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Hydroxystilbamidine

HCID 5284571
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Basic informationOverviewNames & identifiersPropertiesChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
1071752-67-4
Standard SMILES
N=C(N)c1ccc(/C=C/c2ccc(C(=N)N)cc2O)cc1
InChIKey
TUESWZZJYCLFNL-DAFODLJHSA-N
Molecular formula
C16H16N4O
Average molar mass
280.32 g/mol
Monoisotopic mass
280.13241115

Overview

Hydroxystilbamidine is a stilbenoid.

Names & identifiers

Preferred name
Hydroxystilbamidine
IUPAC
4-[(E)-2-(4-carbamimidoylphenyl)ethenyl]-3-hydroxybenzenecarboximidamide

Names & synonyms

HYDROXYSTILBAMIDINE495-99-8OxistilbamidinumHidroxiestilbamidina2-Hydroxy-4,4'-diguanylstilbeneIdrossistilbamidinaHydroxystilbamidinum2-Hydroxy-4,4'-stilbenedicarboxamidine39J262E49WDTXSID3023136RefChem:789572DTXCID803136
Show more names
4-((1E)-2-(4-carbamimidoylphenyl)ethenyl)-3-hydroxybenzene-1-carboximidamide207-811-01071752-67-44-[(E)-2-(4-carbamimidoylphenyl)ethenyl]-3-hydroxybenzenecarboximidamide(E)-4-(4-carbamimidoylstyryl)-3-hydroxybenzimidamideOHSANCGC00166289-01SMR000449023

Database identifiers

CAS
1071752-67-4、495-99-8
PubChem CID
5284571
DTXSID
DTXSID80873552
ChEMBL
CHEMBL1301
ChEBI
CHEBI:135161
UNII
39J262E49W
Nikkaji
J9.866C

Properties

Computed structural properties

XLogP
1.8
Topological polar surface area
120 Ų
Hydrogen bond donors
5
Hydrogen bond acceptors
3
Rotatable bonds
4
Heavy atoms
21
Formal charge
0
Complexity
413

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15

Chemistry & industry

Pharmacology

Pharmacodynamics · 1 item

Hydroxystilbamidine isethionate is a member of the diamidines, a large family of biochemially and pharmacologically interesting compounds. It has a rather unusual combination of properties, exhibiting antitrypanosomal, antimaliarial, antifungal and carcinostatic activities. It also appears to act as an immunosuppressant. This drug may be used in the treatment of blastomycosis, a disease cased by the dimorphic fungus or mold called Blastomyces dermatitids. Blastomycosis is a pulmonary infection that can lead to fever, cough and (rarely) symptoms similar to tuberculosis. Hydroxystilbamidine has largely been replaced with amphotericin B.

Mechanism of Action · 1 item

Hydroxystilbamidine isethionate (HSB) acts on extracellular DNA and lysosomes. In Trypanosomes there is extensive and selective binding of HSB to the kinetoplastic DNA. This inhibits cell division and reproduction. In yeast there is evidence of binding to extranuclear DNA causing numerous mutations. HSB is also taken up in the lysosomes and leads to a significant increase in the number of lysosome-like bodies and secretion granules in trypanosomal organisms. HSB may also stabilize lysosomal membranes. HSB has also been found to bind RNA and is a powerful inhibitor of cellular ribonucleases.

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Compound notes

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