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
Acute otitis media	AB00	Approved	[1]
Chronic bronchitis	CA20.1	Approved	[2]
Pars planitis	N.A.	Approved	[1]
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Therapeutic Class

Antibiotics

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

410.4

Logarithm of the Partition Coefficient (xlogp)

-0.3

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Absorption: The drug is rapidly absorbed following oral administration []
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 []
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

Repurposed Drugs (RPD)

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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]

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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]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Organic anion transporter 3 (SLC22A8)	OT8BY933	S22A8_HUMAN	Regulation of Drug Effects	[9]
Solute carrier family 22 member 6 (SLC22A6)	OTKRCBVM	S22A6_HUMAN	Regulation of Drug Effects	[9]

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Molecular Interaction Atlas (MIA)

MIA Detail

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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
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⏷ Show the Full List of 15 Pharmaceutical Excipients of This Drug

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

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References

1	Ceftibuten 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	Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
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	Neisseria gonorrhoeae and emerging resistance to extended spectrum cephalosporins. Curr Opin Infect Dis. 2009 Feb;22(1):87-91.
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	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.
9	Human organic anion transporter hOAT3 is a potent transporter of cephalosporin antibiotics, in comparison with hOAT1. Biochem Pharmacol. 2005 Oct 1;70(7):1104-13.