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Identification
NameCinchocaine
Accession NumberDB00527  (APRD00915)
TypeSmall Molecule
GroupsApproved
Description

A 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
SynonymLanguageCode
2-Butoxy-N-(2-(diethylamino)ethyl)cinchoninamideNot AvailableNot Available
2-Butoxy-N-(alpha-diethylaminoethyl)cinchoninamideNot AvailableNot Available
2-Butoxy-N-(beta-diethylaminoethyl)cinchoninamideNot AvailableNot Available
2-Butoxy-N-[2-(diethylamino)ethyl]-4-quinolinecarboxamideNot AvailableNot Available
2-Butoxy-quinoline-4-carboxylic acid (2-diethylamino-ethyl)-amideNot AvailableNot Available
2-Butoxyquinoline-4-carboxylic acid diethylaminoethylamideNot AvailableNot Available
2-N-Butoxy-N-(2-diethylaminoethyl)cinchoninamideNot AvailableNot Available
alpha-Butyloxycinchonic acid-gamma-diethylethylenediamineNot AvailableNot Available
alpha-Butyloxycinchoninic acid diethylethylenediamideNot AvailableNot Available
CINCHOCAINENot AvailableNot Available
CinchocainumNot AvailableNot Available
CincocainioNot AvailableNot Available
DibucaineNot AvailableUSAN
Dibucaine baseNot AvailableNot Available
N-(2-(Diethylamino)ethyl)-2-butoxycinchoninamideNot AvailableNot Available
Salts
Name/CAS Structure Properties
Cinchocaine hydrochloride
Thumb
  • InChI Key: IVHBBMHQKZBJEU-UHFFFAOYSA-N
  • Monoisotopic Mass: 379.202654926
  • Average Mass: 379.924
DBSALT000639
Brand names
NameCompany
CincainNot Available
NupercainalNot Available
NupercaineNot Available
SovcaineNot Available
Brand mixtures
Brand NameIngredients
Nupercainal Antiseptic CreamDibucaine + Domiphen Bromide
Proctol OintmentDibucaine Hydrochloride + Esculin + Framycetin Sulfate + Hydrocortisone
Proctol SuppositoriesDibucaine Hydrochloride + Esculin + Framycetin Sulfate + Hydrocortisone
Proctosedyl OintmentDibucaine Hydrochloride + Esculin + Framycetin Sulfate + Hydrocortisone
Proctosedyl SuppositoriesDibucaine Hydrochloride + Esculin + Framycetin Sulfate + Hydrocortisone
Ratio-ProctosoneDibucaine Hydrochloride + Esculin + Framycetin Sulfate + Hydrocortisone (Hydrocortisone Acetate)
Sab-Proctomyxin HC SuppositoriesDibucaine Hydrochloride + Esculin + Framycetin Sulfate + Hydrocortisone
Sandoz Proctomyxin HCDibucaine Hydrochloride + Esculin + Framycetin Sulfate + Hydrocortisone
Categories
CAS number85-79-0
WeightAverage: 343.4632
Monoisotopic: 343.225977187
Chemical FormulaC20H29N3O2
InChI KeyPUFQVTATUTYEAL-UHFFFAOYSA-N
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)
IUPAC Name
2-butoxy-N-[2-(diethylamino)ethyl]quinoline-4-carboxamide
SMILES
CCCCOC1=NC2=CC=CC=C2C(=C1)C(=O)NCCN(CC)CC
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassQuinolines and Derivatives
SubclassQuinoline Carboxamides
Direct parentQuinoline Carboxamides
Alternative parentsQuinolones and Derivatives; Pyridinecarboxylic Acids and Derivatives; Alkyl Aryl Ethers; Pyridinones; Benzene and Substituted Derivatives; Secondary Carboxylic Acid Amides; Tertiary Amines; Carboxylic Acids; Polyamines; Enolates
Substituentsquinolone; pyridine carboxylic acid or derivative; alkyl aryl ether; pyridinone; pyridine; benzene; secondary carboxylic acid amide; tertiary amine; carboxamide group; carboxylic acid derivative; enolate; polyamine; ether; carboxylic acid; amine; organonitrogen compound
Classification descriptionThis compound belongs to the quinoline carboxamides. These are quinolines in which the quinoline ring system is substituted by one or more carboxamide groups.
Pharmacology
IndicationFor production of local or regional anesthesia by infiltration techniques such as percutaneous injection and intravenous regional anesthesia by peripheral nerve block techniques such as brachial plexus and intercostal and by central neural techniques such as lumbar and caudal epidural blocks.
PharmacodynamicsDibucaine is an amide-type local anesthetic, similar to lidocaine.
Mechanism of actionLocal anesthetics block both the initiation and conduction of nerve impulses by decreasing the neuronal membrane's permeability to sodium ions through sodium channel inhibition. This reversibly stabilizes the membrane and inhibits depolarization, resulting in the failure of a propagated action potential and subsequent conduction blockade.
AbsorptionIn general, ionized forms (salts) of local anesthetics are not readily absorbed through intact skin. However, both nonionized (bases) and ionized forms of local anesthetics are readily absorbed through traumatized or abraded skin into the systemic circulation.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Primarily hepatic.

Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicitySubcutaneous LD50 in rat is 27 mg/kg. Symptoms of overdose include convulsions, hypoxia, acidosis, bradycardia, arrhythmias and cardiac arrest.
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Dibucaine Action PathwayDrug actionSMP00396
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9968
Blood Brain Barrier + 0.9876
Caco-2 permeable + 0.5187
P-glycoprotein substrate Substrate 0.8702
P-glycoprotein inhibitor I Inhibitor 0.7536
P-glycoprotein inhibitor II Non-inhibitor 0.8862
Renal organic cation transporter Non-inhibitor 0.6349
CYP450 2C9 substrate Non-substrate 0.8297
CYP450 2D6 substrate Non-substrate 0.6415
CYP450 3A4 substrate Substrate 0.6842
CYP450 1A2 substrate Inhibitor 0.9107
CYP450 2C9 substrate Non-inhibitor 0.907
CYP450 2D6 substrate Inhibitor 0.8932
CYP450 2C19 substrate Non-inhibitor 0.9025
CYP450 3A4 substrate Non-inhibitor 0.8309
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6424
Ames test AMES toxic 0.6038
Carcinogenicity Non-carcinogens 0.8128
Biodegradation Not ready biodegradable 1.0
Rat acute toxicity 2.6763 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.8924
hERG inhibition (predictor II) Inhibitor 0.6851
Pharmacoeconomics
Manufacturers
  • Novartis pharmaceuticals corp
Packagers
Dosage forms
FormRouteStrength
OintmentRectal
Prices
Unit descriptionCostUnit
Dibucaine hcl powder4.74USDg
Nupercainal 1% ointment0.15USDg
Dibucaine 1% ointment0.12USDg
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point99-101 °C (HCl salt)Not Available
water solubility42 mg/L (at 21 °C)BEILSTEIN
logP4.40HANSCH,C ET AL. (1995)
logS-3.7ADME Research, USCD
pKa8.85SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.0389ALOGPS
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 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity102.12 m3·mol-1ChemAxon
Polarizability40.78 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

DrugSyn.org

US1825623
General Reference
  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
  2. 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
  3. 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
External Links
ResourceLink
KEGG DrugD00733
KEGG CompoundC07879
PubChem Compound3025
PubChem Substance46506734
ChemSpider2917
BindingDB50017687
ChEBI247956
ChEMBL
Therapeutic Targets DatabaseDAP000507
PharmGKBPA449286
Drug Product Database2242528
Drugs.comhttp://www.drugs.com/cdi/dibucaine-ointment.html
WikipediaDibucaine
ATC CodesC05AD04D04AB02N01BB06S02DA04S01HA06
AHFS Codes
  • 84:08.00
PDB EntriesNot Available
FDA labelNot Available
MSDSshow(73.8 KB)
Interactions
Drug InteractionsSearched, but no interactions found.
Food InteractionsNot Available

Targets

1. Sodium channel protein type 10 subunit alpha

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Sodium channel protein type 10 subunit alpha Q9Y5Y9 Details

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
  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
  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
  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

2. Sodium channel protein type 5 subunit alpha

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Sodium channel protein type 5 subunit alpha Q14524 Details

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
  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
  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
  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
  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
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

3. Calmodulin

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Calmodulin P62158 Details

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
  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
  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
  4. Sambandam T, Gunasekaran M: Purification and properties of calmodulin from Phymatotrichum omnivorum. Microbios. 1993;73(294):61-74. Pubmed

Enzymes

1. Cholinesterase

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cholinesterase P06276 Details

References:

  1. Elamin B: Dibucaine inhibition of serum cholinesterase. J Biochem Mol Biol. 2003 Mar 31;36(2):149-53. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on October 08, 2013 14:23