Identification

Name
Ivermectin
Accession Number
DB00602  (APRD01058)
Type
Small Molecule
Groups
Approved, Vet Approved
Description

Ivermectin is a broad-spectrum anti-parasite medication. It was first marketed under the name Stromectol® and used against worms (except tapeworms), but, in 2012, it was approved for the topical treatment of head lice infestations in patients 6 months of age and older, and marketed under the name Sklice™ as well. Ivermectin 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).

Structure
Thumb
Synonyms
  • Ivermectin
  • Ivermectina
  • Ivermectine
  • Ivermectinum
External IDs
MK 933
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
RosiverCream1 %TopicalGalderma2015-05-25Not applicableCanada
SkliceLotion.585 g/117gTopicalSanofi Pasteur Limited2012-07-09Not applicableUs
SkliceLotion5 mg/gTopicalArbor Pharmaceuticals2016-06-30Not applicableUs
SoolantraCream10 mg/gTopicalGalderma2015-01-01Not applicableUs
StromectolTablet3 mg/1OralDepartment Of State Health Services, Pharmacy Branch1996-11-22Not applicableUs
StromectolTablet3 mg/1OralMerck Sharp & Dohme Limited1996-11-22Not applicableUs00006 0032 20 nlmimage10 df16efc7
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
IvermectinTablet3 mg/1OralEdenbridge Pharmaceuticals Llc2014-11-15Not applicableUs42799 0806 01 nlmimage10 04460200
IvermectinTablet3 mg/1OralCentral Texas Community Health Centers2014-11-15Not applicableUs
IvermectinTablet3 mg/1Oralbryant ranch prepack2014-11-15Not applicableUs
International/Other Brands
Ascapil (Abbott) / Detebencil (Roux-Ocefa) / Ermetin (Unipharm) / Gotax (Metlen) / Imectin (Pulse) / Ivectin (Aristopharma) / Ivera (Beximco) / Ivergot (Licol) / Ivermec (UCI) / Ivexterm (Valeant) / Ivori (Invision) / Kaonol (Mediderm) / Kilox (Bussié) / Maikeding (Hisun) / Quanox (Dermacare) / Revectina (Solvay) / Scabo (Delta) / Scavista (Zuventus) / Securo (Valeant) / Vermectin (Atlantic Lab)
Categories
UNII
8883YP2R6D
CAS number
70288-86-7
Weight
Average: 1736.1589
Monoisotopic: 1735.000064088
Chemical Formula
C95H146O28
InChI Key
SPBDXSGPUHCETR-CVSKBELMSA-N
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+/m10/s1
IUPAC Name
(1'R,2R,4'S,5S,6R,8'R,10'E,12'S,13'S,14'E,16'E,20'R,21'R,24'S)-21',24'-dihydroxy-12'-{[(2R,4S,5S,6S)-5-{[(2S,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-5,11',13',22'-tetramethyl-6-(propan-2-yl)-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-2'-one; (1'R,2R,4'S,5S,6R,8'R,10'E,12'S,13'S,14'E,16'E,20'R,21'R,24'S)-6-[(2R)-butan-2-yl]-21',24'-dihydroxy-12'-{[(2R,4S,5S,6S)-5-{[(2S,4S,5S,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[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-2'-one
SMILES

Pharmacology

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.

Structured Indications
Pharmacodynamics

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.

TargetActionsOrganism
AGlycine receptor subunit alpha-3
agonist
Human
UGamma-aminobutyric acid receptor subunit beta-3
agonist
Human
Absorption

Moderately well absorbed. Improved absorption with high fat meal.

Volume of distribution

The volume of distribution is 3 to 3.5 L/kg and it does not cross the blood-brain barrier.

Protein binding

93%

Metabolism

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.

Route of elimination

Ivermectin is metabolized in the liver, and 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)

Clearance
Not Available
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.

Affected organisms
  • Parasitic nematodes and other roundworms
  • Head lice
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AcenocoumarolIvermectin may increase the anticoagulant activities of Acenocoumarol.Approved
AfatinibThe serum concentration of Afatinib can be increased when it is combined with Ivermectin.Approved
AmiodaroneThe metabolism of Ivermectin can be decreased when combined with Amiodarone.Approved, Investigational
AprepitantThe serum concentration of Ivermectin can be increased when it is combined with Aprepitant.Approved, Investigational
AtazanavirThe metabolism of Ivermectin can be decreased when combined with Atazanavir.Approved, Investigational
AtomoxetineThe metabolism of Ivermectin can be decreased when combined with Atomoxetine.Approved
AzithromycinThe serum concentration of Ivermectin can be increased when it is combined with Azithromycin.Approved
BoceprevirThe metabolism of Ivermectin can be decreased when combined with Boceprevir.Approved, Withdrawn
BortezomibThe metabolism of Ivermectin can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Ivermectin can be decreased when it is combined with Bosentan.Approved, Investigational
BosutinibThe serum concentration of Bosutinib can be increased when it is combined with Ivermectin.Approved
Brentuximab vedotinThe serum concentration of Brentuximab vedotin can be increased when it is combined with Ivermectin.Approved
CarbamazepineThe metabolism of Ivermectin can be increased when combined with Carbamazepine.Approved, Investigational
CeritinibThe serum concentration of Ivermectin can be increased when it is combined with Ceritinib.Approved
ClarithromycinThe metabolism of Ivermectin can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Ivermectin can be decreased when combined with Clemastine.Approved
ClorindioneIvermectin may increase the anticoagulant activities of Clorindione.Experimental
ClotrimazoleThe metabolism of Ivermectin can be decreased when combined with Clotrimazole.Approved, Vet Approved
CobicistatThe metabolism of Ivermectin can be decreased when combined with Cobicistat.Approved
ColchicineThe serum concentration of Colchicine can be increased when it is combined with Ivermectin.Approved
ConivaptanThe serum concentration of Conivaptan can be increased when it is combined with Ivermectin.Approved, Investigational
CrizotinibThe metabolism of Ivermectin can be decreased when combined with Crizotinib.Approved
CyclosporineThe metabolism of Ivermectin can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
Dabigatran etexilateThe serum concentration of the active metabolites of Dabigatran etexilate can be increased when Dabigatran etexilate is used in combination with Ivermectin.Approved
DabrafenibThe serum concentration of Ivermectin can be decreased when it is combined with Dabrafenib.Approved
DarunavirThe metabolism of Ivermectin can be decreased when combined with Darunavir.Approved
DasatinibThe serum concentration of Ivermectin can be increased when it is combined with Dasatinib.Approved, Investigational
DeferasiroxThe serum concentration of Ivermectin can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe metabolism of Ivermectin can be decreased when combined with Delavirdine.Approved
DicoumarolIvermectin may increase the anticoagulant activities of Dicoumarol.Approved
DihydroergotamineThe metabolism of Ivermectin can be decreased when combined with Dihydroergotamine.Approved
DiltiazemThe metabolism of Ivermectin can be decreased when combined with Diltiazem.Approved
DiphenadioneIvermectin may increase the anticoagulant activities of Diphenadione.Experimental
DoxorubicinThe serum concentration of Doxorubicin can be increased when it is combined with Ivermectin.Approved, Investigational
DoxycyclineThe metabolism of Ivermectin can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe metabolism of Ivermectin can be decreased when combined with Dronedarone.Approved
EdoxabanThe serum concentration of Edoxaban can be increased when it is combined with Ivermectin.Approved
EltrombopagThe serum concentration of Ivermectin can be increased when it is combined with Eltrombopag.Approved
EnzalutamideThe serum concentration of Ivermectin can be decreased when it is combined with Enzalutamide.Approved
ErythromycinThe metabolism of Ivermectin can be decreased when combined with Erythromycin.Approved, Vet Approved
Ethyl biscoumacetateIvermectin may increase the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
EverolimusThe serum concentration of Everolimus can be increased when it is combined with Ivermectin.Approved
FluconazoleThe metabolism of Ivermectin can be decreased when combined with Fluconazole.Approved
FluindioneIvermectin may increase the anticoagulant activities of Fluindione.Investigational
FluvoxamineThe metabolism of Ivermectin can be decreased when combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe metabolism of Ivermectin can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Ivermectin can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe metabolism of Ivermectin can be increased when combined with Fosphenytoin.Approved
Fusidic AcidThe serum concentration of Ivermectin can be increased when it is combined with Fusidic Acid.Approved
IdelalisibThe metabolism of Ivermectin can be decreased when combined with Idelalisib.Approved
ImatinibThe metabolism of Ivermectin can be decreased when combined with Imatinib.Approved
IndinavirThe metabolism of Ivermectin can be decreased when combined with Indinavir.Approved
IsavuconazoniumThe metabolism of Ivermectin can be decreased when combined with Isavuconazonium.Approved, Investigational
IsradipineThe metabolism of Ivermectin can be decreased when combined with Isradipine.Approved
ItraconazoleThe metabolism of Ivermectin can be decreased when combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Ivermectin can be increased when it is combined with Ivacaftor.Approved
KetoconazoleThe metabolism of Ivermectin can be decreased when combined with Ketoconazole.Approved, Investigational
LedipasvirThe serum concentration of Ledipasvir can be increased when it is combined with Ivermectin.Approved
LopinavirThe metabolism of Ivermectin can be decreased when combined with Lopinavir.Approved
LorpiprazoleThe serum concentration of Ivermectin can be increased when it is combined with Lorpiprazole.Approved
LovastatinThe metabolism of Ivermectin can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Ivermectin can be increased when it is combined with Luliconazole.Approved
LumacaftorThe serum concentration of Ivermectin can be decreased when it is combined with Lumacaftor.Approved
MifepristoneThe serum concentration of Ivermectin can be increased when it is combined with Mifepristone.Approved, Investigational
MitotaneThe serum concentration of Ivermectin can be decreased when it is combined with Mitotane.Approved
NaloxegolThe serum concentration of Naloxegol can be increased when it is combined with Ivermectin.Approved
NefazodoneThe metabolism of Ivermectin can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Ivermectin can be decreased when combined with Nelfinavir.Approved
NetupitantThe serum concentration of Ivermectin can be increased when it is combined with Netupitant.Approved
NevirapineThe metabolism of Ivermectin can be increased when combined with Nevirapine.Approved
NilotinibThe metabolism of Ivermectin can be decreased when combined with Nilotinib.Approved, Investigational
OlaparibThe metabolism of Ivermectin can be decreased when combined with Olaparib.Approved
OsimertinibThe serum concentration of Ivermectin can be increased when it is combined with Osimertinib.Approved
PalbociclibThe serum concentration of Ivermectin can be increased when it is combined with Palbociclib.Approved
PazopanibThe serum concentration of Pazopanib can be increased when it is combined with Ivermectin.Approved
PentobarbitalThe metabolism of Ivermectin can be increased when combined with Pentobarbital.Approved, Vet Approved
PhenindioneIvermectin may increase the anticoagulant activities of Phenindione.Approved, Investigational
PhenobarbitalThe metabolism of Ivermectin can be increased when combined with Phenobarbital.Approved
PhenprocoumonIvermectin may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
PhenytoinThe metabolism of Ivermectin can be increased when combined with Phenytoin.Approved, Vet Approved
PosaconazoleThe metabolism of Ivermectin can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PrimidoneThe metabolism of Ivermectin can be increased when combined with Primidone.Approved, Vet Approved
PrucaloprideThe serum concentration of Prucalopride can be increased when it is combined with Ivermectin.Approved
RanolazineThe serum concentration of Ranolazine can be increased when it is combined with Ivermectin.Approved, Investigational
RifabutinThe metabolism of Ivermectin can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Ivermectin can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Ivermectin can be increased when combined with Rifapentine.Approved
RifaximinThe serum concentration of Rifaximin can be increased when it is combined with Ivermectin.Approved, Investigational
RolapitantThe serum concentration of Ivermectin can be increased when it is combined with Rolapitant.Approved
RucaparibThe metabolism of Ivermectin can be decreased when combined with Rucaparib.Approved, Investigational
SaquinavirThe metabolism of Ivermectin can be decreased when combined with Saquinavir.Approved, Investigational
SarilumabThe therapeutic efficacy of Ivermectin can be decreased when used in combination with Sarilumab.Approved
SildenafilThe metabolism of Ivermectin can be decreased when combined with Sildenafil.Approved, Investigational
SilodosinThe serum concentration of Silodosin can be increased when it is combined with Ivermectin.Approved
SiltuximabThe serum concentration of Ivermectin can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Ivermectin can be increased when it is combined with Simeprevir.Approved
St. John's WortThe serum concentration of Ivermectin can be decreased when it is combined with St. John's Wort.Investigational, Nutraceutical
StiripentolThe serum concentration of Ivermectin can be increased when it is combined with Stiripentol.Approved
SulfisoxazoleThe metabolism of Ivermectin can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
TelaprevirThe metabolism of Ivermectin can be decreased when combined with Telaprevir.Approved, Withdrawn
TelithromycinThe metabolism of Ivermectin can be decreased when combined with Telithromycin.Approved
TeriflunomideThe serum concentration of Ivermectin can be increased when it is combined with Teriflunomide.Approved
TiclopidineThe metabolism of Ivermectin can be decreased when combined with Ticlopidine.Approved
TioclomarolIvermectin may increase the anticoagulant activities of Tioclomarol.Experimental
TocilizumabThe serum concentration of Ivermectin can be decreased when it is combined with Tocilizumab.Approved
TopotecanThe serum concentration of Topotecan can be increased when it is combined with Ivermectin.Approved, Investigational
VemurafenibThe serum concentration of Ivermectin can be increased when it is combined with Vemurafenib.Approved
VenlafaxineThe metabolism of Ivermectin can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Ivermectin can be decreased when combined with Verapamil.Approved
VincristineThe excretion of Vincristine can be decreased when combined with Ivermectin.Approved, Investigational
VoriconazoleThe metabolism of Ivermectin can be decreased when combined with Voriconazole.Approved, Investigational
WarfarinIvermectin may increase the anticoagulant activities of Warfarin.Approved
ZiprasidoneThe metabolism of Ivermectin can be decreased when combined with Ziprasidone.Approved
Food Interactions
  • When administered with a high fat meal, the bioavailability is increased 2.5 times.

References

Synthesis Reference

Shuet-Hing L. Chiu, Josephine R. Carlin, Rae Taub, "Ivermectin derivative compounds and process for preparing the same." U.S. Patent US4963667, issued June, 1982.

US4963667
General References
Not Available
External Links
Human Metabolome Database
HMDB0014740
KEGG Drug
D00804
KEGG Compound
C07970
PubChem Compound
46936176
PubChem Substance
46506810
ChemSpider
30776735
ChEMBL
CHEMBL1200633
Therapeutic Targets Database
DAP000261
PharmGKB
PA450133
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Ivermectin
ATC Codes
P02CF01 — IvermectinD11AX22 — Ivermectin
AHFS Codes
  • 84:04.12 — Scabicides and Pediculicides
FDA label
Download (60.2 KB)
MSDS
Download (73.4 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedBasic ScienceHealthy Volunteers3
1CompletedBasic SciencePlasmodium Infections1
1CompletedTreatmentLice of the head1
1, 2CompletedTreatmentAlcohol Use Disorder (AUD)1
1, 2CompletedTreatmentPlasmodium Infections1
1, 2Not Yet RecruitingTreatmentRosaceas1
2Active Not RecruitingTreatmentLymphatic Filariasis1
2CompletedTreatmentLymphatic Filariasis1
2CompletedTreatmentOnchocerciasis1
2CompletedTreatmentPlasmodium Infections1
2CompletedTreatmentLice of the head1
2, 3CompletedTreatmentLymphatic Filariasis / Plasmodium Infections1
2, 3RecruitingTreatmentDengue Fever1
3Active Not RecruitingTreatmentOesophagostomiasis1
3Active Not RecruitingTreatmentLice of the head / Scabies1
3CompletedPreventionOnchocerciasis1
3CompletedTreatmentLice Infestations1
3CompletedTreatmentModerate to Severe Papulopustular Rosacea1
3CompletedTreatmentOnchocerciasis1
3CompletedTreatmentPapulopustular Rosacea1
3CompletedTreatmentRosaceas1
3CompletedTreatmentLice of the head2
3Enrolling by InvitationPreventionPlasmodium Infections1
3Not Yet RecruitingTreatmentGale / Ivermectin / Oral Parasitic Drug / Severe Forms of Scabies1
3RecruitingTreatmentScabies1
3RecruitingTreatmentLice of the head1
3Unknown StatusTreatmentChronic Strongyloidiasis1
3Unknown StatusTreatmentDemodicidosis / Rosaceas1
4Active Not RecruitingTreatmentImpetigo / Scabies / Yaws1
4Active Not RecruitingTreatmentRosaceas1
4CompletedBasic ScienceLoa Loa / Loiasis1
4CompletedTreatmentLymphatic Filariasis1
4CompletedTreatmentRosaceas1
4Not Yet RecruitingTreatmentEpilepsies / Ivermectin / Onchocerciasis1
4RecruitingTreatmentHelminth Infection / Lymphatic Filariasis1
4WithdrawnNot AvailableLymphatic Filariasis / Trachoma1
Not AvailableActive Not RecruitingPreventionLymphatic Filariasis1
Not AvailableCompletedTreatmentAbdominal Pain (AP) / Lymphoedema / Mansonelliasis / Pruritus1
Not AvailableCompletedTreatmentParasitic Diseases2
Not AvailableCompletedTreatmentScabies1
Not AvailableTerminatedTreatmentHelminthiasis / Human Immunodeficiency Virus (HIV) Infections1
Not AvailableTerminatedTreatmentLymphatic Filariasis1
Not AvailableUnknown StatusTreatmentHelminthiasis / Strongyloides Stercoralis Infection1

Pharmacoeconomics

Manufacturers
  • Merck and co inc
Packagers
Dosage forms
FormRouteStrength
CreamTopical1 %
LotionTopical.585 g/117g
LotionTopical5 mg/g
CreamTopical10 mg/g
TabletOral3 mg/1
Prices
Unit descriptionCostUnit
Stromectol 20 3 mg tablet Box116.13USD box
Ivermectin powder14.0USD g
Stromectol 3 mg tablet5.58USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US8927595No2007-10-122027-10-12Us
US8791153No2007-10-122027-10-12Us
US6103248No1998-05-222018-05-22Us
US9089587No2014-03-132034-03-13Us
US8470788No2004-04-222024-04-22Us
US9233118No2014-03-132034-03-13Us
US9233117No2014-03-132034-03-13Us
US7550440No2004-04-222024-04-22Us
US8815816No2004-04-222024-04-22Us
US8093219No2004-04-222024-04-22Us
US8080530No2004-04-222024-04-22Us
US6133310No1999-04-262019-04-26Us
US5952372No1998-09-182018-09-18Us
US8415311No2004-04-222024-04-22Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)155 °CNot Available
water solubilityInsolubleNot Available
Predicted Properties
PropertyValueSource
logP5.83ChemAxon
pKa (Strongest Acidic)12.47ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area170.06 Å2ChemAxon
Rotatable Bond Count15ChemAxon
Refractivity230.33 m3·mol-1ChemAxon
Polarizability96.87 Å3ChemAxon
Number of Rings14ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8146
Blood Brain Barrier-0.549
Caco-2 permeable-0.8192
P-glycoprotein substrateSubstrate0.8771
P-glycoprotein inhibitor IInhibitor0.805
P-glycoprotein inhibitor IIInhibitor0.8192
Renal organic cation transporterNon-inhibitor0.7384
CYP450 2C9 substrateNon-substrate0.8877
CYP450 2D6 substrateNon-substrate0.886
CYP450 3A4 substrateSubstrate0.7714
CYP450 1A2 substrateNon-inhibitor0.9129
CYP450 2C9 inhibitorNon-inhibitor0.8366
CYP450 2D6 inhibitorNon-inhibitor0.928
CYP450 2C19 inhibitorNon-inhibitor0.8793
CYP450 3A4 inhibitorNon-inhibitor0.7957
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8073
Ames testNon AMES toxic0.8295
CarcinogenicityNon-carcinogens0.9622
BiodegradationNot ready biodegradable0.9759
Rat acute toxicity3.5285 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9471
hERG inhibition (predictor II)Non-inhibitor0.5536
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as milbemycins. These are a group of macrolides with a structure containing a 16-membered lactone ring fused to a 1,7-dioxaspiroundecane ring system and to either a benzofuran (or hydrogenated derivative thereof). In some cases (e.g. Milbemycin E), the tetrahydrofuranyl ring is missing. Milbemycins can be o-glycosylated at C13 to form Avermectins. Milbemycins are produced by Streptomyces species.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Macrolides and analogues
Sub Class
Milbemycins
Direct Parent
Milbemycins
Alternative Parents
O-glycosyl compounds / Disaccharides / Ketals / Oxanes / Tetrahydrofurans / Tertiary alcohols / Secondary alcohols / Lactones / Carboxylic acid esters / Oxacyclic compounds
show 5 more
Substituents
Milbemycin / Disaccharide / Glycosyl compound / O-glycosyl compound / Ketal / Oxane / Tetrahydrofuran / Tertiary alcohol / Carboxylic acid ester / Lactone
show 15 more
Molecular Framework
Not Available
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Transmitter-gated ion channel activity
Specific Function
The glycine receptor is a neurotransmitter-gated ion channel. Binding of glycine to its receptor increases the chloride conductance and thus produces hyperpolarization (inhibition of neuronal firing).
Gene Name
GLRA3
Uniprot ID
O75311
Uniprot Name
Glycine receptor subunit alpha-3
Molecular Weight
53799.775 Da
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:17016423]
  2. Yates DM, Wolstenholme AJ: An ivermectin-sensitive glutamate-gated chloride channel subunit from Dirofilaria immitis. Int J Parasitol. 2004 Aug;34(9):1075-81. [PubMed:15313134]
  3. McCavera S, Rogers AT, Yates DM, Woods DJ, Wolstenholme AJ: An ivermectin-sensitive glutamate-gated chloride channel from the parasitic nematode Haemonchus contortus. Mol Pharmacol. 2009 Jun;75(6):1347-55. doi: 10.1124/mol.108.053363. Epub 2009 Mar 31. [PubMed:19336526]
  4. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Agonist
General Function
Gaba-gated chloride ion channel activity
Specific Function
Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...
Gene Name
GABRB3
Uniprot ID
P28472
Uniprot Name
Gamma-aminobutyric acid receptor subunit beta-3
Molecular Weight
54115.04 Da
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:17016423]
  2. 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:12421359]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Schwab D, Fischer H, Tabatabaei A, Poli S, Huwyler J: Comparison of in vitro P-glycoprotein screening assays: recommendations for their use in drug discovery. J Med Chem. 2003 Apr 24;46(9):1716-25. [PubMed:12699389]
  2. Pouliot JF, L'Heureux F, Liu Z, Prichard RK, Georges E: Reversal of P-glycoprotein-associated multidrug resistance by ivermectin. Biochem Pharmacol. 1997 Jan 10;53(1):17-25. [PubMed:8960059]
  3. Nagy H, Goda K, Fenyvesi F, Bacso Z, Szilasi M, Kappelmayer J, Lustyik G, Cianfriglia M, Szabo G Jr: Distinct groups of multidrug resistance modulating agents are distinguished by competition of P-glycoprotein-specific antibodies. Biochem Biophys Res Commun. 2004 Mar 19;315(4):942-9. [PubMed:14985103]
  4. Schinkel AH, Wagenaar E, van Deemter L, Mol CA, Borst P: Absence of the mdr1a P-Glycoprotein in mice affects tissue distribution and pharmacokinetics of dexamethasone, digoxin, and cyclosporin A. J Clin Invest. 1995 Oct;96(4):1698-705. [PubMed:7560060]
  5. Jani M, Makai I, Kis E, Szabo P, Nagy T, Krajcsi P, Lespine A: Ivermectin interacts with human ABCG2. J Pharm Sci. 2011 Jan;100(1):94-7. doi: 10.1002/jps.22262. Epub 2010 Jun 22. [PubMed:20574995]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Transporter activity
Specific Function
Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o-glucuronide, methotre...
Gene Name
ABCC1
Uniprot ID
P33527
Uniprot Name
Multidrug resistance-associated protein 1
Molecular Weight
171589.5 Da
References
  1. Lespine A, Dupuy J, Orlowski S, Nagy T, Glavinas H, Krajcsi P, Alvinerie M: Interaction of ivermectin with multidrug resistance proteins (MRP1, 2 and 3). Chem Biol Interact. 2006 Feb 25;159(3):169-79. Epub 2005 Dec 27. [PubMed:16384552]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Organic anion transmembrane transporter activity
Specific Function
Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter.
Gene Name
ABCC2
Uniprot ID
Q92887
Uniprot Name
Canalicular multispecific organic anion transporter 1
Molecular Weight
174205.64 Da
References
  1. Lespine A, Dupuy J, Orlowski S, Nagy T, Glavinas H, Krajcsi P, Alvinerie M: Interaction of ivermectin with multidrug resistance proteins (MRP1, 2 and 3). Chem Biol Interact. 2006 Feb 25;159(3):169-79. Epub 2005 Dec 27. [PubMed:16384552]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
Gene Name
ABCG2
Uniprot ID
Q9UNQ0
Uniprot Name
ATP-binding cassette sub-family G member 2
Molecular Weight
72313.47 Da
References
  1. Jani M, Makai I, Kis E, Szabo P, Nagy T, Krajcsi P, Lespine A: Ivermectin interacts with human ABCG2. J Pharm Sci. 2011 Jan;100(1):94-7. doi: 10.1002/jps.22262. Epub 2010 Jun 22. [PubMed:20574995]

Drug created on June 13, 2005 07:24 / Updated on January 19, 2018 10:49