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阿奇霉素 A

阿奇霉素 A

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?阿奇霉素 A名称


















中文名

阿奇霉素 A
英文名

(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-3,4,10-trihydroxy-13-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,8,10,12,14-hexamethyl-1-oxa-6-azacyclopentadecan-15-one
中文别名


9-去氧-9a-氮杂-同型红霉素A 去甲阿奇霉素




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去甲阿奇霉素




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阿奇霉素杂质 A



英文别名
更多





?阿奇霉素 A生物活性












































描述
Azathramycin 是一种抗生素。
相关类别




溶解度

体外:

DMSO:33.33 mg / mL(45.35 mM;需要超声波)

体内:1。逐个添加每种溶剂:10%DMSO 90%(20%SBE-β-CD在盐水中)溶解度:≥2.5mg / mL(3.40 mM);澄清溶液2.逐个添加每种溶剂:10%DMSO 90%玉米油溶解度:≥2.5mg / mL(3.40 mM);澄清溶液3.逐个添加每种溶剂:10%DMSO 40%PEG300 5%吐温-80 45%盐水溶解度:≥2.5mg/ mL(3.40mM);明确解决方案

储备液

1 mM 1.3606 mL 6.8031 mL 13.6062 mL
5 mM 0.2721 mL 1.3606 mL 2.7212 mL
10 mM 0.1361 mL 0.6803 mL 1.3606 mL


存储

粉末 -20℃下 3年
4℃下 2年
在溶剂中 -80℃下 6个月
-20℃下 1个月


运输

室温;可能会有所不同
SMILES

C[C@H]1[C@H](O)[C@](C)(OC)C[C@]([H])(O[C@@H]([C@H](C)[C@@H](O[C@@]2([H])[C@H](O)[C@@H](N(C)C)C[C@@H](C)O2)[C@](C)(O)C[C@@H](C)CN[C@H](C)[C@@H](O)[C@@](O)(C)[C@@H](CC)O3)[C@@H](C)C3=O)O1
参考文献

[1]. Noedl H, Krudsood S, Leowattana W, In vitro antimalarial activity of azithromycin, artesunate, and quinine in combination and correlation with clinical outcome. Antimicrob Agents Chemother. 2007 Feb;51(2):651-6.

[2]. Hiwatashi Y, Maeda M, Fukushima H, Azithromycin suppresses proliferation, interleukin production and mitogen-activated protein kinases in human peripheral-blood mononuclear cells stimulated with bacterial superantigen. J Pharm Pharmacol. 2011 Oct;63(10):1320-6.

[3]. Fernandez-Obregon AC. Azithromycin for the treatment of acne. Int J Dermatol. 2000 Jan;39(1):45-50.


相关活性
小分子




嘌呤霉素盐酸盐



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G-418 硫酸盐



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衣霉素



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潮霉素B



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盐霉素



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阿维巴坦钠



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硫酸新霉素



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法硼巴坦



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甲氧西林钠



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利福平



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甲硝唑



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羧苄青霉素钠



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头孢他啶



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Eravacycline dihydrochloride



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头孢噻肟钠






?阿奇霉素 A物理化学性质









































密度 1.2±0.1 g/cm3
沸点 815.2±65.0 °C at 760 mmHg
熔点 126-136?C
分子式 C37H70N2O12
分子量 734.958
闪点 446.8±34.3 °C
精确质量 734.492859
PSA 188.87000
LogP 3.11
外观性状 白色固体
蒸汽压 0.0±0.6 mmHg at 25°C
折射率 1.536






?阿奇霉素 A安全信息
























符号

GHS07


GHS07
信号词
Warning
危害声明
H319
警示性声明
P305 + P351 + P338
危险品运输编码 NONH for all modes of transport





?阿奇霉素 A合成线路


























~83%







阿奇霉素 A结构式

阿奇霉素 A

76801-85-9






文献:ALEMBIC LIMITED Patent: WO2009/156938 A2, 2009 ; Location in patent: Page/Page column 8 ;





~%







阿奇霉素 A结构式

阿奇霉素 A

76801-85-9






文献:WO2007/80507 A2, ; Page/Page column 11 ;





~44%







阿奇霉素 A结构式

阿奇霉素 A

76801-85-9






文献:Costa, Anna M.; Vilarrasa, Jaume Tetrahedron Letters, 2000 , vol. 41, # 18 p. 3371 – 3375





~%







阿奇霉素 A结构式

阿奇霉素 A

76801-85-9






文献:Lee, Younjoo; Choi, Jun Yong; Fu, Hong; Harvey, Colin; Ravindran, Sandeep; Roush, William R.; Boothroyd, John C.; Khosla, Chaitan Journal of Medicinal Chemistry, 2011 , vol. 54, # 8 p. 2792 – 2804





~%







阿奇霉素 A结构式

阿奇霉素 A

76801-85-9






文献:Journal of Medicinal Chemistry, , vol. 54, # 8 p. 2792 – 2804







?阿奇霉素 A上下游产品













阿奇霉素 A上游产品? 3

阿奇霉素 A下游产品? 1













?阿奇霉素 A文献3

更多文献














Peptide-mediated macrolide resistance reveals possible specific interactions in the nascent peptide exit tunnel.

Mol. Microbiol. 54(2) , 376-85, (2004)

Expression of specific short peptides can render cells resistant to macrolide antibiotics. Peptides conferring resistance to structurally different macrolides including oleandomycin, azithromycin, aza…





Quantitative thin-layer chromatographic method of analysis of azithromycin in pure and capsule forms.

J. Chromatogr. Sci. 41(1) , 10-6, (2003)

A validated stability-indicating thin-layer chromatographic (TLC) method of the analysis of azithromycin (AZT) in bulk and capsule forms is developed. Both AZT potential impurity and degradation produ…





Erythromycin series. XII. Antibacterial in vitro evaluation of 10-dihydro-10-deoxo-11-azaerythromycin A: synthesis and structure-activity relationship of its acyl derivatives.

J. Antibiot. 40(7) , 1006-15, (1987)

Antibacterial in vitro evaluation of 10-dihydro-10-deoxo-11-azaerythromycin A (5), the new 15-membered semi-synthetic macrolide antibiotic with nitrogen as additional atom in the aglycone ring of eryt…









?阿奇霉素 A英文别名




























































9-deokso-9a-aza-9a-homoeritromicin A


Desmethylazithromycin


1-oxa-6-azacyclopentadecan-15-one, 13-[(2,6-dideoxy-3-C-methyl-3-O-methyl-α-L-ribo-hexopyranosyl)oxy]-2-ethyl-3,4,10-trihydroxy-3,5,8,10,12,14-hexamethyl-11-[[3,4,6-trideoxy-3-(dimethylamino)-β-D-xylo-hexopyranosyl]oxy]-, (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-


9a-N-desmethyl azithromycin


(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-2-Ethyl-3,4,10-trihydroxy-3,5,8,10,12,14-hexamethyl-15-oxo-11-{[3,4,6-trideoxy-3-(dimethylamino)-β-D-xylo-hexopyranosyl]oxy}-1-oxa-6-azacyclopentadecan-13-yl 2, 6-dideoxy-3-C-methyl-3-O-methyl-α-L-ribo-hexopyranoside


DD-Azaerythromycin A


10-Dihydro-10-deoxo-11-azaerythromycin A


9-Deoxo-9a-aza-9a-homo Erythromycin A(Desmethyl Azithromycin)


(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-2-Ethyl-3,4,10-trihydroxy-3,5,8,10,12,14-hexamethyl-15-oxo-11-{[3,4,6-trideoxy-3-(dimethylamino)-β-D-xylo-hexopyranosyl]oxy}-1-oxa-6-azacyclopentadecan-13-yl 2,6-dideoxy-3-C-methyl-3-O-methyl-α-L-ribo-hexopyranoside


9-deoxo-9-dihydro-9a-aza-9a-homoerythromycin A


9a-aza-9-deoxo-9a-homoerythromycin A


9-deoxo-9a-aza-9a-homoerythromycin


Azaerythromycin A


UNII-4LSP9FJT5B


1-Oxa-6-azacyclopentadecan-15-one, 13-[(2,6-dideoxy-3-C-methyl-3-O-methyl-α-L-ribo-hexopyranosyl)oxy]-2-ethyl-3,4,10-trihydroxy-3,5,8,10,12,14-hexamethyl-11-[[3,4,6-trideoxy-3-(dimethylamino)-β -D-xylo-hexopyranosyl]oxy]-, (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-


9-deoxo-9a-aza-9a-homoerythromycin A


Azathramycin







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