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Identification
NameHexylcaine
Accession NumberDB00473  (APRD01014)
TypeSmall Molecule
GroupsApproved, Withdrawn
DescriptionHexylcaine 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
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
CyclaineMerck
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Hexylcaine hydrochloride
Thumb
  • InChI Key: MTFCPNHRBINLRQ-UHFFFAOYNA-N
  • Monoisotopic Mass: 297.149556724
  • Average Mass: 297.82
DBSALT000630
CategoriesNot Available
UNII511IU0826Z
CAS number532-77-4
WeightAverage: 261.3593
Monoisotopic: 261.172878985
Chemical FormulaC16H23NO2
InChI KeyInChIKey=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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentBenzoic acid esters
Alternative Parents
Substituents
  • Benzoate ester
  • Benzylether
  • Benzoyl
  • Cyclohexylamine
  • Carboxylic acid ester
  • Secondary amine
  • Monocarboxylic acid or derivatives
  • Secondary aliphatic amine
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationUsed as a local anesthetic for surface application, infiltration or nerve block
PharmacodynamicsHexylcaine 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 actionHexyl 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.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hydrolyzed by plasma esterases to benzoic acid and other derivatives

Route of eliminationNot Available
Half life<10 minutes
ClearanceNot Available
ToxicitySymptoms 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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
Manufacturers
  • Merck and co inc
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point177-178.5U.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 RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis Reference

U.S. Patent 2,486,374.

US2486374
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

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 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 respon...
Gene Name:
SCN5A
Uniprot ID:
Q14524
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 across the membrane, the protein forms a sodium-selective channel through which sodium ions may pass in accordance with their electrochemical gradient. Plays a role in neuropathic pain mechanisms.
Gene Name:
SCN10A
Uniprot ID:
Q9Y5Y9
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 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23