Back سودوإفيدرين Arabic Psevdoefedrin Azerbaijani سودوافدرین AZB সিউডোফেড্রিন Bengali/Bangla Pseudoefedrina Catalan Pseudoefedrin Czech Ffugeffedrin Welsh Pseudoephedrin German Pseudoefedrina Spanish سودوافدرین Persian

Pseudoephedrine

"Sudafed" redirects here. For Sudafed PE, see Phenylephrine.
"Contac" redirects here. Not to be confused with Contact.

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 agents; Sympathomimetics; Nasal decongestants; Psychostimulants
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 psychostimulant,[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 dryness of the mouth among other effects.[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 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.
  30. ^ Cite error: The named reference Drugs@FDA was invoked but never defined (see the help page).
  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.
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