Details of the Drug

General Information of Drug (ID: DMSIMD8)

• Drug Name: Cefuroxime
• Synonyms: Anaptivan; Biociclin; Biofuroksym; Bioxima; CXM; Cefofix; Cefumax; Cefurex; Cefuril; Cefuroxim; Cefuroximesodium; Cefuroximine; Cefuroximo; Cefuroximum; Cephuroxime; Cetroxil; Colifossim; Curocef; Curoxim; Curoxima; Curoxime; Froxal; Furoxil; Kesint; Ketocef; Lifurox; Medoxim; Sharox; Spectrazolr; Ultroxim; Zinacef;CEFUROXIME AND DEXTROSE IN DUPLEX CONTAINER; CEFUROXIME SODIUM; Cefuroxim AJ; Cefuroxim Fresenius; Cefuroxim Genericsn; Cefuroxim Hexal; Cefuroxim Lilly; Cefuroxim MN; Cefuroxim Norcox; Cefuroxim curasan; Cefuroxima Fabra; Cefuroxima Richet; Cefuroxime for Injection and Dextrose for Injection in Duplex Container; Cefuroxime na; Cefuroxime sodium salt; KEFUROX IN PLASTIC CONTAINER; Sodium cefuroxime; ZINACEF IN PLASTIC CONTAINER; Zinacef Danmark; Ceftin (TN); Cefuroxim Norcox [inj.]; Cefuroxime (TN); Cefuroximo [INN-Spanish]; Cefuroximum [INN-Latin]; Cetroxil [inj.]; Froxal [inj.]; KS-1040; Sharox [inj.]; Zinacef (TN); Zinnat (TN); Zinnat [inj.]; Cefuroxime (USAN/INN); Cefuroxime [USAN:INN:BAN]; Cefuroxime sodium (JP15/USP); Cefuroxime sodium [USAN:BAN:JAN]; Sodium (6R-(6alpha,7beta(Z)))-3-(((aminocarbonyl)oxy)methyl)-7-(2-furyl(methoxyimino)acetamido)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate; Sodium (6R,7R)-7-(2-(2-furyl)glyoxylamido)-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate, 7(sup 2)-(Z)-(O-methyloxime), carbamate (ester); (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; (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; (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); 3-[(carbamoyloxy)methyl]-7beta-[(2Z)-2-(furan-2-yl)-2-(methoxyimino)acetamido]-3,4-didehydrocepham-4-carboxylic acid

Indication

Disease Entry	ICD 11	Status	REF
Acute bronchitis	CA42	Approved	[1]

• Therapeutic Class: Antibiotics
• Drug Type: Small molecular drug
• #Ro5 Violations (Lipinski): 0:
  Molecular Weight (mw); 424.4
  Topological Polar Surface Area (xlogp); -0.2
  Rotatable Bond Count (rotbonds); 8
  Hydrogen Bond Donor Count (hbonddonor); 3
  Hydrogen Bond Acceptor Count (hbondacc); 10
• ADMET Property:
  Absorption: The drug absorbed from the gastrointestinal tract [2]
  BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [3]
  Clearance: The drug present in the plasma can be removed from the body at the rate of 2.2 mL/min/kg [4]
  Elimination: 96% of drug is excreted from urine in the unchanged form [3]
  Half-life: The concentration or amount of drug in body reduced by one-half in 80 minutes [4]
  Metabolism: The drug is metabolized to acetaldehyde and acetic acid [2]
  MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 39.35042 micromolar/kg/day [5]
  Vd: Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 0.15 L/kg [4]
  Water Solubility: The ability of drug to dissolve in water is measured as 200 mg/mL [3]
• Chemical Identifiers:
  Formula: C16H16N4O8S
  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
  Canonical 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
  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-IZRZKJBUSA-N
• Cross-matching ID:
  PubChem CID: 5479529
  ChEBI ID: CHEBI:3515
  CAS Number: 55268-75-2
  DrugBank ID: DB01112
  TTD ID: D0Y2IE
  VARIDT ID: DR00706

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Bacterial Penicillin binding protein (Bact PBP)	TTJP4SM	NOUNIPROTAC	Binder	[6]

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Cefuroxime (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Sodium bicarbonate	DMMU6BJ	Moderate	Decreased absorption of Cefuroxime due to altered gastric pH caused by Sodium bicarbonate.	Acidosis [5C73]	[16]
Kanamycin	DM2DMPO	Moderate	Increased risk of nephrotoxicity by the combination of Cefuroxime and Kanamycin.	Bacterial infection [1A00-1C4Z]	[17]
Rabeprazole	DMMZXIW	Moderate	Decreased absorption of Cefuroxime due to altered gastric pH caused by Rabeprazole.	Bacterial infection [1A00-1C4Z]	[16]
SODIUM CITRATE	DMHPD2Y	Moderate	Decreased absorption of Cefuroxime due to altered gastric pH caused by SODIUM CITRATE.	Discovery agent [N.A.]	[16]
Dexlansoprazole	DM1DBV5	Moderate	Decreased absorption of Cefuroxime due to altered gastric pH caused by Dexlansoprazole.	Gastro-oesophageal reflux disease [DA22]	[16]
Givosiran	DM5PFIJ	Moderate	Increased risk of nephrotoxicity by the combination of Cefuroxime and Givosiran.	Inborn porphyrin/heme metabolism error [5C58]	[18]
Plazomicin	DMKMBES	Moderate	Increased risk of nephrotoxicity by the combination of Cefuroxime and Plazomicin.	Urinary tract infection [GC08]	[17]

References

• [1] Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
• [2] FDA approval: ado-trastuzumab emtansine for the treatment of patients with HER2-positive metastatic breast cancer. Clin Cancer Res. 2014 Sep 1;20(17):4436-41.
• [3] BDDCS applied to over 900 drugs
• [4] Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
• [5] Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
• [6] Cefuroxime resistance in non-beta-lactamase Haemophilus influenzae is linked to mutations in ftsI. J Antimicrob Chemother. 2003 Mar;51(3):523-30.
• [7] Effects of amino acid alterations in penicillin-binding proteins (PBPs) 1a, 2b, and 2x on PBP affinities of penicillin, ampicillin, amoxicillin, cefditoren, cefuroxime, cefprozil, and cefaclor in 18 clinical isolates of penicillin-susceptible, -intermediate, and -resistant pneumococci. Antimicrob Agents Chemother. 2002 May;46(5):1273-80.
• [8] Bacteriological characteristics of Staphylococcus aureus isolates from humans and bulk milk. J Dairy Sci. 2008 Feb;91(2):564-9.
• [9] Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
• [10] Activities of antibiotics against methicillin-resistant Staphylococcus aureus with particular reference to synergetic effect between ticarcillin and fosfomycin on penicillinase non-producing methicillin-resistant S. aureus. Jpn J Antibiot. 1993 Jun;46(6):421-7.
• [11] Emerging drugs for bacterial urinary tract infections. Expert Opin Emerg Drugs. 2005 May;10(2):275-98.
• [12] Penicillin-binding protein sensitive to cephalexin in sporulation of Bacillus cereus. Microbiol Res. 1997 Sep;152(3):227-32.
• [13] Clofarabine: past, present, and future. Leuk Lymphoma. 2007 Oct;48(10):1922-30.
• [14] Relationship between penicillin-binding protein patterns and beta-lactamases in clinical isolates of Bacteroides fragilis with different susceptibility to beta-lactam antibiotics. J Med Microbiol. 2004 Mar;53(Pt 3):213-21.
• [15] Resistance of Pseudomonas aeruginosa to cefsulodin: modification of penicillin-binding protein 3 and mapping of its chromosomal gene. J Antimicrob Chemother. 1990 Apr;25(4):513-23.
• [16] Honig PK, Gillespie BK "Clinical significance of pharmacokinetic drug interactions with over-the-counter (OTC) drugs." Clin Pharmacokinet 35 (1998): 167-71. [PMID: 9784931]
• [17] Agencia Espaola de Medicamentos y Productos Sanitarios Healthcare "Centro de informacion online de medicamentos de la AEMPS - CIMA.".
• [18] Cerner Multum, Inc. "Australian Product Information.".