ivermectin   

GtoPdb Ligand ID: 2373

Synonyms: Heartgard® | ivermectin B1a | MK-933 | Sklice® | Soolantra®
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.
2D Structure
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Physico-chemical Properties
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
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
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
(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
INN number INN
4828 ivermectin
Synonyms
Heartgard® | ivermectin B1a | MK-933 | Sklice® | Soolantra®
Database Links
Specialist databases
AntibioticDB 1059
Other databases
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