Identification

Name
Levonordefrin
Accession Number
DB06707
Type
Small Molecule
Groups
Approved
Description

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

Structure
Thumb
Synonyms
  • (-)-cobefrin
  • alpha-Methylnoradrenaline
  • Corbadrine
  • L-alpha-methylnoradrenaline
  • L-Nordefrin
  • Neo-cobefrin
External IDs
BA 2818 / BA-2818
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
2% Polocaine Dental With Levonordefrin 1:20,000Levonordefrin (0.05 mg) + Mepivacaine Hydrochloride (20 mg)SolutionInfiltrationDentsply Pharmaceutical1990-12-312011-08-04Canada
Carbocaine 2% With Neo-cobefrinLevonordefrin (0.05 mg) + Mepivacaine Hydrochloride (20 mg)SolutionInfiltrationNovocol Inc.Not applicableNot applicableCanada
Carbocaine 2% With Neo-cobefrinLevonordefrin (0.05 mg) + Mepivacaine Hydrochloride (20 mg)SolutionInfiltrationKodak Canada Inc.2005-04-222008-07-14Canada
Carbocaine 2% With Neo-cobefrinLevonordefrin (0.05 mg) + Mepivacaine Hydrochloride (20 mg)SolutionInfiltrationCarestream Health Inc.2006-09-01Not applicableCanada
Carbocaine with Neo-CobefrinLevonordefrin (0.05 mg/1mL) + Mepivacaine Hydrochloride (20 mg/1mL)Injection, solutionSubcutaneousCaresteam Health, Inc.2011-01-01Not applicableUs
Isocaine HCl Inj 2%Levonordefrin (0.05 mg) + Mepivacaine Hydrochloride (20 mg)SolutionInfiltrationNovocol Inc.1977-12-31Not applicableCanada
Mepivacaine Hydrochloride and LevonordefrinLevonordefrin (0.05 mg/1mL) + Mepivacaine Hydrochloride (20 mg/1mL)Injection, solutionSubcutaneousDarby Dental Supply Llc2011-01-14Not applicableUs
Mepivacaine Hydrochloride with LevonordefrinLevonordefrin (0.05 mg/1mL) + Mepivacaine Hydrochloride (20 mg/1mL)Injection, solutionSubcutaneousHenry Schein2011-01-01Not applicableUs
Mepivacaine With LevonordefrinLevonordefrin (0.05 mg/1mL) + Mepivacaine Hydrochloride (20 mg/1mL)Injection, solutionSubcutaneousBenco Dental2011-01-012012-05-24Us
Mepivacaine with LevonordefrinLevonordefrin (0.05 mg/1mL) + Mepivacaine Hydrochloride (20 mg/1mL)Injection, solutionSubcutaneousPatterson Dental2011-01-01Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Isocaine with LevonordefrinLevonordefrin (0.05 mg/1mL) + Mepivacaine Hydrochloride (20 mg/1mL)Injection, solutionSubcutaneousNovocol Pharmaceutical of Canada Inc.2006-04-14Not applicableUs
Scandonest LLevonordefrin (0.05 mg/1mL) + Mepivacaine Hydrochloride (20 mg/1mL)Injection, solutionSubcutaneousSeptodont2006-06-08Not applicableUs
International/Other Brands
Neo-Cobefrin / Nordefrin
Categories
UNII
V008L6478D
CAS number
829-74-3
Weight
Average: 183.2044
Monoisotopic: 183.089543287
Chemical Formula
C9H13NO3
InChI Key
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[C@H](N)[C@H](O)C1=CC(O)=C(O)C=C1

Pharmacology

Indication

Used as a topical nasal decongestant and vasoconstrictor in dentistry.

Pharmacodynamics

Levonordefrin is 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 action

It 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.

TargetActionsOrganism
AAlpha-2 adrenergic receptors
agonist
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the hypertensive activities of Levonordefrin.
AlprenololLevonordefrin may increase the atrioventricular blocking (AV block) activities of Alprenolol.
AmineptineAmineptine may decrease the antihypertensive activities of Levonordefrin.
AmitriptylinoxideAmitriptylinoxide may decrease the antihypertensive activities of Levonordefrin.
AmoxapineAmoxapine may decrease the antihypertensive activities of Levonordefrin.
ArotinololLevonordefrin may increase the atrioventricular blocking (AV block) activities of Arotinolol.
AsenapineLevonordefrin may increase the atrioventricular blocking (AV block) activities of Asenapine.
BefunololLevonordefrin may increase the atrioventricular blocking (AV block) activities of Befunolol.
BenmoxinBenmoxin may increase the hypertensive activities of Levonordefrin.
BevantololLevonordefrin may increase the atrioventricular blocking (AV block) activities of Bevantolol.
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0015652
KEGG Drug
D02388
KEGG Compound
C11768
PubChem Compound
164739
PubChem Substance
99443259
ChemSpider
144416
BindingDB
50029048
ChEBI
10304
ChEMBL
CHEMBL677
PharmGKB
PA165958380
IUPHAR
508
Guide to Pharmacology
GtP Drug Page
Wikipedia
Levonordefrin

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
InjectionSubcutaneous
InjectionDental
SolutionInfiltration
Injection, solutionSubcutaneous
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not 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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenylpropanes
Direct Parent
Phenylpropanes
Alternative Parents
Catechols / Aralkylamines / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Secondary alcohols / 1,2-aminoalcohols / Organopnictogen compounds / Monoalkylamines / Hydrocarbon derivatives / Aromatic alcohols
Substituents
Phenylpropane / Catechol / 1-hydroxy-4-unsubstituted benzenoid / 1-hydroxy-2-unsubstituted benzenoid / Phenol / Aralkylamine / 1,2-aminoalcohol / Secondary alcohol / Organic nitrogen compound / Aromatic alcohol
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
catecholamine (CHEBI:10304)

Targets

Kind
Protein group
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Thioesterase binding
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 oxymetazo...

Components:
References
  1. de Andrade CA, de Andrade GM, De Paula PM, De Luca LA Jr, Menani JV: Involvement of central alpha1-adrenoceptors on renal responses to central moxonidine and alpha-methylnoradrenaline. Eur J Pharmacol. 2009 Apr 1;607(1-3):60-7. [PubMed:19326476]

Drug created on May 15, 2010 19:00 / Updated on August 02, 2018 05:38