HYDROXYSTILBAMIDINE

US Previously Marketed

First approved in 1953

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H16N4O
Molecular Weight	280.3244
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0
Stereo Comments	Assumed E-isomer; MM2 minimum energy of E and Z are 8.2496 and 18.2584 kcal/mol respectively

SHOW SMILES / InChI

Structure Search

SMILES

NC(=N)C1=CC=C(\C=C\C2=C(O)C=C(C=C2)C(N)=N)C=C1

InChI

InChIKey=TUESWZZJYCLFNL-DAFODLJHSA-N

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+

HIDE SMILES / InChI

Description
Sources: http://www.springer.com/us/book/9780751404999
Curator's Comment: description was created based on several sources, including, http://www.ncbi.nlm.nih.gov/pubmed/1933270

Hydroxystilbamidine is an organic antimonal derivative with antiprotazoal, antifungal and anticancer activity. It was used in the treatment of blastomicosis and leishmaniasis. Moreover, hydroxystilbamidine (FluoroGold) is used as a tracer for neurons.

CNS Activity

Originator

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Blastomycosis 7 Sources: http://www.ncbi.nlm.nih.gov/pubmed/13104430	Curative		Approved 8429	HYDROXYSTILBAMIDINE ISETHIONATE Approved Use Unknown Launch Date -5.05785614E11

C_max

Value	Dose	Co-administered	Analyte	Population
32.6 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/021876s013lbl.pdf	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: DOXYLAMINE	DOXYLAMINE	PYRIDOXINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
43.4 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/021876s013lbl.pdf	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: DOXYLAMINE	DOXYLAMINE	PYRIDOXINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
0.4 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/021876s013lbl.pdf	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: DOXYLAMINE	DOXYLAMINE	PYRIDOXINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
20% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/021876s013lbl.pdf	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: DOXYLAMINE	DOXYLAMINE	PYRIDOXINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
225 mg 1 times / day multiple, intravenous Dose: 225 mg, 1 times / day Route: intravenous Route: multiple Dose: 225 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/13545726	unhealthy, 7 years n = 1 Health Status: unhealthy Condition: BLASTOMYCOSIS Age Group: 7 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/13545726	Other AEs: Hepatic failure... Other AEs: Hepatic failure (grade 5\|acute) Sources: https://pubmed.ncbi.nlm.nih.gov/13545726
45.2 g 1 times / day multiple, intravenous Highest studied dose Dose: 45.2 g, 1 times / day Route: intravenous Route: multiple Dose: 45.2 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/13545726 https://pubmed.ncbi.nlm.nih.gov/13171792	unhealthy n = 1 Health Status: unhealthy Condition: BLASTOMYCOSIS Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/13545726 https://pubmed.ncbi.nlm.nih.gov/13171792	Sources: https://pubmed.ncbi.nlm.nih.gov/13545726 https://pubmed.ncbi.nlm.nih.gov/13171792

AEs

AE	Significance	Dose	Population
Hepatic failure	grade 5\|acute	225 mg 1 times / day multiple, intravenous Dose: 225 mg, 1 times / day Route: intravenous Route: multiple Dose: 225 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/13545726	unhealthy, 7 years n = 1 Health Status: unhealthy Condition: BLASTOMYCOSIS Age Group: 7 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/13545726

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00BGES
AK Scientific	C459
BOC Sciences	495-99-8
Chem Scene	CS-8085
Chemodex	H0100
MolPort	MolPort-003-931-687
NCI Plated 2007	259242
NCI Plated 2007	78326
Sigma Aldrich	39286
Sigma Aldrich	39286\|SIGMA
Sigma Aldrich	H9160
Sigma Aldrich	H9160\|SIGMA
Tetrahedron	TS34218
ZINC	ZINC000000001547	http://zinc15.docking.org/substances/ZINC000000001547
ZINC	ZINC000004896000	http://zinc15.docking.org/substances/ZINC000004896000
eMolecules	43473789
eMolecules	44841559

PubMed

Title	Date	PubMed
Hydroxystilbamidine in the treatment of Indian kala-azar.	1950 Dec	14813822
Hydroxystilbamidine treatment of North American blastomycosis.	1956 Oct	13371364
Sensitivity of Hartmannella (Acanthamoeba) to 5-fluorocytosine, hydroxystilbamidine, and other substances.	1970 Nov	5536863
Ultrastructural alterations of Trypanosoma cruzi kinetoplast induced by the interaction of a trypanocidal drug (hydroxystilbamidine) with the kinetoplast DNA.	1971 Oct	5000212
Effect of hydroxystilbamidine on the kinetoplast of Trypanosoma gambiense in mice.	1975 Dec	1243650
Interaction between hydroxystilbamidine and DNA. II. Temperature jump relaxation study. Dynamics of nucleic acids and polynucleotides.	1975 Sep 12	1242364
Interaction between hydroxystilbamidine and DNA. I. Binding isotherms and thermodynamics of the association.	1975 Sep 12	1242363
Isolation of giant silk fibroin polysomes and fibroin mRNP particles using a novel ribonuclease inhibitor, hydroxystilbamidine.	1980 Oct	6893456
Chloroquine, hydroxystilbamidine, and dapsone inhibit resorption of fetal rat bone in organ culture.	1982 Sep	6817901

Sample Use Guides

In Vivo Use Guide

A total dose of 8 mg is given in daily doses of 225 mg in 200 ml of 5 percent dextrose by slow infusion.

Route of Administration: Intravenous

In Vitro Use Guide

Hairs infected with Microsporum audouini, M. canis, and Trichophyton schoenleini, respectively, as well as thick nail clippings infected with T. rubrum, were suspended for 72 hours at 30°C in 0.225 % aqueous solutions of hydroxystilbamidine. The minimum fungistatic concentration ranged from 60 ug/ml to 1000 ug/ml of Sabouraud's agar.

Name

Type

Language

HYDROXYSTILBAMIDINE

Official Name

English

hydroxystilbamidine [INN]

Common Name

English

Hydroxystilbamidine [WHO-DD]

Common Name

English

HYDROXYSTILBAMIDINE [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C514