Cinchocaine

Identification

Summary

Cinchocaine is an anesthetic used for local or regional anesthesia.

Brand Names
Nupercainal, Proctol, Proctosedyl
Generic Name
Cinchocaine
DrugBank Accession Number
DB00527
Background

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
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.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination for symptomatic treatment ofHemorrhoidsCombination Product in combination with: Framycetin (DB00452), Hydrocortisone (DB00741)••••••••••••••••••••
Used in combination to treatHemorrhoidsCombination Product in combination with: Framycetin (DB00452), Hydrocortisone (DB00741)••••••••••••••••••••
Symptomatic treatment ofHemorrhoids••• •••
Treatment ofItchy skin••• •••
Symptomatic treatment ofSkin irritation••• •••
Contraindications & Blackbox Warnings
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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.

TargetActionsOrganism
ASodium channel protein type 5 subunit alpha
inhibitor
Humans
ASodium channel protein type 10 subunit alpha
inhibitor
Humans
UCalmodulin
inhibitor
Humans
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
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Toxicity

Subcutaneous LD50 in rat is 27 mg/kg. Symptoms of overdose include convulsions, hypoxia, acidosis, bradycardia, arrhythmias and cardiac arrest.

Pathways
PathwayCategory
Dibucaine Action PathwayDrug 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.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when Cinchocaine is combined with 1,2-Benzodiazepine.
AbemaciclibThe risk or severity of methemoglobinemia can be increased when Abemaciclib is combined with Cinchocaine.
AbirateroneThe risk or severity of methemoglobinemia can be increased when Abiraterone is combined with Cinchocaine.
AcebutololCinchocaine may increase the bradycardic activities of Acebutolol.
AcetaminophenThe risk or severity of methemoglobinemia can be increased when Acetaminophen is combined with Cinchocaine.
Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Cinchocaine hydrochlorideZ97702A5DG61-12-1IVHBBMHQKZBJEU-UHFFFAOYSA-N
International/Other Brands
Cincain / Nupercaine / Sovcaine
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
CVS Hemorrhoidal Topical AnalgesicOintment10 mg/1gTopicalCVS Health2014-01-17Not applicableUS flag
DibucaineOintment0.28 g/28gTopicalAkron Pharma Inc.2021-11-04Not applicableUS flag
DibucaineOintment1 g/100gTopicalChain Drug Marketing Association Inc.2022-09-14Not applicableUS flag
DibucaineOintment0.28 g/28gTopicalGeritrex Llc2015-07-31Not applicableUS flag
DibucaineOintment1 g/100gTopicalE. Fougera & CO., A division of Fougera Pharmaceuticals Inc.1968-01-01Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
DECATYLEN LOZENGECinchocaine hydrochloride (0.03 mg) + Dequalinium chloride (0.25 mg)LozengeOralAPEX PHARMA MARKETING PTE. LTD.1990-06-25Not applicableSingapore flag
FAKTU SUPPOSITORYCinchocaine hydrochloride (2.5 mg) + Policresulen (100 mg)SuppositoryRectalTAKEDA PHARMACEUTICALS (ASIA PACIFIC) PTE. LTD.1988-04-26Not applicableSingapore flag
Nupercainal Antiseptic CreamCinchocaine (0.5 %) + Domiphen bromide (0.05 %)CreamTopicalGlaxosmithkline Inc1967-12-312016-11-29Canada flag
Odan Proctomyxin HCCinchocaine hydrochloride (0.5 %) + Esculin (1 %) + Framycetin sulfate (1 %) + Hydrocortisone (0.5 %)OintmentRectalOdan Laboratories Ltd2001-03-092021-08-11Canada flag
Odan Proctomyxin HC SuppositoriesCinchocaine hydrochloride (5 mg) + Esculin (10 mg) + Framycetin sulfate (10 mg) + Hydrocortisone (5 mg)SuppositoryRectalOdan Laboratories Ltd2001-01-052021-10-07Canada flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
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)OintmentTopicalSincerus Florida, LLC2019-05-11Not applicableUS flag

Categories

ATC Codes
D04AB02 — CinchocaineS01HA06 — CinchocaineS02DA04 — CinchocaineN01BB06 — CinchocaineC05AD04 — Cinchocaine
Drug Categories
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)
Affected organisms
  • Humans and other mammals

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
  1. Abdel-Ghani NT, Youssef AF, Awady MA: Cinchocaine hydrochloride determination by atomic absorption spectrometry and spectrophotometry. Farmaco. 2005 May;60(5):419-24. [Article]
  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. [Article]
  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. [Article]
Human Metabolome Database
HMDB0014668
KEGG Drug
D00733
KEGG Compound
C07879
PubChem Compound
3025
PubChem Substance
46506734
ChemSpider
2917
BindingDB
48532
RxNav
3339
ChEBI
247956
ChEMBL
CHEMBL1086
ZINC
ZINC000001530939
Therapeutic Targets Database
DAP000507
PharmGKB
PA449286
Drugs.com
Drugs.com Drug Page
Wikipedia
Cinchocaine
MSDS
Download (73.8 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
  • Novartis pharmaceuticals corp
Packagers
  • Medisca Inc.
  • Novartis AG
  • Perrigo Co.
Dosage Forms
FormRouteStrength
OintmentTopical10 mg/1g
LozengeOral0.25 mg
LozengeOral
CreamTopical10 mg/1g
OintmentTopical0.01 g/1g
OintmentTopical0.28 g/28g
OintmentTopical1 g/100g
OintmentTopical
Ointment
SuppositoryRectal2.5 mg
OintmentRectal; Topical1 %
CreamTopical
GelBuccal; Dental; Topical
OintmentRectal; Topical
KitCutaneous
OintmentRectal
SuppositoryRectal
Prices
Unit descriptionCostUnit
Dibucaine hcl powder4.74USD g
Nupercainal 1% ointment0.15USD g
Dibucaine 1% ointment0.12USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)99-101 °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 Solubility0.0389 mg/mLALOGPS
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
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9968
Blood Brain Barrier+0.9876
Caco-2 permeable+0.5187
P-glycoprotein substrateSubstrate0.8702
P-glycoprotein inhibitor IInhibitor0.7536
P-glycoprotein inhibitor IINon-inhibitor0.8862
Renal organic cation transporterNon-inhibitor0.6349
CYP450 2C9 substrateNon-substrate0.8297
CYP450 2D6 substrateNon-substrate0.6415
CYP450 3A4 substrateSubstrate0.6842
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorInhibitor0.8932
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6424
Ames testAMES toxic0.6038
CarcinogenicityNon-carcinogens0.8128
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.6763 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8924
hERG inhibition (predictor II)Inhibitor0.6851
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-05br-9272000000-3d2ab0479ffb92d2501b
GC-MS Spectrum - EI-BGC-MSsplash10-000i-9000000000-11b0b035aed1c901a827
GC-MS Spectrum - CI-BGC-MSsplash10-0006-5009000000-4623c33d494376e699f3
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0006-0009000000-396529f9f1539ca4f5d2
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00di-0091000000-f6ba1af6a7e8fcdfaa16
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00xr-0190000000-9cd7408320081da0e435
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-01b9-0960000000-48d5c97824dd28e11f73
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-014i-0900000000-cbd25496ff6fc8a2fa36
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-014i-0900000000-b4f898603ef48a2b9e29
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00xr-3980000000-e5e0b2d6136d950b770a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-006x-0069000000-e2a33891c2322309d77f
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0129000000-9b3ca25dec4c895cf5dd
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0g4l-2192000000-e47d82b22b190b17c572
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-6795000000-055d57092ee630dbf36a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0lk9-4890000000-094309f643f52f986bba
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-08mi-0891000000-a92d49712f190b152492
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-192.1912442
predicted
DarkChem Lite v0.1.0
[M-H]-194.4440442
predicted
DarkChem Lite v0.1.0
[M-H]-179.98798
predicted
DeepCCS 1.0 (2019)
[M+H]+192.6148442
predicted
DarkChem Lite v0.1.0
[M+H]+194.9590442
predicted
DarkChem Lite v0.1.0
[M+H]+182.34598
predicted
DeepCCS 1.0 (2019)
[M+Na]+192.5290442
predicted
DarkChem Lite v0.1.0
[M+Na]+194.5266442
predicted
DarkChem Lite v0.1.0
[M+Na]+188.43912
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
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
  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. [Article]
  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. [Article]
  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. [Article]
  4. Sambandam T, Gunasekaran M: Purification and properties of calmodulin from Phymatotrichum omnivorum. Microbios. 1993;73(294):61-74. [Article]

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

Drug created at June 13, 2005 13:24 / Updated at March 18, 2024 16:48