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(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
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ChemBase ID:
983
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Molecular Formular:
C16H16N4O8S
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Molecular Mass:
424.38524
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Monoisotopic Mass:
424.06888449
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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
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Cite this record
CBID:983 http://www.chembase.cn/molecule-983.html
NAMES AND DATABASE IDS
NAMES AND DATABASE IDS
Names Database IDs
IUPAC name
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(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
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(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
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IUPAC Traditional name
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cefuroxime
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(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
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Brand Name
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Ancef
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Biofuroksym
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Cedax
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Cefizox
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Cefobid
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Cefotan
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Ceftin
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Cefurax
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Cefuril
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Cefzil
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Cepazine
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Cephuroxime
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Duricef
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Elobact
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Kefurox
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Kefzol
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Kerurox
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Mandol
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Maxipime
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Mefoxin
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Monocid
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Oraxim
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Rocephin
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Sharox
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Velosef
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Zinacef
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Zinat
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Zinnat
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Synonyms
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Cefuroxime [USAN:BAN:INN]
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Cefuroximo [INN-Spanish]
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Cefuroximum [INN-Latin]
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Cefuroxim
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Cefuroxime
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Cefuroxime
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头孢呋辛
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CAS Number
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EC Number
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MDL Number
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PubChem SID
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PubChem CID
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DATA SOURCES
DATA SOURCES
All Sources Commercial Sources Non-commercial Sources
CALCULATED PROPERTIES
CALCULATED PROPERTIES
JChem
ALOGPS 2.1
Acid pKa
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3.14945
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H Acceptors
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7
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H Donor
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3
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LogD (pH = 5.5)
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-3.2276237
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LogD (pH = 7.4)
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-4.356998
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Log P
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-0.9029735
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Molar Refractivity
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97.1658 cm3
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Polarizability
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37.301525 Å3
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Polar Surface Area
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173.76 Å2
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Rotatable Bonds
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8
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Lipinski's Rule of Five
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true
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Log P
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-0.24
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LOG S
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-3.17
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Solubility (Water)
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2.84e-01 g/l
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DETAILS
DETAILS
DrugBank
Sigma Aldrich
DrugBank -
DB01112
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Item |
Information |
Drug Groups
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approved |
Description
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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 |
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Enteric bacteria and other eubacteria |
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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 |
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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]
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External Links |
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PATENTS
PATENTS
PubChem Patent
Google Patent