Levonordefrin

Identification

Summary

Levonordefrin is a topical sympathomimetic amine found in local anesthetic products that is used for nasal decongestion or vasoconstriction during dental procedures.

Brand Names
Carbocaine With Neocobefrin, Isocaine With Levonordefrin, Scandonest L
Generic Name
Levonordefrin
DrugBank Accession Number
DB06707
Background

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

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 183.2044
Monoisotopic: 183.089543287
Chemical Formula
C9H13NO3
Synonyms
  • (-)-cobefrin
  • alpha-Methylnoradrenaline
  • Corbadrina
  • Corbadrine
  • Corbadrinum
  • L-alpha-methylnoradrenaline
  • L-Nordefrin
  • Levonordefrin
  • Neo-cobefrin
External IDs
  • BA 2818
  • BA-2818

Pharmacology

Indication

Used as a topical nasal decongestant and vasoconstrictor in dentistry.

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Contraindications & Blackbox Warnings
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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
Humans
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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcebutololThe therapeutic efficacy of Acebutolol can be increased when used in combination with Levonordefrin.
AceclofenacThe risk or severity of hypertension can be increased when Levonordefrin is combined with Aceclofenac.
AcemetacinThe risk or severity of hypertension can be increased when Levonordefrin is combined with Acemetacin.
AcetazolamideThe risk or severity of Cardiac Arrhythmia can be increased when Levonordefrin is combined with Acetazolamide.
AcetyldigitoxinThe risk or severity of Cardiac Arrhythmia can be increased when Levonordefrin is combined with Acetyldigitoxin.
Food Interactions
No interactions found.

Products

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International/Other Brands
Neo-Cobefrin / Nordefrin
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
2% Polocaine Dental With Levonordefrin 1:20,000Levonordefrin (0.05 mg / mL) + Mepivacaine hydrochloride (20 mg / mL)SolutionInfiltrationDentsply Pharmaceutical1990-12-312011-08-04Canada flag
Carbocaine 2% With Neo-cobefrinLevonordefrin (0.05 mg / mL) + Mepivacaine hydrochloride (20 mg / mL)SolutionInfiltrationCarestream Health Inc.2006-09-012018-09-06Canada flag
Carbocaine 2% With Neo-cobefrinLevonordefrin (0.05 mg / mL) + Mepivacaine hydrochloride (20 mg / mL)SolutionInfiltrationNovocol Inc.2019-07-302023-03-20Canada flag
Carbocaine 2% With Neo-cobefrinLevonordefrin (0.05 mg / mL) + Mepivacaine hydrochloride (20 mg / mL)SolutionInfiltrationKodak Canada Inc.2005-04-222008-07-14Canada flag
Carbocaine with Neo-CobefrinLevonordefrin (0.05 mg/1mL) + Mepivacaine hydrochloride (20 mg/1mL)Injection, solutionSubcutaneousCaresteam Health, Inc.2011-01-01Not applicableUS flag

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
1,2-aminoalcohol / 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Alcohol / Amine / Aralkylamine / Aromatic alcohol / Aromatic homomonocyclic compound / Catechol / Hydrocarbon derivative
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
catecholamine (CHEBI:10304)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
V008L6478D
CAS number
829-74-3
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

References

General References
Not Available
Human Metabolome Database
HMDB0015652
KEGG Drug
D02388
KEGG Compound
C11768
PubChem Compound
164739
PubChem Substance
99443259
ChemSpider
144416
BindingDB
50223426
RxNav
132889
ChEBI
10304
ChEMBL
CHEMBL677
ZINC
ZINC000000034157
PharmGKB
PA165958380
Guide to Pharmacology
GtP Drug Page
Wikipedia
Levonordefrin

Clinical Trials

Clinical Trials
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PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns
3CompletedTreatmentLocal Anaesthesia therapy1somestatusstop reasonjust information to hide
Not AvailableUnknown StatusTreatmentEdema / Pain / Trismus1somestatusstop reasonjust information to hide
Not AvailableUnknown StatusTreatmentSuccess of Inferior Alveolar Nerve Block1somestatusstop reasonjust information to hide

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-MSsplash10-000f-9700000000-97a66276892b2b9a6d84
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00kb-1900000000-0d3f1b23bb948e7b2c24
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0900000000-600876d8867e1e320b6f
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-1900000000-b8d913aa0fd0d23c339a
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00dr-0900000000-a615208a196b01db6ced
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-05fs-3900000000-07fbd2d50ac996fbf41d
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-8900000000-e510e84e6f087115f839
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-145.4942228
predicted
DarkChem Lite v0.1.0
[M-H]-148.43163
predicted
DeepCCS 1.0 (2019)
[M+H]+146.5656228
predicted
DarkChem Lite v0.1.0
[M+H]+150.8272
predicted
DeepCCS 1.0 (2019)
[M+Na]+145.8184228
predicted
DarkChem Lite v0.1.0
[M+Na]+156.73972
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein group
Organism
Humans
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. [Article]

Drug created at May 16, 2010 01:00 / Updated at June 12, 2020 16:52