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12650-69-0 分子结构
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9-({4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-{[(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl}oxan-2-yl]-3-methylbut-2-enoyl}oxy)nonanoic acid

ChemBase编号:293
分子式:C26H44O9
平均质量:500.62216
单一同位素质量:500.29853299
SMILES和InChIs

SMILES:
[C@H]1([C@H](CO[C@H]([C@@H]1O)C/C(=C/C(=O)OCCCCCCCCC(=O)O)/C)C[C@H]1[C@H]([C@H]([C@H](C)O)C)O1)O
Canonical SMILES:
OC(=O)CCCCCCCCOC(=O)/C=C(/C[C@@H]1OC[C@@H]([C@H]([C@H]1O)O)C[C@@H]1O[C@H]1[C@H]([C@@H](O)C)C)\C
InChI:
InChI=1S/C26H44O9/c1-16(13-23(30)33-11-9-7-5-4-6-8-10-22(28)29)12-20-25(32)24(31)19(15-34-20)14-21-26(35-21)17(2)18(3)27/h13,17-21,24-27,31-32H,4-12,14-15H2,1-3H3,(H,28,29)/b16-13+/t17-,18-,19-,20-,21-,24+,25-,26-/m0/s1
InChIKey:
MINDHVHHQZYEEK-HBBNESRFSA-N

引用这个纪录

CBID:293 http://www.chembase.cn/molecule-293.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
9-({4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-{[(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl}oxan-2-yl]-3-methylbut-2-enoyl}oxy)nonanoic acid
9-{[(2E)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-{[(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl}oxan-2-yl]-3-methylbut-2-enoyl]oxy}nonanoic acid
IUPAC传统名
mupirocin
9-({4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-{[(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl}oxan-2-yl]-3-methylbut-2-enoyl}oxy)nonanoic acid
商标名
Bactoderm
Bactroban
Bactroban Nasal
Centany
Turixin
别名
Bifido 选择性添加剂 A
MUP 添加剂
莫匹罗星 溶液
莫匹罗星添加剂
mupirocin
Mupirocin
Bifido Selective Supplement A
MUP Supplement
Mupirocin solution
Mupirocin Supplement
5,9-Anhydro-2,3,4,8-tetradeoxy-8-[[3-(2-hydroxy-1-methylpropyl)oxiranyl]methyl]-3-methyl-[2E,8[2S,3S(1S,2S)]]-L-talonon-2-enonic acid 8-carboxyoctyl ester
BRL 4910A
Mupirocin
(2E)-5,9-Anhydro-2,3,4,8-tetradeoxy-8-[[(2S,3S)-3-[(1S,2S)-2-hydroxy-1-methylpropyl]-oxiranyl]methyl]-3-methyl-L-talo-non-2-enonic Acid 8-Carboxyoctyl Ester
Bactoderm
Bactroban
Bactroban Ointment
Mupirocin Neo-Sensitabs
Mupricin
Pseudomonic Acid A
Turixin
trans-Pseudomonic Acid
MRC
Pseudomonic acid
Mupirocine
CAS号
12650-69-0
EC号
231-791-2
MDL号
MFCD01711620
PubChem SID
24724542
160963756
46505594
PubChem CID
446596
ATC码
D06AX09
R01AX06
CHEMBL
719
Chemspider ID
393914
DrugBank ID
DB00410
KEGG ID
D01076
美国药典/FDA物质标识码
D0GX863OA5
维基百科标题
Mupirocin
Medline Plus
a688004

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 4.8340716  质子受体
质子供体 LogD (pH = 5.5) 1.7011259 
LogD (pH = 7.4) -0.07094509  Log P 2.4513257 
摩尔折射率 129.3941 cm3 极化性 51.53534 Å3
极化表面积 146.05 Å2 可自由旋转的化学键 17 
里宾斯基五规则 false 
Log P 2.25  LOG S -4.28 
溶解度 2.65e-02 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
DMSO expand 查看数据来源
DMSO: ≥10 mg/mL expand 查看数据来源
Ethanol expand 查看数据来源
Methanol expand 查看数据来源
外观
White Crystalline Solid expand 查看数据来源
white to tan powder expand 查看数据来源
熔点
77-78°C expand 查看数据来源
比旋光度
[α]/D -15.7 to -20°, c = 1 in methanol expand 查看数据来源
保存条件
-20°C Freezer, Under Inert Atmosphere expand 查看数据来源
RTECS编号
RA6907000 expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
德国WGK号
1 expand 查看数据来源
2 expand 查看数据来源
个人保护装置
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand 查看数据来源
保存温度
2-8°C expand 查看数据来源
room temp expand 查看数据来源
给药途径
topical expand 查看数据来源
半衰期
20 to 40 minutes expand 查看数据来源
蛋白结合率
97% expand 查看数据来源
法定药品分级
Rx Only (US) expand 查看数据来源
妊娠期药物分类
B (US) expand 查看数据来源
美国(FDA)药品许可证
Bactroban expand 查看数据来源
纯度
≥92% (HPLC) expand 查看数据来源
级别
for microbiology expand 查看数据来源
质检报告
下载链接 expand 查看数据来源
有效期
(limited shelf life, expiry date on the label) expand 查看数据来源
Empirical Formula (Hill Notation)
C26H44O9 expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank -  DB00410 external link
Item Information
Drug Groups approved; investigational
Description Mupirocin (pseudomonic acid A, or Bactroban or Centany) is an antibiotic originally isolated from Pseudomonas fluorescens. It is used topically, and is primarily effective against Gram-positive bacteria. Mupirocin is bacteriostatic at low concentrations and bactericidal at high concentrations.
Mupirocin has a unique mechanism of action, which is selective binding to bacterial isoleucyl-tRNA synthetase, which halts the incorporation of isoleucine into bacterial proteins. Because this mechanism of action is not shared with any other antibiotic, mupirocin has few problems of antibiotic cross-resistance.
Indication For the treatment of Staphylococci nasal carriers.
Pharmacology Mupirocin, an antibiotic produced from Pseudomonas fluorescens, is structurally unrelated to any other topical or systemic antibiotics. Mupirocin is used to treat infection caused by Staphylococcus aureus and beta-hemolytic streptococci including Streptococcus pyogenes. This antibiotic has little, if any, potential for cross-resistance with other antibiotics.
Affected Organisms
Enteric bacteria and other eubacteria
Biotransformation Hepatic. Following intravenous or oral administration, mupirocin is rapidly metabolized. The principal metabolite is monic acid, which has no antibacterial activity.
Absorption No measurable systemic absorption
Half Life 20 to 40 minutes
Protein Binding 97%
Elimination Following the application of Centany (mupirocin ointment),2% to a 400 cm2 area on the back of 23 healthy volunteers once daily for 7 days, the mean (range) cumulative urinary excretion of monic acid over 24 hrs following the last administration was 1.25% (0.2% to 3.0%) of the administered dose of mupirocin.
External Links
Wikipedia
RxList
Drugs.com
Sigma Aldrich -  M7694 external link
Biochem/physiol Actions
Antibiotic; inhibits isoleucyl-tRNA synthetase (IRS).
Sigma Aldrich -  89914 external link
Components
(每瓶,足够用于 500mL 培养基) 莫匹罗星 25mg 无菌蒸馏水 5mL
Application
菌落计数法选择性分离奶制品中的双岐杆菌属的选择性添加剂。
Toronto Research Chemicals -  M794000 external link
Mupirocin, is a major component of the pseudomonic acid, an antibiotic complex produced by Pseudomonas fluorescens NCIB 10586. Topical antibacterial.

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Hughes, J., et al.: J. Antibiot., 31, 330 (1978)
  • Ward, A., et al.: Drugs, 32, 425 (1978)
  • Casewell, M.W., et al.: J. Antimicrob. Chemother., 19, 1 (1978)
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专利

专利

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