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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2020-02-26 21:42:00 UTC
HMDB IDHMDB0015656
Secondary Accession Numbers
  • HMDB15656
Metabolite Identification
Common NameNaphazoline
DescriptionNaphazoline is only found in individuals that have used or taken this drug. It is a rapid acting sympathomimetic vasoconstrictor of occular 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 result 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
Data?1582753320
Synonyms
ValueSource
NafazolinKegg
AK CONHMDB
AK-CONHMDB
Akorn brand OF naphazoline hydrochlorideHMDB
Alcon brand 1 OF naphazoline hydrochlorideHMDB
Alcon brand 2 OF naphazoline hydrochlorideHMDB
Alfa, colirioHMDB
Bausch and lomb brand 1 OF naphazoline hydrochlorideHMDB
Ciba vision brand 1 OF naphazoline hydrochlorideHMDB
Febena brand OF naphazoline hydrochlorideHMDB
Hydrochloride, naphazolineHMDB
IdrilHMDB
Iquinosa brand OF naphazoline hydrochlorideHMDB
Naphazoline monohydrochlorideHMDB
Novartis brand 1 OF naphazoline hydrochlorideHMDB
Ross brand OF naphazoline hydrochlorideHMDB
tele StullnHMDB
TeleStullnHMDB
Vasocon regularHMDB
Abbot brand OF naphazoline hydrochlorideHMDB
Ciba vision brand 2 OF naphazoline hydrochlorideHMDB
Clear eyesHMDB
Grin brand OF naphazoline hydrochlorideHMDB
Grin, afazolHMDB
MiraclarHMDB
Monohydrochloride, naphazolineHMDB
Naphazoline hydrochlorideHMDB
Naphazoline nitrateHMDB
Novartis brand 2 OF naphazoline hydrochlorideHMDB
PrivineHMDB
ProculinHMDB
Warner lambert brand OF naphazoline nitrateHMDB
Warner-lambert brand OF naphazoline nitrateHMDB
Winzer brand OF naphazoline hydrochlorideHMDB
Forte, naphconHMDB
Afazol grinHMDB
AlbalonHMDB
Bausch and lomb brand 2 OF naphazoline hydrochlorideHMDB
Chauvin brand OF naphazoline hydrochlorideHMDB
Eyes, clearHMDB
NafazairHMDB
Nitrate, naphazolineHMDB
Optima brand OF naphazoline hydrochlorideHMDB
Pensa, vasoconstrictorHMDB
PrivinHMDB
Stulln brand OF naphazoline hydrochlorideHMDB
tele-StullnHMDB
VasoNitHMDB
VasoclearHMDB
VasoconHMDB
Vasoconstrictor pensaHMDB
AKConHMDB
all ClearHMDB
Allergan brand OF naphazoline hydrochlorideHMDB
Clear, allHMDB
Colirio alfaHMDB
NaphconHMDB
Naphcon forteHMDB
OptazineHMDB
Regular, vasoconHMDB
SiozwoHMDB
Whitehall brand OF naphazoline hydrochlorideHMDB
Chemical FormulaC14H14N2
Average Molecular Weight210.2744
Monoisotopic Molecular Weight210.115698458
IUPAC Name2-(naphthalen-1-ylmethyl)-4,5-dihydro-1H-imidazole
Traditional Namenaphazoline
CAS Registry Number835-31-4
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 KeyCNIIGCLFLJGOGP-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings.
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassNot Available
Direct ParentNaphthalenes
Alternative Parents
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
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.038 g/LALOGPS
logP3.44ALOGPS
logP2.19ChemAxon
logS-3.7ALOGPS
pKa (Strongest Basic)10.19ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area24.39 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity65.52 m³·mol⁻¹ChemAxon
Polarizability23.77 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-2900000000-026b23156746d2a4a1deSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03di-0390000000-bf587920984867425a82Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0090000000-0076ea45eaeedc60e1fbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1490000000-9be572c365d8869eec53Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-5900000000-b07ec5aa4378446ddd21Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-af432db2e56a6f9aed8dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1290000000-46d4b9b044e895d92e64Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ou-1900000000-8c83d33771f2cc032669Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB06711 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB06711 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB06711
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4283
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNaphazoline
METLIN IDNot Available
PubChem Compound4436
PDB IDNot Available
ChEBI ID142468
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot 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 ]