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Identification
Name Hexylcaine
Accession Number DB00473 (APRD01014)
Type small molecule
Groups approved
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.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Salts Not Available
Brand names
Name Company
Cyclaine
Hexilcaina [INN-Spanish]
Hexylcaine hydrochloride
Hexylcainum [INN-Latin]
Osmocaine
Brand mixtures Not Available
Categories
  • Anesthetics
  • Local Anesthetics
CAS number 532-77-4
Weight Average: 261.3593
Monoisotopic: 261.172878985
Chemical Formula C16H23NO2
InChI Key InChIKey=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
Plain Text
IUPAC Name
1-(cyclohexylamino)propan-2-yl benzoate
SMILES
CC(CNC1CCCCC1)OC(=O)C1=CC=CC=C1
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Aminobenzoates
Substructures
  • Aminobenzoates
  • Carboxylic Acids and Derivatives
  • Benzyl Alcohols and Derivatives
  • Acetates
  • Benzoates
  • Aliphatic and Aryl Amines
  • Ethers
  • Benzene and Derivatives
  • Aromatic compounds
  • Benzoyl Derivatives
Pharmacology
Indication Used as a local anesthetic for surface application, infiltration or nerve block
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.
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
Pharmacoeconomics
Manufacturers
  • Merck and co inc
Packagers Not Available
Dosage forms Not Available
Prices Not Available
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
logP 3.9 Not Available
Predicted Properties
Property Value Source
water solubility 9.71e-03 g/l ALOGPS
logP 3.04 ALOGPS
logP 3.83 ChemAxon
logS -4.4 ALOGPS
pKa (strongest basic) 9.87 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 2 ChemAxon
hydrogen donor count 1 ChemAxon
polar surface area 38.33 ChemAxon
rotatable bond count 6 ChemAxon
refractivity 76.24 ChemAxon
polarizability 30.29 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Compound C14172 Link_out
PubChem Compound 10770 Link_out
PubChem Substance 46506241 Link_out
ChemSpider 10315 Link_out
BindingDB 50017670 Link_out
Therapeutic Targets Database DAP000506 Link_out
PharmGKB PA164746489 Link_out
Wikipedia http://en.wikipedia.org/wiki/Hexylcaine Link_out
ATC Codes Not Available
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Sodium channel protein type 5 subunit alpha

Pharmacological action: yes
Actions: inhibitor

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 responsible for the initial upstroke of the action potential in the electrocardiogram

Organism class: human
UniProt ID: Q14524 Link_out
Gene: SCN5A Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: unknown
Actions: inhibitor

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 sodium ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant sodium channel isoform. Its electrophysiological properties vary depending on the type of the associated beta subunits (in vitro). Plays a role in neuropathic pain mechanisms

Organism class: human
UniProt ID: Q9Y5Y9 Link_out
Gene: SCN10A Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19