976-71-6

Basic information

• Product Name: Canrenone
• Synonyms: PREGNA-4,6-DIENE-17-BETA-0L-3-ONE-21-CARBOXYLIC ACID-GAMMA LACTONE;11614r.p;17-(2-Carboxyethyl)17-hydroxy-3-oxoandrosta-4,6-dienelactone;17-(2-Carboxyethyl)17-hydroxyandrosta-4,6-dien-3-onelactone;17-hydroxy-3-oxo-,gamma-lactone,(17-alpha)-pregna-6-diene-21-carboxylicacid;17-Hydroxy-3-oxo-17-pregna-4,6-diene-21-carboxylicacid-lactone;phanurane;pregna-4,6-diene-21-carboxylicacid,17-hydroxy-3-oxo-,gamma-lactone,(17-alph
• CAS NO: 976-71-6
• Molecular Formula: C₂₂H₂₈O₃
• Molecular Weight: 340.46
• EINECS: 213-554-5
• Product Categories: Spironolacrone;Intermediates & Fine Chemicals;Pharmaceuticals;Steroids;ASMANEX
• Mol File: 976-71-6.mol

Chemical Properties

• Melting Point: 158-1600C
• Boiling Point: 416.25°C (rough estimate)
• Flash Point: 237.6 °C
• Appearance: white to beige/
• Density: 1.1236 (rough estimate)
• Vapor Pressure: 8.95E-12mmHg at 25°C
• Refractive Index: 1.5000 (estimate)
• Storage Temp.: Store at RT
• Solubility: DMSO: soluble20mg/mL, clear
• Water Solubility: 272.4ug/L(25 oC)
• CAS DataBase Reference: Canrenone(CAS DataBase Reference)
• NIST Chemistry Reference: Canrenone(976-71-6)
• EPA Substance Registry System: Canrenone(976-71-6)

Safety Data

• Hazard Codes: Xn,N
• Statements: 40-51/53
• Safety Statements: 36/37-61
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 976-71-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Canrenone is used as an aldosterone antagonist for the treatment of hypertension and heart failure. It helps to reduce the levels of aldosterone, which in turn decreases sodium and water retention, leading to a reduction in blood pressure and improvement in heart function.
Used in Diuretic Therapy:
Canrenone is used as a diuretic for the treatment of edema and fluid retention. It promotes the excretion of excess fluid and sodium from the body, thereby reducing the volume of blood and relieving the symptoms of edema.
Used in Heart Failure Management:
Canrenone is used as a heart failure management agent for the treatment of patients with severe heart failure. It helps to improve the heart's pumping function and reduce the workload on the heart, leading to an improvement in the overall condition of the patient.
Used in Hypertension Treatment:
Canrenone is used as an antihypertensive agent for the treatment of patients with hypertension. It helps to lower blood pressure by reducing the levels of aldosterone, which in turn decreases sodium and water retention in the body.

World Health Organization (WHO)

Canrenone, which has aldosterone antagonist activity, is a major metabolite of spironolactone and the major metabolite of potassium canrenoate. See WHO comments for potassium canrenoate and spironolactone.

Flammability and Explosibility

Nonflammable

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.

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+/m0/s1

Synthetic route

SPIRONOLACTONE (52-01-7) → canrenone (976-71-6)

Conditions	Yield
With mercury dichloride In ethanol Ambient temperature;	95%
With sodium methylate In tetrahydrofuran at 20℃; for 18h; Elimination;	72%
With potassium dihydrogenphosphate In ethanol at 40℃; Rate constant; Kinetics; Thermodynamic data; var. buffers, pH, temp., ionic strengh, spironolactone and buffer conc.; energy of activation;

potassium canrenoate → canrenone (976-71-6)

Conditions	Yield
With NH2SO4 In methanol for 0.0833333h; Heating;	92%
With hydrogenchloride In chloroform for 8h; Heating;	86%
With acetic acid for 0.5h; Heating;

17β-hydroxy-3-ethoxy-17α-pregna-3,5-diene-21-carboxylic acid-γ-lactone → canrenone (976-71-6)

Conditions	Yield
With chloranil In methanol; water; 1,2-dichloro-ethane at 20℃; for 1h;	84%

17β-hydroxy-3-ethoxy-17α-pregn-3,5-diene-21-carboxylic acid-γ-lactone → canrenone (976-71-6)

Conditions	Yield
Stage #1: 17β-hydroxy-3-ethoxy-17α-pregn-3,5-diene-21-carboxylic acid-γ-lactone With chloranil In methanol; dichloromethane; water at 20℃; for 1h; Stage #2: With sodium thiosulfate In methanol; water at 20℃; for 1h;	83%

3-oxopregn-4-ene-21,17α-carbolactone (976-70-5) → canrenone (976-71-6)

Conditions	Yield
With chloranil In tert-butyl alcohol Heating;	70%
With chloranil; toluene-4-sulfonic acid; xylene

SPIRONOLACTONE (52-01-7) → canrenone (976-71-6) + Chloronone (79327-11-0)

Conditions	Yield
With mercury dichloride In ethanol for 2h; Heating;	A 38% B 54%

C22H32O3 (13934-61-7, 14009-58-6) → canrenone (976-71-6)

Conditions	Yield
Yield given. Multistep reaction;

levonorgestrel (434-03-7) → canrenone (976-71-6)

Conditions

Yield

Multi-step reaction with 5 steps 1: 98 percent / trimethyl orthoformate, p-toluenesulfonic acid / methanol / 3 h / 50 °C 2: H2, triphenylphosphine, rhodium acetate dimer / ethyl acetate / 20 h / 80 °C / 9000.7 Torr 3: 100 percent / N-methylmorpholine N-oxide (NMO), RuCl2(Ph3P)3 / dimethylformamide / 0.17 h 4: 97 percent / 6 N HCl / tetrahydrofuran / 0.5 h 5: 70 percent / p-chloranil / 2-methyl-propan-2-ol / Heating View Scheme

17α-ethynyl-17β-hydroxy-5-androsten-3-one ethylene ketal (50407-76-6) → canrenone (976-71-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: H2, triphenylphosphine, rhodium acetate dimer / ethyl acetate / 20 h / 80 °C / 9000.7 Torr 2: 100 percent / N-methylmorpholine N-oxide (NMO), RuCl2(Ph3P)3 / dimethylformamide / 0.17 h 3: 97 percent / 6 N HCl / tetrahydrofuran / 0.5 h 4: 70 percent / p-chloranil / 2-methyl-propan-2-ol / Heating View Scheme

5'-hydroxyspiro-5-en-3-one (121936-43-4) → canrenone (976-71-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 100 percent / N-methylmorpholine N-oxide (NMO), RuCl2(Ph3P)3 / dimethylformamide / 0.17 h 2: 97 percent / 6 N HCl / tetrahydrofuran / 0.5 h 3: 70 percent / p-chloranil / 2-methyl-propan-2-ol / Heating View Scheme

C24H34O4 (75219-50-0) → canrenone (976-71-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 97 percent / 6 N HCl / tetrahydrofuran / 0.5 h 2: 70 percent / p-chloranil / 2-methyl-propan-2-ol / Heating View Scheme

3-(3-oxo-7α-thio-17β-hydroxy-4-androsten-17α-yl)propionic acid γ-lactone (38753-76-3) + methyl iodide (74-88-4) → canrenone (976-71-6) + 7-Thiomethylspirolactone (38753-77-4)

Conditions	Yield
With sodium hydride In tetrahydrofuran at 20℃; for 2h;

3-(3-oxo-7α-thio-17β-hydroxy-4-androsten-17α-yl)propionic acid γ-lactone (38753-76-3) → canrenone (976-71-6)

Conditions	Yield
With sodium methylate; methyl iodide In methanol at 20℃; for 1h;

SPIRONOLACTONE (52-01-7) → 3-(3-oxo-7α-thio-17β-hydroxy-4-androsten-17α-yl)propionic acid γ-lactone (38753-76-3) + canrenone (976-71-6)

Conditions	Yield
With sodium hypochlorite; octabromotetrakis(2,6-dichlorophenyl)porphyrin Fe(III)Cl In water; acetonitrile at 80℃; for 0.833333h; Microwave irradiation;
With curvularia lunata Microbiological reaction;

Androstenedione (63-05-8) → canrenone (976-71-6)

Conditions

Yield

Multi-step reaction with 5 steps 1: potassium hydroxide / tetrahydrofuran / 6.5 h / 15 - 20 °C / Inert atmosphere 2: 5%-palladium/activated carbon; hydrogen / ethanol / 5 h / 20 - 30 °C / Inert atmosphere 3: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium bromide; sodium hypochlorite; tetrabutyl-ammonium chloride / dichloromethane / 6 h / 10 - 15 °C 4: pyridine; sodium acetate; acetic acid; N-Bromosuccinimide / acetone; water / 2 h / -2 - 2 °C 5: lithium carbonate; lithium bromide / N,N-dimethyl-formamide / 3 h / 100 - 105 °C View Scheme

C22H29BrO3 → canrenone (976-71-6)

Conditions	Yield
With lithium carbonate; lithium bromide In N,N-dimethyl-formamide at 100 - 105℃; for 3h;	7.8 g

17,23-dihydroxy-21,24-dinor-17βH-chol-4-en-20-yn-3-one (55542-26-2) → canrenone (976-71-6)

Conditions

Yield

Multi-step reaction with 4 steps 1: 5%-palladium/activated carbon; hydrogen / ethanol / 5 h / 20 - 30 °C / Inert atmosphere 2: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium bromide; sodium hypochlorite; tetrabutyl-ammonium chloride / dichloromethane / 6 h / 10 - 15 °C 3: pyridine; sodium acetate; acetic acid; N-Bromosuccinimide / acetone; water / 2 h / -2 - 2 °C 4: lithium carbonate; lithium bromide / N,N-dimethyl-formamide / 3 h / 100 - 105 °C View Scheme

17α-(3-hydroxypropyl)-17β-hydroxy-4-androsten-3-one (55542-27-3) → canrenone (976-71-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium bromide; sodium hypochlorite; tetrabutyl-ammonium chloride / dichloromethane / 6 h / 10 - 15 °C 2: pyridine; sodium acetate; acetic acid; N-Bromosuccinimide / acetone; water / 2 h / -2 - 2 °C 3: lithium carbonate; lithium bromide / N,N-dimethyl-formamide / 3 h / 100 - 105 °C View Scheme

SPIRONOLACTONE (52-01-7) → 3-(17β-hydroxy-3-oxo-1,4,6-androstadien-17α-yl)propionic acid γ-lactone (6785-74-6) + canrenone (976-71-6)

Conditions	Yield
With gibberella fujikuroi for 240h; Microbiological reaction;

SPIRONOLACTONE (52-01-7) → 15α-hydroxycanrenone (58551-67-0) + 1β-hydroxycanronene + 1α-hydroxycanrenone + 1-dehydro-15α-hydroxycanrenone + 3-(3-oxo-7α-thio-17β-hydroxy-4-androsten-17α-yl)propionic acid γ-lactone (38753-76-3) + 3-(17β-hydroxy-3-oxo-1,4,6-androstadien-17α-yl)propionic acid γ-lactone (6785-74-6) + canrenone (976-71-6)

Conditions	Yield
With aspergillus alliaceus Microbiological reaction;

SPIRONOLACTONE (52-01-7) → 15α-hydroxycanrenone (58551-67-0) + 1β-hydroxycanronene + 1α-hydroxycanrenone + 1-dehydro-15α-hydroxycanrenone + 3-(17β-hydroxy-3-oxo-1,4,6-androstadien-17α-yl)propionic acid γ-lactone (6785-74-6) + canrenone (976-71-6)

Conditions	Yield
With fusarium lini Microbiological reaction;

3-ethoxyandrosta-3,5-dien-17-one (972-46-3) → canrenone (976-71-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: lithium bromide; C30H31Cl3N3(1+)*BF4(1-); triethylamine / 1,2-dichloro-ethane / 5 h / 20 °C / Inert atmosphere; Sealed tube 2: chloranil / 1,2-dichloro-ethane; methanol; water / 1 h / 20 °C View Scheme

C25H32O5 → canrenone (976-71-6)

Conditions	Yield
With acetic acid In water; toluene at 0 - 100℃; for 24h; pH=7.1; Temperature; pH-value; Autoclave; Inert atmosphere;	33.1 g

C22H30O4 → canrenone (976-71-6)

Conditions	Yield
With methanesulfonyl chloride; triethylamine In dichloromethane at 0℃; for 4h; Temperature; Reagent/catalyst; Solvent; Inert atmosphere;	8.6 g

dehydroepiandrosterone (53-43-0) → canrenone (976-71-6)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: iodine; mercury dichloride; magnesium / diethyl ether / 0.5 h / 40 °C 1.2: 2.5 h / 0 - 20 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 °C 2.2: 2 h / 0 - 20 °C 2.3: 1 h / 0 - 20 °C 3.1: Dess-Martin periodane / dichloromethane / 4 h / 0 - 20 °C 4.1: chloranil / tert-butyl alcohol / 3 h / 80 °C View Scheme

21,24-dinor-3β,17β-dihydroxy-chol-5-en-22-yne (156894-83-6) → canrenone (976-71-6)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 °C 1.2: 2 h / 0 - 20 °C 1.3: 1 h / 0 - 20 °C 2.1: Dess-Martin periodane / dichloromethane / 4 h / 0 - 20 °C 3.1: chloranil / tert-butyl alcohol / 3 h / 80 °C View Scheme

3β,17β-Dihydroxy-5-androsten-17α-propanoic Acid γ-Lactone (13934-61-7) → canrenone (976-71-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: Dess-Martin periodane / dichloromethane / 4 h / 0 - 20 °C 2: chloranil / tert-butyl alcohol / 3 h / 80 °C View Scheme

C22H30O3 → canrenone (976-71-6)

Conditions	Yield
With chloranil In tert-butyl alcohol at 80℃; for 3h;	7.9 mg

formic acid (64-18-6) + canrenone (976-71-6) → C22H27ClO3 (66175-65-3) + 7α-Chlor-6β-(formyloxy)-17β-hydroxy-3-oxo-4,6-pregnadien-21-carbonsaeure-γ-lacton (110078-67-6)

Conditions	Yield
With tert-butylhypochlorite for 1h; Ambient temperature; Title compound not separated from byproducts;	A n/a B 91%

canrenone (976-71-6) + 4-(t-butyldimethylsilyloxy)-benzyl mercaptan (245076-35-1) → 3-oxo-17α-pregna-4-ene-7α-[4-(t-butyldimethylsilyloxy)-benzylthia]-21,17-carbolactone (245076-30-6)

Conditions	Yield
With sodium at 45℃; for 0.75h; Addition;	91%

canrenone (976-71-6) → 11α-hydroxyl canrenone (192569-17-8)

Conditions	Yield
With D-glucose; peptone In water	90%
With D-glucose In water for 72h;	80%
With D-glucose In water for 72h;	80%

N,N-dimethyl(methylene)ammonium chloride (30354-18-8) + canrenone (976-71-6) → 2α-Dimethylaminomethyl-3-oxo-17α-pregna-4,6-dien-21,17-carbolacton-hydrochlorid

Conditions	Yield
In acetonitrile for 24h; Ambient temperature;	86%

canrenone (976-71-6) + [4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanethiol (245076-36-2) → 3-oxo-17α-pregna-4-ene-7α-{4-[2-(1-piperidinyl)-ethoxy]benzylthia}-21,17-carbolactone

Conditions	Yield
With sodium at 45℃; for 1h; Addition;	82%

canrenone (976-71-6) → 9α,17-dihydroxy-3-oxo-17α-pregna-4,6-diene-21-carboxylic acid γ-lactone

Conditions	Yield
With Nocardia farcinica NCAIM (P)-B 001342 9α-hydroxylase; 13-ethyl-10,11α-dihydroxy-4-gonene-3,17-dione In methanol; water; N,N-dimethyl-formamide at 30℃; for 16h; Enzymatic reaction;	82%
With dipotassium hydrogenphosphate; D-glucose; sodium chloride In methanol; water at 26℃; for 5 - 48h; Conversion of starting material;
With dipotassium hydrogenphosphate; D-glucose; sodium chloride In methanol; water at 26℃; for 5 - 48h; Conversion of starting material;

canrenone (976-71-6) + thioacetic acid (507-09-5) → SPIRONOLACTONE (52-01-7)

Conditions	Yield
Stage #1: tiolacetic acid With trifluoromethylsulfonic anhydride In tetrahydrofuran Stage #2: canrenone In tetrahydrofuran at 20℃; for 1h;	76%
With trimethylsilyl trifluoromethanesulfonate In tetrahydrofuran at 20℃; for 3h;	60%
In water at 20℃; for 2h; Michael addition;

canrenone (976-71-6) + phenylmethanethiol (100-53-8) → 3-oxo-17α-pregna-4-ene-7α-(benzylthia)-21,17-carbolactone

Conditions	Yield
With sodium at 60℃; for 24h; Addition;	74%

canrenone (976-71-6) + allyl-trimethyl-silane (762-72-1) → C25H34O3 (76685-44-4) + C28H42O3Si (116506-59-3)

Conditions	Yield
titanium tetrachloride In dichloromethane at -70℃;	A 73% B 15%

1-thiopropane (107-03-9) + canrenone (976-71-6) → 3-oxo-17α-pregna-4-ene-7α-(propylthia)-21,17-carbolactone

Conditions	Yield
With sodium at 60℃; for 24h; Addition;	72%

acetic anhydride (108-24-7) + canrenone (976-71-6) + acetyl chloride (75-36-5) → 3-Acetoxy-17α-pregna-3,5,7-trien-21,17-carbolacton

Conditions	Yield
With pyridine for 24h; Heating;	70%

2-methylfuran (534-22-5) + canrenone (976-71-6) → 17β-hydroxy-7α-(5'-methyl-2'-furyl)-3-oxo-pregn-4-ene-21-carboxylic acid γ-lactone + 17β-hydroxy-7β-(5'-methyl-2'-furyl)-3-oxo-pregn-4-ene-21-carboxylic acid γ-lactone

Conditions	Yield
With ethanol; boron trifluoride diethyl etherate In nitromethane at -19℃; for 17h;	A 69.5% B 19.8%

canrenone (976-71-6) → 2α,6β,7α-Tribrom-3-oxo-17α-pregn-4-en-21,17-carbolacton

Conditions	Yield
With pyridinium hydrobromide perbromide In acetic acid for 1.5h; Ambient temperature;	69%

methylthiol (74-93-1) + canrenone (976-71-6) → 7-Thiomethylspirolactone (38753-77-4)

Conditions	Yield
With piperidine at 10℃;	69%
With piperidine In methanol at 20℃; for 20h;

canrenone (976-71-6) + thioacetic acid (507-09-5) → β-spironolactone (33784-05-3) + SPIRONOLACTONE (52-01-7)

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In tetrahydrofuran for 1h; Ambient temperature; Yields of byproduct given;	A n/a B 64%
With trimethylsilyl trifluoromethanesulfonate In tetrahydrofuran for 1h; Ambient temperature; Yield given;	A n/a B 64%

Hexanethiol (111-31-9) + canrenone (976-71-6) → 3-oxo-17α-pregna-4-ene-7α-(hexylthia)-21,17-carbolactone

Conditions	Yield
With sodium at 60℃; for 24h; Addition;	62%

canrenone (976-71-6) + thiophenol (108-98-5) → 3-oxo-17α-pregna-4-ene-7α-(phenylthia)-21,17-carbolactone

Conditions	Yield
With sodium at 60℃; for 24h; Addition;	59%

canrenone (976-71-6) + ethanethiol (75-08-1) → 17-hydroxy-7α-thioethyl-3-oxo-4-androstene-17α-pr0pi0nic acid, γ-lactone

Conditions	Yield
With sodium at 60℃; for 24h; Addition;	59%

1-hexene (592-41-6) + canrenone (976-71-6) → (+)-7α-hexyl-17-hydroxy-3-oxo-17α-pregn-4-ene-21-carboxylic acid γ-lactone (1430412-93-3) + (+)-7β-hexyl-17-hydroxy-3-oxo-17α-pregn-4-ene-21-carboxylic acid γ-lactone (1430412-96-6)

Conditions	Yield
Stage #1: 1-hexene With Schwartz's reagent In dichloromethane at 20℃; for 0.666667h; Inert atmosphere; Schlenk technique; Stage #2: canrenone With chloro-trimethyl-silane; copper(I) trifluoromethanesulfonate benzene In diethyl ether; dichloromethane at 20℃; for 15h; Inert atmosphere; Schlenk technique; diastereoselective reaction;	A 59% B 21%
Stage #1: 1-hexene With Schwartz's reagent In dichloromethane at 20℃; for 0.666667h; Inert atmosphere; Stage #2: With C36H30CuNO2P(1+)*CF3O3S(1-) In diethyl ether; dichloromethane at 20℃; for 0.166667h; Inert atmosphere; Stage #3: canrenone With chloro-trimethyl-silane In diethyl ether; dichloromethane at 20℃; for 15h; Inert atmosphere;	A 59% B 21%

canrenone (976-71-6) → γ-lactone of 17α-pregna-4,6-diene-3β,17β-diol-20-carboxylic acid (67605-87-2)

Conditions	Yield
With sodium tetrahydroborate In methanol	56%

canrenone (976-71-6) → 6α,7α-Epoxycanrenone

Conditions	Yield
With 2,6-di-tert-butyl-4-methyl-phenol; 3-chloro-benzenecarboperoxoic acid In chloroform for 1.66667h; Heating;	53%

Upstream product

• 976-70-5 3-oxopregn-4-ene-21,17α-carbolactone 
• 52-01-7 SPIRONOLACTONE 
• 50407-76-6 17α-ethynyl-17β-hydroxy-5-androsten-3-one ethylene ketal 
• 121936-43-4 5'-hydroxyspiro-5-en-3-one 
• 38753-76-3 3-(3-oxo-7α-thio-17β-hydroxy-4-androsten-17α-yl)propionic acid γ-lactone 
• 74-88-4 methyl iodide 
• 63-05-8 Androstenedione 
• 55542-26-2 17,23-dihydroxy-21,24-dinor-17βH-chol-4-en-20-yn-3-one 
• 55542-27-3 17α-(3-hydroxypropyl)-17β-hydroxy-4-androsten-3-one 
• 972-46-3 3-ethoxyandrosta-3,5-dien-17-one 
• 2181-04-6 Potassium canrenoate 
• 801-37-6 C₂₂H₃₀O₃ 
• 434-03-7 levonorgestrel 
• 13934-61-7 C₂₂H₃₂O₃ 

Downstream Products

• 52-01-7 SPIRONOLACTONE 
• 66175-65-3 C₂₂H₂₇ClO₃ 
• 110078-67-6 7α-Chlor-6β-(formyloxy)-17β-hydroxy-3-oxo-4,6-pregnadien-21-carbonsaeure-γ-lacton 
• 106112-12-3 C₂₉H₃₄O₄ 
• 33784-05-3 β-spironolactone 
• 110078-66-5 6β,7β-Epoxy-17β-hydroxy-3-oxo-4,6-pregnadien-21-carbonsaeure-γ-lacton 
• 73726-56-4 C₂₂H₂₈O₄ 
• 73726-57-5 C₂₂H₂₈O₅ 
• 114577-01-4 6α,7α-Epoxycanrenone 
• 245076-30-6 3-oxo-17α-pregna-4-ene-7α-[4-(t-butyldimethylsilyloxy)-benzylthia]-21,17-carbolactone 
• 38753-77-4 7-Thiomethylspirolactone 
• 76676-33-0 RU 26752 
• 192569-17-8 11α-hydroxyl canrenone 

Relevant articles and documents

Preformulation studies of spironolactone: Effect of pH, two buffer species, ionic strength, and temperature on stability

Using a stability-indicating HPLC assay method, the effect of pH, two buffer species (citrate and phosphate), ionic strength, and temperature on the stability of spironolactone in 20% solution of ethyl alcohol in water has been studied. The optimum pH of stability appears to be ~4.5. On increasing the buffer concentration, both species hastened the decomposition of spironolactone. The ionic strength did not affect the stability of the drug. The energy of activation has been estimated to be ~78.8 kJ/mol at pH 4.3. The un-ionized spironolactone is subject to general acid-base catalysis. The K(h) and K(oh) values at 40 °C have been estimated to be 1.63 and 2.8 x 105 day-1, respectively. The HPO4-2 ion had ~10 times more catalytic effect than the H2PO4-1 ion. This data will be used to develop a stable oral liquid dosage form of the drug.

The nitration of canrenone with acetic anhydride/nitric acid

3-Oxo-17α-pregna-4,6-diene-21,17-carbolactone (canrenone, II) is produced from the potassium salt of 17-hydroxy-3-oxo-17α-pregna-4,6-diene- 21-carboxylic acid (I) by acid catalyzed lactonization. II reacts with acetic anhydride/nitric acid to give one main product (III) and some minor products. The structure of III was determined by chemical and spectral analysis to be the 4-nitro derivative of canrenone. This result is in contrast to the known reactions of H with most other reagents that were found to add at Δ6, and also in contrast to the reactions of acetic anhydride/nitric acid with alkenes. Electrophilic substitution at the ambident C4 is discussed as the reaction path. The 4-nitro group enhances the inhibitor), activity of II against Na+/K+-ATPase, the target enzyme of the cardioactive digitalis glycosides, which appears to indicate increased cardioactivity.

Synthesis and reactions of 2-methylene-canrenone

Starting from the Mannich salt 1 of the aldosterone antagonist canrenone or from 2-methylene-canrenone (2) the A-ring annulated hetero- and carbocycles 5, 6, 8-13 were prepared. Receptor (estradiol, progesterone, androgen, gluco- and mineralocorticoid) binding studies and competition studies with the serum proteins SHBG and CBG were carried out using the compounds 2, 3, 4b, 5, 6b, 8 and 12. The relative binding affinities with CBG are below 1%, in all other cases lower than 0.01%.

One-Pot γ-Lactonization of Homopropargyl Alcohols via Intramolecular Ketene Trapping

A one-pot γ-lactonization of homopropargyl alcohols via an alkyne deprotonation/boronation/oxidation sequence has been developed. Oxidation of the generated alkynyl boronate affords the corresponding ketene intermediate, which is trapped by the adjacent hydroxy group to furnish the γ-lactone. We have optimized the conditions as well as examined the substrate scope and synthetic applications of this efficient one-pot lactonization.

Method for preparing spirolactone intermediate canrenone

The invention provides a method for preparing spirolactone intermediate canrenone. The method comprises the following operation steps: a lactone substance (I) is dissolved in an organic solvent, a catalyst and an auxiliary agent are added, and the mixture is stirred at 50-80 DEG C to prepare the canrenone (II), wherein the organic solvent is at least one of cyclohexane, toluene or methyl tetrahydrofuran; the auxiliary agent is at least one of dimethyl formamide, N,N - dimethyl acetamide and N-methyl pyrrolidone; and the catalyst is poly-4-vinylpyridine. The reaction route is shown in the specification. Compared with the prior art, the method has the advantages that the reaction temperature is low, pressurization is not needed, the quality of canrenone can be improved, the energy consumption can be effectively reduced, and the production cost can be reduced.

Synthesis method of canrenone

The invention provides a synthesis method of canrenone, and relates to the technical field of chemical synthesis. The synthesis method of canrenone comprises the following steps: (a) adding a compound in a formula 1 into an organic solvent to obtain a solution containing the compound in the formula 1; and (b) introducing the solution in the step (a) into a micro-channel reactor, and carrying out a decarboxylation reaction to obtain canrenone. The method can completely react within a short time, reduces side reactions caused by long-time high temperature, can continuously react in the microchannel reactor, has the advantages of high mass transfer efficiency, fast reaction, short time and less side reactions, greatly improves the experiment operability, has the yield equivalent to that of the original process, and solves the problems of slow reaction and dangerous and tedious operation, and improves the production applicability of the reaction.

Synthesis process of steroid compound, canrenone and spirolactone

The invention relates to the technical field of medicine synthesis, in particular to a synthesis process of a steroid compound, canrenone and spirolactone. An embodiment of the invention provides thesteroid compound. The steroid compound has a structural formula as shown in the specification. In the structural formula, R is selected from H or an alkyl group. The steroid compound can be used for synthesizing canrenone and spirolactone, synthesis conditions are mild, synthesis efficiency is high, the amount of wastewater is small, the quality of the formed products is high, and production costcan be effectively reduced.

Method for preparing canrenone as spironolactone intermediate

The invention relates to the technical field of canrenone preparation, and particularly discloses a method for preparing canrenone as a spironolactone intermediate. The method for preparing the canrenone as the spironolactone intermediate specifically comprises the steps that a biological fermentation product 7alpha-hydroxylactone is used as a raw material, a 6,7-site double-bond is formed, and the canrenone as the spironolactone intermediate is obtained. The method for preparing the canrenone as the spironolactone intermediate is simple and efficient and low in the production cost, suitable for large-scale industrial production and convenient for people to use.

Preparation method of canrenone

The invention provides a preparation method of canrenone. The preparation method comprises the following steps: synthesizing canrenone by using a dehydrogenation product compound I as a substrate, adding a catalyst, carrying out an internal esterification reaction, and optimizing a reaction line. After the reaction is completed, the product is adjusted to be neutral and is directly concentrated, and a high pressure reaction is carried out directly after a dry solvent is recycled by using methylbenzene with ethyl alcohol, so that the aftertreatment reaction steps are reduced, the hydrolysis ofan E-ring ethyl formate group is avoided, and the high-pressure reaction difficulty is greatly lowered. The operability of the reaction is greatly improved, the production cost is reduced, the side reactions are greatly reduced, the reaction of each step is relatively easy to realize, the yield is greatly improved, the production is more economical and safer, and the preparation method is more applicable for industrial production.

Fungal biotransformation of diuretic and antihypertensive drug spironolactone with Gibberella fujikuroi, Curvularia lunata, Fusarium lini, and Aspergillus alliaceus

Derivatives of spironolactone (1), a diuretic and antihypertensive drug, were synthesized by using fungal cells for the first time. Ten different fungi were screened for their ability to biotransform 1, four of which were able to produce metabolites 2–8. Gibberella fujikuroi produced canrenone (2), 1-dehydrocanrenone (3), Curvularia lunuta provided compound 2, and 7α-thio-spironolactone (4), Fusarium lini yielded compounds 2, 3, 1β-hydroxycanrenone (5), 1α-hydroxycanrenone (6), 1-dehydro-15α-hydroxycanrenone (7), and 15α-hydroxycanrenone (8), while Aspergillus alliaceus was able to produce all the seven metabolites. Metabolites 5, 6, and 7 were identified as new compounds. Their structures were elucidated by using different spectroscopic techniques. Substrate 1 and its metabolites 2, 3, and 5–8 were also evaluated for α-glucosidase inhibitory activity in vitro. Substrate 1 was found to be strongly active with IC50 = 335 ± 4.3 μM as compared to the standard drug acarbose IC50 = 840 ± 1.73 μM, whereas all of resulting metabolites were found to be inactive.