Pseudoephedrine

"Sudafed" redirects here. For Sudafed PE, see Phenylephrine.

Pseudoephedrine
Clinical data
Pronunciation/ˌsuːdoʊ.ɪˈfɛdrɪn, -ˈɛfɪdriːn/
Trade namesAfrinol, Sudafed, Sinutab, others
Other namesPSE; PDE; (+)-ψ-Ephedrine; ψ-Ephedrine; d-Isoephedrine; (1S,2S)-Pseudoephedrine; d-Pseudoephedrine; (+)-Pseudoephedrine; L(+)-Pseudoephedrine; Isoephedrine; (1S,2S)-α,N-Dimethyl-β-hydroxyphenethylamine; (1S,2S)-N-Methyl-β-hydroxyamphetamine
AHFS/Drugs.comMonograph
MedlinePlusa682619
License data
Pregnancy
category
  • AU: B2
Routes of
administration		By mouth[1][2]
Drug classNorepinephrine releasing agent; Nasal decongestant; Stimulant
ATC code
Legal status
Legal status
  • AU: S3 (Pharmacist only) Largely tracked nationwide via “Project STOP” to avoid purchases in large quantities.[3] Use of Project STOP is mandatory in all states and territories except Victoria and Tasmania[4][5]
  • BR: Class D1 (Drug precursors)[6]
  • CA: OTC Removed from the NDS in 2024, for both combination and single ingredient preparations, on 1 Mar & 10 Jun 2024, respectively.[7]
  • UK: P (Pharmacy medicines)
  • US: OTC
Pharmacokinetic data
Bioavailability~100%[8]
Protein binding21–29% (AGPTooltip alpha-1-acid glycoprotein, HSATooltip Human serum albumin)[9][10]
MetabolismNot extensively metabolized[11][1][2]
Metabolites• Norpseudoephedrine[1]
Onset of action30 minutes[1]
Elimination half-life5.4 hours (range 3–16 hours dependent on urine pH)[2][1][11]
Duration of action4–12 hours[1][12]
ExcretionUrine: 43–96% (unchanged)[1][11][2][8]
Identifiers
  • (1S,2S)-2-(methylamino)-1-phenylpropan-1-ol
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.001.835 Edit this at Wikidata
Chemical and physical data
FormulaC10H15NO
Molar mass165.236 g·mol−1
3D model (JSmol)
  • O[C@@H](c1ccccc1)[C@@H](NC)C
  • InChI=1S/C10H15NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,10-12H,1-2H3/t8-,10+/m0/s1 checkY
  • Key:KWGRBVOPPLSCSI-WCBMZHEXSA-N checkY
  (verify)

Pseudoephedrine, sold under the brand name Sudafed among others, is a sympathomimetic medication which is used as a decongestant to treat nasal congestion.[1][13][2] It has also been used off-label for certain other indications, like treatment of low blood pressure.[14][15][16] At higher doses, it may produce various additional effects including stimulant,[17][1] appetite suppressant,[18] and performance-enhancing effects.[19][20] In relation to this, non-medical use of pseudoephedrine has been encountered.[17][1][18][19][20] The medication is taken by mouth.[1][2]

Side effects of pseudoephedrine include insomnia, increased heart rate, increased blood pressure, and dry mouth, among others.[21][2][1][22] Rarely, pseudoephedrine has been associated with serious cardiovascular complications like heart attack and hemorrhagic stroke.[18][23][15] Some people may be more sensitive to its cardiovascular effects.[22][1] Pseudoephedrine acts as a norepinephrine releasing agent, thereby indirectly activating adrenergic receptors.[24][2][25][1] As such, it is an indirectly acting sympathomimetic.[24][2][25][1] Pseudoephedrine significantly crosses into the brain, but has some peripheral selectivity due to its hydrophilicity.[25][26] Chemically, pseudoephedrine is a substituted amphetamine and is closely related to ephedrine, phenylpropanolamine, and amphetamine.[1][13][2] It is the (1S,2S)-enantiomer of β-hydroxy-N-methylamphetamine.[27]

Along with ephedrine, pseudoephedrine occurs naturally in ephedra, which has been used for thousands of years in traditional Chinese medicine.[13][28] It was first isolated from ephedra in 1889.[28][13][29] Subsequent to its synthesis in the 1920s, pseudoephedrine was introduced for medical use as a decongestant.[13] Pseudoephedrine is widely available over-the-counter (OTC) in both single-drug and combination preparations.[30][22][13][2] Availability of pseudoephedrine has been restricted starting in 2005 as it can be used to synthesize methamphetamine.[13][2] Phenylephrine has replaced pseudoephedrine in many over-the-counter oral decongestant products.[2] However, oral phenylephrine appears to be ineffective as a decongestant.[31][32]

  1. ^ a b c d e f g h i j k l m n o p Głowacka K, Wiela-Hojeńska A (May 2021). "Pseudoephedrine—Benefits and Risks". Int J Mol Sci. 22 (10): 5146. doi:10.3390/ijms22105146. PMC 8152226. PMID 34067981.
  2. ^ a b c d e f g h i j k l m Eccles R (January 2007). "Substitution of phenylephrine for pseudoephedrine as a nasal decongeststant. An illogical way to control methamphetamine abuse". British Journal of Clinical Pharmacology. 63 (1): 10–14. doi:10.1111/j.1365-2125.2006.02833.x. PMC 2000711. PMID 17116124.
  3. ^ "Project STOP A Pharmacy Guild Initiative, May 2016" (PDF). The Pharmacy Guild of Australia. 18 May 2016.
  4. ^ "Trends & issues in crime and criminal justice No. 509, March 2016" (PDF). Australian Institute of Criminology. 7 March 2016. Retrieved 11 July 2024.
  5. ^ "Project STOP mandatory for pharmacists in NSW from next month". Pulse.IT. 24 February 2016. Retrieved 11 July 2024.
  6. ^ Anvisa (31 March 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). Archived from the original on 3 August 2023. Retrieved 15 August 2023.
  7. ^ "Background on Update to NAPRA NHP Policy". napra.ca. 10 June 2024. Retrieved 11 July 2024.
  8. ^ a b Brunton LL, Lazo JS, Parker K, eds. (2006). Goodman & Gilman's The Pharmacological Basis of Therapeutics (11th ed.). New York: McGraw-Hill Medical Publishing Division. ISBN 0-07-142280-3.
  9. ^ Volpp M, Holzgrabe U (January 2019). "Determination of plasma protein binding for sympathomimetic drugs by means of ultrafiltration". Eur J Pharm Sci. 127: 175–184. doi:10.1016/j.ejps.2018.10.027. PMID 30391401.
  10. ^ Schmidt S (2023). Lang-etablierte Arzneistoffe genauer unter die Lupe genommen: Enantioselektive Proteinbindung und Stabilitätsstudien [A closer look at long-established drugs: enantioselective protein binding and stability studies] (Thesis) (in German). Universität Würzburg. doi:10.25972/opus-34594.
  11. ^ a b c Cite error: The named reference ChuaBenrimojTriggs1989 was invoked but never defined (see the help page).
  12. ^ Aaron CK (August 1990). "Sympathomimetics". Emerg Med Clin North Am. 8 (3): 513–526. doi:10.1016/S0733-8627(20)30256-X. PMID 2201518.
  13. ^ a b c d e f g Laccourreye O, Werner A, Giroud JP, Couloigner V, Bonfils P, Bondon-Guitton E (February 2015). "Benefits, limits and danger of ephedrine and pseudoephedrine as nasal decongestants". Eur Ann Otorhinolaryngol Head Neck Dis. 132 (1): 31–34. doi:10.1016/j.anorl.2014.11.001. PMID 25532441.
  14. ^ Cite error: The named reference FreemanKaufmann2007 was invoked but never defined (see the help page).
  15. ^ a b Cite error: The named reference VanBerkelFuller2015 was invoked but never defined (see the help page).
  16. ^ Cite error: The named reference Fedorowski2019 was invoked but never defined (see the help page).
  17. ^ a b Cite error: The named reference SchifanoChiappiniMiuli2021 was invoked but never defined (see the help page).
  18. ^ a b c Cite error: The named reference MunafòFraraPerico2021 was invoked but never defined (see the help page).
  19. ^ a b Cite error: The named reference TrinhKimRitsma2015 was invoked but never defined (see the help page).
  20. ^ a b Cite error: The named reference GheorghievHosseiniMoran2018 was invoked but never defined (see the help page).
  21. ^ Taverner D, Latte J (January 2007). Latte GJ (ed.). "Nasal decongestants for the common cold". Cochrane Database Syst Rev (1): CD001953. doi:10.1002/14651858.CD001953.pub3. PMID 17253470.
  22. ^ a b c Cite error: The named reference SalernoJackson2005 was invoked but never defined (see the help page).
  23. ^ Cite error: The named reference CantuArauzMurillo-Bonilla2003 was invoked but never defined (see the help page).
  24. ^ a b Cite error: The named reference RothmanVuPartilla2003 was invoked but never defined (see the help page).
  25. ^ a b c Cite error: The named reference ODonnell1995 was invoked but never defined (see the help page).
  26. ^ Cite error: The named reference BouchardWeberGeiger2002 was invoked but never defined (see the help page).
  27. ^ Cite error: The named reference PubChem was invoked but never defined (see the help page).
  28. ^ a b Abourashed EA, El-Alfy AT, Khan IA, Walker L (August 2003). "Ephedra in perspective--a current review". Phytother Res. 17 (7): 703–712. doi:10.1002/ptr.1337. PMID 12916063.
  29. ^ Chen KK, Kao CH (1926). "Ephedrine and Pseudoephedrine, their Isolation, Constitution, Isomerism, Properties, Derivatives and Synthesis. (with a Bibliography) **The expense of this work has been defrayed by a part of a grant from the Committee on Therapeutic Research, Council on Pharmacy and Chemistry, American Medical Association". The Journal of the American Pharmaceutical Association (1912). 15 (8): 625–639. doi:10.1002/jps.3080150804.
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  31. ^ Hatton RC, Hendeles L (March 2022). "Why Is Oral Phenylephrine on the Market After Compelling Evidence of Its Ineffectiveness as a Decongestant?". Ann Pharmacother. 56 (11): 1275–1278. doi:10.1177/10600280221081526. PMID 35337187. S2CID 247712448.
  32. ^ Hendeles L, Hatton RC (July 2006). "Oral phenylephrine: an ineffective replacement for pseudoephedrine?". J Allergy Clin Immunol. 118 (1): 279–280. doi:10.1016/j.jaci.2006.03.002. PMID 16815167.