| Stereochemistry | ABSOLUTE |
| Molecular Formula | C22H28O3 |
| Molecular Weight | 340.4559 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 6 / 6 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CC[C@@]3(CCC(=O)O3)[C@@]1(C)CC[C@@]4([H])[C@@]2([H])C=CC5=CC(=O)CC[C@]45C
InChI
InChIKey=UJVLDDZCTMKXJK-WNHSNXHDSA-N
InChI=1S/C22H28O3/c1-20-9-5-15(23)13-14(20)3-4-16-17(20)6-10-21(2)18(16)7-11-22(21)12-8-19(24)25-22/h3-4,13,16-18H,5-12H2,1-2H3/t16-,17+,18+,20+,21+,22-/m1/s1
| Molecular Formula | C22H28O3 |
| Molecular Weight | 340.4559 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 6 / 6 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Canrenone, a spironolactone metabolite, is a mineralocorticoid receptor antagonist. Canrenone is used as a diuretic in Europe and, in particular, in Italy under brand name Luvion. Luvion is a tablet for oral application which is effective for the treatment Hyperaldosteronism primary, secondary hyperaldosteronism from edematous states ( heart failure congestive, cirrhosis of the liver in phase ascites , nephrotic syndrome ) and arterial hypertension essential where other therapies were not sufficiently effective or tolerate. In addition was suggested that canrenone might represent an effective therapy for idiopathic post-puberal hirsutism and it normalizds the cardiac response to the postural challenge in patients with preascitic cirrhosis. Canrenone seems to be effective in reducing blood pressure in patients with metabolic syndrome. Moreover, canrenone seems also to improve MPO, Lp(a), and metalloproteinases in these patients.
Approval Year
PubMed
Patents
Sample Use Guides
In the majority of cases are sufficient 50-200 mg per day, divided into one or more daily doses. In severe cases this dosage resistant or can be raised to 300 mg or more, according to medical prescription.
Route of Administration:
Oral
Canrenone (in concentration range: 0-10000 nM) decreased [3H]-progesterone binding to isolated uterine cytosolic progesterone receptors. The inhibition was concentration-dependent. Canrenone (in concentration range: 0-25150 nM) did not alter [3H]-oestradiol binding to isolated uterine cytosolic oestrogen receptors. Canrenone inhibition of progesterone binding to isolated cytosolic receptors was strictly competitive: Kd (apparent dissociation constant for progesterone binding) was increased in a concentration-dependent manner by canrenone, whereas Bmax (maximal number of progesterone binding sites/mg cytosolic protein) was unaltered. There was marked cooperativity in progesterone binding at high canrenone and low progesterone concentrations. The implication is that canrenone alters the subunit interaction of the receptor protein. Kd for progesterone was 3.2 X 10(-9)M. Ki (the inhibition constant for canrenone with respect to progesterone binding) was 300 X 10(-9)M.
