SPIRORENONE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C24H28O3
Molecular Weight	364.4773
Optical Activity	UNSPECIFIED
Defined Stereocenters	10 / 10
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12C[C@]1([H])[C@@]3([H])[C@]4([H])[C@]5([H])C[C@]5([H])[C@@]6(CCC(=O)O6)[C@@]4(C)CC[C@]3([H])[C@@]7(C)C=CC(=O)C=C27

InChI

InChIKey=NZUIUYWHFPQZBH-HXCATZOESA-N

InChI=1S/C24H28O3/c1-22-6-3-12(25)9-17(22)13-10-14(13)20-16(22)4-7-23(2)21(20)15-11-18(15)24(23)8-5-19(26)27-24/h3,6,9,13-16,18,20-21H,4-5,7-8,10-11H2,1-2H3/t13-,14+,15-,16+,18+,20-,21+,22-,23+,24+/m1/s1

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Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6628506 | https://www.ncbi.nlm.nih.gov/pubmed/6329237

Spirorenone is an androstadienone derivative patented by Schering A.-G as a highly effective aldosterone antagonist. Spirorenone is 8.6 times as potent as spironolactone, but showed a lower affinity for the mineralocorticoid receptors. In phase I clinical trials Spirorenone was absorbed with a half-life of 20-30 min, achieving maximum concentrations of about 100 ng/ml (10 mg) and 260 ng/ml (40 mg) after 1-2 h. Disposition of the parent drug was biphasic with half-lives of 50-60 min (distribution) and 5-6 h (elimination). Neither significant accumulation nor enzyme induction was observed after prolonged treatment.

Originator

Approval Year

PubMed

Title	Date	PubMed
Determination of plasma levels of spirorenone, a new aldosterone antagonist, and one of its metabolites by high-performance liquid chromatography.	1982 Jun 11	7107766
Pharmacokinetics of the new aldosterone antagonist, spirorenone, in healthy volunteers after single and repeated daily doses.	1983	6628506

Patents

Sample Use Guides

In Vivo Use Guide

10 and 40 mg for 14 days

Route of Administration: Oral

Name

Type

Language

SPIRORENONE

Official Name

English

(6R,7R,8R,9S,10R,13S,14R,15S,16S,17S)-3',4',6,7,8,9,11,12,13,14,15,16,20,21-TETRADECAHYDRO-10,13-DIMETHYLSPIRO(17H-DICYCLOPROPA(6,7:15,16)CYCLOPENTA(A)PHENANTHRENE-17,2'(5'H)-FURAN)-3(10H),5'-DIONE

Common Name

English

spirorenone [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C101255