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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2017-10-23 19:06:21 UTC
HMDB IDHMDB0014668
Secondary Accession Numbers
  • HMDB14668
Metabolite Identification
Common NameDibucaine
DescriptionA local anesthetic of the amide type now generally used 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. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1006)
Structure
Thumb
Synonyms
ValueSource
2-Butoxy-N-(2-(diethylamino)ethyl)cinchoninamideChEBI
2-Butoxy-N-(alpha-diethylaminoethyl)cinchoninamideChEBI
2-Butoxy-N-(beta-diethylaminoethyl)cinchoninamideChEBI
2-Butoxy-N-[2-(diethylamino)ethyl]-4-quinolinecarboxamideChEBI
2-Butoxy-quinoline-4-carboxylic acid (2-diethylamino-ethyl)-amideChEBI
2-Butoxyquinoline-4-carboxylic acid diethylaminoethylamideChEBI
2-N-Butoxy-N-(2-diethylaminoethyl)cinchoninamideChEBI
alpha-Butyloxycinchonic acid-gamma-diethylethylenediamineChEBI
alpha-Butyloxycinchoninic acid diethylethylenediamideChEBI
CinchocainumChEBI
CincocainioChEBI
Dibucaine baseChEBI
N-(2-(diethylamino)Ethyl)-2-butoxycinchoninamideChEBI
2-Butoxy-N-(a-diethylaminoethyl)cinchoninamideGenerator
2-Butoxy-N-(α-diethylaminoethyl)cinchoninamideGenerator
2-Butoxy-N-(b-diethylaminoethyl)cinchoninamideGenerator
2-Butoxy-N-(β-diethylaminoethyl)cinchoninamideGenerator
2-Butoxy-quinoline-4-carboxylate (2-diethylamino-ethyl)-amideGenerator
2-Butoxyquinoline-4-carboxylate diethylaminoethylamideGenerator
a-Butyloxycinchonate-g-diethylethylenediamineGenerator
a-Butyloxycinchonic acid-g-diethylethylenediamineGenerator
alpha-Butyloxycinchonate-gamma-diethylethylenediamineGenerator
α-butyloxycinchonate-γ-diethylethylenediamineGenerator
α-butyloxycinchonic acid-γ-diethylethylenediamineGenerator
a-Butyloxycinchoninate diethylethylenediamideGenerator
a-Butyloxycinchoninic acid diethylethylenediamideGenerator
alpha-Butyloxycinchoninate diethylethylenediamideGenerator
α-butyloxycinchoninate diethylethylenediamideGenerator
α-butyloxycinchoninic acid diethylethylenediamideGenerator
CincainMeSH
NupercaineMeSH
NupercainalMeSH
SovcaineMeSH
CinchocaineMeSH
Chemical FormulaC20H29N3O2
Average Molecular Weight343.4632
Monoisotopic Molecular Weight343.225977187
IUPAC Name2-butoxy-N-[2-(diethylamino)ethyl]quinoline-4-carboxamide
Traditional Namedibucaine
CAS Registry Number85-79-0
SMILES
CCCCOC1=NC2=CC=CC=C2C(=C1)C(=O)NCCN(CC)CC
InChI Identifier
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)
InChI KeyPUFQVTATUTYEAL-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as quinolones and derivatives. These are compounds containing a quinoline moiety which bears a ketone group.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassQuinolines and derivatives
Direct ParentQuinolones and derivatives
Alternative Parents
Substituents
  • Quinolone
  • Alkyl aryl ether
  • Pyridine
  • Benzenoid
  • Heteroaromatic compound
  • Tertiary amine
  • Tertiary aliphatic amine
  • Carboximidic acid
  • Carboximidic acid derivative
  • Ether
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Role

Industrial application:

  Pharmaceutical industry:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point99 - 101 °C (hydrochloride salt)Not Available
Boiling PointNot AvailableNot Available
Water Solubility0.039 g/LNot Available
LogP4.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.039 g/LALOGPS
logP3.79ALOGPS
logP3.7ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)14.57ChemAxon
pKa (Strongest Basic)9.04ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.46 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity102.12 m³·mol⁻¹ChemAxon
Polarizability40.78 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-9000000000-11b0b035aed1c901a827View in MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0006-5009000000-4623c33d494376e699f3View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05br-9272000000-3d2ab0479ffb92d2501bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0006-0009000000-396529f9f1539ca4f5d2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00di-0091000000-f6ba1af6a7e8fcdfaa16View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00xr-0190000000-9cd7408320081da0e435View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-01b9-0960000000-48d5c97824dd28e11f73View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-0900000000-cbd25496ff6fc8a2fa36View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-0900000000-b4f898603ef48a2b9e29View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00xr-3980000000-e5e0b2d6136d950b770aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-3559000000-63b39814c87e3867b4c8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zmi-8891000000-b554e300f3adf4d3ece4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pi0-9310000000-e2dff930dc76d5752208View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-2069000000-55885f8ff7612dc6aaebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-8396000000-06d05a3147875a59f5b0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-5910000000-c55a93ba4d932f2362abView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Dibucaine PathwayPw000402Pw000402 greyscalePw000402 simpleNot Available
Displaying 1 entry
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00527 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00527 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00527
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2917
KEGG Compound IDC07879
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDibucaine
METLIN IDNot Available
PubChem Compound3025
PDB IDNot Available
ChEBI ID247956
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Abdel-Ghani NT, Youssef AF, Awady MA: Cinchocaine hydrochloride determination by atomic absorption spectrometry and spectrophotometry. Farmaco. 2005 May;60(5):419-24. [PubMed:15910814 ]
  2. Nounou MM, El-Khordagui LK, Khalafallah N: Effect of various formulation variables on the encapsulation and stability of dibucaine base in multilamellar vesicles. Acta Pol Pharm. 2005 Sep-Oct;62(5):369-79. [PubMed:16459486 ]
  3. Souto-Padron T, Lima AP, Ribeiro Rde O: Effects of dibucaine on the endocytic/exocytic pathways in Trypanosoma cruzi. Parasitol Res. 2006 Sep;99(4):317-20. Epub 2006 Apr 13. [PubMed:16612626 ]

Enzymes

General function:
Involved in carboxylesterase activity
Specific function:
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:
BCHE
Uniprot ID:
P06276
Molecular weight:
68417.575
References
  1. Elamin B: Dibucaine inhibition of serum cholinesterase. J Biochem Mol Biol. 2003 Mar 31;36(2):149-53. [PubMed:12689511 ]
General function:
Involved in calcium ion binding
Specific function:
Calmodulin mediates the control of a large number of enzymes and other proteins by Ca(2+). Among the enzymes to be stimulated by the calmodulin-Ca(2+) complex are a number of protein kinases and phosphatases. Together with CEP110 and centrin, is involved in a genetic pathway that regulates the centrosome cycle and progression through cytokinesis
Gene Name:
CALM1
Uniprot ID:
P62158
Molecular weight:
16837.5
References
  1. Muto Y, Kudo S, Nozawa Y: Effects of local anesthetics on calmodulin-dependent guanylate cyclase in the plasma membrane of Tetrahymena pyriformis. Biochem Pharmacol. 1983 Dec 1;32(23):3559-63. [PubMed:6140014 ]
  2. Volpi M, Sha'afi RI, Epstein PM, Andrenyak DM, Feinstein MB: Local anesthetics, mepacrine, and propranolol are antagonists of calmodulin. Proc Natl Acad Sci U S A. 1981 Feb;78(2):795-9. [PubMed:6262771 ]
  3. Liu SH, Fu WM, Lin-Shiau SY: Studies on the inhibition by chlorpromazine of myotonia induced by ion channel modulators in mouse skeletal muscle. Eur J Pharmacol. 1993 Jan 26;231(1):23-30. [PubMed:7680317 ]
  4. Sambandam T, Gunasekaran M: Purification and properties of calmodulin from Phymatotrichum omnivorum. Microbios. 1993;73(294):61-74. [PubMed:8382768 ]
General function:
Involved in ion channel activity
Specific function:
This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant Na(+) channel isoform. This channel is responsible for the initial upstroke of the action potential in the electrocardiogram
Gene Name:
SCN5A
Uniprot ID:
Q14524
Molecular weight:
226937.5
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Oka M, Itoh Y, Fujita T: 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. [PubMed:12354567 ]
  4. Louro SR, Anteneodo C, Wajnberg E: Carboxyl groups at the membrane interface as molecular targets for local anesthetics. Biophys Chem. 1998 Aug 4;74(1):35-43. [PubMed:9742684 ]
  5. Ryan SE, Demers CN, Chew JP, Baenziger JE: Structural effects of neutral and anionic lipids on the nicotinic acetylcholine receptor. An infrared difference spectroscopy study. J Biol Chem. 1996 Oct 4;271(40):24590-7. [PubMed:8798723 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
General function:
Involved in ion channel activity
Specific function:
This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which sodium ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant sodium channel isoform. Its electrophysiological properties vary depending on the type of the associated beta subunits (in vitro). Plays a role in neuropathic pain mechanisms
Gene Name:
SCN10A
Uniprot ID:
Q9Y5Y9
Molecular weight:
220623.6
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Louro SR, Anteneodo C, Wajnberg E: Carboxyl groups at the membrane interface as molecular targets for local anesthetics. Biophys Chem. 1998 Aug 4;74(1):35-43. [PubMed:9742684 ]
  4. Ryan SE, Demers CN, Chew JP, Baenziger JE: Structural effects of neutral and anionic lipids on the nicotinic acetylcholine receptor. An infrared difference spectroscopy study. J Biol Chem. 1996 Oct 4;271(40):24590-7. [PubMed:8798723 ]