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Identification
Name Dibucaine
Accession Number DB00527 (APRD00915)
Type small molecule
Groups approved
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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Salts Not Available
Brand names
Name Company
Cinchocaine
Cinchocaine HCL
cinchocaine hydrochloride
Dermacaine
Dibucain
Dibucaine base
Dibucaine hydrochloride
Heavy Solution Nupercaine
Nupercainal
Nupercaine
Sovcaine
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Brand mixtures
Brand Name Ingredients
Nupercainal Antiseptic Crm Dibucaine + Domiphen Bromide
Proctol Ointment Dibucaine Hydrochloride + Esculin + Framycetin Sulfate + Hydrocortisone
Proctol Suppositories Dibucaine Hydrochloride + Esculin + Framycetin Sulfate + Hydrocortisone
Proctosedyl Ointment Dibucaine Hydrochloride + Esculin + Framycetin Sulfate + Hydrocortisone
Proctosedyl Sup Dibucaine Hydrochloride + Esculin + Framycetin Sulfate + Hydrocortisone
Proctosedyl Suppositories Dibucaine Hydrochloride + Esculin + Framycetin Sulfate + Hydrocortisone
Proctosone Ont Dibucaine Hydrochloride + Esculin + Hydrocortisone Acetate + Neomycin Sulfate
Proctosone Sup Dibucaine Hydrochloride + Esculin + Hydrocortisone Acetate + Neomycin Sulfate
Ratio-Proctosone Dibucaine Hydrochloride + Esculin + Framycetin Sulfate + Hydrocortisone (Hydrocortisone Acetate)
Sab-Proctomyxin Hc Suppositories Dibucaine Hydrochloride + Esculin + Framycetin Sulfate + Hydrocortisone
Sandoz Proctomyxin Hc Dibucaine Hydrochloride + Esculin + Framycetin Sulfate + Hydrocortisone
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Categories
  • Anesthetics, Local
CAS number 85-79-0
Weight Average: 343.4632
Monoisotopic: 343.225977187
Chemical Formula C20H29N3O2
InChI Key InChIKey=PUFQVTATUTYEAL-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)
Plain Text
IUPAC Name
2-butoxy-N-[2-(diethylamino)ethyl]quinoline-4-carboxamide
SMILES
CCCCOC1=NC2=CC=CC=C2C(=C1)C(=O)NCCN(CC)CC
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • (Iso)quinolines and Derivatives
  • Fluoroquinolones and Quinolones
Substructures
  • Amino Ketones
  • Pyridines and Derivatives
  • Ethers
  • Benzene and Derivatives
  • Carboxylic Acids and Derivatives
  • Aliphatic and Aryl Amines
  • Pyridines
  • Heterocyclic compounds
  • Aromatic compounds
  • Carboxamides and Derivatives
  • (Iso)quinolines and Derivatives
  • Fluoroquinolones and Quinolones
Pharmacology
Indication For 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.
Pharmacodynamics Dibucaine is an amide-type local anesthetic, similar to lidocaine.
Mechanism of action Local 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.
Absorption In 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 distribution Not Available
Protein binding Not Available
Metabolism Primarily hepatic.
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity Subcutaneous 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
Pathway Name SMPDB ID
Smp00396 Dibucaine Pathway SMP00396
Pharmacoeconomics
Manufacturers
  • Novartis pharmaceuticals corp
Packagers
Dosage forms
Form Route Strength
Ointment Rectal
Prices
Unit description Cost Unit
Dibucaine hcl powder 4.74 USD g
Nupercainal 1% ointment 0.15 USD g
Dibucaine 1% ointment 0.12 USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 99-101 °C (HCl salt) Not Available
water solubility 42 mg/L (at 21 °C) BEILSTEIN
logP 4.40 HANSCH,C ET AL. (1995)
logS -3.7 ADME Research, USCD
pKa 8.85 SANGSTER (1994)
Predicted Properties
Property Value Source
water solubility 3.89e-02 g/l ALOGPS
logP 3.79 ALOGPS
logP 3.7 ChemAxon
logS -4 ALOGPS
pKa (strongest acidic) 14.57 ChemAxon
pKa (strongest basic) 9.04 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 4 ChemAxon
hydrogen donor count 1 ChemAxon
polar surface area 54.46 ChemAxon
rotatable bond count 10 ChemAxon
refractivity 102.12 ChemAxon
polarizability 40.78 ChemAxon
References
Synthesis Reference Not Available
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
Resource Link
KEGG Drug D00733 Link_out
KEGG Compound C07879 Link_out
PubChem Compound 3025 Link_out
PubChem Substance 46506734 Link_out
ChemSpider 2917 Link_out
BindingDB 50017687 Link_out
ChEBI 247956 Link_out
ChEMBL 247956 Link_out
Therapeutic Targets Database DAP000507 Link_out
PharmGKB PA449286 Link_out
Drug Product Database 2242528 Link_out
Drugs.com http://www.drugs.com/cdi/dibucaine-ointment.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Dibucaine Link_out
ATC Codes
  • C05AD04
  • D04AB02
  • N01BB06
  • S02DA04
  • S01HA06
AHFS Codes
  • 84:08.00
PDB Entries Not Available
FDA label Not Available
MSDS show (73.8 KB)
Interactions
Drug Interactions Searched, but no interactions found.
Food Interactions Not Available
Targets

1. Sodium channel protein type 10 subunit alpha

Pharmacological action: yes
Actions: inhibitor

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

Organism class: human
UniProt ID: Q9Y5Y9 Link_out
Gene: SCN10A Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: yes
Actions: inhibitor

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

Organism class: human
UniProt ID: Q14524 Link_out
Gene: SCN5A Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: unknown
Actions: inhibitor

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

Organism class: human
UniProt ID: P62158 Link_out
Gene: CALM1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Actions: inhibitor

An acylcholine + H(2)O = choline + a carboxylate

UniProt ID: P06276 Link_out
Gene: BCHE Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Elamin B: Dibucaine inhibition of serum cholinesterase. J Biochem Mol Biol. 2003 Mar 31;36(2):149-53. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19