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60-54-8 分子结构
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(4S,4aS,5aS,6S,12aS)-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide

ChemBase编号:639
分子式:C22H24N2O8
平均质量:444.43456
单一同位素质量:444.15326574
SMILES和InChIs

SMILES:
c12c(C(=O)C3=C([C@]4([C@@H](C[C@@H]3[C@@]1(O)C)[C@@H](C(=C(C4=O)C(=O)N)O)N(C)C)O)O)c(ccc2)O
Canonical SMILES:
CN([C@@H]1C(=C(C(=O)N)C(=O)[C@@]2([C@H]1C[C@H]1C(=C2O)C(=O)c2c([C@@]1(C)O)cccc2O)O)O)C
InChI:
InChI=1S/C22H24N2O8/c1-21(31)8-5-4-6-11(25)12(8)16(26)13-9(21)7-10-15(24(2)3)17(27)14(20(23)30)19(29)22(10,32)18(13)28/h4-6,9-10,15,25,27-28,31-32H,7H2,1-3H3,(H2,23,30)/t9-,10-,15-,21+,22-/m0/s1
InChIKey:
OFVLGDICTFRJMM-WESIUVDSSA-N

引用这个纪录

CBID:639 http://www.chembase.cn/molecule-639.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
(4S,4aS,5aS,6S,12aS)-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
IUPAC传统名
tetracycline
商标名
Abramycin
Abricycline
Achromycin
Achromycin V
Actisite
Agromicina
Ambramicina
Ambramycin
Amycin
Bio-Tetra
Biocycline
Bristaciclin
Bristaciclina
Bristacycline
Cefracycline
Ciclibion
Copharlan
Criseociclina
Cyclopar
Cytome
Democracin
Deschlorobiomycin
Dumocyclin
Enterocycline
Hostacyclin
Lexacycline
Limecycline
Liquamycin
Medocycline
Mericycline
Micycline
Neocycline
Oletetrin
Omegamycin
Orlycycline
Panmycin
Polycycline
Polyotic
Purocyclina
Resteclin
Retet
Robitet
Roviciclina
SK-Tetracycline
Solvocin
Sumycin
TAC
Tetra-CO
Tetrabon
Tetrachel
Tetracycl
Tetracycline II
Tetracyn
Tetradecin
Tetrafil
Tetramed
Tetraverine
Tetrex
Topicycline
Tsiklomistsin
Tsiklomitsin
Veracin
Vetacyclinum
别名
四环素
Tetracycline HCl
TC
Anhydrotetracycline
Tetracycline
Tetracycline
CAS号
60-54-8
EC号
200-481-9
MDL号
MFCD00151232
Beilstein号
2230417
PubChem SID
46506693
24888860
24900120
160964102
PubChem CID
54675776
5280962

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
Sigma Aldrich
87128 external link 加入购物车 请登录
T3258 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 -2.2437224  质子受体
质子供体 LogD (pH = 5.5) -4.3970165 
LogD (pH = 7.4) -6.222226  Log P -3.5476153 
摩尔折射率 114.1883 cm3 极化性 43.205765 Å3
极化表面积 181.62 Å2 可自由旋转的化学键
里宾斯基五规则 false 
Log P -0.56  LOG S -2.52 
溶解度 1.33e+00 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
231 mg/L at 25 oC (SRC PhysProp experimental -- YALKOWSKY,SH & DANNENFELSER,RM (1992)) expand 查看数据来源
熔点
172-174 °C (dec.) expand 查看数据来源
比旋光度
[α]20/D -230±5°, c = 1% in methanol expand 查看数据来源
疏水性(logP)
-0.3 expand 查看数据来源
RTECS编号
QI8750000 expand 查看数据来源
欧盟危险性物质标志
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
德国WGK号
3 expand 查看数据来源
危险公开号
22 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
GHS07 expand 查看数据来源
GHS警示词
Warning expand 查看数据来源
GHS危险声明
H302 expand 查看数据来源
个人保护装置
dust mask type N95 (US), Eyeshields, Gloves expand 查看数据来源
保存温度
-20°C expand 查看数据来源
2-8°C expand 查看数据来源
相关基因信息
human ... CYP1A2(1544), TERT(7015) expand 查看数据来源
纯度
≥88.0% (HPLC) expand 查看数据来源
≥98.0% (NT) expand 查看数据来源
适用性
suitable for 1694 per US EPA expand 查看数据来源
杂质
4-11% water expand 查看数据来源
Empirical Formula (Hill Notation)
C22H24N2O8 · xH2O expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank Sigma Aldrich Sigma Aldrich
DrugBank -  DB00759 external link
Item Information
Drug Groups approved
Description Tetracycline is a broad spectrum polyketide antibiotic produced by the Streptomyces genus of Actinobacteria. It exerts a bacteriostatic effect on bacteria by binding reversible to the bacterial 30S ribosomal subunit and blocking incoming aminoacyl tRNA from binding to the ribosome acceptor site. It also binds to some extent to the bacterial 50S ribosomal subunit and may alter the cytoplasmic membrane causing intracellular components to leak from bacterial cells.
Indication Used to treat bacterial infections such as Rocky Mountain spotted fever, typhus fever, tick fevers, Q fever, rickettsialpox and Brill-Zinsser disease. May be used to treat infections caused by Chlamydiae spp., B. burgdorferi (Lyme disease), and upper respiratory infections caused by typical (S. pneumoniae, H. influenzae, and M. catarrhalis) and atypical organisms (C. pneumoniae, M. pneumoniae, L. pneumophila). May also be used to treat acne. Tetracycline may be an alternative drug for people who are allergic to penicillin.
Pharmacology Tetracycline is a short-acting antibiotic that inhibits bacterial growth by inhibiting translation. It binds to the 30S ribosomal subunit and prevents the amino-acyl tRNA from binding to the A site of the ribosome. It also binds to some extent to the 50S ribosomal subunit. This binding is reversible in nature. Additionally tetracycline may alter the cytoplasmic membrane of bacteria causing leakage of intracellular contents, such as nucleotides, from the cell.
Toxicity LD50=808mg/kg (orally in mice)
Affected Organisms
Enteric bacteria and other eubacteria
Biotransformation Not metabolized
Absorption Bioavailability is less than 40% when administered via intramuscular injection, 100% intravenously, and 60-80% orally (fasting adults). Food and/or milk reduce GI absorption of oral preparations of tetracycline by 50% or more.
Half Life 6-12 hours
Protein Binding 20 - 67% protein bound
Elimination They are concentrated by the liver in the bile and excreted in the urine and feces at high concentrations in a biologically active form.
References
[Link]
Griffin MO, Fricovsky E, Ceballos G, Villarreal F: Tetracyclines: a pleitropic family of compounds with promising therapeutic properties. Review of the literature. Am J Physiol Cell Physiol. 2010 Sep;299(3):C539-48. Epub 2010 Jun 30. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com
Sigma Aldrich -  87128 external link
Other Notes
Review4; Inhibitor of protein synthesis, binds to the 30S subunit and inhibits binding of aminoacyl-tRNAs.
Application
Tetracycline is an inhibitor of protein synthesis and is used in tetracycline controlled gene expression systems (gene switches) such a the tet-on and tet-off systems 1. It is also used to select tetracyline resistant colonies in cell culture 2.
Biochem/physiol Actions
Tetracycline binds to the 30S subunit of the ribosome at the A-site. During protein biosynthesis, the new t-RNA with the amino acid attempts to bind to the A-site of the ribosome. However, since the A-site is blocked by the tetracycline, the aminoacyl-tRNA cannot bind to it. Without the attachment of the tRNA, protein biosynthesis cannot occur. Protein biosynthesis is inhibited and cell death occurs 3.
Sigma Aldrich -  T3258 external link
Application
Tetracycline is a broad spectrum polyketide antibiotic. It is used clinically to treat bacterial infections such as Rocky Mountain spotted fever, typhus fever, tick fevers, Q fever, and Brill-Zinsser disease. It is used to treat upper respiratory infections and acne1. It is used to study multidrug resistance2 as well as potential side effects such as acute pancreatitis3.
Biochem/physiol Actions
Tetracycline inhibits bacterial protein synthesis elongation at the level of aminoacyl-tRNA binding to the 30S ribosome. Tetracycline passively diffuses through porin channels in the bacterial cell membrane. It also binds to the bacterial 50S ribosomal subunit which may alter the cytoplasmic membrane, causing intracellular components to leak from bacterial cells1. Mode of resistance is via loss of cell wall permeability.

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Griffin MO, Fricovsky E, Ceballos G, Villarreal F: Tetracyclines: a pleitropic family of compounds with promising therapeutic properties. Review of the literature. Am J Physiol Cell Physiol. 2010 Sep;299(3):C539-48. Epub 2010 Jun 30. Pubmed
  • Link
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专利

专利

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