Ivermectin

Category	Herpes simplex Virus (HSV)
CAS	70288-86-7
Description	Ivermectin is a glutamate-gated chloride channel (GluCls) activator, which is used as an antiparasitic drug for the treatment of certain parasitic roundworm infections. Ivermectin inhibits the chloride channels of helminthic parasites and has been shown to have clinical efficacy for the treatment of onchocerciasis, strongyloidiasis, and ectoparasitic infection. Ivermectin is a mixture of mostly Ivermectin B1a (>80%) with some Ivermectin B1b (<20%), which are macrolides from Streptomyces avermitilis.

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Product Information

Synonyms	Ivermectin B1a and Ivermectin B1b (Mixture); Avermectin H2B1a and Avermectin H2B1b (Mixture); Dihydroavermectin B1a and Dihydroavermectin B1b (Mixture); 22,23-Dihydroavermectin B1a and 22,23-Dihydroavermectin B1b (Mixture)
IUPAC Name	(1R,4S,5'S,6R,6'R,8R,10E,12S,13S,14E,16E,20R,21R,24S)-6'-[(2S)-butan-2-yl]-21,24-dihydroxy-12-[(2R,4S,5S,6S)-5-[(2S,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-5',11,13,22-tetramethylspiro[3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene-6,2'-oxane]-2-one;(1R,4S,5'S,6R,6'R,8R,10E,12S,13S,14E,16E,20R,21R,24S)-21,24-dihydroxy-12-[(2R,4S,5S,6S)-5-[(2S,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-5',11,13,22-tetramethyl-6'-propan-2-ylspiro[3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene-6,2'-oxane]-2-one
Molecular Weight	1736.16
Molecular Formula	C48H74O14.C47H72O14
Canonical SMILES	CCC(C)C1C(CCC2(O1)CC3CC(O2)CC=C(C(C(C=CC=C4COC5C4(C(C=C(C5O)C)C(=O)O3)O)C)OC6CC(C(C(O6)C)OC7CC(C(C(O7)C)O)OC)OC)C)C
InChI	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
InChIKey	AZSNMRSAGSSBNP-XPNPUAGNSA-N
Melting Point	>155°C (dec.)
Purity	≥95%
Solubility	Soluble in Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly, Heated, Sonicated)
Appearance	White to Off-white Solid
Application	Antiparasitic Agents
Storage	Store at -20°C
Complexity	1680
Exact Mass	874.50785703
In Vitro	In the submicromolar range (EC50=250 nM) the action of Ivermectin (MK-933) is rapid and reversible, resulting in increased amplitude and slowed deactivation of P2X4 channel currents evoked by ATP. Ivermectin (MK-933) markedly increases the potency of ATP and that of the normally low-potency agonist a,b-methylene-ATP in a use- and voltage-independent manner without changing the ion selectivity of P2X4 channels. Ivermectin (MK-933) activates glutamate-gated chloride channels in the nerves and muscles of the parasite, leading to membrane hyperpolarization and muscle paralysis. Ivermectin (MK-933) strongly inhibits the binding of Impα/β1 to NS5 (IC50=17 μM), but not of Impβ1 alone to NS5. Ivermectin (MK-933) has potent antiviral activity towards both HIV-1 and dengue virus, both of which are strongly reliant on importin α/β nuclear import, with respect to the HIV-1 integrase and NS5 (non-structural protein 5) polymerase proteins respectively.
PSA	17.6
Target	Parasite; HIV; Mitophagy; HSV; SARS-CoV; Antibiotic; Autophagy
XLogP3-AA	4.1