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Details

Stereochemistry ABSOLUTE
Molecular Formula C48H74O14
Molecular Weight 875.0928
Optical Activity UNSPECIFIED
Defined Stereocenters 20 / 20
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of IVERMECTIN B1A

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@@H](C)CC)O6)OC(=O)[C@]([H])(C=C(C)[C@H]1O)[C@@]23O

InChI

InChIKey=AZSNMRSAGSSBNP-XPNPUAGNSA-N
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

HIDE SMILES / InChI

Molecular Formula C48H74O14
Molecular Weight 875.0928
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 20 / 20
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including: http://evans.rc.fas.harvard.edu/pdf/smnr_2000-2001_Raymer_Brian.pdf | http://www.inchem.org/documents/pims/pharm/ivermect.htm

22,23-dihydro-avermectin B1a is a major form of Ivermectin mixture (more than 90%). It is a broad-spectrum anthelmintic (worms), microfilaricide (heartworms), and miticide (mites) drug, used for horses, cattle, pigs, household pets. Ivermectin used in humans, especially for river blindness. Ivermectin binds selectively and with high affinity to glutamate-gated chloride ion channels in invertebrate muscle and nerve cells of the microfilaria.

Originator

Curator's Comment: http://biolinks.co.jp/pdf/Ivermectin.pdf

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Glutamate-gated chloride ion channels
0.35 nM [Kd]
33.0 nM [IC50]
156.0 nM [IC50]
9.0 µM [EC50]
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

9.0771843E11
PubMed

PubMed

TitleDatePubMed
Development and validation of a new HPLC-UV method for the simultaneous determination of triclabendazole and ivermectin B1a in a pharmaceutical formulation.
2010 Nov-Dec
Synthesis of photoreactive ivermectin B1a derivatives and their actions on Haemonchus and Bombyx glutamate-gated chloride channels.
2015 May
Designed biosynthesis of 25-methyl and 25-ethyl ivermectin with enhanced insecticidal activity by domain swap of avermectin polyketide synthase.
2015 Sep 24
Patents

Patents

Sample Use Guides

2 mg/mL (1 ml/ 10 Kg body weight)
Route of Administration: Oral
In Vitro Use Guide
The effects of ivermectin B1a (IVM)on K-28 cells expressing the human a7 nAChR was assessed. The application of IVM alone induced no detectable current in every cell tested (n=15). Preapplication of 25 mM IVM elicited a significant increase in the current evoked by low ACh concentration (30 mM).
Substance Class Chemical
Created
by admin
on Wed Jul 05 23:11:22 UTC 2023
Edited
by admin
on Wed Jul 05 23:11:22 UTC 2023
Record UNII
91Y2202OUW
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
IVERMECTIN B1A
Common Name English
IVERMECTIN COMPONENT B1A
MI  
Common Name English
IVERMECTIN COMPONENT B1A [MI]
Common Name English
AVERMECTIN A1A, 5-O-DEMETHYL-22,23-DIHYDRO-
Common Name English
DIHYDROAVERMECTIN B1A
Common Name English
5-O-DEMETHYL-22,23-DIHYDROAVERMECTIN A1A
Common Name English
22,23-DIHYDROAVERMECTIN B1A
Common Name English
Code System Code Type Description
CHEBI
63941
Created by admin on Wed Jul 05 23:11:22 UTC 2023 , Edited by admin on Wed Jul 05 23:11:22 UTC 2023
PRIMARY
MESH
C052102
Created by admin on Wed Jul 05 23:11:22 UTC 2023 , Edited by admin on Wed Jul 05 23:11:22 UTC 2023
PRIMARY
ChEMBL
CHEMBL1200633
Created by admin on Wed Jul 05 23:11:22 UTC 2023 , Edited by admin on Wed Jul 05 23:11:22 UTC 2023
PRIMARY
MERCK INDEX
M6566
Created by admin on Wed Jul 05 23:11:22 UTC 2023 , Edited by admin on Wed Jul 05 23:11:22 UTC 2023
PRIMARY Merck Index
PUBCHEM
6321424
Created by admin on Wed Jul 05 23:11:22 UTC 2023 , Edited by admin on Wed Jul 05 23:11:22 UTC 2023
PRIMARY
FDA UNII
91Y2202OUW
Created by admin on Wed Jul 05 23:11:22 UTC 2023 , Edited by admin on Wed Jul 05 23:11:22 UTC 2023
PRIMARY
EPA CompTox
DTXSID8023181
Created by admin on Wed Jul 05 23:11:22 UTC 2023 , Edited by admin on Wed Jul 05 23:11:22 UTC 2023
PRIMARY
CAS
71827-03-7
Created by admin on Wed Jul 05 23:11:22 UTC 2023 , Edited by admin on Wed Jul 05 23:11:22 UTC 2023
PRIMARY
ECHA (EC/EINECS)
276-046-2
Created by admin on Wed Jul 05 23:11:22 UTC 2023 , Edited by admin on Wed Jul 05 23:11:22 UTC 2023
PRIMARY
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METABOLITE -> PARENT
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