IVERMECTIN B1A

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 Search

SMILES

CC[C@H](C)[C@H]1O[C@]2(CC[C@@H]1C)C[C@@H]3C[C@@H](C\C=C(C)\[C@@H](O[C@H]4C[C@H](OC)[C@@H](O[C@H]5C[C@H](OC)[C@@H](O)[C@H](C)O5)[C@H](C)O4)[C@@H](C)\C=C\C=C6/CO[C@@H]7[C@H](O)C(C)=C[C@@H](C(=O)O3)[C@]67O)O2

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
Sources: http://biolinks.co.jp/pdf/Ivermectin.pdf
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

Approval Year

Targets

Primary Target	Pharmacology	Potency
Glutamate-gated chloride ion channels 1 Target ID: Glutamate-gated chloride ion channels Sources: https://www.ncbi.nlm.nih.gov/pubmed/25987225	Agonist 2752	0.35 nM [Kd]
GABA-A receptor; alpha-1/beta-3/gamma-2 16 Target ID: CHEMBL2094121 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11082440	Agonist 2752	33.0 nM [IC50]
Glycine receptor 13 Target ID: CHEMBL3392921 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11082440	Agonist 2752	156.0 nM [IC50]
Neuronal acetylcholine receptor protein alpha-7 subunit 78 Target ID: CHEMBL2492 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9463487	Positive Allosteric Modulator 186	9.0 µM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Strongyloidiasis 10 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20059830	Curative		Approved 8583	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 1998

PubMed

Title	Date	PubMed
Designed biosynthesis of 25-methyl and 25-ethyl ivermectin with enhanced insecticidal activity by domain swap of avermectin polyketide synthase.	2015-09-24	26400541
Synthesis of photoreactive ivermectin B1a derivatives and their actions on Haemonchus and Bombyx glutamate-gated chloride channels.	2015-05	25987225
Development and validation of a new HPLC-UV method for the simultaneous determination of triclabendazole and ivermectin B1a in a pharmaceutical formulation.	2011-02-15	21313814

Patents

Sample Use Guides

In Vivo Use Guide

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 `Mon Mar 31 18:06:13 GMT 2025` Edited by `admin` on `Mon Mar 31 18:06:13 GMT 2025`
Record UNII	91Y2202OUW
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

IVERMECTIN COMPONENT B1A

Preferred Name

English

IVERMECTIN B1A

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