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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
SaltsNot Available
Brand names
NameCompany
Neo-CobefrinNot Available
NordefrinNot Available
Brand mixturesNot 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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassPhenols and Derivatives
Direct parentCatecholamines and Derivatives
Alternative parentsAmphetamines and Derivatives; Polyols; Secondary Alcohols; 1,2-Aminoalcohols; Enols; Polyamines; Monoalkylamines
Substituents1,2-aminoalcohol; secondary alcohol; polyol; enol; polyamine; amine; primary amine; primary aliphatic amine; alcohol; organonitrogen compound
Classification descriptionThis compound belongs to the 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.
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
Metabolism
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
Property Value Probability
Human Intestinal Absorption + 0.9908
Blood Brain Barrier - 0.9476
Caco-2 permeable - 0.5196
P-glycoprotein substrate Non-substrate 0.6652
P-glycoprotein inhibitor I Non-inhibitor 0.9818
P-glycoprotein inhibitor II Non-inhibitor 0.9946
Renal organic cation transporter Non-inhibitor 0.9341
CYP450 2C9 substrate Non-substrate 0.7936
CYP450 2D6 substrate Non-substrate 0.7668
CYP450 3A4 substrate Non-substrate 0.7456
CYP450 1A2 substrate Non-inhibitor 0.9046
CYP450 2C9 substrate Non-inhibitor 0.9466
CYP450 2D6 substrate Non-inhibitor 0.9789
CYP450 2C19 substrate Non-inhibitor 0.9294
CYP450 3A4 substrate Non-inhibitor 0.9229
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8329
Ames test AMES toxic 0.6857
Carcinogenicity Non-carcinogens 0.8948
Biodegradation Not ready biodegradable 0.7553
Rat acute toxicity 2.0594 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9705
hERG inhibition (predictor II) Non-inhibitor 0.9117
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility14.6ALOGPS
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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ResourceLink
PubChem Compound164739
PubChem Substance99443259
BindingDB50029048
PharmGKBPA165958380
IUPHAR508
Guide to Pharmacology508
WikipediaLevonordefrin
ATC CodesNot Available
AHFS Codes
  • 52:32
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
DesvenlafaxineDesvenlafaxine may increase the tachycardic and vasopressor effects of levonordefrin. Consider alternate therapy or monitor for increased sympathomimetic effects, such as increased blood pressure, chest pain and headache.
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