Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C47H72O14 |
Molecular Weight | 861.0662 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 19 / 19 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12OC\C3=C/C=C/[C@H](C)[C@H](O[C@@]4([H])C[C@H](OC)[C@@H](O[C@@]5([H])C[C@H](OC)[C@@H](O)[C@H](C)O5)[C@H](C)O4)\C(C)=C\C[C@]6([H])C[C@@H](C[C@]7(CC[C@H](C)[C@H](O7)C(C)C)O6)OC(=O)[C@]([H])(C=C(C)[C@H]1O)[C@@]23O
InChI
InChIKey=VARHUCVRRNANBD-PVVXTEPVSA-N
InChI=1S/C47H72O14/c1-24(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/h11-14,18,24-25,27,29-30,32-44,48-49,51H,15-17,19-23H2,1-10H3/b12-11+,26-14+,31-13+/t25-,27-,29-,30-,32+,33-,34-,35-,36-,37-,38-,39+,40-,41+,42-,43-,44+,46+,47+/m0/s1
Ivermectin B1B (dihydroavermectin B1b) is the minor component (<10%) of the commercial anthelmintic, ivermectin. Members of the avermectin/milbemycin anthelmintic class exert their anthelmintic effects by binding to glutamate-gated chloride channels expressed on nematode neurons and pharyngeal muscle cells. The avermectin/milbemycins are also potent insecticides. In vitro, the B1b (25-isopropyl) analog is slightly more potent than the 25-sec-butyl (B1a) analog as an inhibitor of nematode larval development and paralysis, and also a more sensitive probe for ivermectin resistance.
CNS Activity
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6893469
Curator's Comment: # Merck & Co., Inc.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL613142 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8036687 |
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Target ID: CHEMBL2363050 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14639007 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | STROMECTOL Approved UseSTROMECTOL is indicated for the treatment of the following infections:
Strongyloidiasis of the intestinal tract. STROMECTOL is indicated for the treatment of intestinal (i.e., nondisseminated) strongyloidiasis due to the nematode parasite Strongyloides stercoralis.
Onchocerciasis. STROMECTOL is indicated for the treatment of onchocerciasis due to the nematode
parasite Onchocerca volvulus. Launch Date1998 |
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Curative | STROMECTOL Approved UseSTROMECTOL is indicated for the treatment of the following infections:
Strongyloidiasis of the intestinal tract. STROMECTOL is indicated for the treatment of intestinal (i.e., nondisseminated) strongyloidiasis due to the nematode parasite Strongyloides stercoralis.
Onchocerciasis. STROMECTOL is indicated for the treatment of onchocerciasis due to the nematode
parasite Onchocerca volvulus. Launch Date1998 |
Sample Use Guides
The recommended dosage of STROMECTOL for the treatment of strongyloidiasis is a single oral dosedesigned to provide approximately 200 mkg of ivermectin per kg of body weight (~20mkg of Ivermectin B1B).
The recommended dosage of STROMECTOL for the treatment of onchocerciasis is a single oral dose designed to provide approximately 150 mkg of ivermectin per kg of body weight (~15mkg of Ivermectin B1B).
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24576444
Individual adult O. circumcincta (males and females at random) were manually picked from the storage container with a small forceps, washed and placed in groups of 7–8 individuals into the wells of a 24-well plate (Falcon Tissue Plates). For testing the effects of Ivermectin B1B, each well contained in a total volume of 1•5 mL the worms, RPMI medium and a different concentration of the drug at 10-fold dilutions in different wells. The worms were incubated in these plates for 24 h in an atmosphere containing 5%CO2 at 37 °C. Following incubation, the worms from each well were placed into single glass tubes (inner diameter 6 mm) containing the incubation medium (1•5mL) and enough fresh medium to bring the meniscus in line with the window of the light source in the Micromotility Meter The tubes were maintained in a 37 °C warm water bath. For the measurements, a single tube was placed in the channel of the Micromotility Meter (also held at 37 °C). After a settling period of 10 s, motility was measured for 50–60 s. Dead helminths generated a reading comparable to those obtained from medium alone.
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6321425
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0W28CYI3TU
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70209-81-3
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274-384-5
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63943
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DTXSID3023182
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C034045
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m6566
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CHEMBL2079552
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METABOLITE (PARENT)
SUBSTANCE RECORD