U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C25H38O4
Molecular Weight 402.5668
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OXPRENOATE

SMILES

[H][C@@]12CC[C@@](O)(CCC(O)=O)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])[C@H](CCC)CC4=CC(=O)CC[C@]34C

InChI

InChIKey=DNHCHRGCTVRAFT-JEHIOXJOSA-N
InChI=1S/C25H38O4/c1-4-5-16-14-17-15-18(26)6-10-23(17,2)19-7-11-24(3)20(22(16)19)8-12-25(24,29)13-9-21(27)28/h15-16,19-20,22,29H,4-14H2,1-3H3,(H,27,28)/t16-,19+,20+,22-,23+,24+,25-/m1/s1

HIDE SMILES / InChI
RU 28318 also known as OXPRENOATE is a mineralocorticoid receptor (MR) antagonist, inhibiting aldosterone production and secretion. RU 28318 has been studied in normal and diabetic rats. It was revealed, that in combination with angiotensin converting enzyme inhibitors, RU 28318 was the most effective at improving -dP/dt (a measure of diastolic function) and attenuated cardiac dysfunction in diabetes.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Evaluation of RU28318 and RU40555 as selective mineralocorticoid receptor and glucocorticoid receptor antagonists, respectively: receptor measures and functional studies.
1998 Nov
Direct targeting of hippocampal neurons for apoptosis by glucocorticoids is reversible by mineralocorticoid receptor activation.
2005 Aug
Patents

Sample Use Guides

Heart failure (HF) rats: treated for 4 weeks with intracerebroventricular RU28318 (1 μg/hr) had less hypothalamic ACE and AT1-R mRNA and protein, less NAD(P)H-induced superoxide in PVN, fewer excited PVN neurons, and lower plasma NE. RU28318 had no effect on plasma ALDO, or on ACE or AT1-R mRNA expression in brain cortex
Route of Administration: Other
Hearts removed from animals were perfused for 30 min and then subjected to 30 min of global ischemia (I) followed by a period of 30 min of reperfusion (R). Drugs were administered for 30 min either during perfusion before ischemia or during reperfusion after ischemia. Drug regimens tested were RU28318 (RU; 10-5 M), Captopril (Capt; 3.6 × 10-4 M), Losartan (Los; 3 × 10-4 M), RU + Capt, RU + Los, Capt + Los, and RU + Capt + Los (Triple). In ischemia/reperfusion- (I/R-) injury, was shown that combination approaches were better where Capt + Los + RU (Triple) therapy used in normal and diabetes. However, combination therapies with ACEI and ARBs are rarely employed in the clinic possibly due to fear over accumulating adverse effects in patients with heart disorders.
Name Type Language
OXPRENOATE
Common Name English
17-HYDROXY-3-OXO-7.ALPHA.-PROPYL-17.ALPHA.-PREGN-4-ENE-21-CARBOXYLATE
Common Name English
PREGN-4-ENE-21-CARBOXYLIC ACID, 17-HYDROXY-3-OXO-7-PROPYL-,(7.ALPHA.,17.ALPHA.)-
Common Name English
RU-28328
Code English
Classification Tree Code System Code
NCI_THESAURUS C448
Created by admin on Fri Dec 15 16:44:04 GMT 2023 , Edited by admin on Fri Dec 15 16:44:04 GMT 2023
Code System Code Type Description
CAS
786592-95-8
Created by admin on Fri Dec 15 16:44:04 GMT 2023 , Edited by admin on Fri Dec 15 16:44:04 GMT 2023
PRIMARY
PUBCHEM
3034004
Created by admin on Fri Dec 15 16:44:04 GMT 2023 , Edited by admin on Fri Dec 15 16:44:04 GMT 2023
PRIMARY
NCI_THESAURUS
C87707
Created by admin on Fri Dec 15 16:44:04 GMT 2023 , Edited by admin on Fri Dec 15 16:44:04 GMT 2023
PRIMARY
WIKIPEDIA
Oxprenoic acid
Created by admin on Fri Dec 15 16:44:04 GMT 2023 , Edited by admin on Fri Dec 15 16:44:04 GMT 2023
PRIMARY
EPA CompTox
DTXSID90229228
Created by admin on Fri Dec 15 16:44:04 GMT 2023 , Edited by admin on Fri Dec 15 16:44:04 GMT 2023
PRIMARY
FDA UNII
2JGY63UVRO
Created by admin on Fri Dec 15 16:44:04 GMT 2023 , Edited by admin on Fri Dec 15 16:44:04 GMT 2023
PRIMARY