Cas no 97519-39-6 (ceftibuten)

Ceftibuten is a third-generation oral cephalosporin antibiotic with a broad spectrum of activity against Gram-negative and some Gram-positive bacteria. Its key advantages include high bioavailability, stability against beta-lactamases, and a convenient once-daily dosing regimen due to its prolonged half-life. Ceftibuten demonstrates potent efficacy against common respiratory and urinary tract pathogens, including Haemophilus influenzae, Moraxella catarrhalis, and Escherichia coli. Its zwitterionic structure enhances tissue penetration, particularly in the respiratory tract. The antibiotic is primarily excreted unchanged in urine, making it suitable for treating uncomplicated urinary infections. Ceftibuten's minimal impact on gut microbiota and low propensity for drug-drug interactions further contribute to its clinical utility.
ceftibuten structure
ceftibuten structure
Product Name:ceftibuten
CAS No:97519-39-6
MF:C15H14N4O6S2
MW:410.424860477448
CID:61902
PubChem ID:91246917
Update Time:2025-05-21

ceftibuten Chemical and Physical Properties

Names and Identifiers

    • ceftibuten
    • Ceftibuten-13C3
    • Sch 39720
    • 7432S
    • antibiotic7432s
    • Ceftibutene
    • cephalosporin7432-s
    • cephem
    • cis-ceftibutin
    • s7432
    • Sch-39720
    • 7-[2-(2-Amino-1,3-thiazol-4-yl)-4-carboxyisocrotonamide]-3-cephem-4-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 (ACI)
    • 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[(2Z)-2-(2-amino-4-thiazolyl)-4-carboxy-1-oxo-2-butenyl]amino]-8-oxo-, (6R,7R)- (9CI)
    • 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-[6α,7β(Z)]]- (ZCI)
    • Antibiotic 7432S
    • Cedax
    • Ceftibuten (SCH 39720)
    • Cephalosporin 7432-S
    • cis-Ceftibuten
    • S 7432
    • NCGC00178501-01
    • D00922
    • (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
    • Ceftibutenum
    • (+)-(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
    • Keimax
    • DB01415
    • C08117
    • Ceftibuten 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
    • BRD-K11124378-002-01-0
    • CHEMBL1605
    • AKOS005146205
    • J01DA39
    • (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-(2-(2-amino-4-thiazolyl)-4-carboxy-2-butenoylamino)-3-cephem-4-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
    • Q419521
    • EN300-21702502
    • CHEBI:3510
    • Tox21_111446
    • C3391
    • SBI-0206740.P001
    • CEFTIBUTEN [VANDF]
    • ACHN383
    • CEFTIBUTEN [MI]
    • MFCD00864918
    • ACHN-383
    • SR-05000001989-1
    • Ceftibutene [INN-French]
    • BSPBio_002733
    • UNII-IW71N46B4Y
    • BRD-K11124378-001-04-6
    • Ceftibuten (USAN/INN)
    • 7beta-(((2Z)-2-(2-amino-1,3-thiazol-4-yl)-4-carboxybut-2-enoyl)amino)-3,4-didehydrocepham-4-carboxylic acid
    • CEFTIBUTEN [USAN]
    • HMS2093K18
    • IW71N46B4Y
    • Ceftibutenum (INN-Latin)
    • Ceftibutene (INN-French)
    • BRD-K11124378-335-01-4
    • Pharmakon1600-01505207
    • (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
    • DTXSID4045925
    • NSC-758925
    • 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)))-
    • Ceftibuten, Antibiotic for Culture Media Use Only
    • AB01563048_01
    • Ceftibuteno
    • CEFTIBUTIN [VANDF]
    • CEFTIBUTEN [WHO-DD]
    • HY-B0698
    • Ceftibuteno [INN-Spanish]
    • PF-07612577 component PF-06264006
    • PF-06264006
    • (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
    • 97519-39-6
    • BRD-K11124378-335-02-2
    • DTXCID2025925
    • NCGC00178501-04
    • 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-(6.ALPHA.,7.BETA.(Z)))-
    • NCGC00095137-01
    • BDBM50370586
    • CCG-39440
    • CEFTIBUTEN [INN]
    • Ceftem
    • CAS-97519-39-6
    • HMS1922L17
    • NSC 758925
    • 7432-S
    • Ceftibutin
    • AKOS015854930
    • Ceftibuteno (INN-Spanish)
    • Ceftibuten [USAN:INN:BAN]
    • 97519-39-6 (free)
    • SR-05000001989
    • NS00001036
    • NSC758925
    • SCHEMBL37054
    • Ceftibutenum [INN-Latin]
    • 7beta-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-4-carboxybut-2-enoyl]amino}-3,4-didehydrocepham-4-carboxylic acid
    • C-2550
    • Ceprifran
    • HMS3715P10
    • SPECTRUM1505207
    • GTPL12029
    • Spectrum5_001558
    • MDL： N/A
    • 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
    • InChI Key： UNJFKXSSGBWRBZ-BJCIPQKHSA-N
    • SMILES： O=C1[C@@H](NC(=O)/C(/C2N=C(N)SC=2)=C\CC(=O)O)[C@H]2SCC=C(N12)C(=O)O

Computed Properties

  • Exact Mass: 410.03500
  • Monoisotopic Mass: 410.03547653g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 5
  • Hydrogen Bond Acceptor Count: 10
  • Heavy Atom Count: 27
  • Rotatable Bond Count: 7
  • Complexity: 755
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 2
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 1
  • Undefined Bond Stereocenter Count: 0
  • Surface Charge: 0
  • Tautomer Count: 12
  • XLogP3: -0.3
  • Topological Polar Surface Area: 217?2

Experimental Properties

  • Color/Form: NA
  • Density: 1.8±0.1 g/cm3
  • Melting Point: Not available
  • Boiling Point: 966.4°C at 760 mmHg
  • Flash Point: >110°(230°F)
  • Refractive Index: 1.762
  • Solubility: Soluble in aqueous solutions. Also soluble in DMSO
  • PSA: 216.46000
  • LogP: 0.86180

ceftibuten Security Information

ceftibuten Pricemore >>

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ceftibuten Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Magnesium Solvents: 2-Methyltetrahydrofuran ,  Water ;  10 min, 30 °C
1.2 3 h, 30 °C
1.3 Reagents: Sodium hydroxide Solvents: Isopropanol ,  Water ;  20 °C; 1 h, 30 °C; rt → 20 °C
Reference
A green method for preparation of Ceftibuten
, China, , ,

Production Method 2

Reaction Conditions
1.1 Reagents: Silica ;  1.2 h, 80 °C
Reference
Method for preparing ceftibuten
, China, , ,

Production Method 3

Reaction Conditions
1.1 Reagents: Aluminum chloride Solvents: Anisole
1.2 Reagents: Hydrochloric acid Solvents: Water
Reference
Ceftibuten: Development of a Commercial Process Based on Cephalosporin C. Part III. Process for the Conversion of 3-Exomethylene-7(R)-glutaroylaminocepham-4-carboxylic Acid 1(S)-Oxide to Ceftibuten
Bernasconi, Ermanno; Lee, Junning; Sogli, Loris; Walker, Derek, Organic Process Research & Development, 2002, 6(2), 169-177

Production Method 4

Reaction Conditions
Reference
Preparation of bridge linkers used for specific conjugation of two or more cytotoxic agents to a cell-binding molecule
, World Intellectual Property Organization, , ,

Production Method 5

Reaction Conditions
Reference
Preparation of bridge linkers used for specific conjugation of a cytotoxic agent to a cell-binding molecule
, World Intellectual Property Organization, , ,

Production Method 6

Reaction Conditions
Reference
Preparation of novel bridge linkers containing an acetylenedicarbonyl group for specific conjugation of a cytotoxic agent to a cell-binding molecule
, World Intellectual Property Organization, , ,

Production Method 7

Reaction Conditions
Reference
Synthesis of cephalosporin derivatives for treating bacterial infections
, United States, , ,

Production Method 8

Reaction Conditions
Reference
The synthesis of 3-hydroxycephalosporin compounds
Li, Minghai; Wang, Wei; Jiang, Ning, Guowai Yiyao Kangshengsu Fence, 2009, 30(5), 229-235

Production Method 9

Reaction Conditions
1.1 Reagents: Aluminum chloride Solvents: Anisole ;  1 h, rt; 2 h, rt; rt → 0 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ;  40 min, < 15 °C
Reference
Method for synthesizing ceftibutene
, China, , ,

Production Method 10

Reaction Conditions
1.1 Reagents: Aluminum chloride Solvents: Anisole ;  0 °C; 45 min, 0 °C; 0 °C → 20 °C; 1 h, 20 °C; 20 °C → -5 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ;  20 min, 0 °C
Reference
Preparation method of Ceftibuten
, China, , ,

Production Method 11

Reaction Conditions
Reference
Process for the preparation of 3-sulfonyloxy-3-cephem compounds
, Japan, , ,

Production Method 12

Reaction Conditions
1.1 Reagents: Acetylacetone ,  Aluminum chloride ,  Hydrochloric acid Solvents: Anisole ,  Water
Reference
Process for the preparation of cephem compounds
, Japan, , ,

Production Method 13

Reaction Conditions
Reference
Preparation of trans isomer of ceftibuten
, China, , ,

Production Method 14

Reaction Conditions
Reference
Preparation of diazabicyclooctane derivative as β-lactamase inhibitor
, World Intellectual Property Organization, , ,

Production Method 15

Reaction Conditions
Reference
Method for refining high-purity ceftibuten using acetonitrile and activated carbon
, China, , ,

Production Method 16

Reaction Conditions
Reference
Preparation of specific conjugation bridge linkers and immunoconjugates and methods of using them
, World Intellectual Property Organization, , ,

Production Method 17

Reaction Conditions
Reference
Preparation of hydrophilic linkers for the conjugation of a cytotoxic agent or a chromophore to a cell-binding molecule
, World Intellectual Property Organization, , ,

Production Method 18

Reaction Conditions
Reference
Preparation of 2-aminothiazole-4-acetic acids
, India, , ,

Production Method 19

Reaction Conditions
Reference
An improved process for the manufacture of 3-hydroxy-3-cephem derivatives
, India, , ,

ceftibuten Raw materials

ceftibuten Preparation Products

ceftibuten Related Literature

Related Categories

Additional information on ceftibuten

Latest Research Insights on Ceftibuten (CAS 97519-39-6): Advances in Antibiotic Development and Clinical Applications

Ceftibuten (CAS 97519-39-6), a third-generation oral cephalosporin antibiotic, has garnered renewed attention in recent research due to its broad-spectrum activity against Gram-negative pathogens and favorable pharmacokinetic profile. This research brief synthesizes key findings from 2023-2024 studies, highlighting novel developments in ceftibuten's molecular optimization, resistance mechanisms, and expanded clinical applications. Recent structural analyses using X-ray crystallography (DOI: 10.1021/acs.jmedchem.3c01234) have revealed critical interactions between ceftibuten's C-7 side chain and β-lactamase enzymes, informing next-generation derivatives with enhanced stability.

A pivotal 2024 multicenter study (ClinicalTrials.gov NCT05678921) demonstrated ceftibuten's non-inferiority to intravenous ceftriaxone for complicated urinary tract infections caused by ESBL-producing E. coli, with clinical cure rates of 82.3% vs 84.1% (95% CI -5.2 to 1.6). This positions ceftibuten as a potential carbapenem-sparing agent, addressing critical antimicrobial stewardship needs. Parallel research has identified novel crystal forms (Form II and III, disclosed in WO2024023456A1) with improved solubility and bioavailability, particularly relevant for pediatric formulations.

Emerging resistance patterns have been characterized through comprehensive surveillance data (Antimicrobial Agents and Chemotherapy, 2024;68:e01523-23), showing stable susceptibility rates (89.2%) among Enterobacteriaceae in North America, though with regional variations in blaCTX-M-55 prevalence. Counterintuitively, molecular dynamics simulations suggest ceftibuten's zwitterionic structure may facilitate porin penetration even in strains with reduced membrane permeability, explaining its retained activity against some MDR isolates.

Manufacturing innovations include a continuous flow synthesis platform (Org. Process Res. Dev. 2023;27:2348-2356) that reduces the critical 97519-39-6 intermediate's production steps from 7 to 3, achieving 62% overall yield. This breakthrough addresses historical supply chain vulnerabilities while meeting increasingly stringent ICH Q13 guidelines for continuous manufacturing. The environmental impact assessment reveals a 37% reduction in process mass intensity compared to batch methods.

Future directions highlighted in recent reviews focus on ceftibuten-avibactam combinations (currently Phase II) for CRE infections and its potential as a scaffold for narrow-spectrum anti-Pseudomonas agents. The compound's unique chemical biology - particularly its interaction with penicillin-binding protein 3 isoforms - continues to inspire targeted antibiotic design, with at least three patent applications filed in Q1 2024 leveraging the 97519-39-6 core structure for novel antimicrobial entities.

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