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Identification
NameHexylcaine
Accession NumberDB00473  (APRD01014)
TypeSmall Molecule
GroupsApproved, Withdrawn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
SynonymLanguageCode
CyclaineNot AvailableNot Available
HexilcainaSpanishINN
HexylcaineNot AvailableNot Available
HexylcainumLatinINN
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot 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
Categories
CAS number532-77-4
WeightAverage: 261.3593
Monoisotopic: 261.172878985
Chemical FormulaC16H23NO2
InChI KeyDKLKMKYDWHYZTD-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.
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 substrateNon-inhibitor0.907
CYP450 2D6 substrateInhibitor0.8932
CYP450 2C19 substrateNon-inhibitor0.9026
CYP450 3A4 substrateNon-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
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
SpectraNot Available
References
Synthesis Reference

U.S. Patent 2,486,374.

US2486374
General ReferenceNot 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

1. Sodium channel protein type 5 subunit alpha

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Sodium channel protein type 5 subunit alpha Q14524 Details

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. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

2. Sodium channel protein type 10 subunit alpha

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Sodium channel protein type 10 subunit alpha Q9Y5Y9 Details

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

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Drug created on June 13, 2005 07:24 / Updated on April 28, 2014 17:46