(7R)-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-7-[2-(1H-1,2,3,4-tetrazol-1-yl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• ChemBase编号: 1161
• 分子式: C14H14N8O4S3
• 平均质量: 454.50716
• 单一同位素质量: 454.03001397
• SMILES: S1C2N(C(=O)[C@H]2NC(=O)Cn2nnnc2)C(=C(C1)CSc1sc(nn1)C)C(=O)O
• Canonical SMILES: O=C(N[C@@H]1C(=O)N2C1SCC(=C2C(=O)O)CSc1nnc(s1)C)Cn1cnnn1
• InChI: InChI=1S/C14H14N8O4S3/c1-6-17-18-14(29-6)28-4-7-3-27-12-9(11(24)22(12)10(7)13(25)26)16-8(23)2-21-5-15-19-20-21/h5,9,12H,2-4H2,1H3,(H,16,23)(H,25,26)/t9-,12?/m1/s1
• InChIKey: MLYYVTUWGNIJIB-PKEIRNPWSA-N

名称和登记号

名称

• IUPAC标准名: (7R)-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-7-[2-(1H-1,2,3,4-tetrazol-1-yl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC传统名: cefazolin
• 商标名: Ancef
• 别名: Cefazoline; Cephazolin; CEZ; Cefazolin sodium; Cefazolin

登记号

• CAS号: 25953-19-9
• PubChem SID: 160964624
• PubChem CID: 656510

理论计算性质

JChem

• Acid pKa: 3.0265586
• 质子受体: 9
• 质子供体: 2
• LogD (pH = 5.5): -3.9590034
• LogD (pH = 7.4): -4.991068
• Log P: -1.5194101
• 摩尔折射率: 119.8562 cm^3
• 极化性: 39.86288 Å^3
• 极化表面积: 156.09 Å^2
• 可自由旋转的化学键: 7
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -0.4
• LOG S: -2.97
• 溶解度: 4.87e-01 g/l

分子性质

理化性质

• 疏水性(logP): -0.58 [HANSCH,C ET AL. (1995)]

详细说明

DrugBank - DB01327

• Drug Groups: approved
• Description: A semisynthetic cephalosporin analog with broad-spectrum antibiotic action due to inhibition of bacterial cell wall synthesis. It attains high serum levels and is excreted quickly via the urine. [PubChem]
• Indication: Mainly used to treat bacterial infections of the skin. It can also be used to treat moderately severe bacterial infections involving the lung, bone, joint, stomach, blood, heart valve, and urinary tract. It is clinically effective against infections caused by staphylococci and streptococci species of Gram positive bacteria. May be used for surgical prophylaxis; if required metronidazole may be added to cover B. fragilis.
• Pharmacology: Cefazolin (also known as cefazoline or cephazolin) is a semi-synthetic first generation cephalosporin for parenteral administration. Cefazolin has broad-spectrum antibiotic action due to inhibition of bacterial cell wall synthesis. It attains high serum levels and is excreted quickly via the urine.
• Affected Organisms: Enteric bacteria and other eubacteria
• Biotransformation: Not metabolized.
• Absorption: Not absorbed from GI tract. Must be administered parenterally. Peak serum concentrations attained 1-2 hours post intramuscular injection.
• Half Life: The serum half-life is approximately 1.8 hours following IV administration and approximately 2.0 hours following IM administration.
• Protein Binding: 74-86%
• Elimination: Cefazolin is present in very low concentrations in the milk of nursing mothers. Cefazolin is excreted unchanged in the urine. In the first six hours approximately 60% of the drug is excreted in the urine and this increases to 70%-80% within 24 hours.
• External Links: Wikipedia; RxList; Drugs.com