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Ephedrine
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-Ephedrine_molecule_from_xtal_ball.png) (−)-(1R,2S)-ephedrine chemical structure (top) and ball-and-stick model (bottom) | |
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| Pronunciation | /ɪˈfɛdrɪn/ ⓘ or /ˈɛfɪdriːn/ |
| Trade names | Akovaz, Corphedra, Emerphed, others |
| Other names | (−)-Ephedrine; (1R,2S)-Ephedrine; (1R,2S)-β-Hydroxy-N-methylamphetamine; (1R,2S)-β-Hydroxy-N-methyl-α-methyl-β-phenethylamine |
| AHFS/Drugs.com | Ephedrine: Monograph HCl: Monograph Sulfate: Monograph |
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| Routes of administration | By mouth, intravenous (IV), intramuscular (IM), subcutaneous (SC) |
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| Pharmacokinetic data | |
| Bioavailability | 88%[6] |
| Protein binding | ~24–29% (5–10% to albumin)[7][8][9] |
| Metabolism | Largely unmetabolized[6][10] |
| Metabolites | • Norephedrine[6][10] |
| Onset of action | Oral: 15–60 minutes[11] IM: 10–20 minutes[11] IV: Rapid[11] |
| Elimination half-life | 6 hours[6] |
| Duration of action | Oral: 2–4 hours IV/IM: 60 minutes |
| Excretion | Mainly urine (60% unchanged)[6] |
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| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.005.528 |
| Chemical and physical data | |
| Formula | C10H15NO |
| Molar mass | 165.236 g·mol−1 |
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Ephedrine is a central nervous system (CNS) stimulant and sympathomimetic agent that is often used to prevent low blood pressure during anesthesia.[11] It has also been used for asthma, narcolepsy, and obesity but is not the preferred treatment.[11] It is of unclear benefit in nasal congestion.[11] It can be taken by mouth or by injection into a muscle, vein, or just under the skin.[11] Onset with intravenous use is fast, while injection into a muscle can take 20 minutes, and by mouth can take an hour for effect.[11] When given by injection, it lasts about an hour, and when taken by mouth, it can last up to four hours.[11]
Common side effects include trouble sleeping, anxiety, headache, hallucinations, high blood pressure, fast heart rate, loss of appetite, and urinary retention.[11] Serious side effects include stroke and heart attack.[11] While likely safe in pregnancy, its use in this population is poorly studied.[12][13] Use during breastfeeding is not recommended.[13] Ephedrine works by inducing the release of norepinephrine and hence indirectly activating the α- and β-adrenergic receptors.[11] Chemically, ephedrine is a substituted amphetamine and is the (1R,2S)-enantiomer of β-hydroxy-N-methylamphetamine.[14]
Ephedrine was first isolated in 1885 and came into commercial use in 1926.[15][16] It is on the World Health Organization's List of Essential Medicines.[17] It is available as a generic medication.[11] It can normally be found in plants of the Ephedra genus.[11][18] Over-the-counter dietary supplements containing ephedrine are illegal in the United States,[11] with the exception of those used in traditional Chinese medicine, where its presence is noted by má huáng.[11][18]
- ^ Anvisa (2023-03-31). "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 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-15.
- ^ "Ephedrine Hydrochloride 15mg Tablets Summary of Product Characteristics (SmPC)". emc. Retrieved 8 October 2020.
- ^ "Ephedrine Nasal Drops 1.0% Summary of Product Characteristics (SmPC)". emc. 11 March 2015. Archived from the original on 24 October 2020. Retrieved 8 October 2020.
- ^ "Akovaz- ephedrine sulfate injection". DailyMed. 16 April 2020. Retrieved 8 October 2020.
- ^ "Title 21: Food And Drugs Part 341—Cold, Cough, Allergy, Bronchodilator, And Antiasthmatic Drug Products For Over-The-Counter Human Use". Electronic Code of Federal Regulations. Retrieved 8 October 2020.
- ^ a b c d e "Ephedrine: Uses, Interactions, Mechanism of Action". DrugBank Online. 29 April 2016. Retrieved 14 July 2024.
- ^ 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.
- ^ 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.
- ^ Gad MZ, Azab SS, Khattab AR, Farag MA (October 2021). "Over a century since ephedrine discovery: an updated revisit to its pharmacological aspects, functionality and toxicity in comparison to its herbal extracts". Food Funct. 12 (20): 9563–9582. doi:10.1039/d1fo02093e. PMID 34533553.
- ^ a b Chua SS, Benrimoj SI, Triggs EJ (1989). "Pharmacokinetics of non-prescription sympathomimetic agents". Biopharm Drug Dispos. 10 (1): 1–14. doi:10.1002/bdd.2510100102. PMID 2647163.
- ^ a b c d e f g h i j k l m n o p "Ephedrine". The American Society of Health-System Pharmacists. Archived from the original on 2017-09-09. Retrieved 8 September 2017.
- ^ Briggs GG, Freeman RK, Yaffe SJ (2011). Drugs in pregnancy and lactation: a reference guide to fetal and neonatal risk (9th ed.). Philadelphia: Lippincott Williams & Wilkins. p. 495. ISBN 9781608317080. Archived from the original on 2017-09-08.
- ^ a b "Ephedrine Pregnancy and Breastfeeding Warnings". Archived from the original on 5 August 2017. Retrieved 8 October 2017.
- ^ Cite error: The named reference
PubChemwas invoked but never defined (see the help page). - ^ Soni MG, Shelke K, Amin R, Talati (2013). "A Lessons from the Use of Ephedra Products as a Dietary Supplement". In Bagchi D, Preuss HG (eds.). Obesity epidemiology, pathophysiology, and prevention (2nd ed.). Boca Raton, Florida: CRC Press. p. 692. ISBN 9781439854266. Archived from the original on 2017-09-08.
- ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 541. ISBN 9783527607495.
- ^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
- ^ a b Abourashed EA, El-Alfy AT, Khan IA, Walker L (August 2003). "Ephedra in perspective—a current review". Phytotherapy Research. 17 (7): 703–712. doi:10.1002/ptr.1337. PMID 12916063. S2CID 41083359.
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