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]
Pruritus	EC90	Investigative	[2]
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Therapeutic Class

Anesthetics

Affected Organisms

Humans and other mammals

ATC Code

C05AD04: Dibucaine

C05AD: Local anesthetics

C05A: AGENTS FOR TREATMENT OF HEMORRHOIDS AND ANAL FISSURES FOR TOPICAL USE

C05: VASOPROTECTIVES

C: CARDIOVASCULAR SYSTEM

D04AB02: Dibucaine

D04AB: Anesthetics for topical use

D04A: ANTIPRURITICS, INCL. ANTIHISTAMINES, ANESTHETICS, ETC.

D04: ANTIPRURITICS, INCL. ANTIHISTAMINES, ANESTHETICS, ETC.

D: DERMATOLOGICALS

N01BB06: Dibucaine

N01BB: Amides

N01B: ANESTHETICS, LOCAL

N01: ANESTHETICS

N: NERVOUS SYSTEM

S01HA06: Dibucaine

S01HA: Local anesthetics

S01H: LOCAL ANESTHETICS

S01: OPHTHALMOLOGICALS

S: SENSORY ORGANS

S02DA04: Dibucaine

S02DA: Analgesics and anesthetics

S02D: OTHER OTOLOGICALS

S02: OTOLOGICALS

S: SENSORY ORGANS

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

343.5

Logarithm of the Partition Coefficient (xlogp)

4.4

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Metabolism: The drug is metabolized via the hepatic []

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
UNII: L6JW2TJG99
DrugBank ID: DB00527
TTD ID: D0P5GE

Combinatorial Drugs (CBD)

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Repurposed Drugs (RPD)

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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	[3]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Cholinesterase (BCHE)	OTOH3WQ9	CHLE_HUMAN	Drug Response	[4]
Nuclear receptor subfamily 1 group I member 2 (NR1I2)	OTC5U0N5	NR1I2_HUMAN	Gene/Protein Processing	[5]
Potassium voltage-gated channel subfamily H member 2 (KCNH2)	OTZX881H	KCNH2_HUMAN	Gene/Protein Processing	[6]

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Molecular Interaction Atlas (MIA)

MIA Detail

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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]	[7]
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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	Dibucaine FDA Label
3	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.
4	A further factor contributing to inherited suxamethonium sensitivity. Br J Anaesth. 1969 Dec;41(12):1023-8. doi: 10.1093/bja/41.12.1023.
5	Screening of a chemical library reveals novel PXR-activating pharmacologic compounds. Toxicol Lett. 2015 Jan 5;232(1):193-202. doi: 10.1016/j.toxlet.2014.10.009. Epub 2014 Oct 16.
6	Why are most phospholipidosis inducers also hERG blockers?. Arch Toxicol. 2017 Dec;91(12):3885-3895. doi: 10.1007/s00204-017-1995-9. Epub 2017 May 27.
7	Cerner Multum, Inc. "Australian Product Information.".