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Naphazoline

July 24, 2017
Common Name

Naphazoline Description

Naphazoline is only found in individuals that have used or taken this drug. It is a rapid acting sympathomimetic vasoconstrictor of occliar artierioles. It acts to decrease congestion of the conjunctiva and is found in many over-the-counter eye drops.Naphazoline is a direct acting sympathomimetic drug, which acts on alpha-adrenergic receptors in the arterioles of the nasal mucosa. This activates the adrenal system to yield systemic vasoconstrction. In producing vasoconstriction, the reslit is a decrease in blood flow in the nasal passages and consequently decreased nasal congestion. The vasoconstriction means that there is less pressure in the capillaries and less water can filter out, thus less discharge is made. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source NafazolinKegg AK CONMeSH AK-CONMeSH Akorn brand OF naphazoline hydrochlorideMeSH Alcon brand 1 OF naphazoline hydrochlorideMeSH Alcon brand 2 OF naphazoline hydrochlorideMeSH Alfa, colirioMeSH Bausch and lomb brand 1 OF naphazoline hydrochlorideMeSH Ciba vision brand 1 OF naphazoline hydrochlorideMeSH Febena brand OF naphazoline hydrochlorideMeSH Hydrochloride, naphazolineMeSH IdrilMeSH Iquinosa brand OF naphazoline hydrochlorideMeSH Naphazoline monohydrochlorideMeSH Novartis brand 1 OF naphazoline hydrochlorideMeSH Ross brand OF naphazoline hydrochlorideMeSH tele StlilnMeSH TeleStlilnMeSH Vasocon regliarMeSH Abbot brand OF naphazoline hydrochlorideMeSH Ciba vision brand 2 OF naphazoline hydrochlorideMeSH Clear eyesMeSH Grin brand OF naphazoline hydrochlorideMeSH Grin, afazolMeSH MiraclarMeSH Monohydrochloride, naphazolineMeSH Naphazoline hydrochlorideMeSH Naphazoline nitrateMeSH Novartis brand 2 OF naphazoline hydrochlorideMeSH PrivineMeSH ProcliinMeSH Warner lambert brand OF naphazoline nitrateMeSH Warner-lambert brand OF naphazoline nitrateMeSH Winzer brand OF naphazoline hydrochlorideMeSH Forte, naphconMeSH Afazol grinMeSH AlbalonMeSH Bausch and lomb brand 2 OF naphazoline hydrochlorideMeSH Chauvin brand OF naphazoline hydrochlorideMeSH Eyes, clearMeSH NafazairMeSH Nitrate, naphazolineMeSH Optima brand OF naphazoline hydrochlorideMeSH Pensa, vasoconstrictorMeSH PrivinMeSH Stliln brand OF naphazoline hydrochlorideMeSH tele-StlilnMeSH VasoNitMeSH VasoclearMeSH VasoconMeSH Vasoconstrictor pensaMeSH AKConMeSH all ClearMeSH Allergan brand OF naphazoline hydrochlorideMeSH Clear, allMeSH colirio AlfaMeSH NaphconMeSH Naphcon forteMeSH OptazineMeSH Regliar, vasoconMeSH SiozwoMeSH Whitehall brand OF naphazoline hydrochlorideMeSH

Chemical Formlia

C14H14N2 Average Molecliar Weight

210.2744 Monoisotopic Molecliar Weight

210.115698458 IUPAC Name

2-(naphthalen-1-ylmethyl)-4,5-dihydro-1H-imidazole Traditional Name

naphazoline CAS Registry Number

835-31-4 SMILES

C(C1=NCCN1)C1=CC=CC2=CC=CC=C12

InChI Identifier

InChI=1S/C14H14N2/c1-2-7-13-11(4-1)5-3-6-12(13)10-14-15-8-9-16-14/h1-7H,8-10H2,(H,15,16)

InChI Key

CNIIGCLFLJGOGP-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as naphthalenes. These are compounds containing a naphthalene moiety, which consists of two fused benzene rings. Kingdom

Chemical entities Super Class

Organic compounds Class

Benzenoids Sub Class

Naphthalenes Direct Parent

Naphthalenes Alternative Parents

  • Imidolactams
  • Imidazolines
  • Propargyl-type 1,3-dipolar organic compounds
  • Carboximidamides
  • Carboxamidines
  • Azacyclic compounds
  • Organopnictogen compounds
  • Hydrocarbon derivatives

    • Substituents

  • Naphthalene
  • Imidolactam
  • 2-imidazoline
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Carboxylic acid amidine
  • Amidine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound

    • Molecliar Framework

    Aromatic heteropolycyclic compounds External Descriptors

    Not Available Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Adrenergic alpha-Agonists
  • Sympathomimetic

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water SolubilityNot AvailableNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility0.038 mg/mLALOGPS logP3.44ALOGPS logP2.19ChemAxon logS-3.7ALOGPS pKa (Strongest Basic)10.19ChemAxon Physiological Charge1ChemAxon Hydrogen Acceptor Count2ChemAxon Hydrogen Donor Count1ChemAxon Polar Surface Area24.39 Å2ChemAxon Rotatable Bond Count2ChemAxon Refractivity65.52 m3·mol-1ChemAxon Polarizability23.77 Å3ChemAxon Number of Rings3ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Not 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 DB06711

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06711

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB06711 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

    4283 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Naphazoline NuGOwiki Link

    HMDB15656 Metagene Link

    HMDB15656 METLIN ID

    Not Available PubChem Compound

    4436 PDB ID

    Not Available ChEBI ID

    142468

    Product: Hygromycin B

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References Not Available

    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. Piletz JE, Zhu H, Chikkala DN: Comparison of ligand binding affinities at human I1-imidazoline binding sites and the high affinity state of alpha-2 adrenoceptor subtypes. J Pharmacol Exp Ther. 1996 Nov;279(2):694-702. [PubMed:8930173 ]
    2. Fukushima H, Norimoto K, Seki T, Nishiguchi T, Nakamura T, Konobu T, Nishio K, Okuchi K: Acute pulmonary edema associated with naphazoline ingestion. Clin Toxicol (Phila). 2008 Mar;46(3):254-6. [PubMed:17852165 ]
    3. Ogidigben MJ, Chu TC, Potter DE: Naphazoline-induced suppression of aqueous humor pressure and flow: involvement of central and peripheral alpha(2)/I(1) receptors. Exp Eye Res. 2001 Mar;72(3):331-9. [PubMed:11180982 ]
    General function:
    Involved in G-protein coupled receptor protein signaling pathway
    Specific function:
    This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins
    Gene Name:
    ADRA1A
    Uniprot ID:
    P35348
    Molecular weight:
    51486.0
    References
    1. Bogacka E: [Decongestants in treatment of nasal obstruction]. Otolaryngol Pol. 1999;53(3):347-52. [PubMed:10481510 ]
    2. Leonardi A: Emerging drugs for ocular allergy. Expert Opin Emerg Drugs. 2005 Aug;10(3):505-20. [PubMed:16083326 ]
    3. Piletz JE, Zhu H, Chikkala DN: Comparison of ligand binding affinities at human I1-imidazoline binding sites and the high affinity state of alpha-2 adrenoceptor subtypes. J Pharmacol Exp Ther. 1996 Nov;279(2):694-702. [PubMed:8930173 ]
    4. Hrometz SL, Edelmann SE, McCune DF, Olges JR, Hadley RW, Perez DM, Piascik MT: Expression of multiple alpha1-adrenoceptors on vascular smooth muscle: correlation with the regulation of contraction. J Pharmacol Exp Ther. 1999 Jul;290(1):452-63. [PubMed:10381812 ]
    5. Kai T: [Effects of topical alpha 1- and beta 2-adrenoceptor stimulants on nasal nitric oxide level]. Nihon Jibiinkoka Gakkai Kaiho. 1999 Jul;102(7):898-906. [PubMed:10459292 ]
    6. Ogidigben MJ, Chu TC, Potter DE: Naphazoline-induced suppression of aqueous humor pressure and flow: involvement of central and peripheral alpha(2)/I(1) receptors. Exp Eye Res. 2001 Mar;72(3):331-9. [PubMed:11180982 ]

    PMID: 22998799

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