(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 ID: 1161
• Molecular Formular: C14H14N8O4S3
• Molecular Mass: 454.50716
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (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 Traditional name: cefazolin
• Brand Name: Ancef
• Synonyms: Cefazoline; Cephazolin; CEZ; Cefazolin sodium; Cefazolin

Database IDs

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

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.0265586
• H Acceptors: 9
• H Donor: 2
• LogD (pH = 5.5): -3.9590034
• LogD (pH = 7.4): -4.991068
• Log P: -1.5194101
• Molar Refractivity: 119.8562 cm^3
• Polarizability: 39.86288 Å^3
• Polar Surface Area: 156.09 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.4
• LOG S: -2.97
• Solubility (Water): 4.87e-01 g/l

PROPERTIES

Physical Property

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

DETAILS

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