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Cinchocaine
Identification
- Name
- Cinchocaine
- Accession Number
- DB00527
- 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)
- Type
- Small Molecule
- Groups
- Approved, Vet approved
- Structure
Structure for Cinchocaine (DB00527)
- Weight
- Average: 343.4632
Monoisotopic: 343.225977187 - Chemical Formula
- C20H29N3O2
- Synonyms
- 2-butoxy-N-(2-(diethylamino)ethyl)cinchoninamide
- 2-butoxy-N-(α-diethylaminoethyl)cinchoninamide
- 2-butoxy-N-(β-diethylaminoethyl)cinchoninamide
- 2-butoxy-N-[2-(diethylamino)ethyl]-4-quinolinecarboxamide
- 2-Butoxy-quinoline-4-carboxylic acid (2-diethylamino-ethyl)-amide
- 2-butoxyquinoline-4-carboxylic acid diethylaminoethylamide
- 2-N-butoxy-N-(2-diethylaminoethyl)cinchoninamide
- Cinchocaine
- Cinchocainum
- Cincocainio
- Dibucaine
- N-(2-(diethylamino)ethyl)-2-butoxycinchoninamide
- α-butyloxycinchonic acid-γ-diethylethylenediamine
- α-butyloxycinchoninic acid diethylethylenediamide
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.
- Associated Conditions
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- 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.
Target Actions Organism ASodium channel protein type 10 subunit alpha inhibitorHumans ASodium channel protein type 5 subunit alpha inhibitorHumans UCalmodulin inhibitorHumans - 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
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- 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 Category Dibucaine Action Pathway Drug action - Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Unlock Additional DataAcebutolol Cinchocaine may increase the bradycardic activities of Acebutolol. Acetylcholine The risk or severity of adverse effects can be increased when Cinchocaine is combined with Acetylcholine. Aclidinium Cinchocaine may increase the neuromuscular blocking activities of Aclidinium. Amantadine The therapeutic efficacy of Amantadine can be decreased when used in combination with Cinchocaine. Amifampridine The risk or severity of adverse effects can be increased when Cinchocaine is combined with Amifampridine. Amitriptyline The therapeutic efficacy of Amitriptyline can be decreased when used in combination with Cinchocaine. Amobarbital The therapeutic efficacy of Amobarbital can be decreased when used in combination with Cinchocaine. Amoxapine The therapeutic efficacy of Amoxapine can be decreased when used in combination with Cinchocaine. Anisotropine methylbromide The therapeutic efficacy of Anisotropine methylbromide can be decreased when used in combination with Cinchocaine. Aripiprazole The therapeutic efficacy of Aripiprazole can be decreased when used in combination with Cinchocaine. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- No interactions found.
Products
- Product Ingredients
Ingredient UNII CAS InChI Key Cinchocaine hydrochloride Z97702A5DG 61-12-1 IVHBBMHQKZBJEU-UHFFFAOYSA-N - International/Other Brands
- Cincain / Nupercaine / Sovcaine
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataCVS Hemorrhoidal Topical Analgesic Ointment 10 mg/1g Topical CVS Health 2014-01-17 Not applicable US 
Dibucaine Ointment 1 g/100g Topical E. Fougera & CO., A division of Fougera Pharmaceuticals Inc. 1968-01-01 Not applicable US Dibucaine Ointment 0.28 g/28g Topical Akron Pharma Inc. 2020-07-28 Not applicable US Dibucaine Ointment 0.28 g/28g Topical Geritrex Llc 2015-07-31 Not applicable US Dibucaine Ointment 1 g/100g Topical Perrigo New York Inc. 2011-06-20 Not applicable US Dibucaine Cream 10 mg/1g Topical CVS Health 2010-07-16 Not applicable US Dibucaine Topical Anesthetic 1% Hemorrhoidal Ointment 10 mg/1g Topical Rugby Laboratories Inc. 2019-08-19 Not applicable US Nupercainal Ointment 1 g/100g Topical Dr. Reddy's Laboratories Inc. 2016-05-24 Not applicable US Nupercainal Anesthetic Ointment 1% Ointment Rectal; Topical Glaxosmithkline Inc 1944-12-31 2016-11-24 Canada 
Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Nupercainal Antiseptic Cream Cinchocaine (0.5 %) + Domiphen bromide (0.05 %) Cream Topical Glaxosmithkline Inc 1967-12-31 2016-11-29 Canada Proctol Ointment Cinchocaine hydrochloride (0.5 %) + Esculin (1 %) + Framycetin sulfate (1 %) + Hydrocortisone (0.5 %) Ointment Rectal Odan Laboratories Ltd 2003-08-06 Not applicable Canada Proctol Suppositories Cinchocaine hydrochloride (5 mg) + Esculin (10 mg) + Framycetin sulfate (10 mg) + Hydrocortisone (5 mg) Suppository Rectal Odan Laboratories Ltd 2004-03-15 Not applicable Canada Proctosedyl Cinchocaine hydrochloride (0.5 %) + Esculin (1 %) + Framycetin sulfate (1 %) + Hydrocortisone (0.5 %) Ointment Rectal Aptalis Pharma Canada Ulc 2003-04-01 Not applicable Canada Proctosedyl Cinchocaine hydrochloride (5 mg) + Esculin (10 mg) + Framycetin sulfate (10 mg) + Hydrocortisone (5 mg) Suppository Rectal Aptalis Pharma Canada Ulc 1997-01-23 2020-05-27 Canada Proctosedyl Ointment Cinchocaine hydrochloride (5 mg) + Esculin (10 mg) + Framycetin sulfate (10 mg) + Hydrocortisone (5 mg) Ointment Rectal Roussel Canada Inc. 1959-12-31 1997-08-05 Canada Proctosedyl Ointment Cinchocaine hydrochloride (5 mg) + Esculin (10 mg) + Framycetin sulfate (10 mg) + Hydrocortisone (5 mg) Ointment Rectal Hoechst Roussel Canada Inc. 1971-12-31 2006-07-28 Canada Proctosedyl Sup Cinchocaine hydrochloride (5 mg) + Esculin (10 mg) + Framycetin sulfate (10 mg) + Hydrocortisone (5 mg) Suppository Rectal Roussel Canada Inc. 1959-12-31 1996-09-09 Canada Proctosedyl Suppositories Cinchocaine hydrochloride (5 mg) + Esculin (10 mg) + Framycetin sulfate (10 mg) + Hydrocortisone (5 mg) Suppository Rectal Hoechst Roussel Canada Inc. 1959-12-31 1999-08-11 Canada Proctosone Ont Cinchocaine hydrochloride (.5 %) + Esculin (1 %) + Hydrocortisone acetate (.5 %) + Neomycin sulfate (1 %) Ointment Rectal Technilab Pharma Inc. 1981-12-31 2004-08-03 Canada - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Dibucaine HCl 0.5% / Lidocaine 15% / Phenylephrine HCl 1% / Prilocaine 5% Cinchocaine hydrochloride (0.5 g/100g) + Lidocaine (15 g/100g) + Phenylephrine hydrochloride (1 g/100g) + Prilocaine (5 g/100g) Ointment Topical Sincerus Florida, LLC 2019-05-11 Not applicable US
Categories
- ATC Codes
- D04AB02 — Cinchocaine
- D04AB — Anesthetics for topical use
- D04A — ANTIPRURITICS, INCL. ANTIHISTAMINES, ANESTHETICS, ETC.
- D04 — ANTIPRURITICS, INCL. ANTIHISTAMINES, ANESTHETICS, ETC.
- D — DERMATOLOGICALS
- Drug Categories
- Agents for Treatment of Hemorrhoids and Anal Fissures for Topical Use
- Amides
- Analgesics and Anesthetics
- Anesthetics
- Anesthetics for Topical Use
- Anesthetics, Local
- Antipruritics and Local Anesthetics
- Antipruritics, Incl. Antihistamines, Anesthetics, Etc.
- Cell-mediated Immunity
- Central Nervous System Agents
- Central Nervous System Depressants
- Cholinesterase Inhibitors
- Dermatologicals
- Heterocyclic Compounds, Fused-Ring
- Increased Histamine Release
- Local Anesthetics (Amide)
- Nervous System
- Ophthalmologicals
- Otologicals
- Peripheral Nervous System Agents
- Quinolines
- Sensory Organs
- Sensory System Agents
- Standardized Chemical Allergen
- Vasoprotectives
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as quinolones and derivatives. These are compounds containing a quinoline moiety which bears a ketone group.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Quinolines and derivatives
- Sub Class
- Quinolones and derivatives
- Direct Parent
- Quinolones and derivatives
- Alternative Parents
- Alkyl aryl ethers / Pyridines and derivatives / Benzenoids / Heteroaromatic compounds / Trialkylamines / Propargyl-type 1,3-dipolar organic compounds / Carboximidic acids / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
- Substituents
- Alkyl aryl ether / Amine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carboximidic acid / Carboximidic acid derivative / Ether / Heteroaromatic compound / Hydrocarbon derivative
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- tertiary amino compound, aromatic ether, monocarboxylic acid amide (CHEBI:247956)
Chemical Identifiers
- UNII
- L6JW2TJG99
- CAS number
- 85-79-0
- InChI Key
- 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)
- IUPAC Name
- 2-butoxy-N-[2-(diethylamino)ethyl]quinoline-4-carboxamide
- SMILES
- CCCCOC1=NC2=CC=CC=C2C(=C1)C(=O)NCCN(CC)CC
References
- Synthesis Reference
- US1825623
- General References
- 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]
- 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]
- 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]
- External Links
- Human Metabolome Database
- HMDB0014668
- KEGG Drug
- D00733
- KEGG Compound
- C07879
- PubChem Compound
- 3025
- PubChem Substance
- 46506734
- ChemSpider
- 2917
- BindingDB
- 48532
- 3339
- ChEBI
- 247956
- ChEMBL
- CHEMBL1086
- ZINC
- ZINC000001530939
- Therapeutic Targets Database
- DAP000507
- PharmGKB
- PA449286
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Dibucaine
- AHFS Codes
- 84:08.00 — Antipruritics and Local Anesthetics
- MSDS
- Download (73.8 KB)
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Novartis pharmaceuticals corp
- Packagers
- Medisca Inc.
- Novartis AG
- Perrigo Co.
- Dosage Forms
Form Route Strength Ointment Topical 10 mg/1g Cream Topical 10 mg/1g Ointment Topical 0.28 g/28g Ointment Topical 1 g/100g Ointment Topical Ointment Rectal; Topical Cream Topical Gel Buccal; Dental; Topical Ointment Rectal Suppository Rectal - Prices
Unit description Cost Unit Dibucaine hcl powder 4.74USD g Nupercainal 1% ointment 0.15USD g Dibucaine 1% ointment 0.12USD 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 (°C) 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 0.0389 mg/mL 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 Å2 ChemAxon Rotatable Bond Count 10 ChemAxon Refractivity 102.12 m3·mol-1 ChemAxon Polarizability 40.78 Å3 ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - 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 inhibitor Non-inhibitor 0.907 CYP450 2D6 inhibitor Inhibitor 0.8932 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor 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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Voltage-gated sodium channel activity
- Specific Function
- Tetrodotoxin-resistant channel that mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference acro...
- Gene Name
- SCN10A
- Uniprot ID
- Q9Y5Y9
- Uniprot Name
- Sodium channel protein type 10 subunit alpha
- Molecular Weight
- 220623.605 Da
References
- 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]
- 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]
- 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]
- 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]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Voltage-gated sodium channel activity involved in sa node cell action potential
- 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 pr...
- Gene Name
- SCN5A
- Uniprot ID
- Q14524
- Uniprot Name
- Sodium channel protein type 5 subunit alpha
- Molecular Weight
- 226937.475 Da
References
- 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]
- 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]
- 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]
- 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]
- 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]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Titin binding
- Specific Function
- Calmodulin mediates the control of a large number of enzymes, ion channels, aquaporins and other proteins by Ca(2+). Among the enzymes to be stimulated by the calmodulin-Ca(2+) complex are a number...
- Gene Name
- CALM1
- Uniprot ID
- P0DP23
- Uniprot Name
- Calmodulin
- Molecular Weight
- 16837.47 Da
References
- 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]
- 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]
- 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]
- Sambandam T, Gunasekaran M: Purification and properties of calmodulin from Phymatotrichum omnivorum. Microbios. 1993;73(294):61-74. [PubMed:8382768]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Identical protein binding
- 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
- Uniprot Name
- Cholinesterase
- Molecular Weight
- 68417.575 Da
References
- Elamin B: Dibucaine inhibition of serum cholinesterase. J Biochem Mol Biol. 2003 Mar 31;36(2):149-53. [PubMed:12689511]
Drug created on June 13, 2005 07:24 / Updated on August 14, 2020 04:24
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