Tìm theo
Spironolactone
Các tên gọi khác (4 ) :
  • Espironolactona
  • Spironolactone
  • Spironolactonum
  • Spironolattone
Thuốc lợi tiểu
Thuốc Gốc
Small Molecule
CAS: 52-01-7
ATC: C03DA01
ĐG : Actavis Group , http://www.actavis.com
CTHH: C24H32O4S
PTK: 416.573
A potassium sparing diuretic that acts by antagonism of aldosterone in the distal renal tubules. It is used mainly in the treatment of refractory edema in patients with congestive heart failure, nephrotic syndrome, or hepatic cirrhosis. Its effects on the endocrine system are utilized in the treatments of hirsutism and acne but they can lead to adverse effects. (From Martindale, The Extra Pharmacopoeia, 30th ed, p827)
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C24H32O4S
Phân tử khối
416.573
Monoisotopic mass
416.202130202
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
InChI Key
InChIKey=LXMSZDCAJNLERA-ZHYRCANASA-N
IUPAC Name
(1'S,2R,2'R,9'R,10'R,11'S,15'S)-9'-(acetylsulfanyl)-2',15'-dimethylspiro[oxolane-2,14'-tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan]-6'-ene-5,5'-dione
Traditional IUPAC Name
spironolactone
SMILES
[H][C@@]12CC[C@@]3(CCC(=O)O3)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@@]([H])(CC2=CC(=O)CC[C@]12C)SC(C)=O
Độ tan chảy
134.5 °C
Độ hòa tan
22 mg/L (at 25 °C)
logP
2.78
logS
-4.28
pKa (strongest acidic)
18.01
pKa (Strongest Basic)
-4.9
PSA
60.44 Å2
Refractivity
113.5 m3·mol-1
Polarizability
46.03 Å3
Rotatable Bond Count
2
H Bond Acceptor Count
3
H Bond Donor Count
0
Physiological Charge
0
Number of Rings
5
Bioavailability
1
Rule of Five
true
Ghose Filter
true
Dược Lực Học : Spironolactone is a synthetic 17-lactone steroid which is a renal competitive aldosterone antagonist in a class of pharmaceuticals called potassium-sparing diuretics. On its own, spironolactone is only a weak diuretic, but it can be combined with other diuretics. Due to its anti-androgen effect, it can also be used to treat hirsutism, and is a common component in hormone therapy for male-to-female transgendered people. Spironolactone inhibits the effect of aldosterone by competing for intracellular aldosterone receptor in the distal tubule cells. This increases the secretion of water and sodium, while decreasing the excretion of potassium. Spironolactone has a fairly slow onset of action, taking several days to develop and similarly the effect diminishes slowly.
Cơ Chế Tác Dụng : A potassium sparing diuretic that acts by antagonism of aldosterone in the distal renal tubules. It is used mainly in the treatment of refractory edema in patients with congestive heart failure, nephrotic syndrome, or hepatic cirrhosis. Its effects on the endocrine system are utilized in the treatments of hirsutism and acne but they can lead to adverse effects. (From Martindale, The Extra Pharmacopoeia, 30th ed, p827) Spironolactone is a specific pharmacologic antagonist of aldosterone, acting primarily through competitive binding of receptors at the aldosterone-dependent sodium-potassium exchange site in the distal convoluted renal tubule. Spironolactone causes increased amounts of sodium and water to be excreted, while potassium is retained. Spironolactone acts both as a diuretic and as an antihypertensive drug by this mechanism. It may be given alone or with other diuretic agents which act more proximally in the renal tubule. Aldosterone interacts with a cytoplasmic mineralocorticoid receptor to enhance the expression of the Na+, K+-ATPase and the Na+ channel involved in a Na+ K+ transport in the distal tubule . Spironolactone bind to this mineralcorticoid receptor, blocking the actions of aldosterone on gene expression. Aldosterone is a hormone; its primary function is to retain sodium and excrete potassium in the kidneys.
Dược Động Học :
▧ Absorption :
Fairly rapidly absorbed from the gastrointestinal tract. Food increases the bioavailability of unmetabolized spironolactone by almost 100%.
▧ Protein binding :
Spironolactone and its metabolites are more than 90% bound to plasma proteins.
▧ Metabolism :
Rapidly and extensively metabolized. The metabolic pathway of spironolactone is complex and can be divided into two main routes: those in which the sulfur moiety is retained and those in which the sulfur moiety is removed by dethioacetylation. Spironolactone is transformed to a reactive metabolite that can inactivate adrenal and testicular cytochrome P450 enzymes. It also has anti-androgenic activity.
▧ Route of Elimination :
The metabolites are excreted primarily in the urine and secondarily in bile.
▧ Half Life :
10 minutes
Độc Tính : The oral LD50 of spironolactone is greater than 1,000 mg/kg in mice, rats, and rabbits. Acute overdosage of spironolactone may be manifested by drowsiness, mental confusion, maculopapular or erythematous rash, nausea, vomiting, dizziness, or diarrhea. Spironolactone has been shown to be a tumorigen in chronic toxicity studies in rats.
Chỉ Định : Used primarily to treat low-renin hypertension, hypokalemia, and Conn's syndrome.
Tương Tác Thuốc :
  • Benazepril Increased risk of hyperkalemia
  • Candesartan Increased risk of hyperkalemia
  • Captopril Increased risk of hyperkalemia
  • Cholestyramine Increased risk of acidosis and hyperkalemia
  • Cilazapril Increased risk of hyperkalemia
  • Digoxin Increased digoxin levels and decreased effect in presence of spironolactone
  • Enalapril Increased risk of hyperkalemia
  • Eplerenone This association presents an increased risk of hyperkalemia
  • Eprosartan Increased risk of hyperkalemia
  • Fosinopril Increased risk of hyperkalemia
  • Irbesartan Increased risk of hyperkalemia
  • Lisinopril Increased risk of hyperkalemia
  • Losartan Increased risk of hyperkalemia
  • Mitotane Spironolactone antagonizes the effect of mitotane
  • Perindopril Increased risk of hyperkalemia
  • Polystyrene sulfonate Risk of alkalosis in renal impairment
  • Potassium Increased risk of hyperkalemia
  • Quinapril Increased risk of hyperkalemia
  • Ramipril Increased risk of hyperkalemia
  • Telmisartan Telmisartan may increase the hyperkalemic effect of Spironolactone. Monitor for increased serum potassium concentrations during concomitant therapy.
  • Tobramycin Increased risk of nephrotoxicity
  • Trandolapril Increased risk of hyperkalemia. Monitor serum potassium levels.
  • Treprostinil Additive hypotensive effect. Monitor antihypertensive therapy during concomitant use.
Liều Lượng & Cách Dùng : Tablet, film coated - Oral - 100 mg
Tablet, film coated - Oral - 25 mg
Tablet, film coated - Oral - 50 mg
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Công ty :
    Sản phẩm biệt dược : Aldactone
  • Công ty :
    Sản phẩm biệt dược : Osyrol
  • Công ty :
    Sản phẩm biệt dược : Spiresis
  • Công ty :
    Sản phẩm biệt dược : Spiretic
  • Công ty :
    Sản phẩm biệt dược : Spiroctan
  • Công ty :
    Sản phẩm biệt dược : Uractone
  • Công ty :
    Sản phẩm biệt dược : Verospiron
  • Công ty :
    Sản phẩm biệt dược : Xenalon
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00421
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=5833
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46508525
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C07310
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D00443
ChemSpider
http://www.chemspider.com/Chemical-Structure.5628.html
BindingDB
http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50228080
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0781-1599-01
PharmGKB
http://www.pharmgkb.org/drug/PA451483
Wikipedia
http://en.wikipedia.org/wiki/Spironolactone
RxList
http://www.rxlist.com/cgi/generic/spiron.htm
PDRhealth
http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/ald1010.shtml
Drugs.com
http://www.drugs.com/spironolactone.html
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