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153-61-7 molecular structure
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(6R,7R)-3-[(acetyloxy)methyl]-8-oxo-7-[2-(thiophen-2-yl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

ChemBase ID: 339
Molecular Formular: C16H16N2O6S2
Molecular Mass: 396.43804
Monoisotopic Mass: 396.04497824
SMILES and InChIs

SMILES:
S1[C@H]2N(C(=O)[C@H]2NC(=O)Cc2sccc2)C(=C(C1)COC(=O)C)C(=O)O
Canonical SMILES:
CC(=O)OCC1=C(C(=O)O)N2[C@H](SC1)[C@@H](C2=O)NC(=O)Cc1cccs1
InChI:
InChI=1S/C16H16N2O6S2/c1-8(19)24-6-9-7-26-15-12(14(21)18(15)13(9)16(22)23)17-11(20)5-10-3-2-4-25-10/h2-4,12,15H,5-7H2,1H3,(H,17,20)(H,22,23)/t12-,15-/m1/s1
InChIKey:
XIURVHNZVLADCM-IUODEOHRSA-N

Cite this record

CBID:339 http://www.chembase.cn/molecule-339.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(6R,7R)-3-[(acetyloxy)methyl]-8-oxo-7-[2-(thiophen-2-yl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
IUPAC Traditional name
cefalotin
cephalothin
(6R,7R)-3-[(acetyloxy)methyl]-8-oxo-7-[2-(thiophen-2-yl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Brand Name
Averon-1
Cemastin
Coaxin
Keflin
Seffin
Synonyms
Cefalotina [INN-Spanish]
Cefalotine [INN-French]
Cefalotinum [INN-Latin]
Cephalothin Sodium
Cephalothinum
Cephalothin
Cephalotin
CLS
Cefalothin
Cefalotin
(6R,7R)-3-(Acetoxymethyl)-8-oxo-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
7-(2-Thiopheneacetamido)cephalosporanic acid
Cephalosporin 871
Cefalotin
CAS Number
153-61-7
MDL Number
MFCD00242614
PubChem SID
46509079
160963802
PubChem CID
6024

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 3.625907  H Acceptors
H Donor LogD (pH = 5.5) -1.8540871 
LogD (pH = 7.4) -3.3175669  Log P 0.016272906 
Molar Refractivity 93.794 cm3 Polarizability 36.38155 Å3
Polar Surface Area 113.01 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 0.63  LOG S -3.88 
Solubility (Water) 5.21e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
158 mg/L expand Show data source
Hydrophobicity(logP)
-0.2 expand Show data source
Storage Warning
IRRITANT expand Show data source
MSDS Link
Download expand Show data source
TSCA Listed
false expand Show data source
Mechanism of Action
Mucopeptide synthesis inhibitor expand Show data source
Purity
95+% expand Show data source
97% expand Show data source
Application(s)
Parenteral antibiotic expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00456 external link
Item Information
Drug Groups approved
Description A cephalosporin antibiotic. [PubChem]
Indication Used to prevent infection during surgery and to treat many kinds of infections of the blood, bone or joints, respiratory tract, skin, and urinary tract.
Pharmacology Cefalotin (INN) or cephalothin (USAN) is a semisynthetic first generation cephalosporin having a broad spectrum of antibiotic activity that is administered parenterally.
Toxicity Rat intravenous LD50 is 4000 mg/kg.
Affected Organisms
Enteric bacteria and other eubacteria
Biotransformation Metabolized to a less active desacetyl metabolite, although 50-75% of the drug is eliminated unchanged in the urine.
Half Life 30 minutes
Protein Binding 65-80%
External Links
Wikipedia

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Chauvette, R.R. et al., J.A.C.S., 1962, 84, 3401, (synth)
  • • Woodward, R.B. et al., J.A.C.S., 1966, 88, 852, (synth)
  • • Simmons, R.J., Anal. Profiles Drug Subst., 1972, 1, 319, (rev)
  • • Welles, J.S., Cephalosporins Penicillins: Chem. Biol., (Flynn, E.H., Ed.), Academic Press, 1972, 583, (rev)
  • • Ratcliffe, R. et al., Tet. Lett., 1973, 4649
  • • Nishikawa, J. et al., J. Antibiot., 1982, 35, 1724, (ir, cmr)
  • • Cowley, B.R. et al., Tetrahedron, 1983, 39, 461, (synth)
  • • Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 3941, (synonyms)
  • • Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 138
  • • Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, CCX250; SFQ500
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PATENTS

PATENTS

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INTERNET

INTERNET

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