Identification

Name
Hexylcaine
Accession Number
DB00473  (APRD01014)
Type
Small Molecule
Groups
Approved, Withdrawn
Description

Hexylcaine hydrochloride, also called cyclaine (Merck) or osmocaine, is a short-acting local anesthetic. It acts by inhibiting sodium channel conduction. Overdose can lead to headache, tinnitus, numbness and tingling around the mouth and tongue, convulsions, inability to breathe, and decreased heart function. Hexylcaine has been discontinued in the US market.

Structure
Thumb
Synonyms
  • Cyclaine
  • Hexilcaina
  • Hexylcaine
  • Hexylcainum
Product Ingredients
IngredientUNIICASInChI Key
Hexylcaine hydrochlorideV00NQ7SDYI532-76-3MTFCPNHRBINLRQ-UHFFFAOYSA-N
International/Other Brands
Cyclaine (Merck)
Categories
UNII
511IU0826Z
CAS number
532-77-4
Weight
Average: 261.3593
Monoisotopic: 261.172878985
Chemical Formula
C16H23NO2
InChI Key
DKLKMKYDWHYZTD-UHFFFAOYSA-N
InChI
InChI=1S/C16H23NO2/c1-13(12-17-15-10-6-3-7-11-15)19-16(18)14-8-4-2-5-9-14/h2,4-5,8-9,13,15,17H,3,6-7,10-12H2,1H3
IUPAC Name
1-(cyclohexylamino)propan-2-yl benzoate
SMILES
CC(CNC1CCCCC1)OC(=O)C1=CC=CC=C1

Pharmacology

Indication

Used as a local anesthetic for surface application, infiltration or nerve block

Structured Indications
Not Available
Pharmacodynamics

Hexylcaine is a local ester-class anesthetic. Local anesthetics produce a transient block of nerve conduction by interfering with sodium channels. This effect of the anesthetic interferes with the development of an action potential across the nerve.

Mechanism of action

Hexyl caine acts mainly by inhibiting sodium influx through voltage gated sodium channels in the neuronal cell membrane of peripheral nerves. When the influx of sodium is interrupted, an action potential cannot arise and signal conduction is thus inhibited. The receptor site is thought to be located at the cytoplasmic (inner) portion of the sodium channel.

TargetActionsOrganism
ASodium channel protein type 5 subunit alpha
inhibitor
Human
USodium channel protein type 10 subunit alpha
inhibitor
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

Hydrolyzed by plasma esterases to benzoic acid and other derivatives

Route of elimination
Not Available
Half life

<10 minutes

Clearance
Not Available
Toxicity

Symptoms of anesthetic overdose include headache, tinnitus, circumoral and tongue paresthesias, restlessness, talkativeness, facial twitching, convulsions, respiratory arrest, and cardiac depression

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

U.S. Patent 2,486,374.

US2486374
General References
Not Available
External Links
Human Metabolome Database
HMDB14616
KEGG Compound
C14172
PubChem Compound
10770
PubChem Substance
46506241
ChemSpider
10315
BindingDB
50017670
ChEBI
34791
ChEMBL
CHEMBL1197
Therapeutic Targets Database
DAP000506
PharmGKB
PA164746489
Wikipedia
Hexylcaine

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
  • Merck and co inc
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)177-178.5U.S. Patent 2,486,374.
logP3.9Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00971 mg/mLALOGPS
logP3.04ALOGPS
logP3.83ChemAxon
logS-4.4ALOGPS
pKa (Strongest Basic)9.87ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area38.33 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity76.24 m3·mol-1ChemAxon
Polarizability30.29 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9571
Caco-2 permeable+0.686
P-glycoprotein substrateNon-substrate0.5289
P-glycoprotein inhibitor IInhibitor0.6342
P-glycoprotein inhibitor IIInhibitor0.706
Renal organic cation transporterNon-inhibitor0.6049
CYP450 2C9 substrateNon-substrate0.7135
CYP450 2D6 substrateNon-substrate0.6854
CYP450 3A4 substrateNon-substrate0.5558
CYP450 1A2 substrateInhibitor0.6091
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorInhibitor0.8932
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.8308
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6452
Ames testNon AMES toxic0.6997
CarcinogenicityNon-carcinogens0.8884
BiodegradationReady biodegradable0.7395
Rat acute toxicity2.3873 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7066
hERG inhibition (predictor II)Non-inhibitor0.5195
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-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzoic acids and derivatives
Direct Parent
Benzoic acid esters
Alternative Parents
Benzoyl derivatives / Cyclohexylamines / Carboxylic acid esters / Amino acids and derivatives / Monocarboxylic acids and derivatives / Dialkylamines / Organopnictogen compounds / Organooxygen compounds / Organic oxides / Hydrocarbon derivatives
Substituents
Benzoate ester / Benzoyl / Cyclohexylamine / Amino acid or derivatives / Carboxylic acid ester / Carboxylic acid derivative / Secondary aliphatic amine / Monocarboxylic acid or derivatives / Secondary amine / Organic nitrogen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
benzoate ester (CHEBI:34791)

Targets

Kind
Protein
Organism
Human
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. [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. 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
Human
Pharmacological action
Unknown
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. [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]

Drug created on June 13, 2005 07:24 / Updated on November 07, 2017 01:38