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110871-86-8 分子结构
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5-amino-1-cyclopropyl-7-[(3R,5S)-3,5-dimethylpiperazin-1-yl]-6,8-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

ChemBase编号:1078
分子式:C19H22F2N4O3
平均质量:392.3997864
单一同位素质量:392.16599702
SMILES和InChIs

SMILES:
Fc1c2n(C3CC3)cc(c(=O)c2c(N)c(F)c1N1C[C@@H](N[C@@H](C1)C)C)C(=O)O
Canonical SMILES:
C[C@@H]1N[C@H](C)CN(C1)c1c(F)c(N)c2c(c1F)n(cc(c2=O)C(=O)O)C1CC1
InChI:
InChI=1S/C19H22F2N4O3/c1-8-5-24(6-9(2)23-8)17-13(20)15(22)12-16(14(17)21)25(10-3-4-10)7-11(18(12)26)19(27)28/h7-10,23H,3-6,22H2,1-2H3,(H,27,28)/t8-,9+
InChIKey:
DZZWHBIBMUVIIW-DTORHVGOSA-N

引用这个纪录

CBID:1078 http://www.chembase.cn/molecule-1078.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
5-amino-1-cyclopropyl-7-[(3R,5S)-3,5-dimethylpiperazin-1-yl]-6,8-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
IUPAC传统名
sparfloxacin
5-amino-1-cyclopropyl-7-[(3R,5S)-3,5-dimethylpiperazin-1-yl]-6,8-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
商标名
Zagam
别名
5-氨基-1-环丙基-7-(顺式-3,5-二甲基-1-哌嗪基)-6,8-二氟-1,4-二氢-4-氧代-3-喹啉羧酸
司帕沙星
Sparfloxacin
5-Amino-1-cyclohexyl-7-(cis-3,5-dimethylpiperazino)-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid
Sparfloxacin
5-amino-1-cyclopropyl-7-((3R,5S)-3,5-dimethylpiperazin-1-yl)-6,8-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
cis-5-Amino-1-cyclopropyl-7-(3,5-dimethyl-1-piperazinyl)-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid
Parox
Spara
Sparcin
Zagam
CAS号
110871-86-8
MDL号
MFCD00869619
Beilstein号
9170271
PubChem SID
24860661
24880518
46506453
160964541
PubChem CID
60464

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 5.7532086  质子受体
质子供体 LogD (pH = 5.5) -0.36936733 
LogD (pH = 7.4) -0.04052399  Log P -0.043228146 
摩尔折射率 101.6938 cm3 极化性 36.853016 Å3
极化表面积 98.9 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P -0.07  LOG S -3.54 
溶解度 1.13e-01 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
Chloroform expand 查看数据来源
Ethanol expand 查看数据来源
Practically insoluble expand 查看数据来源
外观
Yellow Solid expand 查看数据来源
熔点
>245°C (dec.) expand 查看数据来源
疏水性(logP)
2.5 expand 查看数据来源
保存条件
-20°C Freezer expand 查看数据来源
RTECS编号
VB1986500 expand 查看数据来源
欧盟危险性物质标志
刺激性(Irritant) 刺激性(Irritant) (Xi) 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
2 expand 查看数据来源
危险公开号
36/37/38 expand 查看数据来源
安全公开号
26-36 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
H315-H319-H335 expand 查看数据来源
GHS警示性声明
P261-P305 + P351 + P338 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
相关基因信息
human ... KCNH1(3756), TOP2A(7153) expand 查看数据来源
生物活性机理
Eukaryotic cells do not contain DNA gyrase or topoisomerase IV. expand 查看数据来源
For many gram-negative bacteria DNA gyrase is the target, whereas topoisomerase IV is the target for many gram-positive bacteria. expand 查看数据来源
Inhibitor of bacterial DNA gyrase or the topoisomerase IV enzyme, thereby inhibiting DNA replication and transcription. expand 查看数据来源
Quinolones can enter cells easily and therefore are often used to treat intracellular pathogens such as Legionella pneumophila and Mycoplasma pneumoniae. expand 查看数据来源
纯度
≥98.0% (HPLC) expand 查看数据来源
95+% expand 查看数据来源
级别
VETRANAL™, analytical standard expand 查看数据来源
质检报告
下载链接 expand 查看数据来源
应用领域
Broad spectrum antibacterial agent expand 查看数据来源
Leprostatic and antitubercular agent expand 查看数据来源
Empirical Formula (Hill Notation)
C19H22F2N4O3 expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank -  DB01208 external link
Item Information
Drug Groups approved
Description Sparfloxacin is a fluoroquinolone antibiotic used in the treatment of bacterial infections. Sparfloxacin exerts its antibacterial activity by inhibiting DNA gyrase, a bacterial topoisomerase. DNA gyrase is an essential enzyme which controls DNA topology and assists in DNA replication, repair, deactivation, and transcription.
Indication For the treatment of adults with the following infections caused by susceptible strains microorganisms: community-acquired pneumonia (caused by Chlamydia pneumoniae, Haemophilus influenzae, Haemophilus parainfluenzae, Moraxella catarrhalis, Mycoplasma pneumoniae, or Streptococcus pneumoniae) and acute bacterial exacerbations of chronic bronchitis (caused by Chlamydia pneumoniae, Enterobacter cloacae, Haemophilus influenzae, Haemophilus parainfluenzae, Klebsiella pneumoniae, Moraxella catarrhalis, Staphylococcus aureus, or Streptococcus pneumoniae).
Pharmacology Sparfloxacin is a synthetic fluoroquinolone broad-spectrum antimicrobial agent in the same class as ofloxacin and norfloxacin. Sparfloxacin has in vitro activity against a wide range of gram-negative and gram-positive microorganisms. Sparfloxacin exerts its antibacterial activity by inhibiting DNA gyrase, a bacterial topoisomerase. DNA gyrase is an essential enzyme which controls DNA topology and assists in DNA replication, repair, deactivation, and transcription. Quinolones differ in chemical structure and mode of action from (beta)-lactam antibiotics. Quinolones may, therefore, be active against bacteria resistant to (beta)-lactam antibiotics. Although cross-resistance has been observed between sparfloxacin and other fluoroquinolones, some microorganisms resistant to other fluoroquinolones may be susceptible to sparfloxacin. In vitro tests show that the combination of sparfloxacin and rifampin is antagonistic against Staphylococcus aureus.
Toxicity Single doses of sparfloxacin were relatively non-toxic via the oral route of administration in mice, rats, and dogs. No deaths occurred within a 14-day post-treatment observation period at the highest oral doses tested, up to 5000 mg/kg in either rodent species, or up to 600 mg/kg in the dog. Clinical signs observed included inactivity in mice and dogs, diarrhea in both rodent species, and vomiting, salivation, and tremors in dogs.
Affected Organisms
Enteric bacteria and other eubacteria
Biotransformation Hepatic. Metabolized primarily by phase II glucuronidation to form a glucuronide conjugate. Metabolism does not utilize or interfere with the cytochrome P450 enzyme system.
Absorption Well absorbed following oral administration with an absolute oral bioavailability of 92%. Unaffected by administration with milk or food, however concurrent administration of antacids containing magnesium hydroxide and aluminum hydroxide reduces the oral bioavailability of sparfloxacin by as much as 50%.
Half Life Mean terminal elimination half-life of 20 hours (range 16-30 hours). Prolonged in patients with renal impairment (creatinine clearance <50 mL/min).
Protein Binding Low plasma protein binding in serum at about 45%.
External Links
Wikipedia
RxList
Drugs.com
Sigma Aldrich -  56968 external link
Biochem/physiol Actions
Inhibits bacterial DNA gyrase (topoisomerase II) and/or topoisomerase IV. Used to modulate (inhibit) bacterial DNA gyrase-dependent processes such as DNA polymerization, (ATP-dependent) DNA supercoiling, and chromosome fragmentation.
Other Notes
Antibacterial agents against respiratory tract infections2
Application
Sparfoxacin is a fluoroquinolone antibiotic used to study antimicrobial activity against mycobacteria and respiratory tract infections 1.
Sigma Aldrich -  33967 external link
法律信息
VETRANAL 商标 Sigma-Aldrich Co. LLC
Toronto Research Chemicals -  S679250 external link
A fluorianted quinolone antibacterial.

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
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  • Yasuba, M., et al.: chemotherapy, 39, Suppl. 4, 180 (1989)
  • Borner, K. et al., J. Chromatogr., 1992, 579, 285, (hplc)
  • Shimada, J. et al., Clin. Pharmacokinet., 1993, 25, 358, (pharmacokinet, rev)
  • Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 202
  • Goa, K.L. et al., Drugs, 1997, 54, 700-725, (rev)
  • Nakamura, S. et al., Antimicrob. Agents Chemother., 1989, 33, 1167; 1990, 34, 89, (pharmacol, activity)
  • Drugs of the Future, 1989, 14, 413, (rev)
  • Chaudhry, A.Z. et al., Antimicrob. Agents Chemother., 1990, 34, 1843; 2442, (activity)
  • Miyamoto, T. et al., J. Med. Chem., 1990, 33, 1645, (cryst struct, synth, pharmacol)
  • Kagemoto, A. et al., Arzneim.-Forsch., 1991, 41, 744, (synth)
  • Matsunaga, Y. et al., Arzneim.-Forsch., 1991, 41, 747; 760, (metab)
  • Nogita, T. et al., J. Antimicrob. Chemother., 1991, 28, 313, (pharmacokinet)
  • Qadri, S.M. et al., Chemotherapy (Basel), 1992, 38, 99, (activity)
  • Lewin, C.S. et al., J. Antimicrob. Chemother., 1992, 30, 625, (activity)
  • Richard, P. et al., J. Antimicrob. Chemother., 1992, 30, 739, (rev)
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专利

专利

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