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Showing drug card for Ivermectin (DB00602)

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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-02-19 16:03:51
Primary Accession Number DB00602
Secondary Accession Number
  • APRD01058
Name Ivermectin
Drug Type
  • Approved
  • Small Molecule
Description Ivermectin (22,23-dihydroavermectin B1a + 22,23-dihydroavermectin B1b) is a broad-spectrum anti-parasite medication, traditionally used against worms (except tapeworms), but more recently found to be effective against most mites and some lice too. It is mainly used in humans in the treatment of onchocerciasis, but is also effective against other worm infestations (such as strongyloidiasis, ascariasis, trichuriasis and enterobiasis).
Synonyms
  1. 22,23-Dihydroxy-avermectin B
  2. 22,23-Dihyroavermectin B1
  3. 5-O-demethyl-22,23-dihydro-avermectin A1a
Brand Names
  1. Ivermectin B1
  2. Ivermectin-luminol
  3. Mectizan
  4. Stromectol
Brand Mixtures
  1. Heel 170 Tab (Calcium Iodide + Fucus Vesiculosus + Ivermectin B1b + Silicon Dioxide)
Chemical IUPAC Name Not Available
Chemical Formula C95H146O28
Chemical Structure Structure
CAS Registry Number 70288-86-7
InChI Identifier InChI=1/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
InChI Key SPBDXSGPUHCETR-MVGRHBATBN
KEGG Drug D00804 Link Image
KEGG Compound C07970 Link Image
PubChem Compound 6474909 Link Image
PubChem Substance 10171 Link Image
ChEBI ID Not Available
PharmGKB ID PA450133 Link Image
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] 02248882 Link Image
RxList Link http://www.rxlist.com/cgi/generic3/ivermectin.htm Link Image
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Ivermectin Link Image
FDA Label
Material Safety Data Sheet (MSDS)
Synthesis Reference Not Available
Average Molecular Weight 1736.1589
Monoisotopic Molecular Weight 1735.0001
State Solid
Melting Point 155 oC
Experimental Water Solubility Insoluble Source: PhysProp
Predicted Water Solubility Not Available Calculated using ALOGPS
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP Not Available Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS Not Available Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES CO[C@H]1C[C@@H](O[C@@H](C)[C@@H]1O)O[C@H]1[C@H](C)O[C@H](C[C@@H]1OC)O[C@H]1[C@@H](C)\C=C\C=C2/CO[C@@H]3[C@H](O)C(C)=C[C@@H](C(=O)O[C@H]4C[C@@H](C\C=C1/C)O[C@@]1(CC[C@H](C)[C@H](O1)C(C)C)C4)[C@]23O.CC[C@@H](C)[C@H]1O[C@]2(CC[C@@H]1C)C[C@@H]1C[C@@H](C\C=C(C)\[C@@H](O[C@H]3C[C@H](OC)[C@@H](O[C@H]4C[C@H](OC)[C@@H](O)[C@H](C)O4)[C@H](C)O3)[C@@H](C)\C=C\C=C3/CO[C@@H]4[C@H](O)C(C)=C[C@@H](C(=O)O1)[C@]34O)O2
Canonical SMILES COC1CC(OC(C)C1O)OC1C(C)OC(CC1OC)OC1C(C)C=CC=C2COC3C(O)C(C)=CC(C(=O)OC4CC(CC=C1C)OC1(CCC(C)C(O1)C(C)C)C4)C23O.CCC(C)C1OC2(CCC1C)CC1CC(CC=C(C)C(OC3CC(OC)C(OC4CC(OC)C(O)C(C)O4)C(C)O3)C(C)C=CC=C3COC4C(O)C(C)=CC(C(=O)O1)C34O)O2
Drug Category
  • Anthelmintics
  • Antinematodal Agents
  • Antiprotozoal Agents
ATC Codes
AHFS Codes Not Available
Indication For the treatment of intestinal (i.e., nondisseminated) strongyloidiasis due to the nematode parasite Strongyloides stercoralis. Also for the treatment of onchocerciasis (river blindness) due to the nematode parasite Onchocerca volvulus. Can be used to treat scabies caused by Sarcoptes scabiei.
Pharmacology Ivermectin is a semisynthetic, anthelminitic agent. It is an avermectin which a group of pentacyclic sixteen-membered lactone (i.e. a macrocyclic lactone disaccharide) derived from the soil bacterium Streptomyces avermitilis. Avermectins are potent anti-parasitic agents. Ivermectin is the most common avermectin. It is a broad spectrum antiparasitic drug for oral administration. It is sometimes used to treat human onchocerciasis (river blindness). It is the mixture of 22,23-dihydro-avermectin B1a (at least 90%) and 22,23-dihydro-avermectin B1b (less than 10%).
Mechanism of Action Ivermectin binds selectively and with high affinity to glutamate-gated chloride ion channels in invertebrate muscle and nerve cells of the microfilaria. This binding causes an increase in the permeability of the cell membrane to chloride ions and results in hyperpolarization of the cell, leading to paralysis and death of the parasite. Ivermectin also is believed to act as an agonist of the neurotransmitter gamma-aminobutyric acid (GABA), thereby disrupting GABA-mediated central nervous system (CNS) neurosynaptic transmission. Ivermectin may also impair normal intrauterine development of O. volvulus microfilariae and may inhibit their release from the uteri of gravid female worms.
Absorption Moderately well absorbed. Improved absorption with high fat meal.
Toxicity LD50 = 29.5 mg/kg (Mouse, oral). LD50 = 10 mg/kg (Rat, oral). Adverse effects include muscle or joint pain, dizziness, fever, headache, skin rash, fast heartbeat.
Protein Binding 93%
Biotransformation Primarily hepatic. Ivermectin and/or its metabolites are excreted almost exclusively in the feces over an estimated 12 days, with less than 1 % of the administered dose excreted in the urine.
Half Life 16 hours (also reported at 22-28 hours)
Dosage Forms
Form Route
Tablet Oral
Patient Information Show Link Image
Contraindications Show Link Image
Interactions Not Available
Drug Interactions Not Available
Food Interactions Not Available
Pathways Not Available
General References
  1. Drugs.com Link Image
  2. Wikipedia Link Image
  3. RxList Link Image
Organisms Affected
  • Parasitic nematodes and other roundworms
Targets
  1. GABA-A receptor subunit
  2. Glutamate-gated chloride channel subunit beta
Drug Target 1 [top]
Target 1 ID 348
Target 1 Name GABA-A receptor subunit
Target 1 Synonyms Not Available
Target 1 Gene Name ZC482.1
Target 1 Protein Sequence >GABA-A receptor subunit 
MRRSKTRRIFHVSITSLLVSTIFCQNGTKPHNNSTSDQMSSSWSNRSQTMYSNASSLLSD
LLLDYDIRLRPGFGGDALLLTMDIIIASFDSISEVDMDYTLTMYLHQYWTDERLRWSNEI
PIDEMTLSGEFSQNIWVPDTFLANDKHSYLHEVTERNKMLRINVDGKVAYGMRLTSTLSC
SMNLRNFSLDSQNCTVEIESYGYTTSEVLMKWNYPLAVHGVEQADVPQFTITGFHTEDSI
VSTATGSYQRLSLVFQLRRSVGYFIFETYLPCDLIVMLSWVSFWINHEATSARVALGITT
VLTMTTISTGVRQSLPRISYVKSIDIYLVMCFVFVFAALLEYAAVNYSYWGRERGKGGGG
NEWPVNGANKEDRESAVNVQKWVPSGLMDGVPQPQDRRVEALEEAMSTSNTAAQNNNFES
TSKPKKRSSSPIPPLCRAGNTISEESESPDYPRYSTTSLKGARPHASLNHKTHHLKGRSS
ARAKRRMTLARMNVSMKQSISGIGRRARKVIPTIRVRDVNLIDKYSRVVFPVCFIVFNLF
YWSYYMMVPS
Target 1 Number of Residues 559
Target 1 Molecular Weight 62439
Target 1 Theoretical pI 8.99
Target 1 GO Classification
Function
neurotransmitter receptor activity
transporter activity
ion transporter activity
ion channel activity
ligand-gated ion channel activity
extracellular ligand-gated ion channel activity
signal transducer activity
receptor activity
transmembrane receptor activity
GABA receptor activity
GABA-A receptor activity
Process
physiological process
cellular physiological process
transport
ion transport
Component
postsynaptic membrane
cell
membrane
intrinsic to membrane
integral to membrane
Target 1 General Function Involved in GABA-A receptor activity
Target 1 Specific Function Not Available
Target 1 Pathways Not Available
Target 1 Reactions Not Available
Target 1 Pfam Domain Function
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • 263-285; 292-311; 326-348; 525-547
Target 1 Essentiality Essential
Target 1 GenBank ID Protein 24943213 Link Image
Target 1 UniProtKB/Swiss-Prot ID Q8ITG2 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name Q8ITG2_CAEEL Link Image
Target 1 PDB ID Not Available
Target 1 Cellular Location
  • Membrane
  • multi-pass membrane protein
Target 1 Gene Sequence >1653 bp 
ATGCGTCGAAGTAAAACTCGGAGGATATTCCACGTGTCCATCACATCGCTGCTGGTTTCA
ACGATTTTTTGCCAAAATGGGACAAAACCTCACAACAACTCAACTTCGGACCAAATGAGC
TCATCTTGGAGCAACCGGAGCCAGACAATGTACTCGAATGCTTCTTCTCTGCTTAGTGAC
CTACTCTTGGACTATGATATCAGGCTGAGGCCTGGTTTTGGAGGAGACGCTCTTCTTCTG
ACGATGGACATCATCATTGCCTCGTTCGACTCGATTTCCGAAGTTGATATGGACTACACT
CTCACAATGTACTTGCATCAATATTGGACAGATGAGCGGTTACGGTGGAGCAATGAGATT
CCGATTGATGAGATGACGTTGAGCGGAGAATTTTCACAAAACATCTGGGTACCTGACACA
TTTCTGGCCAATGACAAGCATTCTTATTTGCATGAGGTCACTGAACGAAACAAGATGCTC
CGAATAAATGTCGATGGAAAGGTTGCATATGGGATGAGGCTCACGTCAACATTGAGTTGC
TCCATGAATCTTAGAAATTTTTCGCTGGATTCGCAGAATTGCACAGTTGAGATTGAATCT
TACGGGTACACAACTTCCGAGGTCCTAATGAAATGGAACTACCCACTAGCAGTGCACGGC
GTCGAACAAGCCGATGTTCCCCAGTTCACCATAACCGGATTCCACACCGAAGATAGCATT
GTCTCCACTGCAACAGGATCTTATCAACGACTGTCTCTCGTTTTCCAACTCAGACGATCA
GTTGGATACTTTATATTCGAAACCTATCTTCCATGTGATCTTATTGTAATGCTATCGTGG
GTATCGTTCTGGATTAATCATGAAGCTACAAGTGCTCGAGTGGCTCTTGGTATTACAACT
GTGCTCACGATGACGACGATTTCGACGGGAGTTCGGCAGAGTTTGCCGAGGATCAGTTAT
GTGAAGAGTATTGATATTTATCTGGTTATGTGCTTCGTCTTCGTTTTCGCCGCACTTCTA
GAGTACGCAGCCGTCAACTACTCCTACTGGGGACGTGAACGAGGAAAGGGTGGCGGAGGA
AACGAGTGGCCAGTCAACGGAGCGAATAAAGAGGACCGCGAGTCGGCGGTGAATGTTCAA
AAATGGGTGCCCAGTGGGTTGATGGATGGTGTACCTCAACCTCAAGATCGGCGGGTTGAA
GCTCTTGAAGAGGCGATGAGCACGAGTAACACAGCTGCTCAGAATAATAATTTTGAAAGC
ACCTCAAAACCCAAGAAGCGTTCATCTTCACCAATTCCACCACTATGCCGAGCTGGTAAC
ACGATAAGTGAAGAATCGGAATCGCCTGACTATCCGAGATATTCAACGACTTCCCTGAAA
GGAGCAAGGCCGCATGCTTCCTTAAATCACAAGACACATCATCTCAAAGGGAGAAGCTCG
GCTAGAGCTAAGCGAAGAATGACTTTGGCTCGAATGAATGTATCCATGAAACAATCAATA
TCAGGAATTGGGCGAAGAGCACGGAAAGTGATTCCGACGATTCGTGTTCGAGATGTTAAT
CTTATTGATAAATACTCACGGGTTGTGTTTCCAGTATGCTTTATTGTTTTTAACTTATTC
TACTGGAGCTACTACATGATGGTCCCTTCCTAG
Target 1 GenBank Gene ID
Target 1 GeneCard ID Not Available
Target 1 GenAtlas ID Not Available
Target 1 HGNC ID Not Available
Target 1 Chromosome Location Not Available
Target 1 Locus Not Available
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Feng XP, Hayashi J, Beech RN, Prichard RK: Study of the nematode putative GABA type-A receptor subunits: evidence for modulation by ivermectin. J Neurochem. 2002 Nov;83(4):870-8. [PubMed Link Image]
Target 1 Drug References
  1. Feng XP, Hayashi J, Beech RN, Prichard RK: Study of the nematode putative GABA type-A receptor subunits: evidence for modulation by ivermectin. J Neurochem. 2002 Nov;83(4):870-8. [PubMed Link Image]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed Link Image]
  3. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed Link Image]
Drug Target 2 [top]
Target 2 ID 538
Target 2 Name Glutamate-gated chloride channel subunit beta
Target 2 Synonyms
  1. Avermectin- sensitive glutamate-gated chloride channel subunit
  2. Glu-Cl beta subunit
  3. Glutamate-gated chloride channel subunit beta precursor
Target 2 Gene Name glc-2
Target 2 Protein Sequence >Avermectin-sensitive glutamate-gated chloride channel GluCl beta 
MTTPSSFSILLLLLLMPVVTNGEYSMQSEQEILNALLKNYDMRVRPPPANSSTEGAVNVR
VNIMIRMLSKIDVVNMEYSIQLTFREQWIDPRLAYENLGFYNPPAFLTVPHVKKSLWIPD
TFFPTEKAAHRHLIDMENMFLRIYPDGKILYSSRISLTSSCPMRLQLYPLDYQSCNFDLV
SYAHTMNDIMYEWDPSTPVQLKPGVGSDLPNFILKNYTTNADCTSHTNTGSYGCLRMQLL
FKRQFSYYLVQLYAPTTMIVIVSWVSFWIDLHSTAGRVALGVTTLLTMTTMQSAINAKLP
PVSYVKVVDVWLGACQTFVFGALLEYAFVSYQDSVRQNDRSREKAARKAQRRREKLEMVD
AEVYQPPCTCHTFEARETFRDKVRRYFTKPDYLPAKIDFYARFVVPLAFLAFNVIYWVSC
LIMSANASTPESLV
Target 2 Number of Residues 441
Target 2 Molecular Weight 49893
Target 2 Theoretical pI 8.34
Target 2 GO Classification
Function
neurotransmitter receptor activity
transporter activity
ion transporter activity
ion channel activity
ligand-gated ion channel activity
extracellular ligand-gated ion channel activity
signal transducer activity
receptor activity
transmembrane receptor activity
GABA receptor activity
GABA-A receptor activity
Process
physiological process
cellular physiological process
transport
ion transport
Component
postsynaptic membrane
cell
membrane
intrinsic to membrane
integral to membrane
Target 2 General Function Involved in GABA-A receptor activity
Target 2 Specific Function Not Available
Target 2 Pathways Not Available
Target 2 Reactions Not Available
Target 2 Pfam Domain Function
Target 2 Signals
  • None
Target 2 Transmembrane Regions
  • 247-269; 276-295; 310-332; 403-425
Target 2 Essentiality Essential
Target 2 GenBank ID Protein 559561 Link Image
Target 2 UniProtKB/Swiss-Prot ID Q17328 Link Image
Target 2 UniProtKB/Swiss-Prot Entry Name Q17328_CAEEL Link Image
Target 2 PDB ID Not Available
Target 2 Cellular Location
  • Membrane
  • multi-pass membrane protein
Target 2 Gene Sequence >1305 bp 
ATGACTACACCTAGTTCATTTTCAATTCTGCTCCTCCTGCTACTGATGCCCGTCGTCACA
AATGGCGAGTACAGTATGCAATCGGAGCAGGAGATTCTCAATGCGTTGCTCAAAAATTAT
GACATGCGGGTACGGCCACCACCGGCCAACTCATCAACGGAAGGTGCTGTCAATGTTCGT
GTTAATATTATGATTCGGATGCTATCGAAAATTGATGTAGTTAATATGGAATATTCAATT
CAACTAACATTCCGCGAGCAATGGATAGATCCTCGACTGGCCTATGAAAATTTGGGTTTC
TACAATCCTCCGGCATTTCTCACAGTCCCACATGTTAAAAAGAGTCTATGGATTCCTGAC
ACATTCTTTCCCACCGAAAAAGCAGCTCATAGACATTTGATTGATATGGAAAACATGTTC
TTGAGGATATATCCGGATGGAAAAATCCTCTACAGTTCCCGGATAAGTTTGACAAGTTCC
TGCCCAATGCGTCTCCAACTCTACCCACTCGACTATCAATCGTGTAACTTTGATCTTGTC
AGCTACGCGCACACAATGAATGATATCATGTACGAGTGGGATCCATCAACACCAGTTCAA
CTGAAACCCGGCGTTGGCTCGGATCTTCCCAATTTTATACTCAAAAACTACACAACAAAT
GCAGATTGCACAAGCCACACGAACACAGGATCATATGGATGTCTCCGAATGCAACTTTTG
TTCAAACGGCAATTCAGTTATTACTTGGTACAACTGTATGCTCCAACCACTATGATTGTG
ATTGTCTCATGGGTTTCATTTTGGATTGATCTTCATTCAACTGCTGGACGTGTCGCTTTA
GGAGTCACTACGCTTCTTACAATGACTACAATGCAATCTGCAATCAACGCCAAGCTTCCA
CCAGTTAGCTACGTAAAAGTTGTGGATGTCTGGCTTGGAGCGTGCCAAACATTTGTATTC
GGAGCACTTCTGGAATACGCATTTGTCAGTTATCAAGATAGTGTCCGGCAAAATGACAGG
TCAAGAGAGAAAGCTGCAAGGAAGGCGCAGAGAAGGAGAGAAAAGTTGGAAATGGTGGAT
GCAGAAGTCTATCAGCCACCGTGCACCTGTCATACTTTCGAAGCCCGCGAGACATTCCGT
GACAAAGTCCGCCGTTACTTCACAAAACCAGATTATCTACCGGCAAAAATTGATTTCTAT
GCCAGATTTGTCGTCCCACTTGCCTTTCTCGCTTTCAATGTTATCTACTGGGTATCATGT
CTTATCATGTCTGCCAATGCTTCCACTCCAGAGTCTCTCGTTTAG
Target 2 GenBank Gene ID
Target 2 GeneCard ID Not Available
Target 2 GenAtlas ID Not Available
Target 2 HGNC ID Not Available
Target 2 Chromosome Location Not Available
Target 2 Locus Not Available
Target 2 SNPs SNPJam Report Link Image
Target 2 General References
  1. Cully DF, Vassilatis DK, Liu KK, Paress PS, Van der Ploeg LH, Schaeffer JM, Arena JP: Cloning of an avermectin-sensitive glutamate-gated chloride channel from Caenorhabditis elegans. Nature. 1994 Oct 20;371(6499):707-11. [PubMed Link Image]
  2. Genome sequence of the nematode C. elegans: a platform for investigating biology. Science. 1998 Dec 11;282(5396):2012-8. [PubMed Link Image]
Target 2 Drug References
  1. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed Link Image]
  2. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed Link Image]

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.