Corbadrine

Corbadrine
Clinical data
Trade namesNeo-Cobefrine
Other namesLevonordefrin; α-Methylnorepinephrine; (–)-3,4-Dihydroxynorephedrine; 3,4,β-Trihydroxy-α-methylphenethylamine; 3,4,β-Trihydroxyamphetamine
ATC code
  • None
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
  • 4-[(1R,2S)-2-amino-1-hydroxypropyl]benzene-1,2-diol
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.113.606 Edit this at Wikidata
Chemical and physical data
FormulaC9H13NO3
Molar mass183.207 g·mol−1
3D model (JSmol)
  • Oc1ccc(cc1O)[C@@H](O)[C@@H](N)C
  • 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 checkY
  • Key:GEFQWZLICWMTKF-CDUCUWFYSA-N checkY
  (verify)

Corbadrine, sold under the brand name Neo-Cobefrine and also known as levonordefrin and α-methylnorepinephrine, is a catecholamine sympathomimetic used as a topical nasal decongestant and vasoconstrictor in dentistry in the United States. It is usually used in a pre-mixed solution with local anesthetics, such as mepivacaine.

The drug acts as a non-selective agonist of the α1-, α2-, and β-adrenergic receptors. It is said to have preferential activity at the α2-adrenergic receptor.

Corbadrine is also a metabolite of the antihypertensive drug methyldopa and plays a role in its pharmacology and effects.

Pharmacology

Pharmacokinetics

Corbadrine is metabolized primarily by catechol O-methyltransferase (COMT).

Chemistry

Corbadrine, also known as 3,4,β-trihydroxy-α-methylphenethylamine or as 3,4,β-trihydroxyamphetamine, as well as α-methylnorepinephrine or (–)-3,4-dihydroxynorephedrine, is a substituted phenethylamine and amphetamine derivative.

Analogues of corbadrine include α-methyldopamine, dioxifedrine (3,4-dihydroxyephedrine; α-methylepinephrine), dioxethedrin (3,4-dihydroxy-N-ethylnorephedrine; α-methyl-N-ethylnorepinephrine), and hydroxyamphetamine (4-hydroxyamphetamine; α-methyltyramine).

Society and culture

Names

Corbadrine is the generic name of the drug and its INNTooltip International Nonproprietary Name. It is also known as levonordefrin, which is its USANTooltip United States Adopted Name. Synonyms of corbadrine include α-methylnorepinephrine and (–)-3,4-dihydroxynorephedrine. The drug has been sold under the brand name Neo-Cobefrine.

References

  1. 1 2 3 4 Elks, J. (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 55. ISBN 978-1-4757-2085-3. Retrieved 30 August 2024.
  2. 1 2 3 Morton I, Morton IK, Hall JM (31 October 1999). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 164–. ISBN 978-0-7514-0499-9.
  3. 1 2 3 4 5 Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 275–. ISBN 978-3-88763-075-1.
  4. ↑ "DailyMed — Search results for levonordefrin". DailyMed. Retrieved 20 February 2016.
  5. 1 2 Logothetis, D.D. (2016). Local Anesthesia for the Dental Hygienist. Elsevier Health Sciences. p. 46. ISBN 978-0-323-43050-0. Retrieved 30 August 2024.
  6. ↑ Abraham, Donald J. (15 January 2003). Burger's Medicinal Chemistry and Drug Discovery. Wiley. doi:10.1002/0471266949.bmc093. ISBN 978-0-471-26694-5.
  7. 1 2 3 Naftalin LW, Yagiela JA (October 2002). "Vasoconstrictors: indications and precautions". Dent Clin North Am. 46 (4): 733–746, ix. doi:10.1016/s0011-8532(02)00021-6. PMID 12436828.
  8. ↑ Sjoerdsma A, Vendsalu A, Engelman K (October 1963). "Studies on the Metabolism and Mechanism of Action of Methyldopa". Circulation. 28 (4): 492–502. doi:10.1161/01.CIR.28.4.492. PMID 14068757.
  9. ↑ "Levonordefrin". PubChem. Retrieved 30 August 2024.