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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

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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 20 / 20
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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 TargetPharmacologyConditionPotency
0.35 nM [Kd]
33.0 nM [IC50]
156.0 nM [IC50]
9.0 µM [EC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
STROMECTOL

PubMed

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
Record UNII
91Y2202OUW
Record Status Validated (UNII)
Record Version