7-(Acetylthio)-17-hydroxy-3-oxopregn-4-ene-21-carboxylic acid gamma-lactone
Basic information
- CAS
52-01-7- Standard SMILES
CC(=O)S[C@@H]1CC2=CC(=O)CC[C@]2(C)[C@H]2CC[C@H]3[C@@H](CC[C@@]34CCC(=O)O4)[C@H]12- InChIKey
UTCPYQMSANLUTE-FCFLTHKLSA-N- Molecular formula
- C23H30O4S
- Average molar mass
- 402.5 g/mol
- Monoisotopic mass
- 402.18648061
Names & identifiers
- Preferred name
- 7-(Acetylthio)-17-hydroxy-3-oxopregn-4-ene-21-carboxylic acid gamma-lactone
- IUPAC
- S-[(7R,8S,9S,10R,13S,14R,17R)-10-methyl-3,5'-dioxospiro[1,2,6,7,8,9,11,12,13,14,15,16-dodecahydrocyclopenta[a]phenanthrene-17,2'-oxolane]-7-yl] ethanethioate
- English name
- Spironolactone
- Molecular formula
- C24H32O4S
- Molecular weight
- 416.58
Names & synonyms
7-(Acetylthio)-17-hydroxy-3-oxopregn-4-ene-21-carboxylic acid gamma-lactonePregn-4-ene-21-carboxylic acid, 7-(acetylthio)-17-hydroxy-3-oxo-, g-lactone, (7a,17a)-S-[(7R,8S,9S,10R,13S,14R,17R)-10-methyl-3,5'-dioxo-spiro[1,2,6,7,8,9,11,12,13,14,15,16-dodecahydrocyclopenta[a]phenanthrene-17,2'-tetrahydrofuran]-7-yl] ethanethioateOsyrolDiraSpirolactoneALDACTONESpironolacAbbolactone17-hydroxy-7alpha-mercapto-3-oxo-17alpha-pregn-4-ene-21-carboxylicacigamm7ALPHA-[ACETYLTHIO]-17ALPHA-HYDROXY-3-OXOPREGN-4-ENE-21-CARBOXYLIC ACID GAMMA-LACTONE17-hydroxy-7-alpha-mercapto-3-oxo-17-alpha-pregn-4-ene-21-carboxylic acid-gamma-lactone-7-acetate
Show more names
17-HYDROXY-7-ALPHA-MERCAPTO-3-OXO-17-ALPHA-PREGU-4-ENE-2[CARBOXYLIC ACID-GAMMA-LACTONE-7-ACETATE]
Database identifiers
Properties
Computed structural properties
- XLogP
- 3.3
- Topological polar surface area
- 85.7 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 2
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 773
Physicochemical properties
- Melting point
- 207 · 207-208 °C (lit.)
- alpha
- -37 · -37 º (c=1, CHCl3)
- Boiling point
- 504.87 °C · 504.87°C (rough estimate)
- Density
- 1.1061 · 1.1061 (rough estimate)
- refractive index
- -36 ° · -36 ° (C=1, CHCl3)
- storage temp.
- 2 · 2-8°C
- solubility
- Practically insoluble in water, soluble in ethanol (96 per cent).
- form
- Powder
- color
- White to yellow-white
- Water Solubility
- practically insoluble
- Merck
- 14 · 14,8760
- Henry's Law Constant
- 9 · 9.0×104 mol/(m3Pa) at 25℃, HSDB (2015)
- BCS Class
- 2 · 2,4,3
- Major Application
- pharmaceutical (small molecule)
- InChIKey
- LXMSZDCAJNLERA-ZHYRCANASA-N
- SMILES
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- TU4725000
- hs_code
- 29321900
- Toxicity
- LD50 in rats, mice, rabbits (mg/kg): 790, 360, 870 i.p. (IARC, 1980)
- risk_code
- 60-40-36/37/38
- Signal word
- Danger
- Symbol(GHS)
- GHS08
- hazard_code
- T,Xn,Xi
- safety_code
- 53-22-36/37/39-45-36-26
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard statements
- H360
- Hazard Classifications
- Carc. 2Repr. 1BSTOT RE 2
- Precautionary statements
- P201-P280-P308+P313
- Hazardous Substances Data
- 52-01-7(Hazardous Substances Data)
Chemistry & industry
Applications
UsesIt can be used as a kind of inefficient diuretic drugs. It is a synthetic 17-lactone steroid which is a kind of 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 and hypokalemia. The active metabolite of lactone (spironolactone); It can be used for the Inhibition of aldosterone biosynthesis. It can also be used as the blocker of the Quabain effect.
UsesSpironolactone, an aldosterone-, and competitive androgen-receptor-antagonist and 5-alpharductase- inhibitor, indicated for the treatment of androgen dependent hirsutism, ideally in doses of 50 to 200 mg per day accompanying the intake of oral contraceptives with the same seven day break in between. Side effects concerning the length of the menstrual cycle, the increase of blood pressure or potassium levels may occur. Spironolactone is the number one drug in the treatment of hirsutism in the US (Farquhar et al., 2003). In other countries the prescription of spironolactone for the treatment of hirsutism may be off-label.
UsesIt 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, hypokalemia
Usesdiuretic, aldosterone antagonist
General DescriptionSpironolactone, 7α-(acetylthio)-17α-hydroxy-3-oxopregn-4-ene-3-one-21-carboxylic acidγ-lactone (Aldactone) is an aldosterone antagonist of greatmedical importance because of its diuretic activity.
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