Details of the Drug

General Information of Drug (ID: DMWV2AG)

• Drug Name: Ceftibuten
• Synonyms: CETB; Cedax; Ceftem; Ceftibutene; Ceftibuteno; Ceftibutenum; Cephem; Ceprifran; Isocef; Keimax; Antibiotic 7432S; S 7432; Sch 39720; Cedax (TN); Ceftibutene [INN-French]; Ceftibuteno [INN-Spanish]; Ceftibutenum [INN-Latin]; Cephalosporin 7432-S; Cis-Ceftibutin; Cis-ceftibuten; Sch-39720; Trans-Ceftibuten; Ceftibuten(USAN/INN); Ceftibuten [USAN:INN:BAN]; (+)-(6R,7R)-7-((Z)-2-(2-Amino-4-thiazolyl)-4-carboxycrotonamido)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid; (6R,7R)-7-[[(E)-2-(2-amino-1,3-thiazol-4-yl)-5-hydroxy-5-oxopent-2-enoyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7R)-7-[[(Z)-2-(2-amino-1,3-thiazol-4-yl)-5-hydroxy-5-oxopent-2-enoyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-5-hydroxy-5-oxopent-2-enoyl]amino]-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)-4-carboxybut-2-enoyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; 7-[[(E)-2-(2-amino-1,3-thiazol-4-yl)-5-hydroxy-5-oxopent-2-enoyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; 7-[[(Z)-2-(2-amino-1,3-thiazol-4-yl)-5-hydroxy-5-oxopent-2-enoyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; 7-[[2-(2-amino-1,3-thiazol-4-yl)-5-hydroxy-5-oxopent-2-enoyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; 7432-S; 7beta-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-4-carboxybut-2-enoyl]amino}-3,4-didehydrocepham-4-carboxylic acid

Indication

Disease Entry	ICD 11	Status	REF
Chronic bronchitis	CA20.1	Approved	[1]

• Therapeutic Class: Antibiotics
• Drug Type: Small molecular drug
• #Ro5 Violations (Lipinski): 0:
  Molecular Weight (mw); 410.4
  Topological Polar Surface Area (xlogp); -0.3
  Rotatable Bond Count (rotbonds); 6
  Hydrogen Bond Donor Count (hbonddonor); 4
  Hydrogen Bond Acceptor Count (hbondacc); 10
• ADMET Property:
  Absorption: The drug is rapidly absorbed following oral administration [2]
  BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 4: low solubility and low permeability [3]
  Bioavailability: 82.5% of drug becomes completely available to its intended biological destination(s) [4]
  Elimination: 71% of drug is excreted from urine in the unchanged form [3]
  MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 13.9227 micromolar/kg/day [5]
  Vd: The volume of distribution (Vd) of drug is 0.21 L/kg [6]
  Water Solubility: The ability of drug to dissolve in water is measured as 0.08 mg/mL [3]
• Chemical Identifiers:
  Formula: C15H14N4O6S2
  IUPAC Name: (6R,7R)-7-[[(Z)-2-(2-amino-1,3-thiazol-4-yl)-4-carboxybut-2-enoyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  Canonical SMILES: C1C=C(N2[C@H](S1)[C@@H](C2=O)NC(=O)/C(=C\\CC(=O)O)/C3=CSC(=N3)N)C(=O)O
  InChI: InChI=1S/C15H14N4O6S2/c16-15-17-7(5-27-15)6(1-2-9(20)21)11(22)18-10-12(23)19-8(14(24)25)3-4-26-13(10)19/h1,3,5,10,13H,2,4H2,(H2,16,17)(H,18,22)(H,20,21)(H,24,25)/b6-1-/t10-,13-/m1/s1
  InChIKey: UNJFKXSSGBWRBZ-BJCIPQKHSA-N
• Cross-matching ID:
  PubChem CID: 5282242
  ChEBI ID: CHEBI:3510
  CAS Number: 97519-39-6
  DrugBank ID: DB01415
  TTD ID: D05JDR
  VARIDT ID: DR00537
  ACDINA ID: D00111

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	[7]

Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
Peptide transporter 2 (SLC15A2)	DT8QKNP	S15A2_HUMAN	Substrate	[8]
Peptide transporter 1 (SLC15A1)	DT9G7XN	S15A1_HUMAN	Substrate	[9]

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

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Benzyl alcohol	E00010	244	Antimicrobial preservative; Solvent
Butylparaben	E00142	7184	Antimicrobial preservative
methylparaben	E00149	7456	Antimicrobial preservative
Propyl 4-hydroxybenzoate	E00141	7175	Antimicrobial preservative
Sodium benzoate	E00432	517055	Antimicrobial preservative; lubricant
Sodium lauryl sulfate	E00464	3423265	Emulsifying agent; Modified-release agent; Penetration agent; Solubilizing agent; Surfactant; lubricant
Simethicone	E00575	6433516	Antifoaming agent; Diluent; Water-repelling agent
Edetate calcium disodium	E00487	6093170	Complexing agent
Magnesium stearate	E00208	11177	lubricant
Polysorbate 80	E00665	Not Available	Dispersing agent; Emollient; Emulsifying agent; Plasticizing agent; Solubilizing agent; Surfactant; Suspending agent
Saccharose	E00091	5988	Binding agent; Coating agent; Cryoprotectant; Diluent; Flavoring agent; Suspending agent; Viscosity-controlling agent
Silicon dioxide	E00670	Not Available	Anticaking agent; Opacifying agent; Viscosity-controlling agent
Sodium propionate	E00445	2723816	Antimicrobial preservative
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
Xanthan gum	E00694	Not Available	Bioadhesive material; Emulsifying agent; Gelling agent; Modified-release agent; Suspending agent; Viscosity-controlling agent

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Ceftibuten 400 mg capsule	400 mg	Oral Capsule	Oral
Ceftibuten Dihydrate eq 400mg base capsule	eq 400mg base	Capsule	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

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• [4] Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
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• [9] Increased protein level of PEPT1 intestinal H+-peptide cotransporter upregulates absorption of glycylsarcosine and ceftibuten in 5/6 nephrectomized rats. Am J Physiol Gastrointest Liver Physiol. 2005 Apr;288(4):G664-70.
• [10] Interactions of amoxicillin and cefaclor with human renal organic anion and peptide transporters. Drug Metab Dispos. 2006 Apr;34(4):547-55.
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• [12] Several hPepT1-transported drugs are substrates of the Escherichia coli proton-coupled oligopeptide transporter YdgR. Res Microbiol. 2017 Jun;168(5):443-449.
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• [15] Three-dimensional quantitative structure-activity relationship analyses of beta-lactam antibiotics and tripeptides as substrates of the mammalian H+/peptide cotransporter PEPT1. J Med Chem. 2005 Jun 30;48(13):4410-9.
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• [19] Species Differences in Human and Rodent PEPT2-Mediated Transport of Glycylsarcosine and Cefadroxil in Pichia Pastoris Transformants. Drug Metab Dispos. 2017 Feb;45(2):130-136.
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• [22] Transport of angiotensin-converting enzyme inhibitors by H+/peptide transporters revisited. J Pharmacol Exp Ther. 2008 Nov;327(2):432-41.
• [23] 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.
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• [26] 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.
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• [29] Clofarabine: past, present, and future. Leuk Lymphoma. 2007 Oct;48(10):1922-30.
• [30] 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.
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