Cefuroxime

C₁₆H₁₆N₄O₈SCAS 55268-75-2424.38 g/mol

Open in Covalent MOL file

Alkene Amide Carbamate Carboxylic acid Lactam Oxime Sulfide

Properties

Molecular formula: C₁₆H₁₆N₄O₈S
Molar mass: 424.38 g/mol
Exact mass: 424.0689 Da
Melting point: 171.5–173 °C (decomposes)
logP: -0.54Crippen estimate
Polar surface area: 173.8 Å²
H-bond donors / acceptors: 3 / 9
Rotatable bonds: 7
Stereocentres: R, Rin SMILES atom order
Double bonds: ZE/Z, in SMILES order

Hazards

Danger

H317 May cause an allergic skin reaction31% of notifiers
H334 May cause allergy or asthma symptoms or breathing difficulties if inhaled97.6% of notifiers
H373 May causes damage to organs through prolonged or repeated exposure66.7% of notifiers

Aggregated from 42 ECHA notifications, via PubChem; a share says how many notifiers assign that statement.

Precautionary statements

P233, P260, P261, P271, P272, P280, P284, P302+P352, P304+P340, P319, P321, P333+P317, P342+P316, P362+P364, P403, P501

Identifiers

CAS number

55268-75-2

SMILES

CO/N=C(/C1=CC=CO1)\C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)COC(=O)N)C(=O)O

InChIKey

JFPVXVDWJQMJEE-IZRZKJBUSA-N

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

Characterization data

Calculated from the structure, in the form journals print them.

[M + H]+

[M + H]+ Calcd for C16H17N4O8S 425.0762

[M + Na]+

[M + Na]+ Calcd for C16H16N4NaO8S 447.0581

[M − H]−

[M − H]− Calcd for C16H15N4O8S 423.0616

Elemental analysis

Anal. Calcd for C16H16N4O8S: C, 45.28; H, 3.80; N, 13.20; S, 7.55.

Weigh it out

Type any one amount. The others follow from the molar mass.

Names and synonyms

15 names · show all

5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[[(aminocarbonyl)oxy]methyl]-7-[[2-furanyl(methoxyimino)acetyl]amino]-8-oxo-, [6R-[6α,7β(Z)]]-
5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[[(aminocarbonyl)oxy]methyl]-7-[[(2Z)-2-(2-furanyl)-2-(methoxyimino)acetyl]amino]-8-oxo-, (6R,7R)-
5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[[(aminocarbonyl)oxy]methyl]-7-[[(2Z)-2-furanyl(methoxyimino)acetyl]amino]-8-oxo-, (6R,7R)-
(6R,7R)-3-[[(Aminocarbonyl)oxy]methyl]-7-[[(2Z)-2-(2-furanyl)-2-(methoxyimino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Cefuroxim
Cephuroxime
Cefaloxime
Biofuroksym
Cefuroxime acid
Ketocef
Cefasyn
Biofuroxim
Multisef
Maxalac
Zefu

Work with Cefuroxime

Predict the NMR spectrum1H and 13C shifts with multiplicities Make a solutionWhat to weigh for any molarity and volume Check drug-likenessLipinski, Veber and lead-likeness Isotope patternExact mass and the mass spectrum pattern

Stereoisomers, salts and isotopologues

The same compound in another form: other stereochemistry, a salt or hydrate, the free acid or base, or an isotope-labelled version.

Cefuroxime sodium56238-63-2Salt

Similar compounds

Cefuroxime axetil64544-07-673 % similar Ceftiofur80370-57-663 % similar Ceftiofur hydrochloride103980-44-561 % similar Cefotaxime63527-52-658 % similar Cefpodoxime80210-62-457 % similar Cefetamet65052-63-351 % similar Ceftiofur sodium104010-37-950 % similar Cefuzonam82219-78-149 % similar

Tanimoto similarity of circular fingerprints over the whole catalogue.

All similar compounds

Elsewhere

PubChem CAS Common Chemistry NIST WebBook