Details of the Drug

General Information of Drug (ID: DMY60I8)

• Drug Name: Cefixime
• Synonyms: CFIX; Cefixima; Cefiximum; Denvar; Necopen; Tricef; CL-284635; FK-027; FR-17027; Ofex (TN); Suprax (TN); Cefixime (JP15/USP/INN); (6R,7R)-7-({(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(carboxymethoxy)imino]acetyl}amino)-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(carboxymethyloxyimino)acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7R)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-{[(carboxymethyl)oxy]imino}acetyl]amino}-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6r,7r)-7-[-2-(2-amino-thiazol-4-yl)-2-carboxymethoxyimino-acetylamino]-8-oxo-3-vinyl-5-thia-1-aza-b; 7beta-{(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(carboxymethoxy)imino]acetamido}-3-ethenyl-3,4-didehydrocepham-4-carboxylic acid

Indication

Disease Entry	ICD 11	Status	REF
Acute gonococcal cervicitis	N.A.	Approved	[1]
Acute otitis media	AB00	Approved	[1]
Bacterial infection	1A00-1C4Z	Approved	[2]
Bronchitis	CA20	Approved	[1]
Cervicitis	N.A.	Approved	[1]
Pars planitis	N.A.	Approved	[1]
Respiratory tract infection	CA45	Approved	[1]
Urinary tract infection	GC08	Approved	[1]

• Therapeutic Class: Antibiotics
• Drug Type: Small molecular drug
• #Ro5 Violations (Lipinski): 1:
  Molecular Weight (mw); 453.5
  Logarithm of the Partition Coefficient (xlogp); -0.7
  Rotatable Bond Count (rotbonds); 8
  Hydrogen Bond Donor Count (hbonddonor); 4
  Hydrogen Bond Acceptor Count (hbondacc); 12
• ADMET Property:
  BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 4: low solubility and low permeability [3]
  Clearance: The drug present in the plasma can be removed from the body at the rate of 1 mL/min/kg [4]
  Elimination: 41% 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 3 - 4 hours [4]
  Metabolism: The drug is metabolized via the hepatic []
  MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 29.33035 micromolar/kg/day [5]
  Unbound Fraction: The unbound fraction of drug in plasma is 0.31% [4]
  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 0.24 L/kg [4]
  Water Solubility: The ability of drug to dissolve in water is measured as 0.05511 mg/mL [3]
• Chemical Identifiers:
  Formula: C16H15N5O7S2
  IUPAC Name: (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(carboxymethoxyimino)acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  Canonical SMILES: C=CC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)/C(=N\\OCC(=O)O)/C3=CSC(=N3)N)SC1)C(=O)O
  InChI: InChI=1S/C16H15N5O7S2/c1-2-6-4-29-14-10(13(25)21(14)11(6)15(26)27)19-12(24)9(20-28-3-8(22)23)7-5-30-16(17)18-7/h2,5,10,14H,1,3-4H2,(H2,17,18)(H,19,24)(H,22,23)(H,26,27)/b20-9-/t10-,14-/m1/s1
  InChIKey: OKBVVJOGVLARMR-QSWIMTSFSA-N
• Cross-matching ID:
  PubChem CID: 5362065
  ChEBI ID: CHEBI:472657
  CAS Number: 79350-37-1
  DrugBank ID: DB00671
  TTD ID: D06OVY
  VARIDT ID: DR00546
  ACDINA ID: D00108
• Repurposed Drugs (RPD): Click to Jump to the Detailed RPD Information of This Drug

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 Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
Peptide transporter 2 (SLC15A2)	DT8QKNP	S15A2_HUMAN	Substrate	[7]
Peptide transporter 1 (SLC15A1)	DT9G7XN	S15A1_HUMAN	Substrate	[8]

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Same Disease as Cefixime

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Disease	REF
Kanamycin	DM2DMPO	Moderate	Increased risk of nephrotoxicity by the combination of Cefixime and Kanamycin.	Bacterial infection [1A00-1C4Z]	[9]
Streptomycin	DME1LQN	Moderate	Increased risk of nephrotoxicity by the combination of Cefixime and Streptomycin.	Bacterial infection [1A00-1C4Z]	[9]
Gentamicin	DMKINJO	Moderate	Increased risk of nephrotoxicity by the combination of Cefixime and Gentamicin.	Bacterial infection [1A00-1C4Z]	[9]
Netilmicin	DMRD1QK	Moderate	Increased risk of nephrotoxicity by the combination of Cefixime and Netilmicin.	Bacterial infection [1A00-1C4Z]	[9]
Tobramycin	DMUI0CH	Moderate	Increased risk of nephrotoxicity by the combination of Cefixime and Tobramycin.	Bacterial infection [1A00-1C4Z]	[9]

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

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Framycetin	DMF8DNE	Moderate	Increased risk of nephrotoxicity by the combination of Cefixime and Framycetin.	Alcoholic liver disease [DB94]	[9]
Nifedipine	DMSVOZT	Minor	Altered absorption of Cefixime caused by Nifedipine.	Angina pectoris [BA40]	[10]
Mycophenolic acid	DMRBMAU	Moderate	Altered absorption of Cefixime due to GI flora changes caused by Mycophenolic acid.	Crohn disease [DD70]	[11]
Ethacrynic acid	DM60QMR	Moderate	Increased risk of nephrotoxicity by the combination of Cefixime and Ethacrynic acid.	Essential hypertension [BA00]	[12]
Furosemide	DMMQ8ZG	Moderate	Increased risk of nephrotoxicity by the combination of Cefixime and Furosemide.	Heart failure [BD10-BD1Z]	[12]
Bumetanide	DMRV7H0	Moderate	Increased risk of nephrotoxicity by the combination of Cefixime and Bumetanide.	Heart failure [BD10-BD1Z]	[12]
Givosiran	DM5PFIJ	Moderate	Increased risk of nephrotoxicity by the combination of Cefixime and Givosiran.	Inborn porphyrin/heme metabolism error [5C58]	[13]
Probenecid	DMMFWOJ	Moderate	Decreased elimination of Cefixime caused by Probenecid mediated competitive inhibition of renal tubular secretion.	Inborn purine/pyrimidine/nucleotide metabolism error [5C55]	[14]
Mycophenolate mofetil	DMPQAGE	Moderate	Altered absorption of Cefixime due to GI flora changes caused by Mycophenolate mofetil.	Transplant rejection [NE84]	[11]
Plazomicin	DMKMBES	Moderate	Increased risk of nephrotoxicity by the combination of Cefixime and Plazomicin.	Urinary tract infection [GC08]	[9]

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Allura red AC dye	E00338	33258	Colorant
Aspartame	E00402	134601	Flavoring agent
Mannitol	E00103	6251	Diluent; Flavoring agent; Lyophilization aid; Plasticizing agent; Tonicity agent
Sodium lauryl sulfate	E00464	3423265	Emulsifying agent; Modified-release agent; Penetration agent; Solubilizing agent; Surfactant; lubricant
Brushite	E00392	104805	Diluent
Crospovidone	E00626	Not Available	Disintegrant
Eisenoxyd	E00585	56841934	Colorant
Ferrosoferric oxide	E00231	14789	Colorant
Lactose monohydrate	E00393	104938	Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Magnesium stearate	E00208	11177	lubricant
Potassium hydroxide	E00233	14797	Alkalizing agent
Propylene glycol	E00040	1030	Antimicrobial preservative; Humectant; Plasticizing agent; Solvent
Silicon dioxide	E00670	Not Available	Anticaking agent; Opacifying agent; Viscosity-controlling agent
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
Triacetin	E00080	5541	Humectant; Plasticizing agent; Solvent

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Cefixime 400 mg capsule	400 mg	Oral Capsule	Oral
Cefixime 100 mg tablet	100 mg	Chewable Tablet	Oral
Cefixime 200 mg tablet	200 mg	Chewable Tablet	Oral
Cefixime 400 mg tablet	400 mg	Oral Tablet	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

• [1] Cefixime FDA Label
• [2] Natural products as sources of new drugs over the last 25 years. J Nat Prod. 2007 Mar;70(3):461-77.
• [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] Genetics of chromosomally mediated intermediate resistance to ceftriaxone and cefixime in Neisseria gonorrhoeae. Antimicrob Agents Chemother. 2009 Sep;53(9):3744-51.
• [7] Transport characteristics of a novel peptide transporter 1 substrate, antihypotensive drug midodrine, and its amino acid derivatives. J Pharmacol Exp Ther. 2006 Jul;318(1):455-60.
• [8] Flavonoids with epidermal growth factor-receptor tyrosine kinase inhibitory activity stimulate PEPT1-mediated cefixime uptake into human intestinal epithelial cells. J Pharmacol Exp Ther. 2001 Oct;299(1):351-7.
• [9] Agencia Espaola de Medicamentos y Productos Sanitarios Healthcare "Centro de informacion online de medicamentos de la AEMPS - CIMA.".
• [10] Duverne C, Bouten A, Deslandes A "Modification of cefixime bioavailabity by nifedipine in humans: involvement of the dipeptide carrier system." Antimicrob Agents Chemother 36 (1992): 2462-7. [PMID: 1489189]
• [11] Product Information. CellCept (mycophenolate mofetil). Roche Laboratories, Nutley, NJ.
• [12] Chrysos G, Gargalianos P, Lelekis M, Stefanou J, Kosmidis J "Pharmacokinetic interactions of ceftazidime and frusemide." J Chemother 7 Suppl (1995): 107-10. [PMID: 8904125]
• [13] Cerner Multum, Inc. "Australian Product Information.".
• [14] Brown G, Zemcov SJ, Clarke AM "Effect of probenecid on cefazolin serum concentrations." J Antimicrob Chemother 31 (1993): 1009-11. [PMID: 8360120]