(6R,7R)-7-[(2R)-2-hydroxy-2-phenylacetamido]-3-{[(1-methyl-1H-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• ChemBase ID: 1160
• Molecular Formular: C18H18N6O5S2
• Molecular Mass: 462.50272
• Monoisotopic Mass: 462.07800971
• SMILES: S1[C@H]2N(C(=O)[C@H]2NC(=O)[C@H](O)c2ccccc2)C(=C(C1)CSc1n(nnn1)C)C(=O)O
• Canonical SMILES: O[C@@H](C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)CSc1nnnn1C)c1ccccc1
• InChI: InChI=1S/C18H18N6O5S2/c1-23-18(20-21-22-23)31-8-10-7-30-16-11(15(27)24(16)12(10)17(28)29)19-14(26)13(25)9-5-3-2-4-6-9/h2-6,11,13,16,25H,7-8H2,1H3,(H,19,26)(H,28,29)/t11-,13-,16-/m1/s1
• InChIKey: OLVCFLKTBJRLHI-AXAPSJFSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-7-[(2R)-2-hydroxy-2-phenylacetamido]-3-{[(1-methyl-1H-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: cefamandole
• Brand Name: Mandol
• Synonyms: Cefadole; Cefamandole nafate; Cefamandole

Database IDs

• CAS Number: 34444-01-4
• PubChem SID: 46508882; 160964623
• PubChem CID: 456255

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.3241954
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -2.132789
• LogD (pH = 7.4): -3.3938322
• Log P: 0.027085615
• Molar Refractivity: 126.6455 cm^3
• Polarizability: 43.361332 Å^3
• Polar Surface Area: 150.54 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.05
• LOG S: -2.9
• Solubility (Water): 5.81e-01 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 0.50 [SANGSTER (1994)]

DETAILS

DrugBank - DB01326

• Drug Groups: approved
• Description: Cefamandole (INN, also known as cephamandole) is a broad-spectrum cephalosporin antibiotic. The clinically used form of cefamandole is the formate ester cefamandole nafate, a prodrug which is administered parenterally. Cefamandole is no longer available in the United States.
• Indication: For the treatment of serious infections caused by susceptible strains of microorganisms.
• Pharmacology: Cefamandole is a broad-spectrum cephalosporin antibiotic. The clinically used form of cefamandole is the formate ester cefamandole nafate, a prodrug which is administered parenterally. The bactericidal action of cefamandole results from inhibition of cell-wall synthesis. Cephalosporins have in vitro activity against a wide range of gram-positive and gram-negative organisms.
• Toxicity: Symptoms of overdose include blood in the urine, diarrhea, nausea, upper abdominal pain, and vomiting.
• Affected Organisms: Enteric bacteria and other eubacteria
• Half Life: The half-life after an intravenous dose is 32 minutes; after intramuscular administration, the half-life is 60 minutes.
• Protein Binding: 75%
• External Links: Wikipedia; RxList