Introduction：Basic information about Canrenone CAS 976-71-6, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Canrenone Basic information
| Product Name: | Canrenone |
| Synonyms: | phanurane;pregna-4,6-diene-21-carboxylicacid,17-hydroxy-3-oxo-,gamma-lactone,(17-alph;sc9376;spirolactonesc14266;CANRENOIC ACID GAMMA LACTONE;CANRENONE;CANRENONE-D4;4,6-ANDROSTADIEN[(17(B-1')-SPIRO-5')]-PERHYDROFURAN-2,3-DIONE |
| CAS: | 976-71-6 |
| MF: | C22H28O3 |
| MW: | 340.46 |
| EINECS: | 213-554-5 |
| Product Categories: | Spironolacrone;ASMANEX;Intermediates & Fine Chemicals;Pharmaceuticals;Steroids |
| Mol File: | 976-71-6.mol |
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Canrenone Chemical Properties
| Melting point | 158-1600C |
| alpha | D +24.5° (chloroform) |
| Boiling point | 416.25°C (rough estimate) |
| density | 1.1236 (rough estimate) |
| refractive index | 1.5000 (estimate) |
| storage temp. | room temp |
| solubility | DMSO: soluble20mg/mL, clear |
| form | powder |
| color | white to beige |
| Optical Rotation | [α]/D +17 to +24°, c = 1 in chloroform-d |
| Water Solubility | 272.4ug/L(25 ºC) |
| Major Application | pharmaceutical (small molecule) |
| InChI | InChI=1/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-/s3 |
| InChIKey | UJVLDDZCTMKXJK-MUWITHSMNA-N |
| SMILES | [C@@]12(CCC(=O)O1)CC[C@@]1([H])[C@]3([H])C=CC4=CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]21C |&1:0,8,10,20,22,26,r| |
| LogP | 2.54 at 25℃ |
| CAS DataBase Reference | 976-71-6 |
| NIST Chemistry Reference | Canrenone(976-71-6) |
Safety Information
| Hazard Codes | Xn,N |
| Risk Statements | 40-51/53 |
| Safety Statements | 36/37-61 |
| RIDADR | UN 3077 9 / PGIII |
| WGK Germany | 3 |
| HazardClass | 9 |
| HS Code | 29329990 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Aquatic Chronic 2
Carc. 2 Oral |
Canrenone Usage And Synthesis
| Chemical Properties | Pale yellow to pale Green Solid |
| Originator | Spiroctan,BoehringerMannheim,Switz.,1968 |
| Uses | Aldosterone antagonist. Diuretic |
| Uses | antiinflammatory, glucocorticoid |
| Uses | Inhibits aldosterone biosynthesis and blocks ouabain effects |
| Definition | ChEBI: Canrenone is a steroid lactone. |
| Manufacturing Process | The lactone is prepared as follows: A solution of 5 parts of 17α-carboxyethyl-17β-hydroxyandrost-4-en-3-one lactone and 5 parts of chloranil in 400 partsof xylene containing a trace of p-toluenesulfonic acid is heated at the boilingpoint of the solvent under reflux overnight. The solution is then cooled andfiltered through approximately 200 parts of silica gel. The gel is successivelywashed with 5%, 10%, and 15% ethyl acetate-benzene solutions, and thewashings comprising 15% ethyl acetate are thereupon purified bychromatography on a further quantity of silica gel, using benzene and ethylacetate as developing solvents. From the 15% ethyl acetate eluate there isobtained pure 17α-carboxyethyl-17β-hydroxyandrost-4,6-dien-3-one lactone,melting at 148° to 151°C. The product solidifies above this melting point andmelts again at 165°C. |
| Brand name | Luvion. |
| Therapeutic Function | Aldosterone antagonist, Diuretic |
| World Health Organization (WHO) | Canrenone, which has aldosterone antagonist activity, is a majormetabolite of spironolactone and the major metabolite of potassium canrenoate.See WHO comments for potassium canrenoate and spironolactone. |
| Flammability and Explosibility | Non flammable |
| Biological Activity | Mineralocorticoid receptor antagonist. Active metabolite of spironolactone ((7a,17a)-7-(Acetylthio)-17-hydroxy-3-oxopregn-4-ene-21-carboxylic acid g-lactone ). |
| Biochem/physiol Actions | Canrenone is a mineralocorticoid (aldosterone) inhibitor. |
Canrenone Preparation Products And Raw materials
| Raw materials | Iodomethane-->Potassium Propionate-->Androstenediol-->Chloranil |
