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
(-)-cobefrin
alpha-Methylnoradrenaline
Corbadrine
L-alpha-methylnoradrenaline
L-Nordefrin
Neo-cobefrin
External IDs BA 2818 / BA-2818
Product Ingredients 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 Pharmaceutical
Carbocaine 2% With Neo-cobefrinCarestream Health Inc.
Carbocaine With Neo-cobefrinCaresteam Health, Inc.
Isocaine HCl Inj 2%Novocol Inc.
Mepivacaine Hydrochloride and LevonordefrinDarby Dental Supply Llc
Mepivacaine Hydrochloride With LevonordefrinHenry Schein
Mepivacaine With LevonordefrinPatterson Dental
Scandonest 2% With LevonordefrinNovocol Inc.
Scandonest LNovocol Inc.
Categories
UNIIV008L6478D
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[[email protected]](N)[[email protected]](O)C1=CC(O)=C(O)C=C1
Pharmacology
Indication

Used as a topical nasal decongestant and vasoconstrictor in dentistry.

Structured Indications Not Available
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.

TargetKindPharmacological actionActionsOrganismUniProt ID
Alpha-2 adrenergic receptorsProtein groupyes
agonist
Humannot applicabledetails
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 organisms
  • Humans and other mammals
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions
DrugInteractionDrug group
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline7,8-DICHLORO-1,2,3,4-TETRAHYDROISOQUINOLINE may increase the hypertensive activities of Levonordefrin.Experimental
BenmoxinBenmoxin may increase the hypertensive activities of Levonordefrin.Withdrawn
CaroxazoneCaroxazone may increase the hypertensive activities of Levonordefrin.Withdrawn
FurazolidoneFurazolidone may increase the hypertensive activities of Levonordefrin.Approved, Vet Approved
HydracarbazineHydracarbazine may increase the hypertensive activities of Levonordefrin.Experimental
IproclozideIproclozide may increase the hypertensive activities of Levonordefrin.Withdrawn
IproniazidIproniazid may increase the hypertensive activities of Levonordefrin.Withdrawn
IsocarboxazidIsocarboxazid may increase the hypertensive activities of Levonordefrin.Approved
MebanazineMebanazine may increase the hypertensive activities of Levonordefrin.Withdrawn
Methylene blueMethylene blue may increase the hypertensive activities of Levonordefrin.Investigational
MinaprineMinaprine may increase the hypertensive activities of Levonordefrin.Approved
MoclobemideMoclobemide may increase the hypertensive activities of Levonordefrin.Approved
NialamideNialamide may increase the hypertensive activities of Levonordefrin.Withdrawn
OctamoxinOctamoxin may increase the hypertensive activities of Levonordefrin.Withdrawn
PargylinePargyline may increase the hypertensive activities of Levonordefrin.Approved
PhenelzinePhenelzine may increase the hypertensive activities of Levonordefrin.Approved
PheniprazinePheniprazine may increase the hypertensive activities of Levonordefrin.Withdrawn
PhenoxypropazinePhenoxypropazine may increase the hypertensive activities of Levonordefrin.Withdrawn
PirlindolePirlindole may increase the hypertensive activities of Levonordefrin.Approved
PivhydrazinePivhydrazine may increase the hypertensive activities of Levonordefrin.Withdrawn
RasagilineRasagiline may increase the hypertensive activities of Levonordefrin.Approved
SafrazineSafrazine may increase the hypertensive activities of Levonordefrin.Withdrawn
SelegilineSelegiline may increase the hypertensive activities of Levonordefrin.Approved, Investigational, Vet Approved
ToloxatoneToloxatone may increase the hypertensive activities of Levonordefrin.Approved
Trans-2-PhenylcyclopropylamineTrans-2-Phenylcyclopropylamine may increase the hypertensive activities of Levonordefrin.Experimental
TranylcypromineTranylcypromine may increase the hypertensive activities of Levonordefrin.Approved
Food InteractionsNot 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
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
Injection, solutionSubcutaneous
SolutionInfiltration
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 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
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct ParentPhenylpropanes
Alternative ParentsCatechols / Aralkylamines / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Secondary alcohols / 1,2-aminoalcohols / Organopnictogen compounds / Monoalkylamines / Hydrocarbon derivatives / Aromatic alcohols
SubstituentsPhenylpropane / Catechol / 1-hydroxy-4-unsubstituted benzenoid / 1-hydroxy-2-unsubstituted benzenoid / Phenol / Aralkylamine / 1,2-aminoalcohol / Secondary alcohol / Organic nitrogen compound / Aromatic alcohol
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptorscatecholamine (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 oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol.
Components:
NameUniProt IDDetails
Alpha-2A adrenergic receptorP08913 Details
Alpha-2B adrenergic receptorP18089 Details
Alpha-2C adrenergic receptorP18825 Details
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 June 11, 2017 16:44