ivermectin   Click here for help

GtoPdb Ligand ID: 2373

Synonyms: Heartgard® | ivermectin B1a | MK-933 | Sklice® | Soolantra®
Approved drug
ivermectin is an approved drug (FDA (1996), UK (2015))
Compound class: Synthetic organic
Comment: Ivermectin is a broad-spectrum anti-parasitic drug. The approved drug is a mixture of mainly avermectin H2B1a (CAS # 71827-03-7) with some avermectin H2B1b (CAS # 70209-81-3). The avermectins are bacterial marcrolides isolated from Streptomyces avermitilis.

SARS-CoV-2 and COVID-19: There is speculation that ivermectin could be used to treat COVID-19, which is principally founded on in vitro evidence of anti-viral activity, and limited evidence of anti-inflammatory action. The evidence that ivermectin is appropriate to prevent or treat coronavirus infection is not compelling. To date (Jan 2021) there is no persuasive efficacy data available from an adequately sized, appropriately designed and controlled randomised clinical trial.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 14
Hydrogen bond donors 3
Rotatable bonds 8
Topological polar surface area 170.06
Molecular weight 874.51
XLogP 2.84
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES COC1CC(OC2C(C)C=CC=C3COC4C3(O)C(C=C(C4O)C)C(=O)OC3CC(CC=C2C)OC2(C3)CCC(C(O2)C(CC)C)C)OC(C1OC1CC(OC)C(C(O1)C)O)C
Isomeric SMILES CO[C@H]1C[C@H](OC2C(C)/C=C/C=C/3\COC4C3(O)[C@@H](C=C([C@H]4O)C)C(=O)O[C@H]3CC(C/C=C/2\C)O[C@]2(C3)CCC(C(O2)C(CC)C)C)O[C@H](C1O[C@H]1C[C@H](OC)C([C@@H](O1)C)O)C
InChI InChI=1S/C48H74O14/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/h12-15,19,25-26,28,30-31,33-45,49-50,52H,11,16-18,20-24H2,1-10H3/b13-12+,27-15+,32-14+/t25?,26?,28?,30-,31-,33?,34-,35-,36-,37-,38-,39-,40+,41?,42?,43?,44?,45?,47+,48?/m0/s1
InChI Key AZSNMRSAGSSBNP-ZLRQRZFZSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1996), UK (2015))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name Click here for help
(1'R,2R,4'S,10'E,14'E,16'E,21'R)-6-(butan-2-yl)-21',24'-dihydroxy-12'-{[(2R,4S,6S)-5-{[(2S,4S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-5,11',13',22'-tetramethyl-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1^{4,8}.0^{20,24}]pentacosane]-10',14',16',22'-tetraen-2'-one
International Nonproprietary Names Click here for help
INN number INN
4828 ivermectin
Synonyms Click here for help
Heartgard® | ivermectin B1a | MK-933 | Sklice® | Soolantra®
Database Links Click here for help
CAS Registry No. 70288-86-7 (source: Scifinder)
ChEBI CHEBI:6078
DrugBank Ligand DB00602
GtoPdb PubChem SID 135650439
PubChem CID 6427057
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Wikipedia Ivermectin