(6R,7S)-7-{2-[(cyanomethyl)sulfanyl]acetamido}-7-methoxy-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: 159
• Molecular Formular: C15H17N7O5S3
• Molecular Mass: 471.53438
• Monoisotopic Mass: 471.04532968
• SMILES: S1[C@H]2N(C(=O)[C@@]2(OC)NC(=O)CSCC#N)C(=C(C1)CSc1n(nnn1)C)C(=O)O
• Canonical SMILES: N#CCSCC(=O)N[C@]1(OC)C(=O)N2[C@@H]1SCC(=C2C(=O)O)CSc1nnnn1C
• InChI: InChI=1S/C15H17N7O5S3/c1-21-14(18-19-20-21)30-6-8-5-29-13-15(27-2,17-9(23)7-28-4-3-16)12(26)22(13)10(8)11(24)25/h13H,4-7H2,1-2H3,(H,17,23)(H,24,25)/t13-,15+/m1/s1
• InChIKey: SNBUBQHDYVFSQF-HIFRSBDPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7S)-7-{2-[(cyanomethyl)sulfanyl]acetamido}-7-methoxy-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: cefmetazole; cefmetazole sodium
• Brand Name: Zefazone
• Synonyms: (6R,7S)-7-[[2-[(Cyanomethyl)thio]acetyl]amino]-7-methoxy-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; SKF 83088; U 72791; U 72791a; Cefmetazole sodium; Cefmetazolo [INN-Spanish]; Cefmetazolum [INN-Latin]; Cefmetazole

Database IDs

• CAS Number: 56796-20-4
• PubChem SID: 46504461; 160963622
• PubChem CID: 42008

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.3825634
• H Acceptors: 9
• H Donor: 2
• LogD (pH = 5.5): -2.7527611
• LogD (pH = 7.4): -4.0735326
• Log P: -0.6482912
• Molar Refractivity: 124.5707 cm^3
• Polarizability: 42.419262 Å^3
• Polar Surface Area: 163.33 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.38
• LOG S: -2.34
• Solubility (Water): 2.16e+00 g/l

PROPERTIES

Physical Property

• Solubility: 94.2 mg/L; Acetone; Methanol; Water
• Apperance: White Solid
• Melting Point: 163-165°C
• Hydrophobicity(logP): -2.2

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

DrugBank - DB00274

• Drug Groups: approved
• Description: A semisynthetic cephamycin antibiotic with a broad spectrum of activity against both gram-positive and gram-negative microorganisms. It has a high rate of efficacy in many types of infection and to date no severe side effects have been noted. [PubChem]
• Indication: For the treatment of infections caused by susceptible organisms.
• Pharmacology: Cefmetazole is a second-generation cephalosporin. The cephalosporins are bactericidal drugs with both gram-positive and gram-negative activity. They inhibit bacterial cell wall synthesis in a way similar to the penicillins. Cefmetazole is more active than 1st-generation cephalosporins against indole-positive Proteus, Serratia, anaerobic gram-negative bacilli (including B. fragilis), and some E. coli, Klebsiella, and P. mirabilis, but is less active than cefoxitin or cefotetan against most gram-negative bacilli.
• Toxicity: Oral LD₅₀ in rats is 3,204 mg/kg. With other b-lactam antibiotics, adverse effects following overdosage have included nausea, vomiting, epigastric distress, diarrhea, and convulsions.
• Affected Organisms: Enteric bacteria and other eubacteria
• Biotransformation: No appreciable metabolism.
• Absorption: Bioavailability is approximately 100% following intramuscular injection.
• Half Life: 1.50 ±0.14 hours
• External Links: Wikipedia

Toronto Research Chemicals - C242850

Semi-synthetic antibiotic derived from Cephamycin. Antibacterial.

REFERENCES

• Nakao, H., et al.: J. Antibiot., 29, 554 (1976)
• Iwata, M., et al.: Jpn. J. Exp. Med., 48, 401 (1976)
• Shindo, H., et al.: Chemoterapy, 27, 64 (1976)
• Nishida, M., et al.: J. Antibiot., 32, 1319 (1976)