Ivermectin

Ivermectin
Clinical data
Pronunciation	/ˌaɪvərˈmɛktɪn/, EYE-vər-MEK-tin
Trade names	Stromectol, others
Other names	MK-933
AHFS/Drugs.com	Systemic Monograph; Topical Monograph;
MedlinePlus	a607069
License data	US DailyMed: Ivermectin;
Pregnancy; category	AU: B3;
Routes of; administration	By mouth, topical
ATC code	D11AX22 (WHO) , P02CF01 (WHO), QP54AA01 (WHO), QS02QA03 (WHO);
Legal status
Legal status	CA: ℞-only; US: ℞-only ; EU: Rx-only;
Pharmacokinetic data
Bioavailability	not determined
Protein binding	93%
Metabolism	Liver (CYP450)
Elimination half-life	38.9 ± 20.8 h
Excretion	Feces; <1% urine
Identifiers
	IUPAC name 22,23-dihydroavermectin B1a + 22,23-dihydroavermectin B1b;
CAS Number	70288-86-7 71827-03-7;
PubChem CID	6321424;
DrugBank	DB00602 ;
ChemSpider	7988461 ;
UNII	8883YP2R6D;
KEGG	D00804 ;
ChEBI	CHEBI:6078;
ChEMBL	ChEMBL1200633 ;
PDB ligand	IVM (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID7040235 ;
ECHA InfoCard	100.067.738
Chemical and physical data
Formula	C; 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 ; Key:SPBDXSGPUHCETR-JFUDTMANSA-N ;
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Ivermectin is an antiparasitic drug. After its discovery in 1975, its first uses were in veterinary medicine to prevent and treat heartworm and acariasis. Approved for human use in 1987, it is used to treat infestations including head lice, scabies, river blindness (onchocerciasis), strongyloidiasis, trichuriasis, ascariasis and lymphatic filariasis. It works through many mechanisms to kill the targeted parasites, and can be taken by mouth, or applied to the skin for external infestations. It belongs to the avermectin family of medications.

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

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