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Details

Stereochemistry ABSOLUTE
Molecular Formula C47H72O14
Molecular Weight 861.068
Optical Activity UNSPECIFIED
Defined Stereocenters 19 / 19
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of IVERMECTIN B1B

SMILES

CC(C)[C@]1([H])[C@@]([H])(C)CC[C@]2(C[C@]3([H])C[C@@]([H])(C/C(/[H])=C(\C)/[C@]([H])([C@@]([H])(C)/C(/[H])=C(\[H])/C(/[H])=C/4\CO[C@]5([H])[C@@]([H])(C(=C[C@@]([H])(C(=O)O3)[C@]45O)C)O)O[C@@]6([H])C[C@@]([H])([C@]([H])([C@]([H])(C)O6)O[C@@]7([H])C[C@@]([H])([C@]([H])([C@]([H])(C)O7)O)OC)OC)O2)O1

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

HIDE SMILES / InChI

Molecular Formula C47H72O14
Molecular Weight 861.068
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 19 / 19
E/Z Centers 0
Optical Activity UNSPECIFIED

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.

Originator

Curator's Comment:: # Merck & Co., Inc.

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
STROMECTOL

Approved Use

STROMECTOL 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 Date

907632000000
Curative
STROMECTOL

Approved Use

STROMECTOL 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 Date

907632000000
PubMed

PubMed

TitleDatePubMed
Ivermectin, a new broad-spectrum antiparasitic agent.
1980 Oct
Patents

Patents

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).
Route of Administration: Oral
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.
Substance Class Chemical
Created
by admin
on Sat Jun 26 01:55:21 UTC 2021
Edited
by admin
on Sat Jun 26 01:55:21 UTC 2021
Record UNII
0W28CYI3TU
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
IVERMECTIN B1B
Common Name English
22,23-DIHYDROAVERMECTIN B1B
Common Name English
AVERMECTIN A1A, 5-O-DEMETHYL-25-DE(1-METHYLPROPYL)-22,23-DIHYDRO-25-(1-METHYLETHYL)-
Common Name English
IVERMECTIN COMPONENT B1B
MI  
Common Name English
IVERMECTIN COMPONENT B1B [MI]
Common Name English
5-O-DEMETHYL-25-DE(1-METHYLPROPYL)-22,23-DIHYDRO-25-(1-METHYLETHYL)AVERMECTIN A1A
Common Name English
Code System Code Type Description
PUBCHEM
6321425
Created by admin on Sat Jun 26 01:55:21 UTC 2021 , Edited by admin on Sat Jun 26 01:55:21 UTC 2021
PRIMARY
FDA UNII
0W28CYI3TU
Created by admin on Sat Jun 26 01:55:21 UTC 2021 , Edited by admin on Sat Jun 26 01:55:21 UTC 2021
PRIMARY
CAS
70209-81-3
Created by admin on Sat Jun 26 01:55:21 UTC 2021 , Edited by admin on Sat Jun 26 01:55:21 UTC 2021
PRIMARY
ECHA (EC/EINECS)
274-384-5
Created by admin on Sat Jun 26 01:55:21 UTC 2021 , Edited by admin on Sat Jun 26 01:55:21 UTC 2021
PRIMARY
EPA CompTox
70209-81-3
Created by admin on Sat Jun 26 01:55:21 UTC 2021 , Edited by admin on Sat Jun 26 01:55:21 UTC 2021
PRIMARY
MESH
C034045
Created by admin on Sat Jun 26 01:55:21 UTC 2021 , Edited by admin on Sat Jun 26 01:55:21 UTC 2021
PRIMARY
MERCK INDEX
M6566
Created by admin on Sat Jun 26 01:55:21 UTC 2021 , Edited by admin on Sat Jun 26 01:55:21 UTC 2021
PRIMARY Merck Index
ChEMBL
CHEMBL2079552
Created by admin on Sat Jun 26 01:55:21 UTC 2021 , Edited by admin on Sat Jun 26 01:55:21 UTC 2021
PRIMARY
Related Record Type Details
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