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3562-63-8 分子结构
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(1S,2R,10R,11S,14R,15S)-14-acetyl-14-hydroxy-2,8,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-6,8-dien-5-one

ChemBase编号:235
分子式:C22H30O3
平均质量:342.4718
单一同位素质量:342.21949482
SMILES和InChIs

SMILES:
O[C@]1([C@@]2([C@H]([C@H]3[C@@H]([C@@]4(C(=CC(=O)CC4)C(=C3)C)C)CC2)CC1)C)C(=O)C
Canonical SMILES:
O=C1CC[C@]2(C(=C1)C(=C[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@]2(O)C(=O)C)C)C)C
InChI:
InChI=1S/C22H30O3/c1-13-11-16-17(20(3)8-5-15(24)12-19(13)20)6-9-21(4)18(16)7-10-22(21,25)14(2)23/h11-12,16-18,25H,5-10H2,1-4H3/t16-,17+,18+,20-,21+,22+/m1/s1
InChIKey:
VXIMPSPISRVBPZ-NWUMPJBXSA-N

引用这个纪录

CBID:235 http://www.chembase.cn/molecule-235.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
(1S,2R,10R,11S,14R,15S)-14-acetyl-14-hydroxy-2,8,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-6,8-dien-5-one
(1S,2R,10R,11S,14R,15S)-14-acetyl-14-hydroxy-2,8,15-trimethyltetracyclo[8.7.0.02,7.011,15]heptadeca-6,8-dien-5-one
IUPAC传统名
megestrol
商标名
Magestin
Maygace
Megace
Megeron
Megestat
Megestil
Megestin
Nia
Niagestin
Ovaban
Ovarid
Volidan
别名
17-Hydroxy-6-methylpregna-4,6-diene-3,20-dione
Megestrol Acetate
Megestrolo [DCIT]
Megestrolum [INN-Latin]
Megestryl acetate
MGA
Megestrol
CAS号
3562-63-8
PubChem SID
160963698
PubChem CID
1909019090
19090
Chemspider ID
18023
维基百科标题
Megestrol

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 价格
TRC
M208040 external link 加入购物车 请登录

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 12.6991005  质子受体
质子供体 LogD (pH = 5.5) 3.2826188 
LogD (pH = 7.4) 3.2826166  Log P 3.282619 
摩尔折射率 99.5039 cm3 极化性 38.614105 Å3
极化表面积 54.37 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P 2.7  LOG S -4.52 
溶解度 1.04e-02 g/l 

分子性质

分子性质

理化性质 安全信息 产品相关信息 生物活性(PubChem)
溶解度
2 µg/mL (at 37°C for the acetate salt) expand 查看数据来源
疏水性(logP)
3.2 expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
质检报告
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详细说明

详细说明

DrugBank DrugBank Wikipedia Wikipedia TRC TRC
DrugBank -  DB00351 external link
Item Information
Drug Groups approved
Description 17-Hydroxy-6-methylpregna-3,6-diene-3,20-dione. A progestational hormone used most commonly as the acetate ester. As the acetate, it is more potent than progesterone both as a progestagen and as an ovulation inhibitor. It has also been used in the palliative treatment of breast cancer. [PubChem]
Indication For the treatment of anorexia, cachexia, or an unexplained, significant weight loss in patients with a diagnosis of acquired immunodeficiency syndrome (AIDS). Also used for the palliative management of recurrent, inoperable, or metastatic breast cancer, endometrial cancer, and prostate cancer in Canada and some other countries.
Pharmacology Megestrol is a synthetic progestin and has the same physiologic effects as natural progesterone. These effects include induction of secretory changes in the endometrium, increase in basal body temperature, pituitary inhibition, and production of withdrawal bleeding in the presence of estrogen. Mestrogel has slight glucocorticoid activity and very slight mineralocorticoid activity. This drug has no estrogenic, androgenic, or anabolic activity. The precise mechanism of megestrol’s antianorexic and anticachetic effects is unknown. Initially developed as a contraceptive, it was first evaluated in breast cancer treatment in 1967.
Toxicity No serious unexpected side effects have resulted from studies involving megestrol acetate oral suspension administered in dosages as high as 1200 mg/day. Treatment with megestrol acetate, an orexigenic agent, has also resulted in iatrogenic adrenal suppression. The mechanism is presumably related to the glucocorticoid properties of megestrol acetate [PMID: 12872362].
Affected Organisms
Humans and other mammals
Biotransformation Primarily hepatic. Megestrol metabolites which were identified in urine constituted 5% to 8% of the dose administered. Respiratory excretion as labeled carbon dioxide and fat storage may have accounted for at least part of the radioactivity not found in urine and feces. No active metabolites have been identified.
Absorption Variable, but well absorbed orally.
Half Life 34 hours
Elimination The major route of drug elimination in humans is urine.
Respiratory excretion as labeled carbon dioxide and fat storage may have accounted for at least part of the radioactivity not found in urine and feces.
References
Berenstein EG, Ortiz Z: Megestrol acetate for the treatment of anorexia-cachexia syndrome. Cochrane Database Syst Rev. 2005 Apr 18;(2):CD004310. [Pubmed]
Pascual Lopez A, Roque i Figuls M, Urrutia Cuchi G, Berenstein EG, Almenar Pasies B, Balcells Alegre M, Herdman M: Systematic review of megestrol acetate in the treatment of anorexia-cachexia syndrome. J Pain Symptom Manage. 2004 Apr;27(4):360-9. [Pubmed]
Rao GG, Miller DS: Hormonal therapy in epithelial ovarian cancer. Expert Rev Anticancer Ther. 2006 Jan;6(1):43-7. [Pubmed]
Schindler AE, Campagnoli C, Druckmann R, Huber J, Pasqualini JR, Schweppe KW, Thijssen JH: Classification and pharmacology of progestins. Maturitas. 2008 Sep-Oct;61(1-2):171-80. [Pubmed]
Orme LM, Bond JD, Humphrey MS, Zacharin MR, Downie PA, Jamsen KM, Mitchell SL, Robinson JM, Grapsas NA, Ashley DM: Megestrol acetate in pediatric oncology patients may lead to severe, symptomatic adrenal suppression. Cancer. 2003 Jul 15;98(2):397-405. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com
Toronto Research Chemicals -  M208040 external link
Megestrol is an orally active progestogen. Megestrol is used in combinations as oral contraceptive and as antineoplastic agent.

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Berenstein EG, Ortiz Z: Megestrol acetate for the treatment of anorexia-cachexia syndrome. Cochrane Database Syst Rev. 2005 Apr 18;(2):CD004310. Pubmed
  • Pascual Lopez A, Roque i Figuls M, Urrutia Cuchi G, Berenstein EG, Almenar Pasies B, Balcells Alegre M, Herdman M: Systematic review of megestrol acetate in the treatment of anorexia-cachexia syndrome. J Pain Symptom Manage. 2004 Apr;27(4):360-9. Pubmed
  • Rao GG, Miller DS: Hormonal therapy in epithelial ovarian cancer. Expert Rev Anticancer Ther. 2006 Jan;6(1):43-7. Pubmed
  • Schindler AE, Campagnoli C, Druckmann R, Huber J, Pasqualini JR, Schweppe KW, Thijssen JH: Classification and pharmacology of progestins. Maturitas. 2008 Sep-Oct;61(1-2):171-80. Pubmed
  • Orme LM, Bond JD, Humphrey MS, Zacharin MR, Downie PA, Jamsen KM, Mitchell SL, Robinson JM, Grapsas NA, Ashley DM: Megestrol acetate in pediatric oncology patients may lead to severe, symptomatic adrenal suppression. Cancer. 2003 Jul 15;98(2):397-405. Pubmed
  • Dea-Ayuela, M., et al.: Bioorg. Med. Chem., 16, 7770 (2008)
  • Santana, L., et al.: J. Med. Chem., 51, 6740 (2008)
  • Gonzalez-Diaz, H., et al.: Curr. Pharm. Des., 16, 2737 (2008)
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专利

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