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97164-56-2 分子结构
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(6R,7R)-7-[(2E)-2-(2-amino-1,3-thiazol-4-yl)-2-[(carboxymethoxy)imino]acetamido]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

ChemBase编号:553
分子式:C16H15N5O7S2
平均质量:453.4496
单一同位素质量:453.04128985
SMILES和InChIs

SMILES:
S1[C@H]2N(C(=O)[C@H]2NC(=O)/C(=N/OCC(=O)O)/c2nc(sc2)N)C(=C(C1)C=C)C(=O)O
Canonical SMILES:
Nc1nc(cs1)/C(=N\OCC(=O)O)/C(=O)N[C@H]1[C@H]2SCC(=C(N2C1=O)C(=O)O)C=C
InChI:
InChI=1S/C16H15N5O7S2/c1-2-6-4-29-14-10(13(25)21(14)11(6)15(26)27)19-12(24)9(20-28-3-8(22)23)7-5-30-16(17)18-7/h2,5,10,14H,1,3-4H2,(H2,17,18)(H,19,24)(H,22,23)(H,26,27)/t10-,14-/m1/s1
InChIKey:
OKBVVJOGVLARMR-QMTHXVAHSA-N

引用这个纪录

CBID:553 http://www.chembase.cn/molecule-553.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
(6R,7R)-7-[(2E)-2-(2-amino-1,3-thiazol-4-yl)-2-[(carboxymethoxy)imino]acetamido]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
(6R,7R)-7-[2-(2-amino-1,3-thiazol-4-yl)-2-[(carboxymethoxy)imino]acetamido]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
IUPAC传统名
cefixim
cefixime
商标名
CFIX
Cefixoral
Cefspan
Cephoral
Oroken
Suprax
Unixime
别名
(6R,7R)-7-[[(2E)-2-(2-Amino-4-thiazolyl)-2-[(carboxymethoxy)imino]acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid
Cefixime E-isomer
[6R-[6α,7β(E)]]-7-[[(2-Amino-4-thiazolyl)[(carboxymethoxy)imino]acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid
(E)-Cefixime (Cefixime EP Impurity D)
Cefixima [Spanish]
Cefixime Anhydrous
Cefiximum [Latin]
Cefixim
Cefixime
CAS号
97164-56-2
79350-37-1
PubChem SID
160964016
PubChem CID
6321411

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
C242820 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 3.4486887  质子受体 10 
质子供体 LogD (pH = 5.5) -4.517875 
LogD (pH = 7.4) -7.089293  Log P -1.5863124 
摩尔折射率 104.9118 cm3 极化性 39.59456 Å3
极化表面积 184.51 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P 0.25  LOG S -3.64 
溶解度 1.04e-01 g/l 

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
55.11 mg/L expand 查看数据来源
疏水性(logP)
-0.4 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 -  DB00671 external link
Item Information
Drug Groups approved
Description Cefixime, an antibiotic, is a third-generation cephalosporin like ceftriaxone and cefotaxime. Cefixime is highly stable in the presence of beta-lactamase enzymes. As a result, many organisms resistant to penicillins and some cephalosporins due to the presence of beta-lactamases, may be susceptible to cefixime. The antibacterial effect of cefixime results from inhibition of mucopeptide synthesis in the bacterial cell wall.
Indication For use in the treatment of the following infections when caused by susceptible strains of the designated microorganisms: (1) uncomplicated urinary tract infections caused by Escherichia coli and Proteus mirabilis, (2) otitis media caused by Haemophilus influenzae (beta-lactamase positive and negative strains), Moraxella catarrhalis (most of which are beta-lactamase positive), and S. pyogenes, (3) pharyngitis and tonsillitis caused by S. pyogenes, (4) acute bronchitis and acute exacerbations of chronic bronchitis caused by Streptococcus pneumoniae and Haemophilus influenzae (beta-lactamase positive and negative strains), and (5) uncomplicated gonorrhea (cervical/urethral) caused by Neisseria gonorrhoeae (penicillinase- and non-penicillinase-producing strains).
Pharmacology Cefixime, an antibiotic, is a third-generation cephalosporin like ceftriaxone and cefotaxime. Cefixime is highly stable in the presence of beta-lactamase enzymes. As a result, many organisms resistant to penicillins and some cephalosporins due to the presence of beta-lactamases, may be susceptible to cefixime. The antibacterial effect of cefixime results from inhibition of mucopeptide synthesis in the bacterial cell wall.
Toxicity Symptoms of overdose include blood in the urine, diarrhea, nausea, upper abdominal pain, and vomiting.
Affected Organisms
Enteric bacteria and other eubacteria
Biotransformation Hepatic. Approximately 50% of the absorbed dose is excreted unchanged in the urine in 24 hours.
Absorption About 40%-50% absorbed orally whether administered with or without food, however, time to maximal absorption is increased approximately 0.8 hours when administered with food.
Half Life 3-4 hours (may range up to 9 hours). In severe renal impairment (5 to 20 mL/min creatinine clearance), the half-life increased to an average of 11.5 hours.
Protein Binding 65% (concentration independent)
References
McMillan A, Young H: The treatment of pharyngeal gonorrhoea with a single oral dose of cefixime. Int J STD AIDS. 2007 Apr;18(4):253-4. [Pubmed]
Adam D, Hostalek U, Troster K: 5-day cefixime therapy for bacterial pharyngitis and/or tonsillitis: comparison with 10-day penicillin V therapy. Cefixime Study Group. Infection. 1995;23 Suppl 2:S83-6. [Pubmed]
External Links
Wikipedia
RxList
PDRhealth
Drugs.com
Toronto Research Chemicals -  C242820 external link
(E)-Cefixime is an isomeric impurity of the third generation cephalosporin antibiotic, Cefixime (C242800).

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • McMillan A, Young H: The treatment of pharyngeal gonorrhoea with a single oral dose of cefixime. Int J STD AIDS. 2007 Apr;18(4):253-4. Pubmed
  • Adam D, Hostalek U, Troster K: 5-day cefixime therapy for bacterial pharyngitis and/or tonsillitis: comparison with 10-day penicillin V therapy. Cefixime Study Group. Infection. 1995;23 Suppl 2:S83-6. Pubmed
  • Bian, L. et al.: Yao. Fen. Zaz., 30, 872 (2010)
  • Rajadurai, R. et al.: Anal. Chem. Ind. J., 9, 265 (2010)
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专利

专利

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