DIBUCAINE

US Approved OTC

First marketed in 1930

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 Search

SMILES

CCCCOC1=CC(C(=O)NCCN(CC)CC)=C2C=CC=CC2=N1

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

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=e3807a1b-c375-456a-bd7e-de3a1607c8fc | https://www.ncbi.nlm.nih.gov/pubmed/9742684

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 Target	Pharmacology	Condition	Potency
Sodium channel protein type V alpha subunit 49 Target ID: CHEMBL1980 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9742684	Blocker 555
Sodium channel protein type X alpha subunit 9 Target ID: CHEMBL5451 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9742684	Blocker 555

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 619 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=e3807a1b-c375-456a-bd7e-de3a1607c8fc	Primary		Approved 8583	Nupercainal Approved Use temporarily relieves pain and itching due to: - hemorrhoids or other anorectal disorders - sunburn - minor burns - minor cuts- scrapes - insect bites - minor skin irritation

C_max

Value	Dose	Co-administered	Analyte	Population
23 ng/mL EXPERIMENT https://www.tandfonline.com/doi/pdf/10.1080/00032718108059837	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:		DIBUCAINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
208 ng × h/mL EXPERIMENT https://www.tandfonline.com/doi/pdf/10.1080/00032718108059837	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:		DIBUCAINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
11 h EXPERIMENT https://www.tandfonline.com/doi/pdf/10.1080/00032718108059837	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:		DIBUCAINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	P-gp 2052

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 2052	substrate 4014 Sources: https://www.tandfonline.com/doi/abs/10.1517/17425255.2.5.733 Page: 2.0	yes

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY574448	https://www.001chemical.com/chem/85-79-0
3B Scientific (Wuhan) Corp	3B2-6004	http://www.3bsc.com/index/pro_info.php?id=88902
AA Blocks	AA008GHY	https://www.aablocks.com/goods/Goods/detail?id=AA008GHY
Aaron Chemicals	AR008H9Q	http://www.aaronchem.com/85-79-0
abcr GmbH	AB443322	http://www.abcr.com/shop/en/AB443322
AbMole Bioscience	M5570	http://www.abmole.com/products/dibucaine.html
Accela ChemBio Inc	SY107339	http://www.accelachem.com/cn/search.html?keyword=SY107339&attname=GoodsCode
Achemo Scientific Limited	AC-20177	http://www.achemo.com/search/?Keyword= 85-79-0
Achemtek	0104-002382	http://www.achemtek.com/85-79-0
AK Scientific, Inc. (AKSCI)	V0074	http://www.aksci.com/item_detail.php?cat=V0074
Alfa Chemistry	85-79-0	https://www.alfa-chemistry.com/cinchocaine-cas-85-79-0-item-293909.htm
Angene	AGN-PC-0JK6F0	http://www.angenechemical.com/productshow/AGN-PC-0JK6F0.html
ApexBio Technology	A8407	http://www.apexbt.com/dibucaine-cinchocaine-hcl.html
ApexBio Technology	B3373	http://www.apexbt.com/dibucaine.html
Ark Pharm	AK161941	http://www.arkpharminc.com/products/85-79-0.html
Aurora Fine Chemicals LLC	A17.913.049	http://online.aurorafinechemicals.com/info?ID=A17.913.049
BioSynth	Q-100863	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/Q-100863.html
Chem Scene	CS-2656	http://www.chemscene.com/85-79-0.html
ChemMol	30110903	http://www.chemmol.com/chemmol/30110903.html
ChemMol	44013477	http://www.chemmol.com/chemmol/44013477.html
ChemMol	49408188	http://www.chemmol.com/chemmol/49408188.html
Chemodex	C0694	http://www.chemodex.com/products/C0694
Chemspace	CSSB00000040244	https://chem-space.com/CSSB00000040244
Clearsynth	CS-O-06228	https://www.clearsynth.com/en/CSO06228.html
Combi-Blocks	QJ-7747	http://www.combi-blocks.com/cgi-bin/find.cgi?QJ-7747
DC Chemicals	DC31648	http://www.dcchemicals.com//product_show-Dibucaine.html
Debye Scientific	DB-056882	http://www.debyesci.com/cas_85-79-0.html
eNovation Chemicals	D485382	https://www.enovationchem.com/ProductDetails.asp?ProductID=D485382
eNovation Chemicals	D673952	https://www.enovationchem.com/ProductDetails.asp?ProductID=D673952
Finetech	FT-0603086	http://www.finetechnology-ind.com/prod/detail/pub/85-79-0.html
iChemical	EBD44268	http://www.ichemical.com/chemicals/cas-85-79-0
Lab Network	LN01342252	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01342252
mcule	MCULE-4397469465	https://mcule.com/MCULE-4397469465/
MedChem Express	HY-B0552	https://www.medchemexpress.com/Dibucaine.html
Molcore	MC574448	https://www.molcore.com/product/85-79-0
MuseChem	I005156	https://www.musechem.com/product/I005156.html
Parchem	18439	http://www.parchem.com/chemical-supplier-distributor/Dibucaine-HCL-008439.aspx
Smolecule	S525923	http://www.smolecule.com/products/s525923
Smolecule	S772554	https://www.smolecule.com/products/s772554
THE BioTek	bt-267688	https://www.thebiotek.com/product/inhibitors/bt-267688
Vitas-M Laboratory	STL483757	http://www.request.vitasmlab.com/index.php?option=com_search_stk&Itemid=22&stk=STL483757&?utm_source=pubchem&utm_medium=p_search_link&utm_campaign=pubchem_search&utm_content=pubchem_slink

PubMed

Title	Date	PubMed
Nitric oxide production by the vacuolar-type (H+)-ATPase inhibitors bafilomycin A1 and concanamycin A and its possible role in apoptosis in RAW 264.7 cells.	2006-11	16895977
Overexpression of RGPR-p117 enhances regucalcin gene promoter activity in cloned normal rat kidney proximal tubular epithelial cells: involvement of TTGGC motif.	2006-10-01	16676356
Involvement of nuclear factor I-A1 in the regulation of regucalcin gene promoter activity in cloned normal rat kidney proximal tubular epithelial cells.	2006-10	16964421
Verapamil, a Ca2+ channel inhibitor acts as a local anesthetic and induces the sigma E dependent extra-cytoplasmic stress response in E. coli.	2006-10	16836975
Inhibition of scratching behavior associated with allergic dermatitis in mice by tacrolimus, but not by dexamethasone.	2006-09-28	16914137
Effects of dibucaine on the endocytic/exocytic pathways in Trypanosoma cruzi.	2006-09	16612626
Regulatory effect of exogenous regucalcin on cell function in osteoblastic MC3T3-E1 cells: involvement of intracellular signaling factor.	2006-08	16820941
Supramolecular binding of protonated amines to a receptor microgel in aqueous medium.	2006-06-21	16758026
Divergence paresis without positional headache: an unusual presentation of cerebrospinal fluid hypovolemia after spinal anesthesia.	2006-06	16717340
[Butyrylcholinesterase deficiency: how to analyse the cholinesterase activity in small children?].	2006-06	16581221
Effect of various formulation variables on the encapsulation and stability of dibucaine base in multilamellar vesicles.	2006-02-08	16459486
Toxicity of polymyxins: a systematic review of the evidence from old and recent studies.	2006-02	16507149
False positives and false negatives with a cocaine-specific field test and modification of test protocol to reduce false decision.	2005-12-20	16226152
[Anogenital dermatoses--allergic and irritative causative factors. Analysis of IVDK data and review of the literature].	2005-12	16405714
Overexpression of RGPR-p117 enhances regucalcin gene expression in cloned normal rat kidney proximal tubular epithelial cells.	2005-12	16273285
Pseudocholinesterase polymorphism in an Irish population.	2005-11	16275543
Overexpression of regucalcin suppresses cell proliferation in cloned rat hepatoma H4-II-E cells: involvement of intracellular signaling factors and cell cycle-related genes.	2005-08-15	15962315
Activation of calcium-independent phospholipase A (iPLA) in brain mitochondria and release of apoptogenic factors by BAX and truncated BID.	2005-08	16092941
Prescription pattern for treatment of hemorrhoids under the universal coverage policy of Thailand.	2005-07	16295562
Hormonal regulation on regucalcin mRNA expression in cloned normal rat kidney proximal tubular epithelial NRK52E cells.	2005-06-01	15786489
Cinchocaine hydrochloride determination by atomic absorption spectrometry and spectrophotometry.	2005-05	15910814
Wetting of surfactant solutions by alkanes.	2005-03	15799482
Genotyping the butyrylcholinesterase in patients with prolonged neuromuscular block after succinylcholine.	2005-03	15731589
Rapid accurate mass desorption electrospray ionisation tandem mass spectrometry of pharmaceutical samples.	2005	16287035
Cd2+ versus Ca2+-produced mitochondrial membrane permeabilization: a proposed direct participation of respiratory complexes I and III.	2004-12-07	15560892
Role of albumin in osteoblastic cells: enhancement of cell proliferation and suppression of alkaline phosphatase activity.	2004-12	15547677
Microfabricated fractal branching networks.	2004-11-01	15376267
Protective actions of various local anesthetics against the membrane dysfunction produced by in vitro ischemia in rat hippocampal CA1 neurons.	2004-11	15488292
Overexpression of regucalcin suppresses cell death and apoptosis in cloned rat hepatoma H4-II-E cells induced by lipopolysaccharide, PD 98059, dibucaine, or Bay K 8644.	2004-10-15	15378600
Preferential partitioning of uncharged local anesthetics into the surface-adsorbed film.	2004-10-10	15465309
[Allergy to formaldehyde].	2004-09	15628056
[Glucose attenuating local anesthetic-induced hemolysis].	2004-09	15500098
A new look at the hemolytic effect of local anesthetics, considering their real membrane/water partitioning at pH 7.4.	2004-08-01	15228957
Local anaesthetics--Nupercaine and Amethcaine.	2004-08	15806723
Randomized, double-blind trial comparing topical nitroglycerine with xylocaine and Proctosedyl in idiopathic chronic anal fissure.	2004-07-15	15250565
Evaluation of antipruritic effects of several agents on scratching behavior by NC/Nga mice.	2004-07-14	15249165
Apoptotic-like mitochondrial events associated to phosphatidylserine exposure in blood platelets induced by local anaesthetics.	2004-07	15213851
Effect of the glycosphingolipid, GM1 on localization of dibucaine in phospholipid vesicles: a fluorescence study.	2004-07	15172834
Some amphiphilic cations block the mitochondrial apoptosis-induced channel, MAC.	2004-06-18	15196916
Interaction of serotonin1A receptors from bovine hippocampus with tertiary amine local anesthetics.	2004-06	15206822
Probing the mechanism of drug/lipid membrane interactions using Biacore.	2004-05-15	15113702
Ethnic differences in the frequency of distribution of serum cholinesterase activity in the Iranian population.	2004-05	15213732
Quantitative evaluation of the effects of mitochondrial permeability transition pore modifiers on accumulation of calcium phosphate: comparison of rat liver and brain mitochondria.	2004-04-01	15019835
[Cauda equina syndrome following intrathecal dibucaine].	2004-04	15160665
Possible mechanism of irreversible nerve injury caused by local anesthetics: detergent properties of local anesthetics and membrane disruption.	2004-04	15087634
Anesthesiology, the birth of pharmacogenetics and Werner Kalow.	2004-03	15010397
[What we can learn from a case of medical malpractice].	2004-02	15027169
p-Bromophenacyl bromide prevents cumene hydroperoxide-induced mitochondrial permeability transition by inhibiting pyridine nucleotide oxidation.	2004	15274248
An improvement in segregation of human butyrylcholinesterase phenotypes having the fluoride-resistant variants.	2003-12	14994645
[Ionic strength influences hemolytic action of dibucaine hydrochloride].	2003-11	14661561

Patents

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 Created by `admin` on `Wed Apr 02 09:30:39 GMT 2025` Edited by `admin` on `Wed Apr 02 09:30:39 GMT 2025`
Record UNII	L6JW2TJG99
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

CINCHOCAINE

Preferred Name

English

DIBUCAINE

Official Name

English

2-Butoxy-N-[2-(diethylamino)ethyl]cinchoninamide

Systematic Name

English

DIBUCAINE [USP IMPURITY]

Common Name

English

DIBUCAINE [USP MONOGRAPH]

Common Name

English

Cinchocaine [WHO-DD]

Common Name

English

NSC-159055

Code

English

DIBUCAINE [MI]

Common Name

English

cinchocaine [INN]

Common Name

English

4-QUINOLINECARBOXAMIDE, 2-BUTOXY-N-(2-(DIETHYLAMINO)ETHYL)

Common Name

English

2-BUTOXY-N-(2-(DIETHYLAMINO)ETHYL)-4-QUINOLINECARBOXAMIDE

Systematic Name

English

DIBUCAINE [HSDB]

Common Name

English

CINCHOCAINE [MART.]

Common Name

English

2-BUTOXY-N-(2-DIETHYLAMINOETHYL)CINCHONINAMIDE

Systematic Name

English

DIBUCAINE [VANDF]

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 310.538