Levonordefrin

Synonyms :
alpha-Methylnoradrenaline, alpha-methylnorepinephrine, Corbadrine, Neo-cobefrin, α-methylnorepinephrine

Status : approved

Description

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

Used

Used as a topical nasal decongestant and vasoconstrictor in dentistry.

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

Dosage

Form Route Strength
Injection, solution subcutaneous 20; .05 mg/mL; mg/mL
Solution block/infiltration 20 mg

Pharmacodynamics

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.

Chemical Classification

This 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.

Catecholamines and derivatives

Organic compounds

Benzenoids

Benzene and substituted derivatives

Phenols and derivatives

Chemical Name

alpha-Methylnoradrenaline

Brands

name Dosage form Country
2% Polocaine Dental With Levonordefrin 1:20,000 solution Canada
Carbocaine 2% With Neo-cobefrin solution Canada
Carbocaine 2% With Neo-cobefrin solution Canada
Carbocaine With Neo-cobefrin injection, solution US
Isocaine Hcl Inj 2% solution Canada
Mepivacaine Hydrochloride and Levonordefrin injection, solution US
Mepivacaine with levonordefrin injection, solution US
Mepivacaine With Levonordefrin injection, solution US
Scandonest 2% With Levonordefrin solution Canada
Scandonest L injection, solution US

Drug Drug Interactions

  •  Acebutolol  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Amphetamine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Atomoxetine  : May enhance the hypertensive effect of Sympathomimetics. Atomoxetine may enhance the tachycardic effect of Sympathomimetics.
  •  Benzphetamine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Benzylpenicilloyl Polylysine  : Alpha-/Beta-Agonists may diminish the diagnostic effect of Benzylpenicilloyl Polylysine.
  •  Chlorphentermine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Clenbuterol  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Dobutamine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Dopamine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Epinephrine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Fenoterol  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Formoterol  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Hyaluronidase  : May enhance the vasoconstricting effect of Alpha-/Beta-Agonists.
  •  Isocarboxazid  : MAO Inhibitors may enhance the hypertensive effect of Levonordefrin.
  •  Isoprenaline  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Labetalol  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Linezolid  : MAO Inhibitors may enhance the hypertensive effect of Levonordefrin.
  •  Mephentermine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Metaraminol  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Methamphetamine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Methoxamine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Midodrine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Moclobemide  : MAO Inhibitors may enhance the hypertensive effect of Levonordefrin.
  •  Naphazoline  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Norepinephrine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Orciprenaline  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Oxymetazoline  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Phenelzine  : MAO Inhibitors may enhance the hypertensive effect of Levonordefrin.
  •  Phenmetrazine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Phentermine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Phenylephrine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Phenylpropanolamine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Procarbazine  : MAO Inhibitors may enhance the hypertensive effect of Levonordefrin.
  •  Rasagiline  : MAO Inhibitors may enhance the hypertensive effect of Levonordefrin.
  •  Ritodrine  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Salmeterol  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Selegiline  : MAO Inhibitors may enhance the hypertensive effect of Levonordefrin.
  •  Spironolactone  : May diminish the vasoconstricting effect of Alpha-/Beta-Agonists.
  •  Tedizolid Phosphate  : MAO Inhibitors may enhance the hypertensive effect of Levonordefrin.
  •  Terbutaline  : May enhance the adverse/toxic effect of other Sympathomimetics.
  •  Tranylcypromine  : MAO Inhibitors may enhance the hypertensive effect of Levonordefrin.

Calculated Property

kind Value Source
logP -0.77 ALOGPS
logS -1.1 ALOGPS
Water Solubility 1.46e+01 g/l ALOGPS
logP -0.39 ChemAxon
IUPAC Name 4-[(1R,2S)-2-amino-1-hydroxypropyl]benzene-1,2-diol ChemAxon
Traditional IUPAC Name levonordefrin ChemAxon
Molecular Weight 183.2044 ChemAxon
Monoisotopic Weight 183.089543287 ChemAxon
SMILES C[C@H](N)[C@H](O)C1=CC(O)=C(O)C=C1 ChemAxon
Molecular Formula C9H13NO3 ChemAxon
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 ChemAxon
InChIKey InChIKey=GEFQWZLICWMTKF-CDUCUWFYSA-N ChemAxon
Polar Surface Area (PSA) 86.71 ChemAxon
Refractivity 48.87 ChemAxon
Polarizability 18.81 ChemAxon
Rotatable Bond Count 2 ChemAxon
H Bond Acceptor Count 4 ChemAxon
H Bond Donor Count 4 ChemAxon
pKa (strongest acidic) 9.63 ChemAxon
pKa (strongest basic) 8.96 ChemAxon
Physiological Charge 1 ChemAxon
Number of Rings 1 ChemAxon
Bioavailability 1 ChemAxon
Rule of Five 1 ChemAxon
Ghose Filter 1 ChemAxon
MDDR-Like Rule 0 ChemAxon

Target within organism

  • Alpha-1A adrenergic receptor : in Human
  • Sodium-dependent noradrenaline transporter : in Human