NAV

Hydroxystilbamidine

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Hydroxystilbamidine
DrugBank Accession Number
DB14753
Background

Hydroxystilbamidine isethionate is used in the therapy of some patients with nonprogressive blastomycosis of the skin, and pulmonary or systemic blastomycosis in children, with fewer side effects than amphotericin B. Hydroxystilbamidine isethionate is also used in pathology for diagnostic purposes.

Type
Small Molecule
Groups
Approved
Structure
3D
Similar Structures
Weight
Average: 280.331
Monoisotopic: 280.132411151
Chemical Formula
C16H16N4O
Synonyms
  • 2-Hydroxy-4,4'-diguanylstilbene
  • 2-Hydroxy-4,4'-stilbenedicarboxamidine
  • Hidroxiestilbamidina
  • Hydroxystilbamidine
  • Hydroxystilbamidinum
  • Idrossistilbamidina
  • Oxistilbamidinum
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Pharmacology

Indication

Used in the treatment of nonprogressive blastomycosis of the skin and other mycoses.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

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

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.

TargetActionsOrganism
ADNA
other/unknown
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Hydroxystilbamidine isethionate0163PVD2QZ533-22-2XVTQTNAKZYLTNZ-HFPMQDOPSA-N

Categories

Drug Categories
Classification
Not classified
Affected organisms
  • Yeast, Molds, Trypanosomes

Chemical Identifiers

UNII
39J262E49W
CAS number
495-99-8
InChI Key
TUESWZZJYCLFNL-DAFODLJHSA-N
InChI
InChI=1S/C16H16N4O/c17-15(18)12-5-2-10(3-6-12)1-4-11-7-8-13(16(19)20)9-14(11)21/h1-9,21H,(H3,17,18)(H3,19,20)/b4-1+
IUPAC Name
4-[(1E)-2-(4-carbamimidoylphenyl)ethenyl]-3-hydroxybenzene-1-carboximidamide
SMILES
NC(=N)C1=CC=C(\C=C\C2=C(O)C=C(C=C2)C(N)=N)C=C1

References

Synthesis Reference

U.S. Patent 2,510,047.

General References
  1. Murgatroyd LB: 2-hydroxystilbamidine isethionate: a new fluorochrome for use in general pathology. II. The selective demonstration of fungi. Diagn Histopathol. 1982 Jul-Sep;5(3):219-22. [Article]
  2. Folds JD, Orlando G, Spitznagel JK: Immunosuppression by hydroxystilbamidine isethionate, a lysosome-stabilizing, anti-proteolytic, antifungal drug. Infect Immun. 1975 Mar;11(3):441-4. [Article]
  3. Link [Link]
Human Metabolome Database
HMDB0240284
ChemSpider
10612853
ChEMBL
CHEMBL1301
ZINC
ZINC000000001547
PharmGKB
PA164745514
Wikipedia
Hydroxystilbamidine

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0644 mg/mLALOGPS
logP1.44ALOGPS
logP1.24Chemaxon
logS-3.6ALOGPS
pKa (Strongest Acidic)8.22Chemaxon
pKa (Strongest Basic)12.14Chemaxon
Physiological Charge2Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area119.97 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity106.84 m3·mol-1Chemaxon
Polarizability30.99 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03e9-0090000000-666127fcf8172eb6a397
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004r-0190000000-af1d4c65b04c2b423ac1
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0090000000-b1b12717bcaec0fd1d1a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-01ot-0190000000-e5dc4444c1baf73ea4cc
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004u-2190000000-0abea7879f206a1252ca
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9210000000-970d630d18070550b524
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-183.063431
predicted
DarkChem Lite v0.1.0
[M-H]-173.44608
predicted
DeepCCS 1.0 (2019)
[M+H]+183.263831
predicted
DarkChem Lite v0.1.0
[M+H]+175.80408
predicted
DeepCCS 1.0 (2019)
[M+Na]+182.651131
predicted
DarkChem Lite v0.1.0
[M+Na]+182.83571
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. DNA
Kind
Nucleotide
Organism
Humans
Pharmacological action
Yes
Actions
Other/unknown
DNA is the molecule of heredity, as it is responsible for the genetic propagation of most inherited traits. It is a polynucleic acid that carries genetic information on cell growth, division, and function. DNA consists of two long strands of nucleotides twisted into a double helix and held together by hydrogen bonds. The sequence of nucleotides determines hereditary characteristics. Each strand serves as the template for subsequent DNA replication and as a template for mRNA production, leading to protein synthesis via ribosomes.
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Folds JD, Orlando G, Spitznagel JK: Immunosuppression by hydroxystilbamidine isethionate, a lysosome-stabilizing, anti-proteolytic, antifungal drug. Infect Immun. 1975 Mar;11(3):441-4. [Article]

Drug created at March 06, 2019 22:09 / Updated at February 21, 2021 18:54