Ivermectin

Ivermectin
Clinical data
Pronunciation/ˌaɪvərˈmɛktɪn/, EYE-vər-MEK-tin
Trade namesStromectol, others
Other namesMK-933
AHFS/Drugs.com
MedlinePlusa607069
License data
Pregnancy
category
  • AU: B3
Routes of
administration		By mouth, topical
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailabilitynot determined
Protein binding93%
MetabolismLiver (CYP450)
Elimination half-life38.9 ± 20.8 h[6]
ExcretionFeces; <1% urine
Identifiers
IUPAC name
  • 22,23-dihydroavermectin B1a + 22,23-dihydroavermectin B1b
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.067.738
Chemical and physical data
FormulaC
48H
74O
14 (22,23-dihydroavermectin B1a)
C
47H
72O
14 (22,23-dihydroavermectin B1b)
Molar mass
  • 875.106 g·mol−1 (22,23-dihydroavermectin B1a)
  • 861.079 g·mol−1 (22,23-dihydroavermectin B1b)
3D model (JSmol)
    SMILES
    • CC[C@H](C)[C@@H]1[C@H](CC[C@@]2(O1)C[C@@H]3C[C@H](O2)C/C=C(/[C@H]([C@H](/C=C/C=C/4\CO[C@H]5[C@@]4([C@@H](C=C([C@H]5O)C)C(=O)O3)O)C)O[C@H]6C[C@@H]([C@H]([C@@H](O6)C)O[C@H]7C[C@@H]([C@H]([C@@H](O7)C)O)OC)OC)\C)C.C[C@H]1CC[C@]2(C[C@@H]3C[C@H](O2)C/C=C(/[C@H]([C@H](/C=C/C=C/4\CO[C@H]5[C@@]4([C@@H](C=C([C@H]5O)C)C(=O)O3)O)C)O[C@H]6C[C@@H]([C@H]([C@@H](O6)C)O[C@H]7C[C@@H]([C@H]([C@@H](O7)C)O)OC)OC)\C)O[C@@H]1C(C)C
    InChI
    • InChI=1S/C48H74O14.C47H72O14/c1-11-25(2)43-28(5)17-18-47(62-43)23-34-20-33(61-47)16-15-27(4)42(26(3)13-12-14-32-24-55-45-40(49)29(6)19-35(46(51)58-34)48(32,45)52)59-39-22-37(54-10)44(31(8)57-39)60-38-21-36(53-9)41(50)30(7)56-38;1-24(2)41-27(5)16-17-46(61-41)22-33-19-32(60-46)15-14-26(4)42(25(3)12-11-13-31-23-54-44-39(48)28(6)18–34(45(50)57-33)47(31,44)51)58-38-21-36(53–10)43(30(8)56–38)59-37-20-35(52–9)40(49)29(7)55-37/h12-15,19,25-26,28,30-31,33-45,49-50,52H,11,16-18,20-24H2,1-10H3;11-14,18,24-25,27,29-30,32-44,48-49,51H,15-17,19-23H2,1-10H3/b13-12+,27-15+,32-14+;12-11+,26-14+,31-13+/t25-,26-,28-,30-,31-,33+,34-,35-,36-,37-,38-,39-,40+,41-,42-,43+,44-,45+,47+,48+;25-,27-,29-,30-,32+,33-,34-,35-,36-,37-,38-,39+,40-,41+,42-,43-,44+,46+,47+/m00/s1 Y
    • Key:SPBDXSGPUHCETR-JFUDTMANSA-N Y
     NY (what is this?)  (verify)

    Ivermectin is an antiparasitic drug.[7] After its discovery in 1975,[8] its first uses were in veterinary medicine to prevent and treat heartworm and acariasis.[9] Approved for human use in 1987,[10] it is used to treat infestations including head lice, scabies, river blindness (onchocerciasis), strongyloidiasis, trichuriasis, ascariasis and lymphatic filariasis.[9][11][12][13] It works through many mechanisms to kill the targeted parasites,[11] and can be taken by mouth, or applied to the skin for external infestations.[11][14] It belongs to the avermectin family of medications.[11]

    William Campbell and Satoshi Ōmura were awarded the 2015 Nobel Prize in Physiology or Medicine for its discovery and applications.[15] It is on the World Health Organization's List of Essential Medicines,[16][17] and is approved by the US Food and Drug Administration (FDA) as an antiparasitic agent.[18] In 2022, it was the 314th most commonly prescribed medication in the United States, with more than 200,000 prescriptions.[19] It is available as a generic medicine.[20][21] Ivermectin is available in a fixed-dose combination with albendazole.[22]

    Misinformation has been widely spread claiming that ivermectin is beneficial for treating and preventing COVID-19.[23][24] Such claims are not backed by credible scientific evidence.[25][26][27] Multiple major health organizations, including the US Food and Drug Administration,[28] the US Centers for Disease Control and Prevention,[29] the European Medicines Agency,[26] and the World Health Organization have advised that ivermectin is not recommended for the treatment of COVID-19.[26][30]

    1. ^ "Regulatory Decision Summary for Stromectol". October 23, 2014. Archived from the original on June 7, 2022. Retrieved June 7, 2022.
    2. ^ "Health Canada New Drug Authorizations: 2015 Highlights". Health Canada. May 4, 2016. Archived from the original on February 20, 2020. Retrieved April 7, 2024.
    3. ^ Cite error: The named reference Stromectol FDA label was invoked but never defined (see the help page).
    4. ^ Cite error: The named reference Soolantra FDA label was invoked but never defined (see the help page).
    5. ^ "List of nationally authorised medicinal products" (PDF). European Medicines Agency. November 26, 2020. Archived (PDF) from the original on December 28, 2020.
    6. ^ Cite error: The named reference mosquito23 was invoked but never defined (see the help page).
    7. ^ Cite error: The named reference Laing was invoked but never defined (see the help page).
    8. ^ Campbell WC (May 2012). "History of avermectin and ivermectin, with notes on the history of other macrocyclic lactone antiparasitic agents". Current Pharmaceutical Biotechnology. 13 (6): 853–865. doi:10.2174/138920112800399095. PMID 22039784.
    9. ^ a b Saunders Handbook of Veterinary Drugs: Small and Large Animal (4 ed.). Elsevier Health Sciences. 2015. p. 420. ISBN 978-0-323-24486-2. Archived from the original on January 31, 2016.
    10. ^ Cite error: The named reference Molyneux2015 was invoked but never defined (see the help page).
    11. ^ a b c d Cite error: The named reference AHFS2016 was invoked but never defined (see the help page).
    12. ^ Sneader W (2005). Drug Discovery a History. Chichester: John Wiley & Sons. p. 333. ISBN 978-0-470-01552-0. Archived from the original on June 15, 2020. Retrieved April 5, 2020.
    13. ^ "Ascariasis – Resources for Health Professionals". U.S. Centers for Disease Control and Prevention (CDC). August 23, 2019. Archived from the original on November 21, 2010. Retrieved December 28, 2019.
    14. ^ Panahi Y, Poursaleh Z, Goldust M (2015). "The efficacy of topical and oral ivermectin in the treatment of human scabies" (PDF). Annals of Parasitology. 61 (1): 11–16. PMID 25911032. Archived (PDF) from the original on April 4, 2020.
    15. ^ Cite error: The named reference nobel-2015 was invoked but never defined (see the help page).
    16. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
    17. ^ 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.
    18. ^ Ahmed S, Karim MM, Ross AG, Hossain MS, Clemens JD, Sumiya MK, et al. (February 2021). "A five-day course of ivermectin for the treatment of COVID-19 may reduce the duration of illness". International Journal of Infectious Diseases. 103: 214–216. doi:10.1016/j.ijid.2020.11.191. PMC 7709596. PMID 33278625.
    19. ^ "Ivermectin Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved August 30, 2024.
    20. ^ "Ivermectin: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Archived from the original on November 28, 2021. Retrieved September 26, 2021.
    21. ^ "Ivermectin lotion: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Archived from the original on September 26, 2021. Retrieved September 25, 2021.
    22. ^ "Ivermectin/Albendazole - opinion on medicine for use outside EU". European Medicines Agency (EMA). January 30, 2025. Retrieved February 16, 2025.
    23. ^ Evershed N, McGowan M, Ball A (March 10, 2021). "Anatomy of a conspiracy theory: how misinformation travels on Facebook". The Guardian. Archived from the original on March 18, 2023. Retrieved May 26, 2021.
    24. ^ "Fact-checking claim about the use of ivermectin to treat COVID-19". PolitiFact. Washington, DC. April 23, 2021. Archived from the original on March 18, 2023. Retrieved May 26, 2021.
    25. ^ Popp M, Reis S, Schießer S, Hausinger RI, Stegemann M, Metzendorf MI, et al. (June 2022). "Ivermectin for preventing and treating COVID-19". The Cochrane Database of Systematic Reviews. 2022 (6): CD015017. doi:10.1002/14651858.CD015017.pub3. PMC 9215332. PMID 35726131.
    26. ^ a b c "EMA advises against use of ivermectin for the prevention or treatment of COVID-19 outside randomised clinical trials". European Medicines Agency. March 22, 2021. Archived from the original on January 17, 2022. Retrieved December 15, 2022.
    27. ^ Garegnani LI, Madrid E, Meza N (April 2021). "Misleading clinical evidence and systematic reviews on ivermectin for COVID-19". BMJ Evidence-Based Medicine. 27 (3): 156–158. doi:10.1136/bmjebm-2021-111678. PMID 33888547.
    28. ^ "Why You Should Not Use Ivermectin to Treat or Prevent COVID-19". U.S. Food and Drug Administration (FDA). December 10, 2021. Archived from the original on August 6, 2021. Retrieved July 13, 2021.
    29. ^ "Rapid Increase in Ivermectin Prescriptions and Reports of Severe Illness Associated with Use of Products Containing Ivermectin to Prevent or Treat COVID-19" (PDF). CDC Health Alert Network. CDCHAN-00449. August 26, 2021. Archived (PDF) from the original on November 3, 2021. Retrieved January 4, 2022.
    30. ^ "WHO advises that ivermectin only be used to treat COVID-19 within clinical trials". World Health Organization (WHO). Archived from the original on August 5, 2021. Retrieved January 4, 2022.
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