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23214-92-8 分子结构
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(8S,10S)-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione

ChemBase编号:870
分子式:C27H29NO11
平均质量:543.51926
单一同位素质量:543.17406075
SMILES和InChIs

SMILES:
O([C@H]1C[C@@](O)(Cc2c1c(O)c1c(c2O)C(=O)c2c(C1=O)c(OC)ccc2)C(=O)CO)[C@@H]1O[C@H]([C@@H](O)[C@@H](N)C1)C
Canonical SMILES:
OCC(=O)[C@@]1(O)C[C@H](O[C@H]2C[C@H](N)[C@@H]([C@@H](O2)C)O)c2c(C1)c(O)c1c(c2O)C(=O)c2c(C1=O)cccc2OC
InChI:
InChI=1S/C27H29NO11/c1-10-22(31)13(28)6-17(38-10)39-15-8-27(36,16(30)9-29)7-12-19(15)26(35)21-20(24(12)33)23(32)11-4-3-5-14(37-2)18(11)25(21)34/h3-5,10,13,15,17,22,29,31,33,35-36H,6-9,28H2,1-2H3/t10-,13-,15-,17-,22+,27-/m0/s1
InChIKey:
AOJJSUZBOXZQNB-TZSSRYMLSA-N

引用这个纪录

CBID:870 http://www.chembase.cn/molecule-870.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
(8S,10S)-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione
IUPAC传统名
doxorubicin
商标名
ADM
Adriablastin
Adriamycin
Adriamycin PFS
Adriamycin RDF
Adriamycin Semiquinone
Adriblastin
Adriblastina
Caelyx
DM2
Doxil
Doxo
RDF Rubex
Rubex
Myocet
Resmycin
别名
Doxorubicin HCl
Doxorubicin Hydrochloride
Doxorubicina [INN-Spanish]
Doxorubicine [INN-French]
Doxorubicinum [INN-Latin]
doxorubicin
Doxorubicin
CAS号
23214-92-8
PubChem SID
160964333
46507641
PubChem CID
31703
CHEBI ID
28748
ATC码
L01DB01
CHEMBL
179
Chemspider ID
29400
DrugBank ID
DB00997
KEGG ID
D03899
美国药典/FDA物质标识码
80168379AG
维基百科标题
Doxorubicin
Medline Plus
a682221

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

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 9.53088  质子受体 12 
质子供体 LogD (pH = 5.5) -1.4428744 
LogD (pH = 7.4) -0.27556196  Log P 0.91642165 
摩尔折射率 134.5937 cm3 极化性 52.692078 Å3
极化表面积 206.07 Å2 可自由旋转的化学键
里宾斯基五规则 false 
Log P 1.41  LOG S -2.67 
溶解度 1.18e+00 g/l 

分子性质

分子性质

理化性质 药理学性质 生物活性(PubChem)
溶解度
Soluble expand 查看数据来源
疏水性(logP)
-0.5 expand 查看数据来源
给药途径
Intravenous expand 查看数据来源
生物利用度
5% (Oral) expand 查看数据来源
排泄
Biliary and fecal expand 查看数据来源
半衰期
12–18.5 hours when released from liposomes expand 查看数据来源
代谢
CYP3A4 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
D (Australia) expand 查看数据来源
D (US) expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank Wikipedia Wikipedia
DrugBank -  DB00997 external link
Item Information
Drug Groups approved; investigational
Description Antineoplastic antibiotic obtained from Streptomyces peucetius. It is a hydroxy derivative of daunorubicin. [PubChem]
Indication For the treatment of Koposi's sarcome connected to AIDS.
Pharmacology Doxorubicin is an antineoplastic in the anthracycline class. General properties of drugs in this class include: interaction with DNA in a variety of different ways including intercalation (squeezing between the base pairs), DNA strand breakage and inhibition with the enzyme topoisomerase II. Most of these compounds have been isolated from natural sources and antibiotics. However, they lack the specificity of the antimicrobial antibiotics and thus produce significant toxicity. The anthracyclines are among the most important antitumor drugs available. Doxorubicin is widely used for the treatment of several solid tumors while daunorubicin and idarubicin are used exclusively for the treatment of leukemia. Doxorubicin may also inhibit polymerase activity, affect regulation of gene expression, and produce free radical damage to DNA. Doxorubicin possesses an antitumor effect against a wide spectrum of tumors, either grafted or spontaneous. The anthracyclines are cell cycle-nonspecific.
Toxicity LD50=21800 ug/kg (rat, subcutaneous)
Affected Organisms
Humans and other mammals
Half Life 55 hours
Protein Binding 70%
Elimination Plasma clearance is in the range 324 to 809 mL/min/m2 and is predominately by metabolism and biliary excretion.
Clearance * 324-809 mL/min/m2
* 1088 mL/min/m2 [Men]
* 433 mL/min/m2 [Women]
* 1540 mL/min/m2 [children greater than 2 years of age receiving administration of 10 to 75 mg/m2 doses]
* 813 mL/min/m2 [infants younger than 2 years of age receiving administration of 10 to 75 mg/m2 doses]
References
Weiss RB: The anthracyclines: will we ever find a better doxorubicin? Semin Oncol. 1992 Dec;19(6):670-86. [Pubmed]
Tan C, Tasaka H, Yu KP, Murphy ML, Karnofsky DA: Daunomycin, an antitumor antibiotic, in the treatment of neoplastic disease. Clinical evaluation with special reference to childhood leukemia. Cancer. 1967 Mar;20(3):333-53. [Pubmed]
Arcamone F, Cassinelli G, Fantini G, Grein A, Orezzi P, Pol C, Spalla C: Adriamycin, 14-hydroxydaunomycin, a new antitumor antibiotic from S. peucetius var. caesius. Biotechnol Bioeng. 1969 Nov;11(6):1101-10. [Pubmed]
Di Marco A, Gaetani M, Scarpinato B: Adriamycin (NSC-123,127): a new antibiotic with antitumor activity. Cancer Chemother Rep. 1969 Feb;53(1):33-7. [Pubmed]
Lomovskaya N, Otten SL, Doi-Katayama Y, Fonstein L, Liu XC, Takatsu T, Inventi-Solari A, Filippini S, Torti F, Colombo AL, Hutchinson CR: Doxorubicin overproduction in Streptomyces peucetius: cloning and characterization of the dnrU ketoreductase and dnrV genes and the doxA cytochrome P-450 hydroxylase gene. J Bacteriol. 1999 Jan;181(1):305-18. [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
  • Tan C, Tasaka H, Yu KP, Murphy ML, Karnofsky DA: Daunomycin, an antitumor antibiotic, in the treatment of neoplastic disease. Clinical evaluation with special reference to childhood leukemia. Cancer. 1967 Mar;20(3):333-53. Pubmed
  • Arcamone F, Cassinelli G, Fantini G, Grein A, Orezzi P, Pol C, Spalla C: Adriamycin, 14-hydroxydaunomycin, a new antitumor antibiotic from S. peucetius var. caesius. Biotechnol Bioeng. 1969 Nov;11(6):1101-10. Pubmed
  • Di Marco A, Gaetani M, Scarpinato B: Adriamycin (NSC-123,127): a new antibiotic with antitumor activity. Cancer Chemother Rep. 1969 Feb;53(1):33-7. Pubmed
  • Lomovskaya N, Otten SL, Doi-Katayama Y, Fonstein L, Liu XC, Takatsu T, Inventi-Solari A, Filippini S, Torti F, Colombo AL, Hutchinson CR: Doxorubicin overproduction in Streptomyces peucetius: cloning and characterization of the dnrU ketoreductase and dnrV genes and the doxA cytochrome P-450 hydroxylase gene. J Bacteriol. 1999 Jan;181(1):305-18. Pubmed
  • Weiss RB: The anthracyclines: will we ever find a better doxorubicin? Semin Oncol. 1992 Dec;19(6):670-86. Pubmed
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专利

专利

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