FComEx: Canrenone (PC000905)

Record Information

Version

1.0

Creation date

2015-10-09 22:33:19 UTC

Update date

2017-01-19 02:36:40 UTC

FoodComEx ID

PC000905

FoodDB Record

FDB023096

Chemical Information

Name

Canrenone

Description

Canrenone is the major metabolite of spironolactone. Spironolactone is a competitive aldosterone receptor antagonist (ARA), has traditionally been the treatment of first choice in idiopathic hyperaldosteronism (IHA) and for preoperative management of aldosterone producing adenoma (APA), and its therapeutic properties are attributable to active metabolite canrenone. Canrenone and the K+ salt of canrenoate are also in clinical use: they avoid the formation of intermediate products with anti-androgenic and progestational actions, resulting in a decreased incidence of side effects. (PMID: 10790593) [HMDB]

CAS Number

976-71-6

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
17-Hydroxy-3-oxo-17a-pregna-4,6-diene-21-carboxylic acid g-lactone	hmdb
17-Hydroxy-3-oxo-17a-pregna-4,6-diene-21-carboxylic acid lactone	hmdb
17a-(2-Carboxyethyl)-17b-hydroxyandrosta-4,6-dien-3-one lactone	hmdb
17b-Hydroxy-3-oxopregna-4,6-diene-21-carboxylic acid	hmdb
20-Spiroxa-4,6-diene-3,21-dione	hmdb
3-(17b-Hydroxy-3-oxoandrosta-4,6-dien-17a-yl)propionic acid g-lactone	hmdb
3-(17b-Hydroxy-3-oxoandrosta-4,6-dien-17a-yl)propionic acid lactone	hmdb
3-(3-Oxo-17b-hydroxy-4,6-androstadien-17a-yl)propionic acid g-lactone	hmdb
3'-(3-Oxo-17b-hydroxyandrosta-4,6-dien-17a-yl)-propionic acid lactone	hmdb
Aldadiene	hmdb
Canrenone	hmdb
Phanurane	hmdb

Chemical Formula

C22H28O3

IUPAC name

(1'S,2R,2'R,10'R,11'S,15'S)-2',15'-dimethylspiro[oxolane-2,14'-tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane]-6',8'-diene-5,5'-dione

InChI Identifier

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

InChI Key

UJVLDDZCTMKXJK-WNHSNXHDSA-N

Isomeric SMILES

[H][C@@]12CC[C@@]3(CCC(=O)O3)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C=CC2=CC(=O)CC[C@]12C

Average Molecular Weight

340.4559

Monoisotopic Molecular Weight

340.203844762

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Steroid lactones

Alternative Parents