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Details

Stereochemistry ABSOLUTE
Molecular Formula C23H34O4
Molecular Weight 374.5137
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ROSTAFUROXIN

SMILES

[H][C@]12CC[C@]3([H])[C@]([H])(CC[C@]4(C)[C@](O)(CC[C@]34O)C5=COC=C5)[C@@]1(C)CC[C@H](O)C2

InChI

InChIKey=AEAPORIZZWBIEX-DTBDINHYSA-N
InChI=1S/C23H34O4/c1-20-8-5-17(24)13-15(20)3-4-19-18(20)6-9-21(2)22(25,10-11-23(19,21)26)16-7-12-27-14-16/h7,12,14-15,17-19,24-26H,3-6,8-11,13H2,1-2H3/t15-,17+,18+,19-,20+,21-,22+,23+/m1/s1

HIDE SMILES / InChI
Rostafuroxin (PST 2238) is a digitoxygenin derivative, which selectively displaces ouabain from the Na ,K -ATPase receptor. PST 2238, at concentrations up to 10−4 M, did not show any significant interaction with a- and b-adrenergic, D1, D2, D3, 5-HT1, 5-HT2, H1, H2, M1, M2, A1, A2, Ca2 , Na , or K channel–associated receptors, AT1, AT2, ETa, ETb, GABA, thromboxane, vasopressin, angiotensin II, or the steorid-hormone receptors (androgen, progestogen, estrogen and mineralocorticoid), confirming that PST 2238 is specific for Na ,K -ATPase. Rostafuroxin has been developed in an attempt to unravel the contribution of mutated adducin and endogenous ouabain in the pathogenesis of hypertension. The compound lowered blood pressure in Milan hypertensive rats and humans. Rostafuroxine had been in phase II clinical trials for the treatment of hypertension. Following adverse events in Rostafuroxin group were described: dizziness, headache, upper respiratory tract infections, high blood pressure.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Sodium-potassium adenosine triphosphatase
1.5 µM [IC50]
Conditions
Doses

Doses

DosePopulationAdverse events​
0.05 mg multiple, oral (unknown)
Studied dose
Dose: 0.05 mg
Route: oral
Route: multiple
Dose: 0.05 mg
Sources:
unhealthy
n = 84
Health Status: unhealthy
Condition: hypertension
Sex: M+F
Food Status: UNKNOWN
Population Size: 84
Sources:
Disc. AE: hypertension...
AEs leading to
discontinuation/dose reduction:
hypertension (1 pt)
Sources:
0.15 mg 1 times / day multiple, oral (unknown)
Studied dose
Dose: 0.15 mg, 1 times / day
Route: oral
Route: multiple
Dose: 0.15 mg, 1 times / day
Sources:
unhealthy
n = 84
Health Status: unhealthy
Condition: hypertension
Sex: M+F
Food Status: UNKNOWN
Population Size: 84
Sources:
Disc. AE: hypertension...
AEs leading to
discontinuation/dose reduction:
hypertension (3 patients)
Sources:
0.5 mg 1 times / day multiple, oral (unknown)
Studied dose
Dose: 0.5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 0.5 mg, 1 times / day
Sources:
unhealthy
n = 81
Health Status: unhealthy
Condition: hypertension
Sex: M+F
Food Status: UNKNOWN
Population Size: 81
Sources:
Disc. AE: hypertension...
AEs leading to
discontinuation/dose reduction:
hypertension (2 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
hypertension 1 pt
Disc. AE
0.05 mg multiple, oral (unknown)
Studied dose
Dose: 0.05 mg
Route: oral
Route: multiple
Dose: 0.05 mg
Sources:
unhealthy
n = 84
Health Status: unhealthy
Condition: hypertension
Sex: M+F
Food Status: UNKNOWN
Population Size: 84
Sources:
hypertension 3 patients
Disc. AE
0.15 mg 1 times / day multiple, oral (unknown)
Studied dose
Dose: 0.15 mg, 1 times / day
Route: oral
Route: multiple
Dose: 0.15 mg, 1 times / day
Sources:
unhealthy
n = 84
Health Status: unhealthy
Condition: hypertension
Sex: M+F
Food Status: UNKNOWN
Population Size: 84
Sources:
hypertension 2 patients
Disc. AE
0.5 mg 1 times / day multiple, oral (unknown)
Studied dose
Dose: 0.5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 0.5 mg, 1 times / day
Sources:
unhealthy
n = 81
Health Status: unhealthy
Condition: hypertension
Sex: M+F
Food Status: UNKNOWN
Population Size: 81
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
17 beta-(3-furyl)-5 beta-androstane-3 beta, 14 beta, 17 alpha-triol (PST 2238). A very potent antihypertensive agent with a novel mechanism of action.
1997 May 23
Adducin- and ouabain-related gene variants predict the antihypertensive activity of rostafuroxin, part 2: clinical studies.
2010 Nov 24
Patents

Sample Use Guides

0.05, 0.15, 0.5, 1.5, or 5.0 mg/day
Route of Administration: Oral
To assess the long-term effect of low concentrations of PST 2238 on the Na+ -K+ pump activity, NRK cells were incubated with PST 2238 for 5 d. PST 2238 stimulated the pump at 10(−6) M (26%, n.s.) and 10(−5) M (27%, p < 0.05).
Name Type Language
ROSTAFUROXIN
INN  
INN  
Official Name English
21,23-EPOXY-24-NOR-14.BETA.,5.BETA.-CHOLA-20,21-DIENE-3.BETA.,14,17.ALPHA.-TRIOL
Common Name English
rostafuroxin [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C270
Created by admin on Fri Dec 15 17:05:28 GMT 2023 , Edited by admin on Fri Dec 15 17:05:28 GMT 2023
Code System Code Type Description
PUBCHEM
153976
Created by admin on Fri Dec 15 17:05:28 GMT 2023 , Edited by admin on Fri Dec 15 17:05:28 GMT 2023
PRIMARY
CAS
156722-18-8
Created by admin on Fri Dec 15 17:05:28 GMT 2023 , Edited by admin on Fri Dec 15 17:05:28 GMT 2023
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WIKIPEDIA
Rostafuroxin
Created by admin on Fri Dec 15 17:05:28 GMT 2023 , Edited by admin on Fri Dec 15 17:05:28 GMT 2023
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ChEMBL
CHEMBL2107775
Created by admin on Fri Dec 15 17:05:28 GMT 2023 , Edited by admin on Fri Dec 15 17:05:28 GMT 2023
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EPA CompTox
DTXSID20870040
Created by admin on Fri Dec 15 17:05:28 GMT 2023 , Edited by admin on Fri Dec 15 17:05:28 GMT 2023
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SMS_ID
300000037040
Created by admin on Fri Dec 15 17:05:28 GMT 2023 , Edited by admin on Fri Dec 15 17:05:28 GMT 2023
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MESH
C106263
Created by admin on Fri Dec 15 17:05:28 GMT 2023 , Edited by admin on Fri Dec 15 17:05:28 GMT 2023
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FDA UNII
P848LCX62B
Created by admin on Fri Dec 15 17:05:28 GMT 2023 , Edited by admin on Fri Dec 15 17:05:28 GMT 2023
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DRUG BANK
DB12350
Created by admin on Fri Dec 15 17:05:28 GMT 2023 , Edited by admin on Fri Dec 15 17:05:28 GMT 2023
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INN
8391
Created by admin on Fri Dec 15 17:05:28 GMT 2023 , Edited by admin on Fri Dec 15 17:05:28 GMT 2023
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NCI_THESAURUS
C90733
Created by admin on Fri Dec 15 17:05:28 GMT 2023 , Edited by admin on Fri Dec 15 17:05:28 GMT 2023
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