(6R,7R)-7-[(2R)-2-amino-2-phenylacetamido]-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• ChemBase编号: 72713
• 分子式: C15H14ClN3O4S
• 平均质量: 367.80736
• 单一同位素质量: 367.03935462
• SMILES: [C@@H]12N(C(=C(CS1)Cl)C(=O)O)C(=O)[C@H]2NC(=O)[C@@H](c1ccccc1)N
• Canonical SMILES: N[C@H](c1ccccc1)C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)Cl
• InChI: InChI=1S/C15H14ClN3O4S/c16-8-6-24-14-10(13(21)19(14)11(8)15(22)23)18-12(20)9(17)7-4-2-1-3-5-7/h1-5,9-10,14H,6,17H2,(H,18,20)(H,22,23)/t9-,10-,14-/m1/s1
• InChIKey: QYIYFLOTGYLRGG-GPCCPHFNSA-N

名称和登记号

名称

• IUPAC标准名: (6R,7R)-7-[(2R)-2-amino-2-phenylacetamido]-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC传统名: cefaclorum; cefaclor
• 别名: Cefaclor; Ceclor; Distaclor; Keflor; Raniclor; Cefaclor (Ceclor); Panoral; 3-Chloro-7-d-(2-phenylglycinamido)-3-cephem-4-carboxylic acid; CEFACLOR

登记号

• CAS号: 53994-73-3
• EC号: 258-909-5
• MDL号: MFCD00151471
• Beilstein号: 8176092
• PubChem SID: 24278331; 162037634
• PubChem CID: 51039

理论计算性质

• Acid pKa: 3.3266125
• 质子受体: 5
• 质子供体: 3
• LogD (pH = 5.5): -2.3051183
• LogD (pH = 7.4): -2.5596933
• Log P: -2.3070648
• 摩尔折射率: 89.5618 cm^3
• 极化性: 34.69509 Å^3
• 极化表面积: 112.73 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

• 溶解度: 1 M HCl: soluble50 mg/mL, clear to very faintly turbid, yellow; DMSO

安全信息

• 保存条件: -20°C; Room Temperature (15-30°C)
• RTECS编号: XI0363000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 2
• 危险公开号: 42/43
• 安全公开号: 22-36/37-45
• GHS危险品标识: GHS08
• GHS警示词: Danger
• GHS危险声明: H317-H334
• GHS警示性声明: P261-P280-P342 + P311
• 个人保护装置: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

产品相关信息

• 纯度: ~98%; ≥99.0% (TLC)
• 成盐信息: Free Base
• 杂质: ≤6% water
• Empirical Formula (Hill Notation): C15H14ClN3O4S

详细说明

MP Biomedicals - 02198943

Purity: ~98%

Selleck Chemicals - S1499

Research Area: Infection
Biological Activity:
Cefaclor belongs to the family of antibiotics known as the cephalosporins (cefalosporins). The cephalosporins are broad-spectrum antibiotics that are used for the treatment of septicaemia, pneumonia, meningitis, biliary-tract infections, peritonitis, and urinary-tract infections. The pharmacology of the cephalosporins is similar to that of the penicillins, excretion being principally renal. Cephalosporins penetrate the cerebrospinal fluid poorly unless the meninges are inflamed; cefotaxime is a more suitable cephalosporin than cefaclor for infections of the central nervous system, e.g. meningitis. Cefaclor is active against many bacteria, including both Gram-negative and Gram-positive organisms. [1]

Sigma Aldrich - C6895

Application
Cefaclor is used to study the mechanism of human renal transporters such as hOAT1, hPEPT1, and hPEPT2. Used to study the effects of inhibition of penicillin-binding proteins on bacterial cell wall mucopeptide synthesis.
Cefaclor is used to study urinary tract, intra-abdominal, and Haemophilus influenzae infections 1. It is used to study the mechanism of human renal organic anion and peptide transporters such as hOAT1, hPEPT1, and hPEPT2 and to study the effects of inhibition of penicillin-binding proteins on bacterial cell wall mucopeptide synthesis .
Biochem/physiol Actions
Cefaclor is active against Gram-negative and Gram-positive bacteria. Excretion of cefaclor is primarily renal. Cefaclor binds to penicillin-binding proteins thereby inhibiting cell wall synthesis 1.

参考文献

• http://en.wikipedia.org/wiki/Cefaclor