Pregn-4-ene-21-carboxylic acid, 7-(acetylthio)-17-hydroxy-3-oxo-, gamma-lactone, (7alpha,17alpha)-

Base Information

• Chemical Name: Pregn-4-ene-21-carboxylic acid, 7-(acetylthio)-17-hydroxy-3-oxo-, gamma-lactone, (7alpha,17alpha)-
• CAS No.: 52-01-7
• Molecular Formula: C24H32O4S
• Molecular Weight: 416.582
• Hs Code.: 29321900
• Wikidata: Q27167012
• ChEMBL ID: CHEMBL1562223
• Mol file: 52-01-7.mol

Synonyms:MLS000678252;SMR000285350;Spiretic;4-(acetylsulfanyl)-9a,11a-dimethyl-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydrospiro[cyclopenta[a]phenanthrene-1,2'-oxolane]-5',7-dione;S-(10,13-dimethyl-3,5'-dioxo-1,2,3,4',5',6,7,8,9,10,11,12,13,14,15,16-hexadecahydro-3'H-spiro[cyclopenta[a]phenanthrene-17,2'-furan]-7-yl) ethanethioate;Aldactazide (Salt/Mix);NCGC00015948-02;S-[(7R,8R,10R,13S,17R)-10,13-dimethyl-3,5'-dioxo-1,2,3,4',5',6,7,8,9,10,11,12,13,14,15,16-hexadecahydro-3'H-spiro[cyclopenta[a]phenanthrene-17,2'-furan]-7-yl] ethanethioate;Opera_ID_551;ChemDiv1_018840;Oprea1_089020;Oprea1_790628;MLS002534805;DivK1c_003624;CHEMBL1562223;SCHEMBL13152854;CHEBI:95199;HMS640I08;7-.alpha.-Acetylthio-3-oxo-17-.alpha.-pregn-4-ene-21,17-.beta.-carbolactone;LXMSZDCAJNLERA-UHFFFAOYSA-N;HMS2637H11;HMS3362I02;17-.alpha.-Pregn-4-ene-21-carboxylic acid, 17-hydroxy-7-.alpha.-mercapto-3-oxo-.gamma.-lactone;17-Hydroxy-7.alpha.-mercapto-3-oxo-17.alpha.-pregn-4-ene-21-carboxylic acid .gamma.-lactone 7-acetate;17-Hydroxy-7.alpha.-mercapto-3-oxo-17.alpha.-pregn-4-ene-21-carboxylic acid .gamma.-lactone acetate;17.alpha.-Pregn-4-ene-21-carboxylic acid, 17-hydroxy-7.alpha.-mercapto-3-oxo-, .gamma.-lactone, acetate;3'-(3-Oxo-7-.alpha.-acetylthio-17-.beta.-hydroxyandrost-4-en-17-.beta.-yl)propionic acid lactone;3-(3-Oxo-7.alpha.-acetylthio-17.beta.-hydroxy-4-androsten-17.alpha.-yl)propionic acid-.gamma.-lactone;Pregn-4-ene-21-carboxylic acid, 7-(acetylthio)-17-hydroxy-3-oxo-, .gamma.-lactone, (7.alpha.,17.alpha.)-;BBL012762;STK763178;AKOS000558644;AKOS022060447;CDS1_002584;VS-03498;FT-0674644;EN300-296098;L001221;Q27167012;F2173-0854;ethanethioic acid S-(10,13-dimethyl-3,5'-dioxo-7-spiro[2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-17,2'-oxolane]yl) ester

Chemical Property of Pregn-4-ene-21-carboxylic acid, 7-(acetylthio)-17-hydroxy-3-oxo-, gamma-lactone, (7alpha,17alpha)-

Chemical Property:

• Appearance/Colour: White to Off White Solid
• Vapor Pressure: 3.24E-14mmHg at 25°C
• Melting Point: 207-208 °C(lit.)
• Refractive Index: -36 ° (C=1, CHCl3)
• Boiling Point: 597 °C at 760 mmHg
• Flash Point: 302.3 °C
• PSA: 85.74000
• Density: 1.24 g/cm³
• LogP: 4.85230
• Storage Temp.: Store at RT
• Solubility.: Practically insoluble in water, soluble in ethanol (96 per cent).
• Water Solubility.: practically insoluble
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 416.20213067
• Heavy Atom Count: 29
• Complexity: 818

Purity/Quality:

99% ^*data from raw suppliers

Spironolactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T, Xn, Xi
• Hazard Codes: T,Xn,Xi
• Statements: 60-40-36/37/38
• Safety Statements: 53-22-36/37/39-45-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)SC1CC2=CC(=O)CCC2(C3C1C4CCC5(C4(CC3)C)CCC(=O)O5)C
• Indications: Spironolactone is a kind of competitive aldosterone inhibitors with the drug itself being not active. Its diuretic effect is through its competitive antagonism against endogenous aldosterone, belonging to potassium-sparing diuretics. 1. edema disease, being used in combination other diuretics for the treatment of congestive heart failure, liver cirrhosis, renal edema, edema disease; the purpose in to correct the increased secondary aldosterone secretion associated with those above diseases and fight against the potassium excretion of other diuretics; it can also used in the treatment of idiopathic edema. 2. Hypertension, as the auxiliary treatment drug of high blood pressure. 3. For primary hyperaldosteronism, spironolactone can be used to diagnose and treat the disease. 4. For the prevention of hypokalemia; being used in combination with thiazide diuretics to enhance the diuretic effect and prevent hypokalemia. The above information is edited by the lookchem of Dai Xiongfeng. Spironolactone (Aldactone) is a compound originally developed as a mineralocorticoid antagonist and is used as a diuretic and antihypertensive agent. However, at high doses spironolactone binds to the androgen receptor. In clinical practice it is a weak androgen antagonist used to treat hirsutism in women by blocking testosterone binding to androgen receptors in hair follicles. Use of spironolactone in women for the treatment of hirsutism or male pattern baldness can result in elevated serum potassium levels; these levels should be checked within 1 month of starting the medication.
• Uses: It 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. Spironolactone, 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. 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, hypokalemia diuretic, aldosterone antagonist
• Therapeutic Function: Diuretic
• Biological Functions: Spironolactone (Aldactone) is structurally related to aldosterone and acts as a competitive inhibitor to prevent the binding of aldosterone to its specific cellular binding protein. Spironolactone thus blocks the hormone-induced stimulation of protein synthesis necessary for Na+ reabsorption and K+ secretion. Spironolactone, in the presence of circulating aldosterone, promotes a modest increase in Na+ excretion associated with a decrease in K+ elimination. The observations that spironolactone is ineffective in adrenalectomized patients and that the actions of spironolactone can be reversed by raising circulating al-dosterone blood levels (surmountable antagonism) support the conclusion that spironolactone acts by competitive inhibition of the binding of aldosterone with receptor sites in the target tissue. Spironolactone acts only when mineralocorticoids are present.
• Clinical Use: Spironolactone has been used clinically in the following conditions: 1. Primary hyperaldosteronism. Used as an aid in preparing patients with adrenal cortical tumors for surgery. 2. Hypokalemia. Used in patients with low serum K+ resulting from diuretic therapy with other agents. Its use should be restricted to patients who are unable to supplement their dietary K+ intake or adequately restrict their salt intake or who cannot tolerate orally available KCl preparations. 3. Hypertension and congestive heart failure. Although spironolactone may be useful in combination with thiazides, the latter remain the drugs of first choice. Fixed-dose combinations of spironolactone and a particular thiazide (e.g., Aldactazide) generally offer no therapeutic advantage over either component given separately and tend to restrict the ability of the clinician to determine the optimal dosage of each drug for a particular patient. 4. Cirrhosis and nephrotic syndrome. Spironolactone is a mild diuretic and may be useful in treating the edema that occurs in these two clinical conditions, that is, when excessive K+ loss is to be avoided.
• Drug interactions: Potentially hazardous interactions with other drugs ACE inhibitors or angiotensin-II antagonists: enhanced hypotensive effect; risk of severe hyperkalaemia. Antibacterials: avoid with lymecycline. Antidepressants: increased risk of postural hypotension with tricyclics. Antihypertensives: enhanced hypotensive effect; increased risk of first dose hypotensive effect with post-synaptic alpha-blockers. Cardiac glycosides: increased digoxin concentration. Ciclosporin: increased risk of hyperkalaemia. Cytotoxics: avoid with mitotane; increased risk of nephrotoxicity and ototoxicity with platinum compounds. Lithium: reduced lithium excretion. NSAIDs: increased risk of hyperkalaemia (especially with indometacin); increased risk of nephrotoxicity; diuretic effect of spironolactone antagonised by aspirin. Potassium salts: increased risk of hyperkalaemia. Tacrolimus: increased risk of hyperkalaemia.

Technology Process of Pregn-4-ene-21-carboxylic acid, 7-(acetylthio)-17-hydroxy-3-oxo-, gamma-lactone, (7alpha,17alpha)-

There total 22 articles about Pregn-4-ene-21-carboxylic acid, 7-(acetylthio)-17-hydroxy-3-oxo-, gamma-lactone, (7alpha,17alpha)- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

→ Spiro[6,7,8,9-tetrahydro-5H-benzocycloheptene-5,1'-(1,3-dihydroisoindole)]03'-one + SPIRONOLACTONE (52-01-7)

Guidance literature:

Reference yield: 76.0%

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

Guidance literature:

tiolacetic acid; With trifluoromethylsulfonic anhydride; In tetrahydrofuran;

canrenone; In tetrahydrofuran; at 20 ℃; for 1h;

Reference yield: 64.0%

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

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; for 1h; Yields of byproduct given; Ambient temperature;

DOI:10.1021/jo00282a041

upstream raw materials:

thioacetic acid

canrenone

tiolacetic acid

levonorgestrel

Downstream raw materials:

15α-hydroxycanrenone

3-(17β-hydroxy-3-oxo-1,4,6-androstadien-17α-yl)propionic acid γ-lactone

canrenone

3-(3-oxo-7α-thio-17β-hydroxy-4-androsten-17α-yl)propionic acid γ-lactone

Refernces

• 1、 -. "Method for preparing spirolactone". Paragraph 0031; 0032. . Retrieved 2017/11/30.
• 2、 -. "Cyclic amino acids and derivatives thereof useful as pharmaceutical agents". . . Retrieved 2008/06/13.