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119413-54-6 分子结构
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(19S)-8-[(dimethylamino)methyl]-19-ethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,11}.0^{4,9}.0^{15,20}]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dione

ChemBase编号:902
分子式:C23H23N3O5
平均质量:421.44582
单一同位素质量:421.16377085
SMILES和InChIs

SMILES:
O1Cc2c([C@@](O)(CC)C1=O)cc1n(Cc3c1nc1c(c3)c(CN(C)C)c(O)cc1)c2=O
Canonical SMILES:
CC[C@@]1(O)C(=O)OCc2c1cc1c3nc4ccc(c(c4cc3Cn1c2=O)CN(C)C)O
InChI:
InChI=1S/C23H23N3O5/c1-4-23(30)16-8-18-20-12(9-26(18)21(28)15(16)11-31-22(23)29)7-13-14(10-25(2)3)19(27)6-5-17(13)24-20/h5-8,27,30H,4,9-11H2,1-3H3/t23-/m0/s1
InChIKey:
UCFGDBYHRUNTLO-QHCPKHFHSA-N

引用这个纪录

CBID:902 http://www.chembase.cn/molecule-902.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
(19S)-8-[(dimethylamino)methyl]-19-ethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,11}.0^{4,9}.0^{15,20}]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dione
(19S)-8-[(dimethylamino)methyl]-19-ethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dione
IUPAC传统名
topotecan
商标名
Hycamptamine
Hycamptin
Hycamtin
别名
TPT
TTC
Topotecanum [INN-Latin]
Topotecane [INN-French]
Topotecan Lactone
Topotecan Hydrochloride
Topotecan Hcl
topotecan
Topotecan
9-[(dimethylamino)methyl]-10-hydroxy-(20S)-camptothecin hydrochloride hydrate
NSC-609669 hydrochloride hydrate
SKF-104864A hydrochloride hydrate
hycamptamine hydrochloride hydrate
Topotecan hydrochloride hydrate
CAS号
119413-54-6
123948-87-8(freebase)
123948-87-8
MDL号
MFCD00870670
PubChem SID
46505204
160964365
PubChem CID
60700

数据来源

数据来源

所有数据来源 商品来源 非商品来源

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 7.999574  质子受体
质子供体 LogD (pH = 5.5) -2.4005558 
LogD (pH = 7.4) -0.9559677  Log P -0.35709506 
摩尔折射率 115.0161 cm3 极化性 44.844234 Å3
极化表面积 103.2 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P 1.84  LOG S -2.69 
溶解度 8.61e-01 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
1 mg/ml expand 查看数据来源
DMSO: ≥20 mg/mL expand 查看数据来源
外观
yellow powder expand 查看数据来源
疏水性(logP)
0.8 expand 查看数据来源
保存条件
desiccated expand 查看数据来源
protect from light expand 查看数据来源
联合国危险货物编号
2811 expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
德国WGK号
3 expand 查看数据来源
联合国危险货物等级
6.1 expand 查看数据来源
联合国危险货物包装类别(PG)
3 expand 查看数据来源
危险公开号
46-48 expand 查看数据来源
安全公开号
22-36 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
Warning expand 查看数据来源
GHS危险声明
H341 expand 查看数据来源
GHS警示性声明
P281 expand 查看数据来源
RID/ADR
UN 2811 6.1/PG 3 expand 查看数据来源
保存温度
-20°C expand 查看数据来源
纯度
≥98% (HPLC and enzymatic) expand 查看数据来源
95+% expand 查看数据来源
Empirical Formula (Hill Notation)
C23H23N3O5 · xHCl · yH2O expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank Sigma Aldrich Sigma Aldrich
DrugBank -  DB01030 external link
Item Information
Drug Groups approved; investigational
Description An antineoplastic agent used to treat ovarian cancer. It works by inhibiting DNA topoisomerases, type I. [PubChem]
Indication For the treatment of advanced ovarian cancer in patients with disease that has recurred or progressed following therapy with platinum-based regimens. Also used as a second-line therapy for treatment-sensitive small cell lung cancer, as well as in combination with cisplatin for the treatment of stage IV-B, recurrent, or persistent cervical cancer not amenable to curative treatment with surgery and/or radiation therapy.
Pharmacology Topotecan, a semi-synthetic derivative of camptothecin (a plant alkaloid obtained from the Camptotheca acuminata tree), is an anti-tumor drug with topoisomerase I-inhibitory activity similar to irinotecan. DNA topoisomerases are enzymes in the cell nucleus that regulate DNA topology (3-dimensional conformation) and facilitate nuclear processes such as DNA replication, recombination, and repair. During these processes, DNA topoisomerase I creates reversible single-stranded breaks in double-stranded DNA, allowing intact single DNA strands to pass through the break and relieve the topologic constraints inherent in supercoiled DNA. The 3'-DNA terminus of the broken DNA strand binds covalently with the topoisomerase enzyme to form a catalytic intermediate called a cleavable complex. After DNA is sufficiently relaxed and the strand passage reaction is complete, DNA topoisomerase reattaches the broken DNA strands to form the unaltered topoisomers that allow transcription to proceed. Topotecan interferes with the growth of cancer cells, which are eventually destroyed. Since the growth of normal cells can be affected by the medicine, other effects may also occur. Unlike irinotecan, topotecan is found predominantly in the inactive carboxylate form at neutral pH and it is not a prodrug.
Toxicity The primary anticipated complication of overdosage would consist of bone marrow suppression.
Affected Organisms
Humans and other mammals
Biotransformation Topotecan undergoes a reversible pH dependent hydrolysis of its lactone moiety; it is the lactone form that is pharmacologically active.
Half Life 2-3 hours
Protein Binding 35%
Elimination Renal clearance is an important determinant of topotecan elimination. In a mass balance/excretion study in 4 patients with solid tumors, the overall recovery of total topotecan and its N-desmethyl metabolite in urine and feces over 9 days averaged 73.4 ± 2.3% of the administered IV dose. Fecal elimination of total topotecan accounted for 9 ± 3.6% while fecal elimination of N-desmethyl topotecan was 1.7 ± 0.6%.
References
Kollmannsberger C, Mross K, Jakob A, Kanz L, Bokemeyer C: Topotecan - A novel topoisomerase I inhibitor: pharmacology and clinical experience. Oncology. 1999;56(1):1-12. [Pubmed]
Herben VM, ten Bokkel Huinink WW, Beijnen JH: Clinical pharmacokinetics of topotecan. Clin Pharmacokinet. 1996 Aug;31(2):85-102. [Pubmed]
Dennis MJ, Beijnen JH, Grochow LB, van Warmerdam LJ: An overview of the clinical pharmacology of topotecan. Semin Oncol. 1997 Feb;24(1 Suppl 5):S5-12-S5-18. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com
Sigma Aldrich -  T2705 external link
Biochem/physiol Actions
Topotecan is a topoisomerase I inhibitor and an apoptosis inducer. It is a potent 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
  • Kollmannsberger C, Mross K, Jakob A, Kanz L, Bokemeyer C: Topotecan - A novel topoisomerase I inhibitor: pharmacology and clinical experience. Oncology. 1999;56(1):1-12. Pubmed
  • Herben VM, ten Bokkel Huinink WW, Beijnen JH: Clinical pharmacokinetics of topotecan. Clin Pharmacokinet. 1996 Aug;31(2):85-102. Pubmed
  • Dennis MJ, Beijnen JH, Grochow LB, van Warmerdam LJ: An overview of the clinical pharmacology of topotecan. Semin Oncol. 1997 Feb;24(1 Suppl 5):S5-12-S5-18. Pubmed
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