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.[1][2][3] It is usually used in a pre-mixed solution with local anesthetics, such as mepivacaine.[4]

The drug acts as a non-selective agonist of the α1-, α2-, and β-adrenergic receptors.[5][6][7] It is said to have preferential activity at the α2-adrenergic receptor.[5][7]

Corbadrine is also a metabolite of the antihypertensive drug methyldopa and lays a role in its pharmacology and effects.[8]

Pharmacology

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Pharmacokinetics

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Corbadrine is metabolized primarily by catechol O-methyltransferase (COMT).[7]

Chemistry

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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.[1][3]

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

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Names

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Corbadrine is the generic name of the drug and its INNTooltip International Nonproprietary Name.[1][3][2] It is also known as levonordefrin, which is its USANTooltip United States Adopted Name.[1][3][2] Synonyms of corbadrine include α-methylnorepinephrine and (–)-3,4-dihydroxynorephedrine.[9] The drug has been sold under the brand name Neo-Cobefrine.[3]

References

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  1. ^ a b c d 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. ^ a b c 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. ^ a b c d e 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. ^ a b 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. ^ a b c 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.
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