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564-25-0 分子结构
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(4S,4aR,5S,5aR,6R,12aS)-4-(dimethylamino)-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide

ChemBase编号:139
分子式:C22H24N2O8
平均质量:444.43456
单一同位素质量:444.15326574
SMILES和InChIs

SMILES:
[C@@H]12[C@](C(=C3[C@H]([C@@H]2O)[C@H](c2c(C3=O)c(ccc2)O)C)O)(C(=O)C(=C([C@H]1N(C)C)O)C(=O)N)O
Canonical SMILES:
CN([C@@H]1C(=C(C(=O)N)C(=O)[C@@]2([C@H]1[C@@H](O)[C@@H]1[C@@H](C)c3cccc(c3C(=O)C1=C2O)O)O)O)C
InChI:
InChI=1S/C22H24N2O8/c1-7-8-5-4-6-9(25)11(8)16(26)12-10(7)17(27)14-15(24(2)3)18(28)13(21(23)31)20(30)22(14,32)19(12)29/h4-7,10,14-15,17,25,27-29,32H,1-3H3,(H2,23,31)/t7-,10+,14+,15-,17-,22-/m0/s1
InChIKey:
JBIWCJUYHHGXTC-AKNGSSGZSA-N

引用这个纪录

CBID:139 http://www.chembase.cn/molecule-139.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,4aR,5S,5aR,6R,12aS)-4-(dimethylamino)-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
IUPAC传统名
vibramycin
商标名
Alti-Doxycycline
Apo-Doxy
Atridox
Doryx
Doxy 100
Doxy-Caps
Doxy-Lemmon
Doxychel
Doxychel Hyclate
Doxycin
Doxylin
Doxytec
Jenacyclin
Monodox
Novo-Doxylin
Nu-Doxycycline
Periostat
Supracyclin
Vibra-Tabs
Vibramycin
Oracea
别名
(4R,4aR,5S,5aR,6R,12aS)-4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamide
6-Deoxy-4-epioxytetracycline
4-Epi Doxycycline (>70%)
Doxcycline anhydrous
Doxycycline Hyclate
Doxycycline Monohydrate
Doxytetracycline
Doxycycline
CAS号
564-25-0
6543-77-7
PubChem SID
160963602
46506491
PubChem CID
5281011
54671203

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
E585900 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
可自由旋转的化学键 里宾斯基五规则 false 
Acid pKa -2.235276  质子受体
质子供体 LogD (pH = 5.5) -4.28254 
LogD (pH = 7.4) -6.187371  Log P -3.435637 
摩尔折射率 113.8919 cm3 极化性 43.13817 Å3
极化表面积 181.62 Å2
溶解度 6.30e-01 g/l  Log P -0.72 
LOG S -2.85 

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
630 mg/L expand 查看数据来源
Methanol expand 查看数据来源
Pyridine expand 查看数据来源
外观
Yellow Solid expand 查看数据来源
熔点
>176°C (dec.) expand 查看数据来源
疏水性(logP)
-0.2 expand 查看数据来源
保存条件
Amber Vial, -20°C Freezer, Under Inert Atmosphere 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
下载链接 expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank TRC TRC
DrugBank -  DB00254 external link
Item Information
Drug Groups approved; investigational
Description A synthetic tetracycline derivative with similar antimicrobial activity. Animal studies suggest that it may cause less tooth staining than other tetracyclines. It is used in some areas for the treatment of chloroquine-resistant falciparum malaria (malaria, falciparum). [PubChem]
Indication Doxycycline is indicated for use in respiratory tract infections caused by Mycoplasma pneumoniae, Haemophilus influenzae, Streptococcus pneumoniae, Legionella spp., or Klebsiella spp. It is also used for prophylaxis of malaria. Doxycycline is indicated for a variety of bacterial infections, from Mycobacterium fortuitum and M. marinum, to susceptible E. coli and Brucella spp. It can be used as an alternative to treating plague, tetanus, Campylobacter fetus
Pharmacology Doxycycline, a long-acting tetracycline derived from oxytetracycline, is used to inhibit bacterial protein synthesis and treat non-gonococcal urethritis and cervicitis, exacerbations of bronchitis in patients with COPD, and adult periodontitis.
Toxicity Symptoms of overdose include anorexia, nausea, diarrhoea, glossitis, dysphagia, enterocolitis and inflammatory lesions (with monilial overgrowth) in the anogenital region, skin reactions such as maculopapular and erythematous rashes, exfoliative dermatitis, photosensitivity, hypersensitivity reactions such as urticaria, angioneurotic oedema, anaphylaxis, anaphyl-actoid purpura, pericarditis, and exacerbation of systemic lupus erythematosus, benign intracranial hypertension in adults disappearing on discontinuation of the medicine, haematologic abnormalities such as haemolytic anaemia, thrombocytopenia, neutropenia, and eosinophilia. LD50=262 mg/kg (I.P. in rat).
Affected Organisms
Enteric bacteria and other eubacteria
Biotransformation Hepatic
Absorption Completely absorbed following oral administration.
Half Life 18-22 hours
Protein Binding >90%
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
Dahl EL, Shock JL, Shenai BR, Gut J, DeRisi JL, Rosenthal PJ: Tetracyclines specifically target the apicoplast of the malaria parasite Plasmodium falciparum. Antimicrob Agents Chemother. 2006 Sep;50(9):3124-31. [Pubmed]
Hoerauf A, Mand S, Fischer K, Kruppa T, Marfo-Debrekyei Y, Debrah AY, Pfarr KM, Adjei O, Buttner DW: Doxycycline as a novel strategy against bancroftian filariasis-depletion of Wolbachia endosymbionts from Wuchereria bancrofti and stop of microfilaria production. Med Microbiol Immunol. 2003 Nov;192(4):211-6. Epub 2003 Mar 5. [Pubmed]
Taylor MJ, Makunde WH, McGarry HF, Turner JD, Mand S, Hoerauf A: Macrofilaricidal activity after doxycycline treatment of Wuchereria bancrofti: a double-blind, randomised placebo-controlled trial. Lancet. 2005 Jun 18-24;365(9477):2116-21. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com
Toronto Research Chemicals -  E585900 external link
An alternative to doxycycline to control gene expression.

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Dahl EL, Shock JL, Shenai BR, Gut J, DeRisi JL, Rosenthal PJ: Tetracyclines specifically target the apicoplast of the malaria parasite Plasmodium falciparum. Antimicrob Agents Chemother. 2006 Sep;50(9):3124-31. Pubmed
  • Hoerauf A, Mand S, Fischer K, Kruppa T, Marfo-Debrekyei Y, Debrah AY, Pfarr KM, Adjei O, Buttner DW: Doxycycline as a novel strategy against bancroftian filariasis-depletion of Wolbachia endosymbionts from Wuchereria bancrofti and stop of microfilaria production. Med Microbiol Immunol. 2003 Nov;192(4):211-6. Epub 2003 Mar 5. Pubmed
  • Taylor MJ, Makunde WH, McGarry HF, Turner JD, Mand S, Hoerauf A: Macrofilaricidal activity after doxycycline treatment of Wuchereria bancrofti: a double-blind, randomised placebo-controlled trial. Lancet. 2005 Jun 18-24;365(9477):2116-21. Pubmed
  • Schiffer, I., et al.: Cancer Res. 63, 7221 (2003)
  • Eger, K., et al.: Biochem. Biophys. Res. Comm., 323, 979, (2004).
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专利

专利

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