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10206-21-0 molecular structure
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(6R,7R)-3-[(acetyloxy)methyl]-7-(2-cyanoacetamido)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

ChemBase ID: 1223
Molecular Formular: C13H13N3O6S
Molecular Mass: 339.32382
Monoisotopic Mass: 339.05250615
SMILES and InChIs

SMILES:
S1[C@H]2N(C(=O)[C@H]2NC(=O)CC#N)C(=C(C1)COC(=O)C)C(=O)O
Canonical SMILES:
CC(=O)OCC1=C(N2[C@H](SC1)[C@@H](C2=O)NC(=O)CC#N)C(=O)O
InChI:
InChI=1S/C13H13N3O6S/c1-6(17)22-4-7-5-23-12-9(15-8(18)2-3-14)11(19)16(12)10(7)13(20)21/h9,12H,2,4-5H2,1H3,(H,15,18)(H,20,21)/t9-,12-/m1/s1
InChIKey:
RRYMAQUWDLIUPV-BXKDBHETSA-N

Cite this record

CBID:1223 http://www.chembase.cn/molecule-1223.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(6R,7R)-3-[(acetyloxy)methyl]-7-(2-cyanoacetamido)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
IUPAC Traditional name
cefacetrile
Brand Name
Celospor
Celtol
Cristacef
Synonyms
(6R,7R)-3-[(Acetyloxy)methyl]-7-[(2-cyanoacetyl)amino]-8-oxo-5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid
7-(2-Cyanoacetamido)-3-(hydroxymethyl)-8-oxo-5-thia--1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid Acetate (Ester)
7-Cyanoacetamidocephalosporanic Acid
Cephacetril
Cephacetrile
Cefacetrilum [inn-latin]
Cefacetrilo [inn-spanish]
7-Cyanacetylamino-cephalosporansaeure
Cefacetrile
CAS Number
10206-21-0
PubChem SID
160964683
46504767
PubChem CID
91562

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
TRC
C231500 external link Add to cart Please log in.

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 3.3054466  H Acceptors
H Donor LogD (pH = 5.5) -4.022756 
LogD (pH = 7.4) -5.9693847  Log P -1.780771 
Molar Refractivity 77.5056 cm3 Polarizability 29.896023 Å3
Polar Surface Area 136.8 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P -0.52  LOG S -2.15 
Solubility (Water) 2.43e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
DMSO expand Show data source
Methanol expand Show data source
Apperance
Pale Beige Solid expand Show data source
Melting Point
133-135°C expand Show data source
Hydrophobicity(logP)
-0.45 [HANSCH,C ET AL. (1995)] expand Show data source
Storage Condition
Hygroscopic, -20°C Freezer, Under Inert Atmosphere 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 - DB01414 external link
Item Information
Drug Groups approved
Description A derivative of 7-aminocephalosporanic acid.
Indication Cefacetrile is a broad-spectrum first generation cephalosporin antibiotic effective in Gram-positive and Gram-negative bacterial infections.
Pharmacology Cefacetrile is effective against many Gram-positive bacterial strains and somewhat less effective against Gram-negative species. It works by 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
Half Life 1.2 hours
Protein Binding 23 to 38%
Distribution Vd of 0.2 to 0.5L/.kg
External Links
Wikipedia
Toronto Research Chemicals - C231500 external link
A cephalosporin antibiotic. Antibacterial.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Dajan, A., et al.: Vet. Microbiol., 35, 213 (1993)
  • • Becker, M., et al.: Anal. Chim. Acta, 520, 19 (1993)
  • • El-Shaboury, S., et al.: J. Pharm. Biomed. Anal., 45, 1 (1993)
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PATENTS

PATENTS

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INTERNET

INTERNET

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