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Spironolactone ( CASNO:52-01-7 )

Identification and Related Records
Name:
Spironolactone
CAS Registry number:
52-01-7
Synonyms:
Alderon
3-(3-Keto-7.alpha.-acetylthio-17.beta.-hydroxy-4-androsten-17.alph a.-yl)propionic acid lactone
Uractone
Spiro(17H-cyclopenta(a)phenauthrene-17,2-(3H)-furan)
Xenalon
Pregn-4-ene-21-carboxylic acid,7-(acetylthio)-17-hydroxy-3-oxo-,?- lactone,(7R,17R)-
Aldactone
17.alpha.-Pregn-4-ene-21-carboxylic acid, 17-hydroxy-7.alpha.-mercapto-3-oxo-, .gamma.-lactone, acetate
Euteberol
Prestwick_449
Pregn-4-ene-21-carboxylic acid, 7-(acetylthio)-17-hydroxy-3-oxo-, gamma-lactone, (7alpha,17alpha)-
Spironolactone A
Urusonin
Verospirone
SC 9420
SC 15983
Spiro(17H-cyclopenta(a)phenanthrene-17,2(5H)-furan), pregn-4-ene-21-carboxylic acid deriv.
Spiro-Tablinen
Spirolang
Spironolactone [BAN:INN:JAN]
7-alpha-Acetylthio-3-oxo-17-alpha-pregn-4-ene-21,17-beta-carbolactone
7-alpha-(acetylthio)-17-alpha-hydroxy-3-oxopregn-4-ene-21-carboxylic acid, gamma-lactone (9CI)
496916-40-6
Spironolactonum [INN-Latin]
Aldactone A
Aldactazide (TN)
Spiroctan
3-(3-Oxo-7-alpha-acetylthio-17-beta-hydroxyandrost-4-en-17-beta-yl)propionic acid lactone
7-(Acetylthio)-17-hydroxy-3-oxopregn-4-ene-21-carboxylic acid gamma-lactone
Pregn-4-ene-21-carboxylic acid, 7-(acetylthio)-17-hydroxy-3-oxo-, g-lactone, (7a,17a)-
Verospiron
EINECS(EC#):
200-133-6
Molecular Formula:
C24H32O4S
Molecular Weight:
416.57
Inchi:
InChI=1/C24H32O4S/c1-14(25)29-19-13-15-12-16(26)4-8-22(15,2)17-5-9-23(3)18(21(17)19)6-10-24(23)11-7-20(27)28-24/h12,17-19,21H,4-11,13H2,1-3H3/t17-,18-,19+,21+,22-,23-,24+/m0/s1
InChIKey:
LXMSZDCAJNLERA-PJKOONHHSA-N
Canonical SMILES:
CC(=O)SC1CC2=CC(=O)CCC2(C3C1C4CCC5(C4(CC3)C)CCC(=O)O5)C
Isomers smiles:
CC(=O)S[C@@H]1CC2=CC(=O)CC[C@@]2([C@@H]3[C@@H]1[C@@H]4CC[C@]5([C@]4(CC3)
C)CCC(=O)O5)C
Chemical and Physical Properties
Appearance:
White powder.
Density:
1.24g/cm3
Melting Point:
198-207℃
Boiling Point:
597℃ at 760mmHg
Refractive Index:
-36 ° (C=1, CHCl3)
Flash Point:
302.3℃
Alpha:
-37 ° (C=1, CHCL3)
Water:
practically insoluble
Solubilities:
practically insoluble
Color/Form:
Crystals from methanol
Light cream-colored to light tan, crystalline powder
Stability:
Stable under normal temperatures and pressures.
Storage temp:
Keep container closed when not in use. Store in a cool, dry, well-ventilated area away from incompatible substances.
Spectral properties:
Specific optical rotation = -33.5 deg (chloroform)
UV max: 238 nm (epsilon 20200)
Computed Properties:
Molecular Weight:416.57348 [g/mol]
Molecular Formula:C24H32O4S
XLogP3:2.9
H-Bond Donor:0
H-Bond Acceptor:5
Rotatable Bond Count:2
Tautomer Count:10
Exact Mass:416.20213
MonoIsotopic Mass:416.20213
Topological Polar Surface Area:85.7
Heavy Atom Count:29
Formal Charge:0
Complexity:818
Isotope Atom Count:0
Defined Atom Stereocenter Count:7
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:2
Feature 3D Ring Count:5
Effective Rotor Count:4.2
Conformer Sampling RMSD:0.8
CID Conformer Count:1
Safety and Handling
Hazard Codes:
T:Toxic
Risk Statements:
R40;R60
Safety Statements:
S53;S22;S36/37/39;S45
Formulations/Preparations:
SPIRONOLACTONE & HYDROCHLOROTHIAZIDE: ALDACTAZIDE (SEARLE). ORAL: EACH TABLET CONTAINS SPIRONOLACTONE 25 MG & HYDROCHLOROTHIAZIDE 25 MG.
Oral: Tablets, film-coated: 25 mg Aldactone (with povidone), (Pfizer) Spironolactone Tablets (Mutual), Spironolactone Tablets (Mylan), Spironolactone Tablets (Sandoz), Spironolactone Tablets (UDL), Spironolactone Tablets, (United Research); 50 mg Aldactone (with povidone; scored), (Pfizer), Spironolactone Tablets (Actavis), Spironolactone Tablets (Mutual), Spironolactone Tablets (Mylan), Spironolactone Tablets (United Research); 100 mg Aldactone (with povidone; scored), (Pfizer), Spironolactone Tablets (Actavis), Spironolactone Tablets (Mutual), Spironolactone Tablets (Mylan), Spironolactone Tablets (United Research).
aldactone
aldactone a
spiresis
spiridon
spirolang
spirone
uractone
verospiron
verospirone
Exposure Standards and Regulations:
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl spironolactone, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
Specification:
The Spironolactone, with the cas registry number 52-01-7, has the IUPAC name of S-[(7R,8R,9S,10R,13S,14S,17R)-10,13-dimethyl-3,5'-dioxospiro[2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-17,2'-oxolane]-7-yl] ethanethioate. This is a kind of white to off white solid, and is practically insoluble. Its product categories are including Active Pharmaceutical Ingredients; Biochemistry; Steroids; Steroids (Others); Intermediates & Fine Chemicals; Pharmaceuticals; API's. As to its usage, it is a kind of diuretic and also used as an antiandrogen.
The physical properties of this chemical are as follows: (1)ACD/LogP: 3.12; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.12; (4)ACD/LogD (pH 7.4): 3.12; (5)ACD/BCF (pH 5.5): 139.34; (6)ACD/BCF (pH 7.4): 139.34; (7)ACD/KOC (pH 5.5): 1192.14; (8)ACD/KOC (pH 7.4): 1192.14; (9)#H bond acceptors: 4; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 85.74; (13)Index of Refraction: 1.585; (14)Molar Refractivity: 112.68 cm3; (15)Molar Volume: 335.7 cm3; (16)Polarizability: 44.67 ×10-24 cm3; (17)Surface Tension: 50.8 dyne/cm; (18)Density: 1.24 g/cm3; (19)Flash Point: 302.3 °C; (20)Enthalpy of Vaporization: 88.93 kJ/mol; (21)Boiling Point: 597 °C at 760 mmHg; (22)Vapour Pressure: 3.24E-14 mmHg at 25°C; (23)Exact Mass: 416.20213; (24)MonoIsotopic Mass: 416.20213; (25)Topological Polar Surface Area: 85.7; (26)Heavy Atom Count: 29; (27)Formal Charge: 0; (28)Complexity: 818.
When you are dealing with this chemical, you should be very cautious. For being a kind of irritant chemical to eyes, respiratory system and skin, it may cause inflammation to the skin or other mucous membranes. Then it is harmful which may cause damage to health. What's more, it is even toxic which could at low levels cause damage to health. This chemical may have impair fertility and may have limited evidence of a carcinogenic effect.
Therefore, you should take the following instructions to protect yourself. Wear suitable protective clothing, gloves and eye/face protection and avoid exposure - obtain special instructions before use. If in case of accident or if you feel unwell seek medical advice immediately (show the label where possible), and if in case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Then do remember not breathe dust. When store it, keep in a dry, cool and well-ventilated place, away from the food raw material.
In addition, you could convert the following datas into the molecular structure:
(1)Canonical SMILES: CC(=O)SC1CC2=CC(=O)CCC2(C3C1C4CCC5(C4(CC3)C)CCC(=O)O5)C
(2)Isomeric SMILES: CC(=O)S[C@@H]1CC2=CC(=O)CC[C@@]2([C@@H]3[C@@H]1[C@@H]4CC[C@]5([C@]4(CC3)C)CCC(=O)O5)C
(3)InChI: InChI=1S/C24H32O4S/c1-14(25)29-19-13-15-12-16(26)4-8-22(15,2)17-5-9-23(3)18(21(17)19)6-10-24(23)11-7-20(27)28-24/h12,17-19,21H,4-11,13H2,1-3H3/t17-,18-,19+,21+,22-,23-,24+/m0/s1
(4)InChIKey: LXMSZDCAJNLERA-ZHYRCANASA-N
Below are the toxicity information of this chemical:
Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
human TDLo oral 5600mg/kg (5600mg/kg) KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED Journal of Laboratory and Clinical Medicine. Vol. 80, Pg. 224, 1972.
man TDLo oral 5714ug/kg/4D- (5.714mg/kg) LUNGS, THORAX, OR RESPIRATION: "FIBROSIS, FOCAL (PNEUMOCONIOSIS)"

BLOOD: AGRANULOCYTOSIS

BLOOD: CHANGES IN CELL COUNT (UNSPECIFIED)
Drug Intelligence and Clinical Pharmacy. Vol. 21, Pg. 974, 1987.
man TDLo oral 7500ug/kg/3W- (7.5mg/kg) BLOOD: AGRANULOCYTOSIS Australian and New Zealand Journal of Medicine. Vol. 30, Pg. 515, 2000.
man TDLo oral 7500ug/kg/3W- (7.5mg/kg) BLOOD: AGRANULOCYTOSIS

BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE
Australian and New Zealand Journal of Medicine. Vol. 30, Pg. 515, 2000.
mouse LD50 intraperitoneal 260mg/kg (260mg/kg) ? Drugs in Japan Vol. 6, Pg. 381, 1982.
mouse LD50 intravenous 260mg/kg (260mg/kg) ? Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 9, Pg. 759, 1967.
mouse LD50 oral > 1gm/kg (1000mg/kg) ? Journal of Environmental Pathology and Toxicology. Vol. 1(5), Pg. 641, 1978.
rabbit LD50 intraperitoneal 866mg/kg (866mg/kg) Journal of Environmental Pathology and Toxicology. Vol. 1(5), Pg. 641, 1978.
rabbit LD50 oral > 1gm/kg (1000mg/kg) Journal of Environmental Pathology and Toxicology. Vol. 1(5), Pg. 641, 1978.
rat LD50 intraperitoneal 277mg/kg (277mg/kg) Drugs in Japan Vol. 6, Pg. 381, 1982.
rat LD50 oral > 1gm/kg (1000mg/kg) Drugs in Japan Vol. 6, Pg. 381, 1982.
women TDLo oral 70mg/kg/5W-I (70mg/kg) BLOOD: AGRANULOCYTOSIS British Medical Journal. Vol. 289, Pg. 731, 1984.
women TDLo oral 122mg/kg/61D- (122mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" New Zealand Medical Journal. Vol. 83, Pg. 147, 1976.
Octanol/Water Partition Coefficient:
log Kow = 2.78
Disposal Methods:
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Use and Manufacturing
Use and Manufacturing:
Methods of Manufacturing
US PATENT 3013012 (1961 TO SEARLE)
Usage:
It is a synthetic 17-lactone steroid which is a renal competitive aldosterone antagonist in a class of pharmaceuticals called potassium-sparing diuretics, used primarily to treat ascites in patients with liver disease, low-renin hypertension, hypok.
Biomedical Effects and Toxicity
Biological Activity:
Competitive mineralocorticoid (aldosterone) receptor antagonist that exhibits antihypertensive activity in vivo . Also displays antiandrogen activity and inhibits steroid hormone biosynthesis.
Pharmacological Action:
- Compounds which inhibit or antagonize the biosynthesis or actions of aldosterone.
- Agents that promote the excretion of urine through their effects on kidney function.
Therapeutic Uses:
Aldosterone Antagonists; Diuretics
EXPL THER: Aldosterone is important in the pathophysiology of heart failure. In a doubleblind study, we enrolled 1663 patients who had severe heart failure and a left ventricular ejection fraction of no more than 35 percent and who were being treated with an angiotensin-converting-enzyme inhibitor, a loop diuretic, and in most cases digoxin. A total of 822 patients were randomly assigned to receive 25 mg of spironolactone daily, and 841 to receive placebo. The primary end point was death from all causes. The trial was discontinued early, after a mean follow-up period of 24 months, because an interim analysis determined that spironolactone was efficacious. There were 386 deaths in the placebo group (46 percent) and 284 in the spironolactone group (35 percent; relative risk of death, 0.70; 95 percent confidence interval, 0.60 to 0.82; P<0.001). This 30 percent reduction in the risk of death among patients in the spironolactone group was attributed to a lower risk of both death from progressive heart failure and sudden death from cardiac causes. The frequency of hospitalization for worsening heart failure was 35 percent lower in the spironolactone group than in the placebo group (relative risk of hospitalization, 0.65; 95 percent confidence interval, 0.54 to 0.77; P<0.001). In addition, patients who received spironolactone had a significant improvement in the symptoms of heart failure, as assessed on the basis of the New York Heart Association functional class (P<0.001). Gynecomastia or breast pain was reported in 10 percent of men who were treated with spironolactone, as compared with 1 percent of men in the placebo group (P<0.001). The incidence of serious hyperkalemia was minimal in both groups of patients. [Pitt B et al; N Engl J Med 341 (10): 709-17 (1999)]
Biomedical Effects and Toxicity:
At the time spironolactone was introduced for clinical use, its bioavailability was inadequate, and this was improved by preparing the drug in finely powdered or micronized form. The absolute bioavailability was indirectly estimated at approximately 73%, which was enhanced in the presence of food. Nearly all absorbed spironolactone (> 90 %) is bound to plasma proteins and, with repeated dosing, a steady state is achieved within 8 days. After oral intake of a 100-mg dose, the plasma half-time of spironolactone was 1-2 h, the time to maximum plasma concentration was 2-3.2 hr, the maximum blood concentration was 92-148 ng/mL, the area under the concentration--time (0-24 hr) curve was 1430-1541 ng/mL per hr and the elimination half-time was 18-20 hr.
The disposition of (14)C spironolactone was studied in male rats, female dogs and female monkeys after intravenous or oral administration of 5 mg/kg bw. Gastrointestinal absorption was estimated to be 82% in rats, 62% in dogs and 103% in monkeys. Spironolactone was extensively metabolized in all three species, and the metabolites were excreted primarily in the urine and feces. The amount of radiolabel excreted in urine or feces of all three species was similar after intravenous and after oral dosing. In monkeys, as in humans, the amounts excreted in urine and feces were about equal, while fecal excretion predominated in rats and dogs as a result of biliary excretion. After the oral dose, the percentage of urinary excretion was 4.7% in rats, 18% in dogs and 46% in monkeys. The high excretion of radiolabel in the feces of rats (90%) after intravenous administration shows the importance of biliary excretion for that species. Species differences were also noted in the biotransformation of spironolactone.
Absorption of spironolactone from the GI tract depends on the formulation in which it is administered. Currently available formulations of spironolactone are well absorbed from the GI tract and bioavailability of the drug exceeds 90% when compared to an optimally absorbed spironolactone solution in polyethylene glycol 400. Following a single oral dose of spironolactone, peak serum concentrations of the drug occur within 1-2 hours, and peak serum concentrations of its principal metabolites are attained within 2-4 hours. When spironolactone is administered concomitantly with food, peak serum concentrations and areas under the serum concentration-time curves (AUCs) of the drug and, to a lesser degree, its principal metabolites are increased substantially compared with the fasting state.
Spironolactone and canrenone, a major metabolite of the drug, are both more than 90% bound to plasma proteins. Spironolactone or its metabolites may cross the placenta. Canrenone, a major metabolite of spironolactone, is distributed into milk.
Environmental Fate and Exposure Potential
Environmental Fate/Exposure Summary:
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 770(SRC), determined from a log Kow of 2.78(2) and a regression-derived equation(3), indicates that spironolactone is expected to have low mobility in soil(SRC). Volatilization of spironolactone from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.1X10-10 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Spironolactone is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.2X10-11 mm Hg(SRC), determined from a fragment constant method(5). Biodegradation data were not available(SRC, 2007).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 770(SRC), determined from a log Kow of 2.78(2) and a regression-derived equation(3), indicates that spironolactone is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.1X10-10 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 27(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data were not available(SRC, 2007).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), spironolactone, which has an estimated vapor pressure of 3.2X10-11 mm Hg at 25 deg C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase spironolactone may be removed from the air by wet or dry deposition(SRC). Spironolactone does not absorb light at wavelengths >290 nm(4) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
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