(6R,7R)-3-[(carbamoyloxy)methyl]-7-[(2E)-2-(furan-2-yl)-2-(methoxyimino)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• ChemBase编号: 983
• 分子式: C16H16N4O8S
• 平均质量: 424.38524
• 单一同位素质量: 424.06888449
• SMILES: S1[C@H]2N(C(=O)[C@H]2NC(=O)/C(=N/OC)/c2occc2)C(=C(C1)COC(=O)N)C(=O)O
• Canonical SMILES: CO/N=C(/C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)COC(=O)N)\c1ccco1
• InChI: InChI=1S/C16H16N4O8S/c1-26-19-9(8-3-2-4-27-8)12(21)18-10-13(22)20-11(15(23)24)7(5-28-16(17)25)6-29-14(10)20/h2-4,10,14H,5-6H2,1H3,(H2,17,25)(H,18,21)(H,23,24)/b19-9+/t10-,14-/m1/s1
• InChIKey: JFPVXVDWJQMJEE-SWWZKJRFSA-N

名称和登记号

名称

• IUPAC标准名: (6R,7R)-3-[(carbamoyloxy)methyl]-7-[(2E)-2-(furan-2-yl)-2-(methoxyimino)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7R)-3-[(carbamoyloxy)methyl]-7-[2-(furan-2-yl)-2-(methoxyimino)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC传统名: cefuroxime; (6R,7R)-3-[(carbamoyloxy)methyl]-7-[2-(furan-2-yl)-2-(methoxyimino)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• 商标名: Ancef; Biofuroksym; Cedax; Cefizox; Cefobid; Cefotan; Ceftin; Cefurax; Cefuril; Cefzil; Cepazine; Cephuroxime; Duricef; Elobact; Kefurox; Kefzol; Kerurox; Mandol; Maxipime; Mefoxin; Monocid; Oraxim; Rocephin; Sharox; Velosef; Zinacef; Zinat; Zinnat
• 别名: 头孢呋辛; Cefuroxime [USAN:BAN:INN]; Cefuroximo [INN-Spanish]; Cefuroximum [INN-Latin]; Cefuroxim; Cefuroxime; Cefuroxime

登记号

• CAS号: 55268-75-2
• EC号: 259-560-1
• MDL号: MFCD00864889
• PubChem SID: 160964446
• PubChem CID: 5361202

理论计算性质

JChem

• Acid pKa: 3.14945
• 质子受体: 7
• 质子供体: 3
• LogD (pH = 5.5): -3.2276237
• LogD (pH = 7.4): -4.356998
• Log P: -0.9029735
• 摩尔折射率: 97.1658 cm^3
• 极化性: 37.301525 Å^3
• 极化表面积: 173.76 Å^2
• 可自由旋转的化学键: 8
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -0.24
• LOG S: -3.17
• 溶解度: 2.84e-01 g/l

分子性质

理化性质

• 溶解度: Freely soluble as sodium salt (145 mg/L)
• 疏水性(logP): -0.8

安全信息

• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

产品相关信息

• 级别: VETRANAL™, analytical standard
• Empirical Formula (Hill Notation): C16H16N4O8S

详细说明

DrugBank - DB01112

• Drug Groups: approved
• Description: Broad-spectrum cephalosporin antibiotic resistant to beta-lactamase. It has been proposed for infections with gram-negative and gram-positive organisms, gonorrhea, and haemophilus. [PubChem]
• Indication: For the treatment of many different types of bacterial infections such as bronchitis, sinusitis, tonsillitis, ear infections, skin infections, gonorrhea, and urinary tract infections.
• Pharmacology: Cefuroxime is a β-lactam type antibiotic. More specifically, it is a second-generation cephalosporin. Cephalosporins work the same way as penicillins: they interfere with the peptidoglycan synthesis of the bacterial wall by inhibiting the final transpeptidation needed for the cross-links. This effect is bactericidal. Cefuroxime is effective against the following organisms: Aerobic Gram-positive Microorganisms: Staphylococcus aureus, Streptococcus pneumoniae, Streptococcus pyogenes. Aerobic Gram-negative Microorganisms: Escherichia coli, Haemophilus influenzae (including beta-lactamase-producing strains), Haemophilus parainfluenzae, Klebsiella pneumoniae, Moraxella catarrhalis (including beta-lactamase-producing strains), Neisseria gonorrhoeae (including beta-lactamase-producing strains). Spirochetes: Borrelia burgdorferi. Cefuroxime axetil is the prodrug
• Toxicity: Allergic reactions might be expected, including rash, nasal congestion, cough, dry throat, eye irritation, or anaphylactic shock. Overdosage of cephalosporins can cause cerebral irritation leading to convulsions.
• Affected Organisms: Enteric bacteria and other eubacteria
• Biotransformation: The axetil moiety is metabolized to acetaldehyde and acetic acid.
• Absorption: Absorbed from the gastrointestinal tract. Absorption is greater when taken after food (absolute bioavailability increases from 37% to 52%).
• Half Life: Approximately 80 minutes following intramuscular or intravenous injection.
• Protein Binding: 50% to serum protein
• References: Perry CM, Brogden RN: Cefuroxime axetil. A review of its antibacterial activity, pharmacokinetic properties and therapeutic efficacy. Drugs. 1996 Jul;52(1):125-58. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Sigma Aldrich - 34218

法律信息
VETRANAL 商标 Sigma-Aldrich Co. LLC

参考文献

• Perry CM, Brogden RN: Cefuroxime axetil. A review of its antibacterial activity, pharmacokinetic properties and therapeutic efficacy. Drugs. 1996 Jul;52(1):125-58. Pubmed