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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
alpha-Methylnoradrenaline
alpha-methylnorepinephrine
Corbadrine
Neo-cobefrin
α-methylnorepinephrine
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
Neo-CobefrinNot Available
NordefrinNot Available
Brand mixtures
NameLabellerIngredients
2% Polocaine Dental With Levonordefrin 1:20,000Dentsply Canada Limited
Carbocaine 2% With Neo-cobefrinCarestream Health Canada Company
Carbocaine With Neo-cobefrinCaresteam Health, Inc.
Isocaine HCl Inj 2%Novocol Pharmaceutical Of Canada Inc
Mepivacaine Hydrochloride and LevonordefrinDarby Dental Supply, LLC
Mepivacaine With LevonordefrinPatterson Dental Supply, Inc.
Scandonest 2% With LevonordefrinNovocol Pharmaceutical Of Canada Inc
Scandonest LNovocol Pharmaceutical Of Canada, Inc
SaltsNot Available
Categories
UNIIV008L6478D
CAS number829-74-3
WeightAverage: 183.2044
Monoisotopic: 183.089543287
Chemical FormulaC9H13NO3
InChI KeyInChIKey=GEFQWZLICWMTKF-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[[email protected]](N)[[email protected]](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
Related Articles
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 inhibitorNon-inhibitor0.9466
CYP450 2D6 inhibitorNon-inhibitor0.9789
CYP450 2C19 inhibitorNon-inhibitor0.9294
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
Injection, solutionsubcutaneous
Solutionblock/infiltration
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 ReferencesNot Available
External Links
ATC CodesNot Available
AHFS Codes
  • 52:32
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AcebutololThe risk or severity of adverse effects can be increased when Acebutolol is combined with Levonordefrin.
AlfuzosinAlfuzosin may decrease the vasoconstricting activities of Levonordefrin.
AmitriptylineAmitriptyline may increase the activities of Levonordefrin.
AmphetamineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Levonordefrin.
BenzphetamineThe risk or severity of adverse effects can be increased when Benzphetamine is combined with Levonordefrin.
CabergolineCabergoline may increase the hypertensive activities of Levonordefrin.
ChlorphentermineThe risk or severity of adverse effects can be increased when Chlorphentermine is combined with Levonordefrin.
ClenbuterolThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Levonordefrin.
DobutamineThe risk or severity of adverse effects can be increased when Dobutamine is combined with Levonordefrin.
DopamineThe risk or severity of adverse effects can be increased when Dopamine is combined with Levonordefrin.
DoxofyllineThe risk or severity of adverse effects can be increased when Levonordefrin is combined with Doxofylline.
DronabinolDronabinol may increase the tachycardic activities of Levonordefrin.
EpinephrineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Levonordefrin.
FenoterolThe risk or severity of adverse effects can be increased when Fenoterol is combined with Levonordefrin.
FormoterolThe risk or severity of adverse effects can be increased when Formoterol is combined with Levonordefrin.
IobenguaneThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Levonordefrin.
IsocarboxazidIsocarboxazid may increase the hypertensive activities of Levonordefrin.
IsoprenalineThe risk or severity of adverse effects can be increased when Isoprenaline is combined with Levonordefrin.
LabetalolThe risk or severity of adverse effects can be increased when Labetalol is combined with Levonordefrin.
LinezolidLinezolid may increase the hypertensive activities of Levonordefrin.
MephentermineThe risk or severity of adverse effects can be increased when Mephentermine is combined with Levonordefrin.
MetaraminolThe risk or severity of adverse effects can be increased when Metaraminol is combined with Levonordefrin.
MethamphetamineThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Levonordefrin.
MethoxamineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Levonordefrin.
MidodrineThe risk or severity of adverse effects can be increased when Midodrine is combined with Levonordefrin.
MoclobemideMoclobemide may increase the hypertensive activities of Levonordefrin.
NadololNadolol may increase the activities of Levonordefrin.
NaphazolineThe risk or severity of adverse effects can be increased when Naphazoline is combined with Levonordefrin.
NorepinephrineThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Levonordefrin.
OrciprenalineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Levonordefrin.
OxymetazolineThe risk or severity of adverse effects can be increased when Oxymetazoline is combined with Levonordefrin.
PhenelzinePhenelzine may increase the hypertensive activities of Levonordefrin.
PhenmetrazineThe risk or severity of adverse effects can be increased when Phenmetrazine is combined with Levonordefrin.
PhentermineThe risk or severity of adverse effects can be increased when Phentermine is combined with Levonordefrin.
PhenylephrineThe risk or severity of adverse effects can be increased when Phenylephrine is combined with Levonordefrin.
PhenylpropanolamineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Levonordefrin.
PrazosinPrazosin may decrease the vasoconstricting activities of Levonordefrin.
ProcarbazineProcarbazine may increase the hypertensive activities of Levonordefrin.
RasagilineRasagiline may increase the hypertensive activities of Levonordefrin.
RitodrineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Levonordefrin.
SalmeterolThe risk or severity of adverse effects can be increased when Salmeterol is combined with Levonordefrin.
SelegilineSelegiline may increase the hypertensive activities of Levonordefrin.
Technetium Tc-99m tilmanoceptLevonordefrin may decrease effectiveness of Technetium Tc-99m tilmanocept as a diagnostic agent.
Tedizolid PhosphateTedizolid Phosphate may increase the hypertensive activities of Levonordefrin.
TerbutalineThe risk or severity of adverse effects can be increased when Terbutaline is combined with Levonordefrin.
TranylcypromineTranylcypromine may increase the hypertensive activities of Levonordefrin.
VenlafaxineVenlafaxine may increase the tachycardic activities of Levonordefrin.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Protein heterodimerization activity
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. Nuclear ADRA1A-ADRA1B heterooligomers regulate phenylephrine(PE)-stimulated ERK signaling in cardiac myocytes.
Gene Name:
ADRA1A
Uniprot ID:
P35348
Molecular Weight:
51486.005 Da
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:6355236 ]
  2. Hersh EV, Giannakopoulos H: Beta-adrenergic blocking agents and dental vasoconstrictors. Dent Clin North Am. 2010 Oct;54(4):687-96. doi: 10.1016/j.cden.2010.06.009. [PubMed:20831932 ]
  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:8894610 ]
  4. 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. doi: 10.1111/j.1472-8206.2009.00805.x. [PubMed:20030735 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Norepinephrine:sodium symporter activity
Specific Function:
Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:
SLC6A2
Uniprot ID:
P23975
Molecular Weight:
69331.42 Da
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:16573647 ]
  2. Bonisch H, Bruss M: The norepinephrine transporter in physiology and disease. Handb Exp Pharmacol. 2006;(175):485-524. [PubMed:16722247 ]
  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:16879714 ]
  4. Gutman DA, Owens MJ: Serotonin and norepinephrine transporter binding profile of SSRIs. Essent Psychopharmacol. 2006;7(1):35-41. [PubMed:16989291 ]
  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:17124432 ]
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Drug created on May 15, 2010 19:00 / Updated on October 03, 2013 23:14