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Identification
NameLevonordefrin
Accession NumberDB06707
TypeSmall Molecule
GroupsApproved
Description

Levonordefrin acts as a topical nasal decongestant and vasoconstrictor, most often used in dentistry.

Structure
Thumb
Synonyms
SynonymLanguageCode
alpha-MethylnoradrenalineNot AvailableNot Available
alpha-methylnorepinephrine Not AvailableNot Available
CorbadrineNot AvailableNot Available
Neo-cobefrinNot AvailableNot Available
α-methylnorepinephrineNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
Neo-CobefrinNot Available
NordefrinNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
CAS number829-74-3
WeightAverage: 183.2044
Monoisotopic: 183.089543287
Chemical FormulaC9H13NO3
InChI KeyGEFQWZLICWMTKF-CDUCUWFYSA-N
InChI
InChI=1S/C9H13NO3/c1-5(10)9(13)6-2-3-7(11)8(12)4-6/h2-5,9,11-13H,10H2,1H3/t5-,9-/m0/s1
IUPAC Name
4-[(1R,2S)-2-amino-1-hydroxypropyl]benzene-1,2-diol
SMILES
C[C@H](N)[C@H](O)C1=CC(O)=C(O)C=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as catecholamines and derivatives. These are compounds containing 4-(2-Aminoethyl)pyrocatechol [4-(2-aminoethyl)benzene-1,2-diol] or a derivative thereof formed by substitution.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenols and derivatives
Direct ParentCatecholamines and derivatives
Alternative Parents
Substituents
  • Catecholamine
  • Phenylpropane
  • Aralkylamine
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationUsed as a topical nasal decongestant and vasoconstrictor in dentistry.
Pharmacodynamicsis a sympathomimetic amine used as a vasoconstrictor in local anesthetic solutions. It has pharmacologic activity similar to that of Epinephrine but it is more stable than Epinephrine. In equal concentrations, Levonordefrin is less potent than Epinephrine in raising blood pressure, and as a vasoconstrictor.
Mechanism of actionIt is designed to mimic the molecular shape of adrenaline. It binds to alpha-adrenergic receptors in the nasal mucosa. Here it can, therefore, cause vasoconstriction
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9908
Blood Brain Barrier-0.9476
Caco-2 permeable-0.5196
P-glycoprotein substrateNon-substrate0.6652
P-glycoprotein inhibitor INon-inhibitor0.9818
P-glycoprotein inhibitor IINon-inhibitor0.9946
Renal organic cation transporterNon-inhibitor0.9341
CYP450 2C9 substrateNon-substrate0.7936
CYP450 2D6 substrateNon-substrate0.7668
CYP450 3A4 substrateNon-substrate0.7456
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 substrateNon-inhibitor0.9466
CYP450 2D6 substrateNon-inhibitor0.9789
CYP450 2C19 substrateNon-inhibitor0.9294
CYP450 3A4 substrateNon-inhibitor0.9229
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8329
Ames testAMES toxic0.6857
CarcinogenicityNon-carcinogens0.8948
BiodegradationNot ready biodegradable0.7553
Rat acute toxicity2.0594 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9705
hERG inhibition (predictor II)Non-inhibitor0.9117
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility14.6 mg/mLALOGPS
logP-0.77ALOGPS
logP-0.39ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)9.63ChemAxon
pKa (Strongest Basic)8.96ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area86.71 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity48.87 m3·mol-1ChemAxon
Polarizability18.81 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ATC CodesNot Available
AHFS Codes
  • 52:32
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AcebutololMay enhance the adverse/toxic effect of other Sympathomimetics.
AmphetamineMay enhance the adverse/toxic effect of other Sympathomimetics.
AtomoxetineMay enhance the hypertensive effect of Sympathomimetics. AtoMOXetine may enhance the tachycardic effect of Sympathomimetics.
BenzphetamineMay enhance the adverse/toxic effect of other Sympathomimetics.
Benzylpenicilloyl PolylysineAlpha-/Beta-Agonists may diminish the diagnostic effect of Benzylpenicilloyl Polylysine.
ChlorphentermineMay enhance the adverse/toxic effect of other Sympathomimetics.
ClenbuterolMay enhance the adverse/toxic effect of other Sympathomimetics.
DobutamineMay enhance the adverse/toxic effect of other Sympathomimetics.
DopamineMay enhance the adverse/toxic effect of other Sympathomimetics.
EpinephrineMay enhance the adverse/toxic effect of other Sympathomimetics.
FenoterolMay enhance the adverse/toxic effect of other Sympathomimetics.
FormoterolMay enhance the adverse/toxic effect of other Sympathomimetics.
HyaluronidaseMay enhance the vasoconstricting effect of Alpha-/Beta-Agonists.
IsocarboxazidMAO Inhibitors may enhance the hypertensive effect of Levonordefrin.
IsoprenalineMay enhance the adverse/toxic effect of other Sympathomimetics.
LabetalolMay enhance the adverse/toxic effect of other Sympathomimetics.
LinezolidMAO Inhibitors may enhance the hypertensive effect of Levonordefrin.
MephentermineMay enhance the adverse/toxic effect of other Sympathomimetics.
MetaraminolMay enhance the adverse/toxic effect of other Sympathomimetics.
MethamphetamineMay enhance the adverse/toxic effect of other Sympathomimetics.
MethoxamineMay enhance the adverse/toxic effect of other Sympathomimetics.
MidodrineMay enhance the adverse/toxic effect of other Sympathomimetics.
MoclobemideMAO Inhibitors may enhance the hypertensive effect of Levonordefrin.
NaphazolineMay enhance the adverse/toxic effect of other Sympathomimetics.
NorepinephrineMay enhance the adverse/toxic effect of other Sympathomimetics.
OrciprenalineMay enhance the adverse/toxic effect of other Sympathomimetics.
OxymetazolineMay enhance the adverse/toxic effect of other Sympathomimetics.
PhenelzineMAO Inhibitors may enhance the hypertensive effect of Levonordefrin.
PhenmetrazineMay enhance the adverse/toxic effect of other Sympathomimetics.
PhentermineMay enhance the adverse/toxic effect of other Sympathomimetics.
PhenylephrineMay enhance the adverse/toxic effect of other Sympathomimetics.
PhenylpropanolamineMay enhance the adverse/toxic effect of other Sympathomimetics.
ProcarbazineMAO Inhibitors may enhance the hypertensive effect of Levonordefrin.
RasagilineMAO Inhibitors may enhance the hypertensive effect of Levonordefrin.
RitodrineMay enhance the adverse/toxic effect of other Sympathomimetics.
SalmeterolMay enhance the adverse/toxic effect of other Sympathomimetics.
SelegilineMAO Inhibitors may enhance the hypertensive effect of Levonordefrin.
SpironolactoneMay diminish the vasoconstricting effect of Alpha-/Beta-Agonists.
Tedizolid PhosphateMAO Inhibitors may enhance the hypertensive effect of Levonordefrin.
TerbutalineMay enhance the adverse/toxic effect of other Sympathomimetics.
TranylcypromineMAO Inhibitors may enhance the hypertensive effect of Levonordefrin.
Food InteractionsNot Available

Targets

1. Alpha-1A adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Alpha-1A adrenergic receptor P35348 Details

References:

  1. Jastak JT, Yagiela JA: Vasoconstrictors and local anesthesia: a review and rationale for use. J Am Dent Assoc. 1983 Oct;107(4):623-30. Pubmed
  2. Hersh EV, Giannakopoulos H: Beta-adrenergic blocking agents and dental vasoconstrictors. Dent Clin North Am. 2010 Oct;54(4):687-96. Pubmed
  3. Yang HT, Endoh M: (+/-)-tamsulosin, an alpha 1A-adrenoceptor antagonist, inhibits the positive inotropic effect but not the accumulation of inositol phosphates in rabbit heart. Eur J Pharmacol. 1996 Oct 3;312(3):281-91. Pubmed# Haenisch B, Walstab J, Herberhold S, Bootz F, Tschaikin M, Ramseger R, Bonisch H: Alpha-adrenoceptor agonistic activity of oxymetazoline and xylometazoline. Fundam Clin Pharmacol. 2010 Dec;24(6):729-39. Pubmed

2. Sodium-dependent noradrenaline transporter

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Sodium-dependent noradrenaline transporter P23975 Details

References:

  1. Habecker BA, Willison BD, Shi X, Woodward WR: Chronic depolarization stimulates norepinephrine transporter expression via catecholamines. J Neurochem. 2006 May;97(4):1044-51. Epub 2006 Mar 29. Pubmed
  2. Bonisch H, Bruss M: The norepinephrine transporter in physiology and disease. Handb Exp Pharmacol. 2006;(175):485-524. Pubmed
  3. Mandela P, Ordway GA: KCl stimulation increases norepinephrine transporter function in PC12 cells. J Neurochem. 2006 Sep;98(5):1521-30. Epub 2006 Jul 31. Pubmed
  4. Gutman DA, Owens MJ: Serotonin and norepinephrine transporter binding profile of SSRIs. Essent Psychopharmacol. 2006;7(1):35-41. Pubmed
  5. Ksiazek P, Buraczynska K, Buraczynska M: Norepinephrine transporter gene (NET) polymorphism in patients with type 2 diabetes. Kidney Blood Press Res. 2006;29(6):338-43. Epub 2006 Nov 23. Pubmed

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Drug created on May 15, 2010 19:00 / Updated on October 03, 2013 23:14