Cefuroxime

Details

• Internal ID: db53ab3a-9fef-496e-ac0f-1a0e8bfeb3c5
• Taxonomy: Organoheterocyclic compounds > Lactams > Beta lactams > Cephalosporins > Cephalosporin 3-carbamates
• IUPAC Name: (6R,7R)-3-(carbamoyloxymethyl)-7-[[(2Z)-2-(furan-2-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• SMILES (Canonical): CON=C(C1=CC=CO1)C(=O)NC2C3N(C2=O)C(=C(CS3)COC(=O)N)C(=O)O
• SMILES (Isomeric): 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
• 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
• InChI Key: JFPVXVDWJQMJEE-IZRZKJBUSA-N
• Popularity: 11,960 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₆N₄O₈S
• Molecular Weight: 424.40 g/mol
• Exact Mass: 424.06888465 g/mol
• Topological Polar Surface Area (TPSA): 199.00 Ų
• XlogP: -0.20

Synonyms

• Cephuroxime
• Cefuroxim
• Cefuroximo
• Cefuroximum
• Sharox
• 55268-75-2
• Zinacef Danmark
• Biofuroksym
• Cefuril
• Zinacef
• Cefuroximum [INN-Latin]
• Cefuroximo [INN-Spanish]
• Cefuroxime Acid
• Cefuroxima
• UNII-O1R9FJ93ED
• EINECS 259-560-1
• O1R9FJ93ED
• BRN 5783190
• CHEBI:3515
• DTXSID5022774
• Kefurox
• (6R,7R)-3-[(carbamoyloxy)methyl]-7-[(2Z)-2-(furan-2-yl)-2-(methoxyimino)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• 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-(6alpha,7beta(Z)))-
• Cefuroximum (INN-Latin)
• Cefuroximo (INN-Spanish)
• CEFUROXIME (MART.)
• CEFUROXIME [MART.]
• CEFUROXIME (USP IMPURITY)
• CEFUROXIME [USP IMPURITY]
• (6r,7r)-3-[(Carbamoyloxy)methyl]-7-{[(2z)-2-(Furan-2-Yl)-2-(Methoxyimino)acetyl]amino}-8-Oxo-5-Thia-1-Azabicyclo[4.2.0]oct-2-Ene-2-Carboxylic Acid
• (6R,7R)-3-[(carbamoyloxy)methyl]-7-{[(2Z)-2-furan-2-yl-2-(methoxyimino)acetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• Cefuroxime [USAN:INN:BAN]
• CXM
• DTXCID302774
• cefurossima
• Cefuroximine
• Cefuroxime [USAN:BAN:INN]
• 4kov
• Cefuroxime (TN)
• (6R,7R)-3-((carbamoyloxy)methyl)-7-(((2Z)-2-furan-2-yl-2-(methoxyimino)acetyl)amino)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid
• 3-((carbamoyloxy)methyl)-7beta-((2Z)-2-(furan-2-yl)-2-(methoxyimino)acetamido)-3,4-didehydrocepham-4-carboxylic acid
• 3-[(carbamoyloxy)methyl]-7beta-[(2Z)-2-(furan-2-yl)-2-(methoxyimino)acetamido]-3,4-didehydrocepham-4-carboxylic acid
• 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)-
• CEFUROXIME [MI]
• CEFUROXIME [INN]
• Cefuroxime (USAN/INN)
• Prestwick3_000720
• CEFUROXIME [USAN]
• CEFUROXIME [VANDF]
• CEFUROXIME [WHO-DD]
• CHEMBL1436
• BSPBio_000939
• (6R,7R)-7-(2-(2-Furyl)glyoxylamido)-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid 7(sup 2)-(Z)-(O-methyloxime) carbamate (ester)
• BIDD:GT0619
• BPBio1_001033
• SCHEMBL1821942
• HY-B1256A
• S01AA27
• BDBM50422689
• MFCD00864889
• AKOS015962849
• AC-4539
• DB01112
• KS-5162
• PD193945
• CS-0013520
• EN300-53016
• C06894
• Cefuroxime, VETRANAL(TM), analytical standard
• D00262
• CEFUROXIME AXETIL IMPURITY D [EP IMPURITY]
• Cefuroxime, Antibiotic for Culture Media Use Only
• W-105575
• BRD-K02733959-236-02-8
• BRD-K02733959-236-07-7
• Q63409033
• Z2382058334
• (6R,7R)-3-(carbamoyloxymethyl)-7-[[(2Z)-2-(2-furyl)-2-methoxyimino-acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• KEF
• KOV

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.05%	96.09%
CHEMBL2581	P07339	Cathepsin D	94.11%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.56%	99.17%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	91.90%	93.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.16%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.20%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.95%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.35%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.73%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.14%	91.11%
CHEMBL4208	P20618	Proteasome component C5	84.90%	90.00%
CHEMBL3891	P07384	Calpain 1	84.70%	93.04%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.51%	95.89%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.23%	95.50%
CHEMBL340	P08684	Cytochrome P450 3A4	81.76%	91.19%
CHEMBL3401	O75469	Pregnane X receptor	80.08%	94.73%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 5479529
• LOTUS: LTS0137157
• wikiData: Q413728