Home > Compound List > Compound details
55268-75-2 molecular structure
click picture or here to close

(6R,7R)-3-[(carbamoyloxy)methyl]-7-[(2E)-2-(furan-2-yl)-2-(methoxyimino)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

ChemBase ID: 983
Molecular Formular: C16H16N4O8S
Molecular Mass: 424.38524
Monoisotopic Mass: 424.06888449
SMILES and InChIs

SMILES:
S1[C@H]2N(C(=O)[C@H]2NC(=O)/C(=N/OC)/c2occc2)C(=C(C1)COC(=O)N)C(=O)O
Canonical SMILES:
CO/N=C(/C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)COC(=O)N)\c1ccco1
InChI:
InChI=1S/C16H16N4O8S/c1-26-19-9(8-3-2-4-27-8)12(21)18-10-13(22)20-11(15(23)24)7(5-28-16(17)25)6-29-14(10)20/h2-4,10,14H,5-6H2,1H3,(H2,17,25)(H,18,21)(H,23,24)/b19-9+/t10-,14-/m1/s1
InChIKey:
JFPVXVDWJQMJEE-SWWZKJRFSA-N

Cite this record

CBID:983 http://www.chembase.cn/molecule-983.html

Collapse All Expand All

NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(6R,7R)-3-[(carbamoyloxy)methyl]-7-[(2E)-2-(furan-2-yl)-2-(methoxyimino)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
(6R,7R)-3-[(carbamoyloxy)methyl]-7-[2-(furan-2-yl)-2-(methoxyimino)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
IUPAC Traditional name
cefuroxime
(6R,7R)-3-[(carbamoyloxy)methyl]-7-[2-(furan-2-yl)-2-(methoxyimino)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Brand Name
Ancef
Biofuroksym
Cedax
Cefizox
Cefobid
Cefotan
Ceftin
Cefurax
Cefuril
Cefzil
Cepazine
Cephuroxime
Duricef
Elobact
Kefurox
Kefzol
Kerurox
Mandol
Maxipime
Mefoxin
Monocid
Oraxim
Rocephin
Sharox
Velosef
Zinacef
Zinat
Zinnat
Synonyms
Cefuroxime [USAN:BAN:INN]
Cefuroximo [INN-Spanish]
Cefuroximum [INN-Latin]
Cefuroxim
Cefuroxime
Cefuroxime
头孢呋辛
CAS Number
55268-75-2
EC Number
259-560-1
MDL Number
MFCD00864889
PubChem SID
160964446
PubChem CID
5361202

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
Sigma Aldrich
34218 external link Add to cart Please log in.

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 3.14945  H Acceptors
H Donor LogD (pH = 5.5) -3.2276237 
LogD (pH = 7.4) -4.356998  Log P -0.9029735 
Molar Refractivity 97.1658 cm3 Polarizability 37.301525 Å3
Polar Surface Area 173.76 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P -0.24  LOG S -3.17 
Solubility (Water) 2.84e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
Freely soluble as sodium salt (145 mg/L) expand Show data source
Hydrophobicity(logP)
-0.8 expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Grade
VETRANAL™, analytical standard expand Show data source
Empirical Formula (Hill Notation)
C16H16N4O8S expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Sigma Aldrich Sigma Aldrich
DrugBank - DB01112 external link
Item Information
Drug Groups approved
Description Broad-spectrum cephalosporin antibiotic resistant to beta-lactamase. It has been proposed for infections with gram-negative and gram-positive organisms, gonorrhea, and haemophilus. [PubChem]
Indication For the treatment of many different types of bacterial infections such as bronchitis, sinusitis, tonsillitis, ear infections, skin infections, gonorrhea, and urinary tract infections.
Pharmacology Cefuroxime is a β-lactam type antibiotic. More specifically, it is a second-generation cephalosporin. Cephalosporins work the same way as penicillins: they interfere with the peptidoglycan synthesis of the bacterial wall by inhibiting the final transpeptidation needed for the cross-links. This effect is bactericidal. Cefuroxime is effective against the following organisms: Aerobic Gram-positive Microorganisms: Staphylococcus aureus, Streptococcus pneumoniae, Streptococcus pyogenes. Aerobic Gram-negative Microorganisms: Escherichia coli, Haemophilus influenzae (including beta-lactamase-producing strains), Haemophilus parainfluenzae, Klebsiella pneumoniae, Moraxella catarrhalis (including beta-lactamase-producing strains), Neisseria gonorrhoeae (including beta-lactamase-producing strains). Spirochetes: Borrelia burgdorferi. Cefuroxime axetil is the prodrug
Toxicity Allergic reactions might be expected, including rash, nasal congestion, cough, dry throat, eye irritation, or anaphylactic shock. Overdosage of cephalosporins can cause cerebral irritation leading to convulsions.
Affected Organisms
Enteric bacteria and other eubacteria
Biotransformation The axetil moiety is metabolized to acetaldehyde and acetic acid.
Absorption Absorbed from the gastrointestinal tract. Absorption is greater when taken after food (absolute bioavailability increases from 37% to 52%).
Half Life Approximately 80 minutes following intramuscular or intravenous injection.
Protein Binding 50% to serum protein
References
Perry CM, Brogden RN: Cefuroxime axetil. A review of its antibacterial activity, pharmacokinetic properties and therapeutic efficacy. Drugs. 1996 Jul;52(1):125-58. [Pubmed]
External Links
Wikipedia
RxList
PDRhealth
Drugs.com
Sigma Aldrich - 34218 external link
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Perry CM, Brogden RN: Cefuroxime axetil. A review of its antibacterial activity, pharmacokinetic properties and therapeutic efficacy. Drugs. 1996 Jul;52(1):125-58. Pubmed
  • Searching...Please wait...

PATENTS

PATENTS

PubChem iconPubChem Patent Google Patent Search IconGoogle Patent

INTERNET

INTERNET

Baidu iconBaidu google iconGoogle