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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 of HYDROXYSTILBAMIDINE

SMILES

NC(=N)C1=CC=C(\C=C\C2=CC=C(C=C2O)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
Molecular Formula C16H16N4O
Molecular Weight 280.3244
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description
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

CNS Penetrant
2588
Curator's Comment: Hydroxystilbamidine enters CNs and thus is used as a retrograde tracer for neurons. All the experiments on CNS penetration were done using rats, although the same is applicable for human.

Originator

Approval Year

1953
193
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8583
HYDROXYSTILBAMIDINE ISETHIONATE

Approved Use

Unknown

Launch Date

1953
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse 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
Health Status: unhealthy
Age Group: 7 years
Sex: F
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
Health Status: unhealthy
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

AEs

AESignificanceDosePopulation
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
Health Status: unhealthy
Age Group: 7 years
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/13545726
Sourcing

Sourcing

Vendor/AggregatorIDURL
1PlusChem LLC
1P00BGES
AK Scientific
C459
BOC Sciences
495-99-8
Chem Scene
CS-8085
Chemodex
H0100
eMolecules
43473789
eMolecules
44841559
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
PubMed

PubMed

TitleDatePubMed
Chloroquine, hydroxystilbamidine, and dapsone inhibit resorption of fetal rat bone in organ culture.
1982-09
Isolation of giant silk fibroin polysomes and fibroin mRNP particles using a novel ribonuclease inhibitor, hydroxystilbamidine.
1980-10
Effect of hydroxystilbamidine on the kinetoplast of Trypanosoma gambiense in mice.
1975-12
Interaction between hydroxystilbamidine and DNA. II. Temperature jump relaxation study. Dynamics of nucleic acids and polynucleotides.
1975-09-12
Interaction between hydroxystilbamidine and DNA. I. Binding isotherms and thermodynamics of the association.
1975-09-12
Ultrastructural alterations of Trypanosoma cruzi kinetoplast induced by the interaction of a trypanocidal drug (hydroxystilbamidine) with the kinetoplast DNA.
1971-10
Sensitivity of Hartmannella (Acanthamoeba) to 5-fluorocytosine, hydroxystilbamidine, and other substances.
1970-11
The affinity of hydroxystilbamidine for psoriatic lesions.
1961-04
Hydroxystilbamidine treatment of North American blastomycosis.
1956-10
Hydroxystilbamidine in the treatment of Indian kala-azar.
1950-12

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.
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:54:35 GMT 2025
Edited
by admin
on Mon Mar 31 17:54:35 GMT 2025
Record UNII
39J262E49W
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
HYDROXYSTILBAMIDINE
INN   MI   WHO-DD  
INN  
Official Name English
HYDROXYSTILBAMIDINE [MI]
Preferred Name English
hydroxystilbamidine [INN]
Common Name English
Hydroxystilbamidine [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C514
Created by admin on Mon Mar 31 17:54:35 GMT 2025 , Edited by admin on Mon Mar 31 17:54:35 GMT 2025
Code System Code Type Description
EVMPD
SUB08085MIG
Created by admin on Mon Mar 31 17:54:35 GMT 2025 , Edited by admin on Mon Mar 31 17:54:35 GMT 2025
PRIMARY
MESH
C100274
Created by admin on Mon Mar 31 17:54:35 GMT 2025 , Edited by admin on Mon Mar 31 17:54:35 GMT 2025
PRIMARY
PUBCHEM
5284571
Created by admin on Mon Mar 31 17:54:35 GMT 2025 , Edited by admin on Mon Mar 31 17:54:35 GMT 2025
PRIMARY
SMS_ID
100000083643
Created by admin on Mon Mar 31 17:54:35 GMT 2025 , Edited by admin on Mon Mar 31 17:54:35 GMT 2025
PRIMARY
DRUG BANK
DB14753
Created by admin on Mon Mar 31 17:54:35 GMT 2025 , Edited by admin on Mon Mar 31 17:54:35 GMT 2025
PRIMARY
INN
456
Created by admin on Mon Mar 31 17:54:35 GMT 2025 , Edited by admin on Mon Mar 31 17:54:35 GMT 2025
PRIMARY
FDA UNII
39J262E49W
Created by admin on Mon Mar 31 17:54:35 GMT 2025 , Edited by admin on Mon Mar 31 17:54:35 GMT 2025
PRIMARY
WIKIPEDIA
HYDROXYSTILBAMIDINE
Created by admin on Mon Mar 31 17:54:35 GMT 2025 , Edited by admin on Mon Mar 31 17:54:35 GMT 2025
PRIMARY
MERCK INDEX
m6153
Created by admin on Mon Mar 31 17:54:35 GMT 2025 , Edited by admin on Mon Mar 31 17:54:35 GMT 2025
PRIMARY Merck Index
CAS
495-99-8
Created by admin on Mon Mar 31 17:54:35 GMT 2025 , Edited by admin on Mon Mar 31 17:54:35 GMT 2025
PRIMARY
EPA CompTox
DTXSID3023136
Created by admin on Mon Mar 31 17:54:35 GMT 2025 , Edited by admin on Mon Mar 31 17:54:35 GMT 2025
PRIMARY
ChEMBL
CHEMBL1301
Created by admin on Mon Mar 31 17:54:35 GMT 2025 , Edited by admin on Mon Mar 31 17:54:35 GMT 2025
PRIMARY
DRUG CENTRAL
1398
Created by admin on Mon Mar 31 17:54:35 GMT 2025 , Edited by admin on Mon Mar 31 17:54:35 GMT 2025
PRIMARY
NCI_THESAURUS
C65870
Created by admin on Mon Mar 31 17:54:35 GMT 2025 , Edited by admin on Mon Mar 31 17:54:35 GMT 2025
PRIMARY
ECHA (EC/EINECS)
207-811-0
Created by admin on Mon Mar 31 17:54:35 GMT 2025 , Edited by admin on Mon Mar 31 17:54:35 GMT 2025
PRIMARY
Related Record Type Details
Structure of Hydroxystilbamidine diisethionate
SALT/SOLVATE -> PARENT
Structure of Hydroxystilbamidine diisethionate
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of HYDROXYSTILBAMIDINE
ACTIVE MOIETY
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