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Tromantadine

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Category Herpes simplex Virus (HSV)
CAS 53783-83-8
Description Tromantadine is a topical antiherpetic drug that has two independent actions on herpes simplex virus type 1 (HSV-1) replication: early, during virus binding or penetration and late, after the initiation of DNA synthesis.
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Product Information

Synonyms N-(1-adamantyl)-2-[2-(dimethylamino)ethoxy]acetamide; D 41; N-(1-adamantyl)-2-(2-dimethylaminoethoxy)acetamide; tromantadin; tromantadine; tromantadine monohydrochloride; tromantadine monohydrochloride, monohydrate; tromantidine; Viru-Merz; Viru-Merz serol; Viru-Serol
Molecular Weight 280.41
Molecular Formula C16H28N2O2
Canonical SMILES CN(C)CCOCC(=O)NC12CC3CC(C1)CC(C3)C2
InChI InChI=1S/C16H28N2O2/c1-18(2)3-4-20-11-15(19)17-16-8-12-5-13(9-16)7-14(6-12)10-16/h12-14H,3-11H2,1-2H3,(H,17,19)
InChIKey UXQDWARBDDDTKG-UHFFFAOYSA-N
Boiling Point 434.5±28.0 °C at 760 Torr
Flash Point 216.6°C
Purity ≥99.0%
Density 1.09±0.1 g/cm3
Solubility In Vitro:
10 mM in DMSO
Appearance Colorless to light yellow (Oil)
Storage Store in a cool and dry place (or refer to the Certificate of Analysis).
Complexity 326
Exact Mass 280.215078140
Index Of Refraction 1.533
In Vitro Tromantadine inhibits herpes simplex virus type 1 (KOS strain)-induced cytopathic effect and virus replication with limited toxicity to the cells. Vero and HEp-2 cells tolerate up to 2 mg of Tromantadine per 2x106 cells for 24-, 48-, or 96-h incubation periods with little change in cell morphology. Treatment of the cells with 10 to 50 μg of Tromantadine reduces herpes simplex virus-induced cytopathic effect. Treatment with 100 to 500 μg of Tromantadine inhibits herpes simplex virus-induced cytopathic effect and reduces virus production. Complete inhibition of virus production is observed with treatments of 500 μg to 1 mg. The antiherpetic activity of Tromantadine is dependent upon the viral inoculum size and the time of addition of the compound with respect to infection. Virion synthesis and viral polypeptide synthesis are inhibited by addition of Tromantadine at the time of infection or 4 h postinfection. Tromantadine raises the bilayer to hexagonal phase transition temperature of synthetic phosphatidylethanolamines and is less disruptive to phospholipid packing. Tromantadine acts similar to cyclosporin A, previously demonstrated to inhibit viral-induced cell-cell fusion.
PSA 41.57000
Target HSV
XLogP3-AA 2.1

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