anorectal conditions.

Pharmacological roles (ChEBI): topical anaesthetic.

Also known as: Cinchocaine, Cincocaina, Dibucaine, NSC-159055, dibucaine, SID11112228, SID855529, SID50100394, SID50100395, SID56424123, SID144203932, SID170464829

Parent form; salt/anhydrous children: CHEMBL1200612

Patent coverage: 4,817 distinct patent families (17,231 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 17,228 (100%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Broader ChEMBL bioactivity targets: 15 (assay-derived). Sample: Lysine-specific demethylase 4E, Survival motor neuron protein, Prelamin-A/C, 15-hydroxyprostaglandin dehydrogenase [NAD(+)], Voltage-dependent L-type calcium channel subunit alpha-1C, Sodium channel protein type 5 subunit alpha, Sodium channel alpha subunits; brain (Types I, II, III), Kappa-type opioid receptor, Voltage-gated inwardly rectifying potassium channel KCNH2, Lysosomal alpha-glucosidase, Cytochrome P450 2D6, Cytochrome P450 1A2, Aldehyde dehydrogenase 1A1, Growth hormone secretagogue receptor type 1, Bile salt export pump.

Bioactivity

ChEMBL activities: 10 potent at pChembl ≥ 5 of 18 total. Top 100 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
LMNA	8.15	Potency	7.1	nM	CHEMBL_ACT_3643945
SMN1	6.05	Potency	891.3	nM	CHEMBL_ACT_3890085
KCNH2	5.85	AC50	1419	nM	CHEMBL_ACT_25118032
SCN1A	5.85	IC50	1400	nM	CHEMBL_ACT_388275
SCN5A	5.75	AC50	1800	nM	CHEMBL_ACT_25158937
CYP1A2	5.3	AC50	5012	nM	CHEMBL_ACT_6059732
OPRK1	5.13	AC50	7357	nM	CHEMBL_ACT_25129532
CYP2D6	5.1	Potency	7943	nM	CHEMBL_ACT_4990296
CYP2D6	5.1	AC50	7943	nM	CHEMBL_ACT_6019822
ALDH1A1	5.05	Potency	8912	nM	CHEMBL_ACT_4155799

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

2 approved indications. FDA phase 4, plus an anticancer drug’s labelled cancer uses (which ChEMBL often logs at phase 3).

Indication	Phase	MONDO	EFO
hemorrhoid	4	MONDO:0004872	EFO:0009552
sunburn	4	MONDO:0005326	EFO:0003958

1 further indication record had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 0.

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.

Related molecules

Related molecules

No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).