(6R,7R)-7-[(2R)-2-amino-2-(4-hydroxyphenyl)acetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• ChemBase编号: 103102
• 分子式: C16H17N3O5S
• 平均质量: 363.38828
• 单一同位素质量: 363.08889166
• SMILES: O=C1N2C(=C(CS[C@@H]2[C@@H]1NC(=O)[C@@H](c1ccc(O)cc1)N)C)C(=O)O
• Canonical SMILES: O=C([C@@H](c1ccc(cc1)O)N)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)C
• InChI: InChI=1S/C16H17N3O5S/c1-7-6-25-15-11(14(22)19(15)12(7)16(23)24)18-13(21)10(17)8-2-4-9(20)5-3-8/h2-5,10-11,15,20H,6,17H2,1H3,(H,18,21)(H,23,24)/t10-,11-,15-/m1/s1
• InChIKey: BOEGTKLJZSQCCD-UEKVPHQBSA-N

名称和登记号

名称

• IUPAC标准名: (6R,7R)-7-[(2R)-2-amino-2-(4-hydroxyphenyl)acetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC传统名: cephadroxil; (6R,7R)-7-[(2R)-2-amino-2-(4-hydroxyphenyl)acetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• 别名: 头孢羟氨苄; Cefadroxil; p-Hydroxycephalexine; Cefamox; CEFADROXIL; (6R,7R)-7-((R)-2-amino-2-(4-hydroxyphenyl)acetamido)-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; Cephadroxil; Baxan; Bidocef; Cefadril; Cefadrox; Cefroxil; Duricef

登记号

• CAS号: 50370-12-2
• EC号: 256-555-6
• MDL号: MFCD00865091
• PubChem SID: 162091217; 24892921
• PubChem CID: 47965

理论计算性质

• Acid pKa: 3.4454033
• 质子受体: 6
• 质子供体: 4
• LogD (pH = 5.5): -2.4450464
• LogD (pH = 7.4): -2.7044444
• Log P: -2.4485235
• 摩尔折射率: 90.9545 cm^3
• 极化性: 35.27431 Å^3
• 极化表面积: 132.96 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

分子性质

理化性质

• 熔点: 197°C

安全信息

• 保存条件: 2-8°C
• RTECS编号: XI0337000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 2
• 危险公开号: 36/37/38-42/43
• 安全公开号: 26-36
• GHS危险品标识: GHS07; GHS08
• GHS警示词: Danger
• GHS危险声明: H315-H317-H319-H334-H335
• GHS警示性声明: P261-P280-P305 + P351 + P338-P342 + P311
• 个人保护装置: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

药理学性质

• 生物活性机理: Cell wall synthesis inhibitor; Mucopeptide-synthesis inhibitor;

产品相关信息

• 应用领域: Broad-spectrum antibiotic effective in Gram-positive and Gram-negative bacterial infections.; It is a bactericidal antibiotic

详细说明

MP Biomedicals - 02150581

White crystalline powder
m.p. 197°C

Sigma Aldrich - C7020

Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C7020.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

参考文献

• Ger. Pat., 1973, 2 263 861; CA, 79, 78822, (synth)
• Ger. Pat., 1975, 2 460 607; CA, 83, 145764, (synth)
• Dunn, G. et al., J. Antibiot., 1976, 29, 65, (synth)
• Neuman, M., Drugs of Today (Barcelona), 1977, 13, 471, (rev)
• U.S. Pat., 1979, 4 160 863; CA, 91, 175376, (synth, cryst struct)
• Leitner, F. et al., J. Antimicrob. Chemother., Suppl. B, 1982, 10, 1, (numerous papers)
• Tanrisever, B. et al., Drugs, 1986, 32, 1, (rev)
• Shin, W. et al., Acta Cryst. C, 1992, 48, 1454, (cryst struct)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 5179, (synonyms)
• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 163
• Kemperman, G.J. et al., Eur. J. Org. Chem., 2001, 1817-1820, (synth)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, DYF700