U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C9H13NO3.ClH
Molecular Weight 219.665
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEVONORDEFRIN HYDROCHLORIDE

SMILES

Cl.C[C@H](N)[C@H](O)C1=CC=C(O)C(O)=C1

InChI

InChIKey=YRJLEOWRVNBAOI-WFZUHFMFSA-N
InChI=1S/C9H13NO3.ClH/c1-5(10)9(13)6-2-3-7(11)8(12)4-6;/h2-5,9,11-13H,10H2,1H3;1H/t5-,9-;/m0./s1

HIDE SMILES / InChI
Levonordefrin acts as a topical nasal decongestant and vasoconstrictor, most often used in dentistry. It is administered in a pre-mixed solution with local anesthetics, such as mepivacaine or procaine.

CNS Activity

Curator's Comment: Levonordefrin doesn't cross BBB; all side-effects are periferial. It is rapidly metabolized by catechol-o-methyltransferase, its elimination half-life is 1-3 minute (https://www.ncbi.nlm.nih.gov/pubmed/22822998)

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
205.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Secondary
CARBOCAINE W/ NEO-COBEFRIN

Approved Use

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.

Launch Date

1960
PubMed

PubMed

TitleDatePubMed
Selectivity of agonists for cloned alpha 1-adrenergic receptor subtypes.
1994 Nov
Parkinson disease: systemic and orofacial manifestations, medical and dental management.
2009 Jun
Beta-adrenergic blocking agents and dental vasoconstrictors.
2010 Oct
Patents

Patents

Sample Use Guides

Mepivacaine and levonordefrin are injected locally. The dose varies and depends upon the area to be anesthetized, the vascularity of the tissues, individual tolerance and the technique of anesthesia. For infiltration and block injections in the upper or lower jaw, the average dose of 1 cartridge, containing 1.7 mL of mepivacaine HCl 2% with levonordefrin 1:20,000 will usually suffice. 5.3 cartridges (180 mg of the 2% solution) are usually adequate to effect anesthesia of the entire oral cavity.
Route of Administration: Intramuscular
In Vitro Use Guide
Alpha-2-adrenergic receptors were labeled using 2.0 nM [3H]rauwolscine (80.5 Ci/mL) in 50 nM Tris buffer, pH 7.4, containing 10 mM EDTA. The final protein concentrations was approximately 500 ug/mL for the a2-assay. Phentolamine (10 uM) was used to determine the fraction of nonspecific binding. Samples were incubated at 30 °C for 30 min and then rapidly filtered (Whatman GF/C glass fiber filters presoaked in 10 uM phentolamine) and washed with 20 mL of ice-cold assay buffer on a Brandel cell harvester. Individual filters were inserted into scintillation vials, shaken, and allowed to equilibrate for 5 h with 5 mL of aqueous scintillation fluid before radioactivity counting on a Beckman LS 6800 liquid scintillation counter. The IC50 was determined by plotting the percentage specific binding at each sigmoidal Emax model. The equilibrium dissociation constant of each compound (Ki) was then calculated using the standard equation. Levonordefrin inhibits binding of radioligand with alpha-2 adrenergic receptors with Ki of 205 nM.
Name Type Language
LEVONORDEFRIN HYDROCHLORIDE
Common Name English
(-)-2-AMINO-1-(3,4-DIHYDROXYPHENYL)PROPAN-1-OL HYDROCHLORIDE
Systematic Name English
CORBADRINE HYDROCHLORIDE
WHO-DD  
Common Name English
LEVONORDEFRIN HCL
Common Name English
Corbadrine hydrochloride [WHO-DD]
Common Name English
1,2-BENZENEDIOL, 4-((1R,2S)-2-AMINO-1-HYDROXYPROPYL)-, HYDROCHLORIDE (1:1)
Systematic Name English
L-NORDEFRIN HYDROCHLORIDE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29747
Created by admin on Fri Dec 15 16:50:49 GMT 2023 , Edited by admin on Fri Dec 15 16:50:49 GMT 2023
Code System Code Type Description
PUBCHEM
20055314
Created by admin on Fri Dec 15 16:50:49 GMT 2023 , Edited by admin on Fri Dec 15 16:50:49 GMT 2023
PRIMARY
FDA UNII
U63S13UAOR
Created by admin on Fri Dec 15 16:50:49 GMT 2023 , Edited by admin on Fri Dec 15 16:50:49 GMT 2023
PRIMARY
SMS_ID
100000087981
Created by admin on Fri Dec 15 16:50:49 GMT 2023 , Edited by admin on Fri Dec 15 16:50:49 GMT 2023
PRIMARY
ECHA (EC/EINECS)
233-853-4
Created by admin on Fri Dec 15 16:50:49 GMT 2023 , Edited by admin on Fri Dec 15 16:50:49 GMT 2023
PRIMARY
EVMPD
SUB01453MIG
Created by admin on Fri Dec 15 16:50:49 GMT 2023 , Edited by admin on Fri Dec 15 16:50:49 GMT 2023
PRIMARY
EPA CompTox
DTXSID00146134
Created by admin on Fri Dec 15 16:50:49 GMT 2023 , Edited by admin on Fri Dec 15 16:50:49 GMT 2023
PRIMARY
NCI_THESAURUS
C99566
Created by admin on Fri Dec 15 16:50:49 GMT 2023 , Edited by admin on Fri Dec 15 16:50:49 GMT 2023
PRIMARY
CAS
10390-18-8
Created by admin on Fri Dec 15 16:50:49 GMT 2023 , Edited by admin on Fri Dec 15 16:50:49 GMT 2023
PRIMARY