Norfenefrine

Norfenefrine
Ball-and-stick model of (R)-Norfenefrine
Clinical data
Other namesNorfenephrine; Norphenephrine; Norphenylephrine; meta-Norsynephrine; meta-Octopamine; 3-Octopamine; Adrianol; 3,β-Dihydroxyphenethylamine; 3,β-Dihydroxy-β-phenylethylamine
AHFS/Drugs.comInternational Drug Names
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Metabolismm-Hydroxymandelic acid[1][2]
Identifiers
  • 3-(2-Amino-1-hydroxyethyl)phenol
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.007.844 Edit this at Wikidata
Chemical and physical data
FormulaC8H11NO2
Molar mass153.181 g·mol−1
3D model (JSmol)
  • OC(c1cc(O)ccc1)CN
  • InChI=1S/C8H11NO2/c9-5-8(11)6-2-1-3-7(10)4-6/h1-4,8,10-11H,5,9H2 checkY
  • Key:LRCXRAABFLIVAI-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Norfenefrine, also known as meta-octopamine or norphenylephrine and sold under the brand name Novadral among others, is a sympathomimetic medication which is used in the treatment of hypotension (low blood pressure).[3][4][5][6] Along with its structural isomer p-octopamine and the tyramines, norfenefrine is a naturally occurring endogenous trace amine and plays a role as a minor neurotransmitter in the brain.[7]

Medical uses

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Norfenefrine is used in the treatment of hypotension (low blood pressure).[3] It is said to be similarly effective or less effective than midodrine.[8][9][10]

Pharmacology

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Pharmacodynamics

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Norfenefrine is described as an α-adrenergic receptor agonist and sympathomimetic agent.[4][6] It is said to act predominantly as an α1-adrenergic receptor agonist.[3]

Chemistry

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Norfenefrine, also known as 3,β-dihydroxyphenethylamine, is a substituted phenethylamine derivative.[4][6] It is an analogue of norepinephrine (3,4,β-trihydroxyphenethylamine), of meta-tyramine (3-hydroxyphenethylamine), of phenylephrine ((R)-β,3-dihydroxy-N-methylphenethylamine), of etilefrine (3,β-dihydroxy-N-ethylphenethylamine), and of metaterol (3,β-dihydroxy-N-isopropylphenethylamine), as well as of metaraminol ((1R,2S)-3,β-dihydroxy-α-methylphenethylamine).[4]

Norfenefrine is used medically as the hydrochloride salt.[4][6]

The predicted log P of norfenefrine is -0.28 to -0.95.[11][12][13]

Society and culture

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Names

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Norfenefrine is the generic name of the drug and its INNTooltip International Nonproprietary Name.[4][6] Synonyms of norfenefrine include hydroxyphenylethanolamine, nor-phenylephrine, and m-norsynephrine, among others.[4][6] Brand names of norfenefrine include Novadral, A.S. COR, Coritat, Energona, Hypolind, Norfenefrin Ziethen, and Norfenefrin-Ratiopharm, among others.[6]

Availability

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Norfenefrine is marketed in Europe, Japan, and Mexico.[6]

References

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  1. ^ Hengstmann JH, Konen W, Konen C, Eichelbaum M, Dengler HJ (1974). "The physiological disposition of p-octopamine in man". Naunyn-Schmiedeberg's Archives of Pharmacology. 283 (1): 93–106. doi:10.1007/bf00500148. PMID 4277715. S2CID 35523412.
  2. ^ D'Andrea G, Nordera G, Pizzolato G, Bolner A, Colavito D, Flaibani R, Leon A (January 2010). "Trace amine metabolism in Parkinson's disease: low circulating levels of octopamine in early disease stages". Neuroscience Letters. 469 (3): 348–351. doi:10.1016/j.neulet.2009.12.025. PMID 20026245. S2CID 12797090.
  3. ^ a b c Docherty JR (June 2008). "Pharmacology of stimulants prohibited by the World Anti-Doping Agency (WADA)". Br J Pharmacol. 154 (3): 606–622. doi:10.1038/bjp.2008.124. PMC 2439527. PMID 18500382.
  4. ^ a b c d e f g Elks, J. (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 61. ISBN 978-1-4757-2085-3. Retrieved 22 July 2024.
  5. ^ Macdonald F (1997). Dictionary of Pharmacological Agents. CRC Press. p. 104. ISBN 978-0-412-46630-4. Retrieved 24 April 2012.
  6. ^ a b c d e f g h Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. p. 750. ISBN 978-3-88763-075-1. Retrieved 24 April 2012.
  7. ^ Danielson TJ, Boulton AA, Robertson HA (December 1977). "m-Octopamine, p-octopamine and phenylethanolamine in rat brain: a sensitive, specific assay and the effects of some drugs". Journal of Neurochemistry. 29 (6): 1131–1135. doi:10.1111/j.1471-4159.1977.tb06519.x. PMID 340613. S2CID 26137006.
  8. ^ McTavish D, Goa KL (November 1989). "Midodrine. A review of its pharmacological properties and therapeutic use in orthostatic hypotension and secondary hypotensive disorders". Drugs. 38 (5): 757–777. doi:10.2165/00003495-198938050-00004. PMID 2480881.
  9. ^ McClellan KJ, Wiseman LR, Wilde MI (January 1998). "Midodrine. A review of its therapeutic use in the management of orthostatic hypotension". Drugs Aging. 12 (1): 76–86. doi:10.2165/00002512-199812010-00007. PMID 9467688.
  10. ^ Maule S, Papotti G, Naso D, Magnino C, Testa E, Veglio F (March 2007). "Orthostatic hypotension: evaluation and treatment". Cardiovasc Hematol Disord Drug Targets. 7 (1): 63–70. doi:10.2174/187152907780059029. PMID 17346129.
  11. ^ "Norfenefrine". PubChem. Retrieved 31 August 2024.
  12. ^ "Norfenefrine: Uses, Interactions, Mechanism of Action". DrugBank Online. 23 June 2017. Retrieved 31 August 2024.
  13. ^ "norfenefrine". ChemSpider. 31 August 2024. Retrieved 31 August 2024.
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