Drug Details

General Information of the Drug (ID: DR3804)
Name
Cefuroxime
Synonyms
cefuroxime; Cephuroxime; Cefuroxim; Cefuroximo; 55268-75-2; Cefuroximum; Zinacef Danmark; Zinacef; Sharox; Cefuroximum [INN-Latin]; Cefuroximo [INN-Spanish]; UNII-O1R9FJ93ED; O1R9FJ93ED; CHEBI:3515; (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; Biofuroksym; Cefuril; Kefurox; Q63409033; (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]; C16H16N4O8S; (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; (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; EINECS 259-560-1; BRN 5783190; Cefuroximine; Cefuroxime [USAN:BAN:INN]; 4kov; Cefuroxime (TN); Cefuroxime (USAN/INN); Prestwick3_000720; 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); 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)))-; BIDD:GT0619; BPBio1_001033; SCHEMBL1821942; HY-B1256A; ZINC3830485; BDBM50422689; MFCD00864889; AKOS015962849; AC-4539; DB01112; KS-5162; P802; AB0010602; CS-0013520; EN300-53016; C06894; Cefuroxime, VETRANAL(TM), analytical standard; D00262; 268C752; A830563; Cefuroxime, Antibiotic for Culture Media Use Only; W-105575; BRD-K02733959-236-02-8; BRD-K02733959-236-07-7; (6R,7R)-3-((Carbamoyloxy)methyl)-7-((Z)-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-(aminocarbonyloxymethyl)-7-[[(2Z)-2-(furan-2-yl)-2-methoxyimino-ethanoyl]amino]-8-oxidanylidene-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7R)-3-(carbamoyloxymethyl)-7-[[(2Z)-2-(2-furanyl)-2-methoxyimino-1-oxoethyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (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; (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-3-ene-2-carboxylic Acid; 3-[(carbamoyloxy)methyl]-7beta-[(2Z)-2-(furan-2-yl)-2-(methoxyimino)acetamido]-3,4-didehydrocepham-4-carboxylic acid; KEF; KOV
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Molecular Type
Small molecule
Disease Acute bronchitis [ICD-11: CA42] Approved [1]
Structure
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2D MOL

3D MOL

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Formula
C16H16N4O8S
PubChem CID
5479529
Canonical SMILES
CON=C(C1=CC=CO1)C(=O)NC2C3N(C2=O)C(=C(CS3)COC(=O)N)C(=O)O
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-IZRZKJBUSA-N
CAS Number
CAS 55268-75-2
ChEBI ID
CHEBI:3515
TTD Drug ID
D0Y2IE
DrugBank ID
DB01112
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          1,4-naphthoquinone      Setaria palmifolia     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model Micrococcus luteus Microorganism model Micrococcus luteus
Bacillus cereus Microorganism model Bacillus cereus
Methicillin-sensitive Staphylococcus aureus Microorganism model Staphylococcus aureus
Methicillin-Resistant Staphylococcus aureus Microorganism model Staphylococcus aureus
Escherichia coli Microorganism model Escherichia coli
Klebsiella pneumoniae Microorganism model Klebsiella pneumoniae
Pseudomonas aeruginosa Microorganism model Pseudomonas aeruginosa
Salmonella choleraesuis Microorganism model Salmonella choleraesuis
                    Experimental
                    Result(s)		 1,4-naphthoquinone combined with ascorbate have significant antitumor effects against MCF-7 cells in vitro and Ehrlich-ascites carcinoma in mice.
Target and Pathway
Target(s) Bacterial Penicillin binding protein (Bact PBP)  Molecule Info  [3]
References
Reference 1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
Reference 2 Synergistic Antibacterial Activity Between 1,4-Naphthoquinone and Beta-Lactam Antibiotics Against Methicillin-Resistant Staphylococcus aureus. Microb Drug Resist. 2021 Feb;27(2):234-240.
Reference 3 Cefuroxime resistance in non-beta-lactamase Haemophilus influenzae is linked to mutations in ftsI. J Antimicrob Chemother. 2003 Mar;51(3):523-30.
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