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Details

Stereochemistry ACHIRAL
Molecular Formula C16H16N4O.2C2H6O4S
Molecular Weight 532.588
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of HYDROXYSTILBAMIDINE ISETHIONATE

SMILES

OCCS(O)(=O)=O.OCCS(O)(=O)=O.NC(=N)C1=CC=C(C=CC2=C(O)C=C(C=C2)C(N)=N)C=C1

InChI

InChIKey=XVTQTNAKZYLTNZ-UHFFFAOYSA-N
InChI=1S/C16H16N4O.2C2H6O4S/c17-15(18)12-5-2-10(3-6-12)1-4-11-7-8-13(16(19)20)9-14(11)21;2*3-1-2-7(4,5)6/h1-9,21H,(H3,17,18)(H3,19,20);2*3H,1-2H2,(H,4,5,6)

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
Molecular Formula C2H6O4S
Molecular Weight 126.132
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
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
2554
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
8429
HYDROXYSTILBAMIDINE ISETHIONATE

Approved Use

Unknown

Launch Date

-5.05785614E11
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
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

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
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

Sourcing

Vendor/AggregatorIDURL
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

PubMed

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

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 Fri Dec 15 14:58:54 UTC 2023
Edited
by admin
on Fri Dec 15 14:58:54 UTC 2023
Record UNII
0163PVD2QZ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
HYDROXYSTILBAMIDINE ISETHIONATE
MI   ORANGE BOOK   WHO-DD  
Systematic Name English
HYDROXYSTILBAMIDINE ISETIONATE [MART.]
Common Name English
2-HYDROXY-4,4'-STILBENEDICARBOXAMIDINE BIS(2-HYDROXYETHANESULFONATE) (SALT)
Common Name English
BENZENECARBOXIMIDAMIDE, 4-(2-(4-(AMINOIMINOMETHYL)PHENYL)ETHENYL)-3-HYDROXY-, BIS(2-HYDROXYETHANESULPHONATE) (SALT)
Common Name English
HYDROXYSTILBAMIDINE ISETHIONATE [ORANGE BOOK]
Common Name English
HYDROXYSTILBAMIDINE ISETHIONATE [MI]
Common Name English
NSC-259242
Code English
2-HYDROXY-4,4'-STILBENEDICARBOXAMIDINE BIS(2-HYDROXYETHANESULPHONATE) (SALT)
Common Name English
Hydroxystilbamidine isethionate [WHO-DD]
Common Name English
BENZENECARBOXIMIDAMIDE, 4-(2-(4-(AMINOIMINOMETHYL)PHENYL)ETHENYL)-3-HYDROXY-, BIS(2-HYDROXYETHANESULFONATE) (SALT)
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C514
Created by admin on Fri Dec 15 14:58:54 UTC 2023 , Edited by admin on Fri Dec 15 14:58:54 UTC 2023
Code System Code Type Description
NCI_THESAURUS
C65871
Created by admin on Fri Dec 15 14:58:54 UTC 2023 , Edited by admin on Fri Dec 15 14:58:54 UTC 2023
PRIMARY
DRUG BANK
DB01040
Created by admin on Fri Dec 15 14:58:54 UTC 2023 , Edited by admin on Fri Dec 15 14:58:54 UTC 2023
PRIMARY
NSC
259242
Created by admin on Fri Dec 15 14:58:54 UTC 2023 , Edited by admin on Fri Dec 15 14:58:54 UTC 2023
PRIMARY
SMS_ID
100000086958
Created by admin on Fri Dec 15 14:58:54 UTC 2023 , Edited by admin on Fri Dec 15 14:58:54 UTC 2023
PRIMARY
PUBCHEM
10779
Created by admin on Fri Dec 15 14:58:54 UTC 2023 , Edited by admin on Fri Dec 15 14:58:54 UTC 2023
PRIMARY
CAS
533-22-2
Created by admin on Fri Dec 15 14:58:54 UTC 2023 , Edited by admin on Fri Dec 15 14:58:54 UTC 2023
PRIMARY
MERCK INDEX
m6153
Created by admin on Fri Dec 15 14:58:54 UTC 2023 , Edited by admin on Fri Dec 15 14:58:54 UTC 2023
PRIMARY Merck Index
ChEMBL
CHEMBL1301
Created by admin on Fri Dec 15 14:58:54 UTC 2023 , Edited by admin on Fri Dec 15 14:58:54 UTC 2023
PRIMARY
FDA UNII
0163PVD2QZ
Created by admin on Fri Dec 15 14:58:54 UTC 2023 , Edited by admin on Fri Dec 15 14:58:54 UTC 2023
PRIMARY
EVMPD
SUB02596MIG
Created by admin on Fri Dec 15 14:58:54 UTC 2023 , Edited by admin on Fri Dec 15 14:58:54 UTC 2023
PRIMARY
ECHA (EC/EINECS)
208-557-3
Created by admin on Fri Dec 15 14:58:54 UTC 2023 , Edited by admin on Fri Dec 15 14:58:54 UTC 2023
PRIMARY
Related Record Type Details
Structure of HYDROXYSTILBAMIDINE
PARENT -> SALT/SOLVATE
Structure of ISETHIONIC ACID
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of HYDROXYSTILBAMIDINE
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