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=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

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 537
Sodium channel protein type X alpha subunit 9 Target ID: CHEMBL5451 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9742684	Blocker 537

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 614 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=e3807a1b-c375-456a-bd7e-de3a1607c8fc	Primary		Approved 8429	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 1537

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 1537	substrate 3367 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
AK Scientific, Inc. (AKSCI)	V0074	http://www.aksci.com/item_detail.php?cat=V0074
Aaron Chemicals	AR008H9Q	http://www.aaronchem.com/85-79-0
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
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
Finetech	FT-0603086	http://www.finetechnology-ind.com/prod/detail/pub/85-79-0.html
Lab Network	LN01342252	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01342252
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
abcr GmbH	AB443322	http://www.abcr.com/shop/en/AB443322
eNovation Chemicals	D485382	https://www.enovationchem.com/ProductDetails.asp?ProductID=D485382
eNovation Chemicals	D673952	https://www.enovationchem.com/ProductDetails.asp?ProductID=D673952
iChemical	EBD44268	http://www.ichemical.com/chemicals/cas-85-79-0
mcule	MCULE-4397469465	https://mcule.com/MCULE-4397469465/

PubMed

Title	Date	PubMed
An improvement in segregation of human butyrylcholinesterase phenotypes having the fluoride-resistant variants.	2003 Dec	14994645
[Ionic strength influences hemolytic action of dibucaine hydrochloride].	2003 Nov	14661561
p-Bromophenacyl bromide prevents cumene hydroperoxide-induced mitochondrial permeability transition by inhibiting pyridine nucleotide oxidation.	2004	15274248
[Cauda equina syndrome following intrathecal dibucaine].	2004 Apr	15160665
Possible mechanism of irreversible nerve injury caused by local anesthetics: detergent properties of local anesthetics and membrane disruption.	2004 Apr	15087634
Quantitative evaluation of the effects of mitochondrial permeability transition pore modifiers on accumulation of calcium phosphate: comparison of rat liver and brain mitochondria.	2004 Apr 1	15019835
Local anaesthetics--Nupercaine and Amethcaine.	2004 Aug	15806723
A new look at the hemolytic effect of local anesthetics, considering their real membrane/water partitioning at pH 7.4.	2004 Aug 1	15228957
Role of albumin in osteoblastic cells: enhancement of cell proliferation and suppression of alkaline phosphatase activity.	2004 Dec	15547677
Cd2+ versus Ca2+-produced mitochondrial membrane permeabilization: a proposed direct participation of respiratory complexes I and III.	2004 Dec 7	15560892
[What we can learn from a case of medical malpractice].	2004 Feb	15027169
Apoptotic-like mitochondrial events associated to phosphatidylserine exposure in blood platelets induced by local anaesthetics.	2004 Jul	15213851
Effect of the glycosphingolipid, GM1 on localization of dibucaine in phospholipid vesicles: a fluorescence study.	2004 Jul	15172834
Evaluation of antipruritic effects of several agents on scratching behavior by NC/Nga mice.	2004 Jul 14	15249165
Interaction of serotonin1A receptors from bovine hippocampus with tertiary amine local anesthetics.	2004 Jun	15206822
Some amphiphilic cations block the mitochondrial apoptosis-induced channel, MAC.	2004 Jun 18	15196916
Anesthesiology, the birth of pharmacogenetics and Werner Kalow.	2004 Mar	15010397
Ethnic differences in the frequency of distribution of serum cholinesterase activity in the Iranian population.	2004 May	15213732
Probing the mechanism of drug/lipid membrane interactions using Biacore.	2004 May 15	15113702
Randomized, double-blind trial comparing topical nitroglycerine with xylocaine and Proctosedyl in idiopathic chronic anal fissure.	2004 May-Jun	15250565
Protective actions of various local anesthetics against the membrane dysfunction produced by in vitro ischemia in rat hippocampal CA1 neurons.	2004 Nov	15488292
Microfabricated fractal branching networks.	2004 Nov 1	15376267
Preferential partitioning of uncharged local anesthetics into the surface-adsorbed film.	2004 Oct 10	15465309
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 Oct 15	15378600
[Allergy to formaldehyde].	2004 Sep	15628056
[Glucose attenuating local anesthetic-induced hemolysis].	2004 Sep	15500098
Rapid accurate mass desorption electrospray ionisation tandem mass spectrometry of pharmaceutical samples.	2005	16287035
Activation of calcium-independent phospholipase A (iPLA) in brain mitochondria and release of apoptogenic factors by BAX and truncated BID.	2005 Aug	16092941
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 Aug 15	15962315
[Anogenital dermatoses--allergic and irritative causative factors. Analysis of IVDK data and review of the literature].	2005 Dec	16405714
Overexpression of RGPR-p117 enhances regucalcin gene expression in cloned normal rat kidney proximal tubular epithelial cells.	2005 Dec	16273285
False positives and false negatives with a cocaine-specific field test and modification of test protocol to reduce false decision.	2005 Dec 20	16226152
Prescription pattern for treatment of hemorrhoids under the universal coverage policy of Thailand.	2005 Jul	16295562
Hormonal regulation on regucalcin mRNA expression in cloned normal rat kidney proximal tubular epithelial NRK52E cells.	2005 Jun 1	15786489
Wetting of surfactant solutions by alkanes.	2005 Mar	15799482
Genotyping the butyrylcholinesterase in patients with prolonged neuromuscular block after succinylcholine.	2005 Mar	15731589
Cinchocaine hydrochloride determination by atomic absorption spectrometry and spectrophotometry.	2005 May	15910814
Pseudocholinesterase polymorphism in an Irish population.	2005 Nov	16275543
Effect of various formulation variables on the encapsulation and stability of dibucaine base in multilamellar vesicles.	2005 Sep-Oct	16459486
Regulatory effect of exogenous regucalcin on cell function in osteoblastic MC3T3-E1 cells: involvement of intracellular signaling factor.	2006 Aug	16820941
Toxicity of polymyxins: a systematic review of the evidence from old and recent studies.	2006 Feb	16507149
Divergence paresis without positional headache: an unusual presentation of cerebrospinal fluid hypovolemia after spinal anesthesia.	2006 Jun	16717340
[Butyrylcholinesterase deficiency: how to analyse the cholinesterase activity in small children?].	2006 Jun	16581221
Supramolecular binding of protonated amines to a receptor microgel in aqueous medium.	2006 Jun 21	16758026
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 Nov	16895977
Involvement of nuclear factor I-A1 in the regulation of regucalcin gene promoter activity in cloned normal rat kidney proximal tubular epithelial cells.	2006 Oct	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 Oct	16836975
Overexpression of RGPR-p117 enhances regucalcin gene promoter activity in cloned normal rat kidney proximal tubular epithelial cells: involvement of TTGGC motif.	2006 Oct 1	16676356
Effects of dibucaine on the endocytic/exocytic pathways in Trypanosoma cruzi.	2006 Sep	16612626
Inhibition of scratching behavior associated with allergic dermatitis in mice by tacrolimus, but not by dexamethasone.	2006 Sep 28	16914137

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.

Name

Type

Language

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

CINCHOCAINE

Official 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