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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

Molecular Formula C23H34O4
Molecular Weight 374.5137
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
1.5 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Doses

AEs

PubMed

Sample Use Guides

In Vivo Use Guide
0.05, 0.15, 0.5, 1.5, or 5.0 mg/day
Route of Administration: Oral
In Vitro Use Guide
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).
Substance Class Chemical
Record UNII
P848LCX62B
Record Status Validated (UNII)
Record Version