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Details

Stereochemistry ABSOLUTE
Molecular Formula C9H13NO3
Molecular Weight 183.2048
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEVONORDEFRIN

SMILES

C[C@@]([H])([C@@]([H])(c1ccc(c(c1)O)O)O)N

InChI

InChIKey=GEFQWZLICWMTKF-CDUCUWFYSA-N
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

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

-3.151872E11
PubMed

PubMed

TitleDatePubMed
Selectivity of agonists for cloned alpha 1-adrenergic receptor subtypes.
1994 Nov
Serum mepivacaine concentrations after intraoral injection in young children.
2003 Oct
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
ORANGE BOOK   USP   USP-RS   VANDF  
Common Name English
NEO-COBEFRIN
Brand Name English
L-.ALPHA.-METHYLNORADRENALINE
Common Name English
NORDEFRIN (-)-FORM [MI]
Common Name English
LEVONORDEFRIN [USP-RS]
Common Name English
1,2-BENZENEDIOL, 4-((1R,2S)-2-AMINO-1-HYDROXYPROPYL)-
Systematic Name English
BA-2818
Code English
NORDEFRIN, L-
Common Name English
(-)-.ALPHA.-(1-AMINOETHYL)-3,4-DIHYDROXYBENZYL ALCOHOL
Systematic Name English
1,2-BENZENEDIOL, 4-(2-AMINO-1-HYDROXYPROPYL)-, (R-(R*,S*))
Common Name English
L-NORDEFRIN
Common Name English
CORBADRINE [INN]
Common Name English
(1R,2S)-(-)-3,4-DIHYDROXYNOREPHEDRINE
Common Name English
BA 2818
Code English
4-((1R,2S)-2-AMINO-1-HYDROXYPROPYL)BENZENE-1,2-DIOL
Systematic Name English
BENZYL ALCOHOL, .ALPHA.-(1-AMINOETHYL)-3,4-DIHYDROXY-, ERYTHRO-(-)-
Common Name English
LEVONORDEFRIN [VANDF]
Common Name English
(-)-COBEFRIN
Common Name English
CORBADRINE [MART.]
Common Name English
L-NOREPHEDRINE, 3,4-DIHYDROXY-
Common Name English
CORBADRINE [WHO-DD]
Common Name English
CORBADRINE
INN   MART.   WHO-DD  
INN  
Official Name English
NSC-757084
Code English
NORDEFRIN (-)-FORM
MI  
Common Name English
LEVONORDEFRIN [USP]
Common Name English
LEVONORDEFRIN [ORANGE BOOK]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29747
Created by admin on Fri Jun 25 22:10:36 UTC 2021 , Edited by admin on Fri Jun 25 22:10:36 UTC 2021
Code System Code Type Description
PUBCHEM
164739
Created by admin on Fri Jun 25 22:10:36 UTC 2021 , Edited by admin on Fri Jun 25 22:10:36 UTC 2021
PRIMARY
EPA CompTox
829-74-3
Created by admin on Fri Jun 25 22:10:36 UTC 2021 , Edited by admin on Fri Jun 25 22:10:36 UTC 2021
PRIMARY
IUPHAR
508
Created by admin on Fri Jun 25 22:10:36 UTC 2021 , Edited by admin on Fri Jun 25 22:10:36 UTC 2021
PRIMARY
DRUG BANK
DB06707
Created by admin on Fri Jun 25 22:10:36 UTC 2021 , Edited by admin on Fri Jun 25 22:10:36 UTC 2021
PRIMARY
DRUG CENTRAL
4482
Created by admin on Fri Jun 25 22:10:36 UTC 2021 , Edited by admin on Fri Jun 25 22:10:36 UTC 2021
PRIMARY
MERCK INDEX
M8051
Created by admin on Fri Jun 25 22:10:36 UTC 2021 , Edited by admin on Fri Jun 25 22:10:36 UTC 2021
PRIMARY Merck Index
WIKIPEDIA
LEVONORDEFRIN
Created by admin on Fri Jun 25 22:10:36 UTC 2021 , Edited by admin on Fri Jun 25 22:10:36 UTC 2021
PRIMARY
INN
50
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PRIMARY
EVMPD
SUB21272
Created by admin on Fri Jun 25 22:10:36 UTC 2021 , Edited by admin on Fri Jun 25 22:10:36 UTC 2021
PRIMARY
NCI_THESAURUS
C47584
Created by admin on Fri Jun 25 22:10:36 UTC 2021 , Edited by admin on Fri Jun 25 22:10:36 UTC 2021
PRIMARY
FDA UNII
V008L6478D
Created by admin on Fri Jun 25 22:10:36 UTC 2021 , Edited by admin on Fri Jun 25 22:10:36 UTC 2021
PRIMARY
ChEMBL
CHEMBL677
Created by admin on Fri Jun 25 22:10:36 UTC 2021 , Edited by admin on Fri Jun 25 22:10:36 UTC 2021
PRIMARY
RXCUI
132889
Created by admin on Fri Jun 25 22:10:36 UTC 2021 , Edited by admin on Fri Jun 25 22:10:36 UTC 2021
PRIMARY RxNorm
USP_CATALOG
1362500
Created by admin on Fri Jun 25 22:10:36 UTC 2021 , Edited by admin on Fri Jun 25 22:10:36 UTC 2021
PRIMARY USP-RS
CAS
829-74-3
Created by admin on Fri Jun 25 22:10:36 UTC 2021 , Edited by admin on Fri Jun 25 22:10:36 UTC 2021
PRIMARY