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Lofexidine

July 24, 2017
Common Name

Lofexidine Description

Lofexidine is an alpha2-adrenergic receptor agonist. It can be used as a short acting anti-hypertensive, but is mostly used to help relieve symptoms of heroin or opiate withdrawal in opiate dependency. It is approved in the United Kingdom, but is still undergoing clinical trials in the United States. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source 2-(alpha-(2,6-Dichlorophenoxy)ethyl)2-imidazolineChEBI LofexidinaChEBI LofexidinumChEBI 2-(a-(2,6-Dichlorophenoxy)ethyl)2-imidazolineGenerator 2-(α-(2,6-dichlorophenoxy)ethyl)2-imidazolineGenerator 2-(1-(2,6-Dichlorophenoxy)ethyl)-4,5-dihydro-1H-imidazoleHMDB BritLofexMeSH 2-(alpha-(2,6-Dichlorophenoxy)ethyl) delta-2-imidazolineMeSH Lofexidine mono-hydrochlorideMeSH Lofexidine, (+-)-isomerMeSH Lofexidine hydrochlorideMeSH Lofexidine monohydrochlorideMeSH

Chemical Formlia

C11H12Cl2N2O Average Molecliar Weight

259.132 Monoisotopic Molecliar Weight

258.03266843 IUPAC Name

2-[1-(2,6-dichlorophenoxy)ethyl]-4,5-dihydro-1H-imidazole Traditional Name

lofexidine CAS Registry Number

31036-80-3 SMILES

CC(OC1=C(Cl)C=CC=C1Cl)C1=NCCN1

InChI Identifier

InChI=1S/C11H12Cl2N2O/c1-7(11-14-5-6-15-11)16-10-8(12)3-2-4-9(10)13/h2-4,7H,5-6H2,1H3,(H,14,15)

InChI Key

KSMAGQUYOIHWFS-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as dichlorobenzenes. These are compounds containing a benzene with exactly two chlorine atoms attached to it. Kingdom

Chemical entities Super Class

Organic compounds Class

Benzenoids Sub Class

Benzene and substituted derivatives Direct Parent

Dichlorobenzenes Alternative Parents

  • Phenoxy compounds
  • Phenol ethers
  • Alkyl aryl ethers
  • Imidolactams
  • Aryl chlorides
  • Imidazolines
  • Propargyl-type 1,3-dipolar organic compounds
  • Carboximidamides
  • Carboxamidines
  • Azacyclic compounds
  • Organopnictogen compounds
  • Organochlorides
  • Hydrocarbon derivatives

    • Substituents

  • Phenoxy compound
  • 1,3-dichlorobenzene
  • Phenol ether
  • Alkyl aryl ether
  • Aryl chloride
  • Aryl halide
  • Imidolactam
  • 2-imidazoline
  • Amidine
  • Carboxylic acid amidine
  • Ether
  • Azacycle
  • Organoheterocyclic compound
  • Carboximidamide
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organic oxygen compound
  • Organohalogen compound
  • Organochloride
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound

    • Molecliar Framework

    Aromatic heteromonocyclic compounds External Descriptors

  • aromatic ether (CHEBI:51368 )
  • imidazoles (CHEBI:51368 )
  • carboxamidine (CHEBI:51368 )
  • dichlorobenzene (CHEBI:51368 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Adrenergic alpha-Agonists
  • Antihypertensive Agents
  • Narcotic Antagonists

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point127 °CNot Available Boiling PointNot AvailableNot Available Water Solubility1.47e-01 g/LNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility0.15 mg/mLALOGPS logP3.31ALOGPS logP2.66ChemAxon logS-3.2ALOGPS pKa (Strongest Basic)7.67ChemAxon Physiological Charge1ChemAxon Hydrogen Acceptor Count3ChemAxon Hydrogen Donor Count1ChemAxon Polar Surface Area33.62 Å2ChemAxon Rotatable Bond Count3ChemAxon Refractivity64.41 m3·mol-1ChemAxon Polarizability25.11 Å3ChemAxon Number of Rings2ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key LC-MS/MS

    LC-MS/MS Spectrum – , positivesplash10-0bta-5090000000-966c69c881b261c7d39dView in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB04948

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB04948

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB04948 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    28460 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Lofexidine NuGOwiki Link

    HMDB15606 Metagene Link

    HMDB15606 METLIN ID

    Not Available PubChem Compound

    30668 PDB ID

    Not Available ChEBI ID

    51368

    Product: WP1067

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. Walsh SL, Strain EC, Bigelow GE: Evaluation of the effects of lofexidine and clonidine on naloxone-precipitated withdrawal in opioid-dependent humans. Addiction. 2003 Apr;98(4):427-39. [PubMed:12653813 ]
    2. Manufacturer Website [Link]

    Enzymes

    General function:
    Involved in G-protein coupled receptor protein signaling pathway
    Specific function:
    Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol
    Gene Name:
    ADRA2A
    Uniprot ID:
    P08913
    Molecular weight:
    48956.3
    References
    1. Jin Y, Verstappen A, Elko E, Cammarata P, Yorio T: Effects of lofexidine, an alpha 2-adrenoreceptor agonist, on ocular blood flow and ion transport of rabbit iris-ciliary body. J Ocul Pharmacol. 1992 Spring;8(1):23-33. [PubMed:1357064 ]
    2. Strang J, Bearn J, Gossop M: Lofexidine for opiate detoxification: review of recent randomised and open controlled trials. Am J Addict. 1999 Fall;8(4):337-48. [PubMed:10598217 ]
    3. Erb S, Hitchcott PK, Rajabi H, Mueller D, Shaham Y, Stewart J: Alpha-2 adrenergic receptor agonists block stress-induced reinstatement of cocaine seeking. Neuropsychopharmacology. 2000 Aug;23(2):138-50. [PubMed:10882840 ]

    PMID: 8410971

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