Details of the Drug

General Information of Drug (ID: DMF9G7L)

Drug Name

Dibucaine

Synonyms

Cincainum; Cinchocaine; Cinchocainum; Cincocaina; Cincocainio; Dermacaine; Dibucain; Dibucainum; Nupercainal; Nupercaine; Percamine; Sovcaine; Cinchocaine HCL; Cinchocaine hydrochloride; Cincocaina [DCIT]; Dibucaine Base; Dibucaine [USP]; Alpha-Butyloxycinchoninic acid diethylethylenediamide; Cincain (TN); Cinchocaine (INN);Cinchocainum [INN-Latin]; Cincocainio [INN-Spanish]; Dibucaine (USP); Nupercainal (TN); Nupercainal (VAN); Nupercaine (TN); Sovcaine (TN); Alpha-Butyloxycinchonic acid-gamma-diethylethylenediamine; N-[2-(Diethylamino)ethyl]-2-butoxycinchoninamide; N-(2-(Diethylamino)ethyl)-2-butoxycinchoninamide; QUINOLINE,2-BUTOXY,4-CARBOXY,(N-TRIETHYLAMINO) AMIDE CINCHOCAIN; 2-Butoxy-N-(2-(diethylamino)ethyl)cinchoninamide; 2-Butoxy-N-(beta-diethylaminoethyl)cinchoninamide; 2-Butoxy-N-(beta.-diethylaminoethyl)cinchoninamide; 2-Butoxy-N-[2-(diethylamino)ethyl]-4-quinolinecarboxamide; 2-Butoxy-N-[2-(diethylamino)ethyl]cinchoninamide; 2-Butoxy-quinoline-4-carboxylic acid (2-diethylamino-ethyl)-amide; 2-Butoxyquinoline-4-carboxylic acid diethylaminoethylamide; 2-N-Butoxy-N-(2-diethylaminoethyl)cinchoninamide; 2-butoxy-N-(2-diethylaminoethyl)quinoline-4-carboxamide; 2-butoxy-N-(alpha-diethylaminoethyl)cinchoninamide; 2-butoxy-N-[2-(diethylamino)ethyl]quinoline-4-carboxamide

Indication

Disease Entry	ICD 11	Status	REF
Anaesthesia	9A78.6	Approved	[1], [2], [3]

Therapeutic Class

Anesthetics

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

343.5

Topological Polar Surface Area (xlogp)

4.4

Rotatable Bond Count (rotbonds)

10

Hydrogen Bond Donor Count (hbonddonor)

1

Hydrogen Bond Acceptor Count (hbondacc)

4

ADMET Property

Metabolism: The drug is metabolized via the hepatic [4]

Chemical Identifiers

Formula: C20H29N3O2
IUPAC Name: 2-butoxy-N-[2-(diethylamino)ethyl]quinoline-4-carboxamide
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

Cross-matching ID

PubChem CID: 3025
ChEBI ID: CHEBI:247956
CAS Number: 85-79-0
DrugBank ID: DB00527
TTD ID: D0P5GE

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Voltage-gated sodium channel alpha Nav1.5 (SCN5A)	TTZOVE0	SCN5A_HUMAN	Blocker	[5]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Dibucaine (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Prilocaine	DMI7DZ2	Major	Increased risk of methemoglobinemia by the combination of Dibucaine and Prilocaine.	Pain [MG30-MG3Z]	[12]
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References

1	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7159).
2	FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (NDA) 006203.
3	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
4	FDA approval: ado-trastuzumab emtansine for the treatment of patients with HER2-positive metastatic breast cancer. Clin Cancer Res. 2014 Sep 1;20(17):4436-41.
5	Halothane attenuates the cerebroprotective action of several Na+ and Ca2+ channel blockers via reversal of their ion channel blockade. Eur J Pharmacol. 2002 Oct 4;452(2):175-81.
6	Lacosamide: a new approach to target voltage-gated sodium currents in epileptic disorders. CNS Drugs. 2009;23(7):555-68.
7	Effect of sodium channel blockers on ST segment, QRS duration, and corrected QT interval in patients with Brugada syndrome. J Cardiovasc Electrophysiol. 2000 Dec;11(12):1320-9.
8	Medicinal chemistry of neuronal voltage-gated sodium channel blockers. J Med Chem. 2001 Jan 18;44(2):115-37.
9	Monoamine transporter and sodium channel mechanisms in the rapid pressor response to cocaine. Pharmacol Biochem Behav. 1998 Feb;59(2):305-12.
10	From first class to third class: recent upheaval in antiarrhythmic therapy--lessons from clinical trials. Am J Cardiol. 1996 Aug 29;78(4A):28-33.
11	How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
12	Cerner Multum, Inc. "Australian Product Information.".