General Information of API (ID: D00111)
Name
Ceftibuten
Synonyms    Click to Show/Hide the Synonyms of This API
ceftibuten; 97519-39-6; Ceftibuteno; Ceftibutenum; Ceftibutene; Sch 39720; cis-ceftibuten; UNII-IW71N46B4Y; Sch-39720; Ceftibuten hydrate; 7432-S; Antibiotic 7432S; CHEBI:3510; IW71N46B4Y; CEFTIBUTEN DIHYDRATE; 97519-39-6 (free); Isocef; MFCD00864918; (+)-(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; cis-Ceftibutin; 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-((2-(2-amino-4-thiazolyl)-4-carboxy-1-oxo-2-butenyl)amino)-8-oxo-, (6R-(6alpha,7beta(Z)))-; Cephalosporin 7432-S; (6R,7R)-7-((Z)-2-(2-Aminothiazol-4-yl)-4-carboxybut-2-enamido)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; Ceftibutene [INN-French]; Ceftibutenum [INN-Latin]; Ceftibuteno [INN-Spanish]; Ceprifran; Ceftem; Keimax; Ceftibuten [USAN:INN:BAN]; S 7432; NCGC00095137-01; Ceftibuten, 95%; Ceftibuten (USAN/INN); Spectrum5_001558; CHEMBL1605; DSSTox_CID_25925; DSSTox_RID_81227; DSSTox_GSID_45925; SCHEMBL37054; ACHN383; BSPBio_002733; SPECTRUM1505207; ACHN-383; DTXSID4045925; HMS1922L17; HMS2093K18; HMS3715P10; Pharmakon1600-01505207; HY-B0698; ZINC3871967; Tox21_111446; BDBM50370586; CC0255; CCG-39440; NSC758925; AKOS005146205; AKOS015854930; DB01415; NSC-758925; NCGC00178501-01; NCGC00178501-04; SBI-0206740.P001; CAS-97519-39-6; C08117; D00922; AB01563048_01; 519C396; Ceftibuten, Antibiotic for Culture Media Use Only; Q419521; SR-05000001989; SR-05000001989-1; 7-[2-(2-Amino-1,3-thiazol-4-yl)-4-carboxyisocrotonamide]-3-cephem-4-carboxylicacid; (6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-4-carboxybut-2-enamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7R)-7-[[(2Z)-2-(2-Amino-4-thiazolyl)-4-carboxy-1-oxo-2-buten-1-yl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; (6R,7R)-7-[[(2Z)-2-(2-Amino-4-thiazolyl)-4-carboxy-1-oxo-2-buten-1-yl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid hydrate; (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; (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; 7beta-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-4-carboxybut-2-enoyl]amino}-3,4-didehydrocepham-4-carboxylic acid
Clinical Status
Approved
Disease Indication Bronchitis ICD-11: CA20 [1]
PubChem CID
5282242
Formula
C15H14N4O6S2
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
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
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=5282242"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 410.4 Topological Polar Surface Area 217
XlogP -0.3 Complexity 755
Heavy Atom Count 27 Rotatable Bond Count 6
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 10
Full List of Drug Formulations (DFMs) Containing This API
          Ceftibuten 400 mg capsule Click to Show/Hide the Full List of Formulation(s):          2 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Methylparaben; Sodium lauryl sulfate; Butylparaben; Benzyl alcohol; Magnesium stearate; Propylparaben; Sodium propionate; Edetate calcium disodium; Titanium dioxide; Polysorbate 80; Cellulose, microcrystalline; Gelatin; Sodium starch glycolate type a potato
                   Dosage Form Oral Capsule
                   Company Macoven Pharmaceuticals; Pernix Therapeutics
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
methylparaben DIG Info Carbonic anhydrase VII (Ki = 780 nM) [2]
Benzyl alcohol DIG Info Indoleamine 2,3-dioxygenase 1 (IC50 = 1400 nM) [3]
Butylparaben DIG Info Estrogen receptor alpha (IC50 = 1420 nM) [4]
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [5]
Propyl 4-hydroxybenzoate DIG Info Estrogen receptor alpha (IC50 = 11 uM) [6]
Polysorbate 80 DIG Info Prostaglandin G/H synthase 1 (IC50 = 1 uM) [6]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [7]
             Drug Formulation 2 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Methylparaben; Sodium lauryl sulfate; Butylparaben; Benzyl alcohol; Propylparaben; Sodium propionate; Edetate calcium disodium; Titanium dioxide; Polysorbate 80; Gelatin
                   Dosage Form Oral Capsule
                   Company Sciele Pharma, Inc.
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
methylparaben DIG Info Carbonic anhydrase VII (Ki = 780 nM) [2]
Benzyl alcohol DIG Info Indoleamine 2,3-dioxygenase 1 (IC50 = 1400 nM) [3]
Butylparaben DIG Info Estrogen receptor alpha (IC50 = 1420 nM) [4]
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [5]
Propyl 4-hydroxybenzoate DIG Info Estrogen receptor alpha (IC50 = 11 uM) [6]
Polysorbate 80 DIG Info Prostaglandin G/H synthase 1 (IC50 = 1 uM) [6]
          Ceftibuten Dihydrate eq 400mg base capsule Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Cherry Flavoring; Polysorbate 80; Silicon Dioxide; Simethicone; Sodium Benzoate; Sucrose; Titanium Dioxide; Xanthan Gum
                   Dosage Form Capsule
                   Company
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Simethicone DIG Info Opioid receptor mu (IC50 = 1.5 nM) [8]
Sodium benzoate DIG Info Carbonic anhydrase II (Ki = 30000 nM) [9]
Polysorbate 80 DIG Info Prostaglandin G/H synthase 1 (IC50 = 1 uM) [6]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [7]
References
1 FDA label for approved ceftibuten from the official website of the U.S. Food and Drug Administration.
2 Mono-/dihydroxybenzoic acid esters and phenol pyridinium derivatives as inhibitors of the mammalian carbonic anhydrase isoforms I, II, VII, IX, XII and XIV. Bioorg Med Chem. 2013 Mar 15; 21(6):1564-9.
3 O-alkylhydroxylamines as rationally-designed mechanism-based inhibitors of indoleamine 2,3-dioxygenase-1. Eur J Med Chem. 2016 Jan 27; 108:564-576.
4 Disconnecting the Estrogen Receptor Binding Properties and Antimicrobial Properties of Parabens through 3,5-Substitution. ACS Med Chem Lett. 2017 Dec 15; 9(1):51-55.
5 Bacterial metabolism rescues the inhibition of intestinal drug absorption by food and drug additives. Proc Natl Acad Sci U S A. 2020 Jul 7;117(27):16009-16018.
6 The activities of drug inactive ingredients on biological targets. Science. 2020 Jul 24;369(6502):403-413.
7 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.
8 From hit to lead. Combining two complementary methods for focused library design. Application to mu opiate ligands. J Med Chem. 2001 Oct 11; 44(21):3378-90.
9 Carbonic anhydrase inhibitors. Interaction of isozymes I, II, IV, V, and IX with carboxylates. Bioorg Med Chem Lett. 2005 Feb 1; 15(3):573-8.

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