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56796-20-4 molecular structure
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(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 and InChIs

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

Cite this record

CBID:159 http://www.chembase.cn/molecule-159.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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 sodium
cefmetazole
Brand Name
Zefazone
Synonyms
Cefmetazole sodium
Cefmetazolo [INN-Spanish]
Cefmetazolum [INN-Latin]
Cefmetazole
(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
CAS Number
56796-20-4
PubChem SID
46504461
160963622
PubChem CID
42008

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
TRC
C242850 external link Add to cart Please log in.

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 3.3825634  H Acceptors
H Donor LogD (pH = 5.5) -2.7527611 
LogD (pH = 7.4) -4.0735326  Log P -0.6482912 
Molar Refractivity 124.5707 cm3 Polarizability 42.419262 Å3
Polar Surface Area 163.33 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P -0.38  LOG S -2.34 
Solubility (Water) 2.16e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
94.2 mg/L expand Show data source
Acetone expand Show data source
Methanol expand Show data source
Water expand Show data source
Apperance
White Solid expand Show data source
Melting Point
163-165°C expand Show data source
Hydrophobicity(logP)
-2.2 expand Show data source
Storage Condition
-20°C Freezer expand Show data source
MSDS Link
Download expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

DrugBank DrugBank TRC TRC
DrugBank - DB00274 external link
Item Information
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 external link
Semi-synthetic antibiotic derived from Cephamycin. Antibacterial.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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)
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PATENTS

PATENTS

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INTERNET

INTERNET

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