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52-01-7 分子结构
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(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

ChemBase编号:304
分子式:C24H32O4S
平均质量:416.57348
单一同位素质量:416.2021305
SMILES和InChIs

SMILES:
S([C@H]1[C@H]2[C@H]3[C@@]([C@@]4(OC(=O)CC4)CC3)(CC[C@@H]2[C@@]2(C(=CC(=O)CC2)C1)C)C)C(=O)C
Canonical SMILES:
CC(=O)S[C@@H]1CC2=CC(=O)CC[C@@]2([C@@H]2[C@@H]1[C@@H]1CC[C@]3([C@]1(CC2)C)CCC(=O)O3)C
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
InChIKey:
LXMSZDCAJNLERA-ZHYRCANASA-N

引用这个纪录

CBID:304 http://www.chembase.cn/molecule-304.html

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
(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
(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?,?.0??,??]heptadecan]-6'-ene-5,5'-dione
(1'S,2R,2'R,9'R,10'R,11'S,15'S)-9'-(acetylsulfanyl)-2',15'-dimethylspiro[oxolane-2,14'-tetracyclo[8.7.0.02,7.011,15]heptadecan]-6'-ene-5,5'-dione
IUPAC传统名
spironolactone
商标名
Abbolactone
Acelat
Aldace
Aldactazide
Aldactide
Aldactone
Aldactone A
Alderon
Aldopur
Almatol
Altex
Aquareduct
Deverol
Diatensec
Dira
Duraspiron
Espironolactona [INN-Spanish]
Euteberol
Lacalmin
Lacdene
Laractone
Melarcon
Nefurofan
Osyrol
SNL
Sagisal
Sincomen
Spiresis
Spiretic
Spiridon
Spiro-Tablinen
Spiroctan
Spiroctanie
Spiroderm
Spirolactone
Spirolakton
Spirolang
Spirolone
Spirone
Spironocompren
Spironolactone A
Spironolactone [BAN:INN:JAN]
Spironolactonum [INN-Latin]
Spironolattone [DCIT]
Sprioderm
Supra-puren
Suracton
Uractone
Urusonin
Verospiron
Verospirone
Verospirone Opianin
Xenalon
别名
Spironolactone
4-Pregnen-21-oic acid-17α-ol-3-one-7α-thiol γ-lactone 7-acetate
7α-(Acetylthio)-17α-hydroxy-3-oxopregn-4-ene-21-carboxylic acid γ-lactone
Spironolactone
(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
(7α,7α)-7-(Acetylthyo)-17-hydroxy-3-oxopregn-4-one-21-carboxylic Acid γ-Lactone
7α-Acetylthio-3-oxo-17α-pregn-4-ene-21,17-carbolactone
SC-9420
Adactone
CAS号
52-01-7
EC号
200-133-6
MDL号
MFCD00071615
MFCD00082250
PubChem SID
24277736
46508525
160963767
PubChem CID
5833
CHEBI ID
9241
ATC码
C03DA01
CHEMBL
1393
Chemspider ID
5628
DrugBank ID
DB00421
IUPHAR配体索引
2875
KEGG ID
D00443
美国药典/FDA物质标识码
27O7W4T232
维基百科标题
Spironolactone
Medline Plus
a682627

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 18.006086  质子受体
质子供体 LogD (pH = 5.5) 3.6367545 
LogD (pH = 7.4) 3.6367545  Log P 3.6367545 
摩尔折射率 113.5043 cm3 极化性 45.06745 Å3
极化表面积 60.44 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P 3.1  LOG S -5.32 
溶解度 1.98e-03 g/l 

分子性质

分子性质

理化性质 安全信息 药理学性质 产品相关信息 生物活性(PubChem)
溶解度
Chloroform expand 查看数据来源
Methanol expand 查看数据来源
Practically insoluble (22 mg/L) expand 查看数据来源
外观
White to Off White Soli- expand 查看数据来源
熔点
205-207°C expand 查看数据来源
207-208 °C(lit.) expand 查看数据来源
疏水性(logP)
2.839 expand 查看数据来源
3.4 expand 查看数据来源
保存条件
Refrigerator expand 查看数据来源
Room Temperature (15-30°C) expand 查看数据来源
RTECS编号
TU4725000 expand 查看数据来源
欧盟危险性物质标志
有毒(Toxic) 有毒(Toxic) (T) expand 查看数据来源
有害性(Harmful) 有害性(Harmful) (Xn) expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
德国WGK号
3 expand 查看数据来源
危险公开号
60 expand 查看数据来源
R:22-40 expand 查看数据来源
安全公开号
53-22-36/37/39-45 expand 查看数据来源
S:36/37/39 expand 查看数据来源
GHS危险品标识
GHS08 expand 查看数据来源
GHS警示词
Danger expand 查看数据来源
GHS危险声明
H360 expand 查看数据来源
GHS警示性声明
P201-P308 + P313 expand 查看数据来源
个人保护装置
Eyeshields, Gloves, type P2 (EN 143) respirator cartridges expand 查看数据来源
给药途径
Oral expand 查看数据来源
排泄
Urine, bile expand 查看数据来源
半衰期
1.3-2 hours expand 查看数据来源
代谢
Hepatic expand 查看数据来源
蛋白结合率
90%+ expand 查看数据来源
法定药品分级
POM (UK) expand 查看数据来源
Rx-only (US) expand 查看数据来源
妊娠期药物分类
B3 (Australia) expand 查看数据来源
C (US) expand 查看数据来源
相关基因信息
human ... HSD17B1(3292), NR3C2(4306)rat ... Ar(24208) expand 查看数据来源
纯度
95% expand 查看数据来源
97.0-103.0% expand 查看数据来源
质检报告
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源

详细说明

详细说明

MP Biomedicals MP Biomedicals DrugBank DrugBank Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals -  02190059 external link
Crystalline Spironolactone is an aldosterone antagonist that also promotes loss of sodium through the kidney but permits retention of potassium.
DrugBank -  DB00421 external link
Item Information
Drug Groups approved
Description 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)
Indication Used primarily to treat low-renin hypertension, hypokalemia, and Conn's syndrome.
Pharmacology 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.
Toxicity 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.
Affected Organisms
Humans and other mammals
Biotransformation 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.
Absorption Fairly rapidly absorbed from the gastrointestinal tract. Food increases the bioavailability of unmetabolized spironolactone by almost 100%.
Half Life 10 minutes
Protein Binding Spironolactone and its metabolites are more than 90% bound to plasma proteins.
Elimination The metabolites are excreted primarily in the urine and secondarily in bile.
References
Berardesca E, Gabba P, Ucci G, Borroni G, Rabbiosi G: Topical spironolactone inhibits dihydrotestosterone receptors in human sebaceous glands: an autoradiographic study in subjects with acne vulgaris. Int J Tissue React. 1988;10(2):115-9. [Pubmed]
Pitt B, Zannad F, Remme WJ, Cody R, Castaigne A, Perez A, Palensky J, Wittes J: The effect of spironolactone on morbidity and mortality in patients with severe heart failure. Randomized Aldactone Evaluation Study Investigators. N Engl J Med. 1999 Sep 2;341(10):709-17. [Pubmed]
Wandelt-Freerksen E: [Aldactone in the treatment of sarcoidosis of the lungs (author's transl)] Z Erkr Atmungsorgane. 1977 Jul;149(1):156-9. [Pubmed]
External Links
Wikipedia
RxList
PDRhealth
Drugs.com
Sigma Aldrich -  S3378 external link
Biochem/physiol Actions
Spironolactone is a competitive aldosterone receptor antagonist. Used as potassium sparing diuretic.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. S3378.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Toronto Research Chemicals -  S683000 external link
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

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Berardesca E, Gabba P, Ucci G, Borroni G, Rabbiosi G: Topical spironolactone inhibits dihydrotestosterone receptors in human sebaceous glands: an autoradiographic study in subjects with acne vulgaris. Int J Tissue React. 1988;10(2):115-9. Pubmed
  • Pitt B, Zannad F, Remme WJ, Cody R, Castaigne A, Perez A, Palensky J, Wittes J: The effect of spironolactone on morbidity and mortality in patients with severe heart failure. Randomized Aldactone Evaluation Study Investigators. N Engl J Med. 1999 Sep 2;341(10):709-17. Pubmed
  • Wandelt-Freerksen E: [Aldactone in the treatment of sarcoidosis of the lungs (author's transl)] Z Erkr Atmungsorgane. 1977 Jul;149(1):156-9. Pubmed
  • Sutter, J.L., et al.: Anal. Profiles Drug Subs., 4, 431 (1975)
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