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164656-23-9 分子结构
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(2R,7R,10S,11S,14S,15S)-N-[2,5-bis(trifluoromethyl)phenyl]-2,15-dimethyl-5-oxo-6-azatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-3-ene-14-carboxamide

ChemBase编号:997
分子式:C27H30F6N2O2
平均质量:528.5297192
单一同位素质量:528.22114753
SMILES和InChIs

SMILES:
FC(F)(F)c1c(NC(=O)[C@@H]2[C@@]3([C@H]([C@H]4C([C@@]5([C@H](NC(=O)C=C5)CC4)C)CC3)CC2)C)cc(cc1)C(F)(F)F
Canonical SMILES:
O=C1C=C[C@]2([C@H](N1)CC[C@@H]1C2CC[C@]2([C@H]1CC[C@@H]2C(=O)Nc1cc(ccc1C(F)(F)F)C(F)(F)F)C)C
InChI:
InChI=1S/C27H30F6N2O2/c1-24-11-9-17-15(4-8-21-25(17,2)12-10-22(36)35-21)16(24)6-7-19(24)23(37)34-20-13-14(26(28,29)30)3-5-18(20)27(31,32)33/h3,5,10,12-13,15-17,19,21H,4,6-9,11H2,1-2H3,(H,34,37)(H,35,36)/t15-,16-,17?,19+,21+,24-,25+/m0/s1
InChIKey:
JWJOTENAMICLJG-VYZSUTEISA-N

引用这个纪录

CBID:997 http://www.chembase.cn/molecule-997.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
(2R,7R,10S,11S,14S,15S)-N-[2,5-bis(trifluoromethyl)phenyl]-2,15-dimethyl-5-oxo-6-azatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-3-ene-14-carboxamide
IUPAC传统名
dutasteride
商标名
Avodart
别名
dutasteride
Dutasteride
CAS号
164656-23-9
PubChem SID
160964460
PubChem CID
152945

数据来源

数据来源

所有数据来源 商品来源 非商品来源
数据来源 数据ID
DrugBank DB01126 external link
PubChem 152945 external link
数据来源 数据ID 价格

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 12.56134  质子受体
质子供体 LogD (pH = 5.5) 5.7926135 
LogD (pH = 7.4) 5.7928123  Log P 5.7928176 
摩尔折射率 127.8962 cm3 极化性 46.833355 Å3
极化表面积 58.2 Å2 可自由旋转的化学键
里宾斯基五规则 false 
Log P 5.45  LOG S -5.77 
溶解度 9.08e-04 g/l 

分子性质

分子性质

理化性质 生物活性(PubChem)
疏水性(logP)
6.8 expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank
DrugBank -  DB01126 external link
Item Information
Drug Groups approved; investigational
Description Dutasteride belongs to a class of drugs called 5-alpha-reductase inhibitors, which block the action of the 5-alpha-reductase enzymes that convert testosterone into dihydrotestosterone (DHT). Finasteride also belongs to this group, but while dutasteride inhibits both isoforms of 5-alpha reductase, finasteride inhibits only one. Even so, a clinical study done by GlaxoSmithKline, the EPICS trial, did not find dutasteride to be more effective than finasteride in treating BPH. [Wikipedia]
Indication For the treatment of symptomatic benign prostatic hyperplasia (BPH) in men with an enlarged prostate gland to improve symptoms, and reduce the risk of acute urinary retention and the need for surgery.
Pharmacology Dutasteride is a synthetic 4-azasteroid compound that is a selective inhibitor of both the type 1 and type 2 isoforms of steroid 5 alpha-reductase (5AR), intracellular enzymes that convert testosterone to 5 alpha-dihydrotestosterone (DHT). Type I 5a-reductase is predominant in the sebaceous glands of most regions of skin, including scalp, and liver. Type I 5a-reductase is responsible for approximately one-third of circulating DHT. The Type II 5a-reductase isozyme is primarily found in prostate, seminal vesicles, epididymides, and hair follicles as well as liver, and is responsible for two-thirds of circulating DHT.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic. Extensively metabolized by CYP3A4 and CYP3A5 to active metabolites.
Absorption 60%
Half Life 5 weeks
Protein Binding Highly bound to albumin (99%) and α-1 acid glycoprotein (96.6%).
Elimination Dutasteride is extensively metabolized in humans. Dutasteride and its metabolites were excreted mainly in feces.
Distribution * 300 to 500 L
References
Keam SJ, Scott LJ: Dutasteride: a review of its use in the management of prostate disorders. Drugs. 2008;68(4):463-85. [Pubmed]
Shah SK, Trump DL, Sartor O, Tan W, Wilding GE, Mohler JL: Phase II study of Dutasteride for recurrent prostate cancer during androgen deprivation therapy. J Urol. 2009 Feb;181(2):621-6. Epub 2008 Dec 16. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Keam SJ, Scott LJ: Dutasteride: a review of its use in the management of prostate disorders. Drugs. 2008;68(4):463-85. Pubmed
  • Shah SK, Trump DL, Sartor O, Tan W, Wilding GE, Mohler JL: Phase II study of Dutasteride for recurrent prostate cancer during androgen deprivation therapy. J Urol. 2009 Feb;181(2):621-6. Epub 2008 Dec 16. Pubmed
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专利

专利

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