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 bronchiolitis N.A. Approved [1]
Acute bronchitis CA42 Approved [2]
Acute gonococcal cervicitis N.A. Approved [1]
Acute maxillary sinusitis N.A. Approved [1]
Acute otitis media AB00 Approved [1]
Bacteremia 1A73 Approved [1]
Staphylococcal pneumonia N.A. Approved [1]
Staphylococcus aureus infection N.A. Approved [1]
Sinusitis CA0A.Z Investigative [1]
⏷ Show the Full List of Indication(s)
Therapeutic Class
Antibiotics
Affected Organisms
Enteric bacteria and other eubacteria
ATC Code
J01DC02: Cefuroxime
J01DC: Second-generation cephalosporins
J01D: OTHER BETA-LACTAM ANTIBACTERIALS
J01: ANTIBACTERIALS FOR SYSTEMIC USE
J: ANTIINFECTIVES FOR SYSTEMIC USE
J01DC02: Cefuroxime
J01DC: Second-generation cephalosporins
J01D: OTHER BETA-LACTAM ANTIBACTERIALS
J01: ANTIBACTERIALS FOR SYSTEMIC USE
J: ANTIINFECTIVES FOR SYSTEMIC USE
S01AA27: Cefuroxime
S01AA: Antibiotics
S01A: ANTIINFECTIVES
S01: OPHTHALMOLOGICALS
S: SENSORY ORGANS
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 424.4
Logarithm of the Partition Coefficient (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 []
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 []
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
CHEMBL1436
CAS Number
55268-75-2
UNII
O1R9FJ93ED
DrugBank ID
DB01112
TTD ID
D0Y2IE
VARIDT ID
DR00706
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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 Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
HLA class I histocompatibility antigen, alpha chain E (HLA-E) OTX1CTFB HLAE_HUMAN Gene/Protein Processing [7]
HLA class II histocompatibility antigen, DQ beta 1 chain (HLA-DQB1) OTVVI3UI DQB1_HUMAN Gene/Protein Processing [7]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

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] [8]
Kanamycin DM2DMPO Moderate Increased risk of nephrotoxicity by the combination of Cefuroxime and Kanamycin. Bacterial infection [1A00-1C4Z] [9]
Rabeprazole DMMZXIW Moderate Decreased absorption of Cefuroxime due to altered gastric pH caused by Rabeprazole. Bacterial infection [1A00-1C4Z] [8]
SODIUM CITRATE DMHPD2Y Moderate Decreased absorption of Cefuroxime due to altered gastric pH caused by SODIUM CITRATE. Discovery agent [N.A.] [8]
Dexlansoprazole DM1DBV5 Moderate Decreased absorption of Cefuroxime due to altered gastric pH caused by Dexlansoprazole. Gastro-oesophageal reflux disease [DA22] [8]
Givosiran DM5PFIJ Moderate Increased risk of nephrotoxicity by the combination of Cefuroxime and Givosiran. Inborn porphyrin/heme metabolism error [5C58] [10]
Plazomicin DMKMBES Moderate Increased risk of nephrotoxicity by the combination of Cefuroxime and Plazomicin. Urinary tract infection [GC08] [9]
⏷ Show the Full List of 7 DDI Information of This Drug

References

1 Cefuroxime FDA Label
2 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
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 Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis. Chem Res Toxicol. 2015 May 18;28(5):927-34. doi: 10.1021/tx5005248. Epub 2015 Apr 3.
8 Honig PK, Gillespie BK "Clinical significance of pharmacokinetic drug interactions with over-the-counter (OTC) drugs." Clin Pharmacokinet 35 (1998): 167-71. [PMID: 9784931]
9 Agencia Espaola de Medicamentos y Productos Sanitarios Healthcare "Centro de informacion online de medicamentos de la AEMPS - CIMA.".
10 Cerner Multum, Inc. "Australian Product Information.".